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  • Christmas in Mount Dora, Florida With Kids: Our Cozy Small-Town Getaway

    Christmas in Mount Dora, Florida With Kids: Our Cozy Small-Town Getaway

    There’s something about visiting a small town during Christmas that makes the holidays feel a little more magical. And Mount Dora, Florida, is one of those places that makes you want to slow down, grab a coffee, and spend the afternoon wandering around.

    We visited Mount Dora with our four-year-old and stayed in a VRBO within walking distance of downtown, which ended up being such a convenient way to experience this charming little town.

    One of my favorite things about Mount Dora is how walkable everything feels. We didn’t need a packed itinerary or a long list of activities to enjoy ourselves. Sometimes the best family getaways are the ones where you can simply explore at your own pace.

    We started with coffee from Foxtail Coffee before making our way through the little shops downtown. I loved being able to wander from store to store, take in the atmosphere, and enjoy a slower kind of family getaway.

    Mount Dora has that friendly, welcoming feeling that makes it especially nice when you’re traveling with younger kids. And during the Christmas season, it becomes an even more charming place to visit.

    If you’re looking for a festive Florida getaway that doesn’t involve theme parks or an overly complicated itinerary, Mount Dora is definitely worth considering.

    Why We Chose to Stay Within Walking Distance of Downtown

    For this trip, we booked a VRBO close enough to walk into downtown Mount Dora.

    And if you’re planning to visit during the holidays, I would absolutely recommend looking for accommodations within walking distance of the historic downtown area.

    Being able to leave our rental and explore without constantly getting back into the car made the trip feel so much more relaxing.

    It also gave us flexibility. With a young child, I love having the option to head back to where we’re staying for a break before going out again.

    Travel tip: When searching for a vacation rental, check the actual walking route to downtown rather than relying only on the distance shown in the listing.

    Find vacation rentals near downtown Mount Dora

    Coffee, Little Shops, and Exploring Downtown Mount Dora

    One of our stops was Foxtail Coffee, which was a nice way to start exploring.

    After grabbing coffee, we spent time checking out the little shops around downtown.

    This is honestly one of my favorite ways to experience a destination. I love finding places where you can walk around, discover local businesses, and enjoy the atmosphere without having to rush from one attraction to another.

    Mount Dora is perfect for that kind of getaway.

    And when you’re visiting with a five-year-old, having a flexible schedule makes such a difference. You can explore a few shops, stop for something to eat, and enjoy the town without feeling like you need to squeeze everything into one afternoon.

  • My Favorite Way to Organize Travel Activities

    My Favorite Way to Organize Travel Activities

    One thing I’ve learned from traveling with Mila is that keeping everything organized makes life so much easier!

    Instead of throwing all her activities into a backpack and digging around whenever she wants something, I love using a foldable travel organizer with clear zippered compartments.

    It’s such a simple idea, but it makes packing activities so much easier.

    Each compartment can hold something different, like coloring books, markers, stickers, small games, and other little activities. I especially love that you can see what’s inside without having to unzip every section.

    And the best part? It folds up compactly and fits right inside a backpack!

    This is especially convenient for flights because I can pull out one activity at a time without having everything scattered across the airplane tray table.

    It’s also great for road trips, Disney vacations, and those moments when we need something to keep Mila entertained while waiting.

    I love finding little travel organization tricks that make packing easier without taking up more space.

    Shop a similar travel activity organizer items

    Travel tip: Choose an organizer with several zippered compartments so smaller supplies stay together. Always check the folded dimensions to make sure it fits your child’s backpack.

  • The Good Witch of Salem With a 5-Year-Old: What We Chose and Would We Go Back?

    The Good Witch of Salem With a 5-Year-Old: What We Chose and Would We Go Back?

    When I was planning our October trip to Salem, I knew I wanted to squeeze in a little Hocus Pocus for me and find something Mila could get excited about, too. The Good Witch of Salem was on my list, and I ended up choosing the potion-making experience for her. By the time she’d finished her potion, she was already excited to try the other activities. So I’d say I picked a good one!

    Some of the hotel links below are affiliate links. If you book through one of them, I may earn a small commission at no extra cost to you. Thank you for supporting Strolling Through Travel!

    🍂 Short on Time? My Top 3 Salem Stays

    ⭐⭐⭐ Hawthone Hotel – Click here for rates & availability

    ⭐⭐ The Salem Inn – Click here for rates & availability

    ⭐ Hampton Inn Salem – Click here for rates & availability

    Making a potion with Mila

    If you know how much we love Disney, you’ll understand why this made me think of Bibbidi Bobbidi Boutique. I had the same feeling watching Mila get into it, except this time my girl was a good witch making her own potion in Salem. How cute is that?

    We heard the story of the Good Witch of Salem, and I got to watch Mila write in the spell book and mix her potion. The spell book is the part I keep going back to in my videos. I love seeing her get that into something she’s doing herself.

    I went in thinking we’d make a potion and carry on with our Salem day. And then she finished and was excited about all the other things she could try! We stuck with the potion this time, but next time I’d let her choose. I could see her having fun decorating a broom or picking out a witch hat.

    And yes, I already signed us up for the monthly potion kit. Apparently we’re bringing a little bit of Salem home with us! The shop lists the Potion of the Month Club at $40 as a recurring subscription.

    What does The Good Witch of Salem cost?

    If I were choosing one thing for a first visit with a five-year-old, I’d do the potion again. It’s $35 for one potion to take home, and the shop says to allow 15–25 minutes. That worked for the kind of Salem day I wanted, with one activity just for Mila and time left over to wander. See the potion-making experience.

    Here’s what the shop listed on November 4, 2026, if your little witch is already eyeing the other options.

    ActivityListed price
    Potion making$35
    Broom decorating$45
    Witch hat decorating$55
    Broom building$65
    Enchanted Witch Transformation$149
    Ultimate Witch Transformation$225

    If your child is all about the outfit, the Enchanted Witch Transformation comes with a sash, a cape, and their choice of witch hat. The shop asks you to reserve a slot for each child. See the witch transformations or browse the broom and hat activities.

    A few things I’d check before going

    The shop is at 281 Essex Street, near the Witch House. If you’re going in September or October, book ahead. The shop requires advance reservations in those months. At other times of year, it takes walk-ins as space allows and recommends booking ahead for weekends and holidays.

    One little detail if you’re bringing a stroller or wagon: it has to stay outside. The potion uses small decorative pieces, so the shop requires adult supervision for ages five and under. I’d also check your timing if you’re planning to pop in late in the day. Activities end 30 minutes before closing, and potion bookings are nonrefundable. Check booking details for your visit.

    Where we booked in Salem

    We only had two night in Salem after our Maine weekend, so we booked Hampton Inn Salem Boston using points. I’m always happy to save a little on the hotel, especially when we’re fitting two destinations into one trip. Free hot breakfast and an indoor pool were nice to have on the list, too. Check Hampton Inn Salem Boston rates.

    If you’re paying cash, I’d compare it with Salem Inn for amazing breakfast and great location. And if you’re going for the full Hocus Pocus weekend, I’d look at Hawthorne Hotel by Salem Common. I still love the idea of waking up and walking right out into historic Salem. Check Salem Inn or check Hawthorne Hotel rates.

    I’d plug in your own dates and check parking when you compare. For more options, I put together a full guide to where to stay in Salem, or you can browse my Salem hotel map.

    Would we go back?

    Absolutely. If you’re taking a little one to Salem and want something festive without the scares, I’d make time for this. I went for the Hocus Pocus nostalgia, and one of my favorite Salem memories ended up being Mila with that spell book. Next time, she gets to pick what we do. 💕

  • Disney Cruise Packing Essentials: What We Actually Used (and What We Didn’t)

    Disney Cruise Packing Essentials: What We Actually Used (and What We Didn’t)

    Before our first Disney cruise, I had a list of things I thought we would need. Now that we’re home, I can tell you which ones were worth bringing—and which one never got used!

    My husband, Mila, and I sailed on a four-night Halloween on the High Seas cruise aboard the Disney Fantasy. Between swimming, island stops, dinners, and Halloween activities, we had plenty going on. But we managed to pack for the three of us with one large suitcase and a couple of smaller tote bags.

    I’m glad we kept it simple. We had the things that helped us stay organized without bringing a suitcase full of extras.

    If you’re packing for your first Disney cruise, here’s my honest take on what I would bring again.

    This post may contain affiliate links. If you shop through one, I may earn a commission at no extra cost to you. As an Amazon Associate, I earn from qualifying purchases.

    In a Rush? These Are the Things I’d Pack Again

    ● Packing cubes: My favorite for organizing our family’s suitcase.

    ● Pop-up hamper: A must-have for keeping dirty clothes together.

    ● Magnetic hooks and a night-light: Small additions that worked great in our room.

    ● Large reusable cups: Helpful throughout the cruise.

    ● A stroller: Useful for helping tote our things around with Mila.

    ● What I’d skip: The over-the-door organizer—we never needed it.

    Want the bigger picture? Read my honest Disney Fantasy Halloween cruise review for our room upgrade, dining experience, island stops, and what Mila loved most.

    Packing Cubes: My Favorite Way to Organize One Family Suitcase

    Packing cubes were amazing to have on this trip.

    When three people are sharing one large suitcase, organization matters. I loved having a way to keep everything together instead of letting our suitcase become one big pile of clothes.

    These are staying on my packing list for future family trips, too. They were one of those things that made our simple packing plan work.

    If you’re using packing cubes for the first time, you could sort them by person or by type of clothing. Choose whichever makes it easiest to find what your family needs.

    My verdict: Definitely bringing them again.

    A Pop-Up Hamper: Small Item, Big Help

    The pop-up hamper was a must for us.

    With swimming and regular outfit changes, having somewhere to collect dirty clothes helped keep our room organized. It was a simple addition, but one I was glad we had packed.

    I would make room for this again before adding another “just in case” outfit to the suitcase.

    My verdict: One of my cruise packing essentials.

    Magnetic Hooks and a Night-Light: Both Earned Their Space

    The magnetic hooks and night-light both worked great in our stateroom.

    Neither took up much luggage space, which is something I appreciate when I’m trying to keep our packing manageable. They were useful little additions rather than things we brought and forgot about.

    We originally booked an oceanview room on Deck 2 and upgraded onboard to a verandah on Deck 10. Even with a room we loved, I was still happy to have these small extras.

    My verdict: I would pack both again.

    Large Reusable Cups: Glad We Brought Them

    We brought large reusable cups, and they were helpful during the cruise.

    These are an easy item to include if your family already has favorites at home. I would bring ours again rather than feeling like I needed to buy an entirely new set of things for another sailing.

    That’s how I want to approach our next packing list: start with what we own and know we’ll use.

    My verdict: Worth bringing.

    A Stroller: Helpful for More Than Getting Around With Mila

    We brought a stroller, and I recommend considering one if it works for your child and your travel plans.

    For us, it was helpful for toting our things around. Family travel comes with bags and belongings even when you make an effort to pack lightly!

    It also fit into the way we handled leaving the ship. We chose to carry our luggage off ourselves instead of having it collected and picking it up in the terminal.

    With one large suitcase, a couple of tote bags, and the stroller, that worked well for our family. Leaving the ship was easy.

    My verdict: I’m glad we brought it. Think about how your family will manage both the stroller and your luggage.

    What We Didn’t Use: The Over-the-Door Organizer

    The over-the-door organizer was the item we brought but did not need at all.

    I can only speak for our family and our room, but it never became part of our routine. With the amount we packed, we were comfortable without using it.

    For another cruise, I would leave it out and stick with the organizing items that actually helped us.

    My verdict: Skipping it next time.

    How We Kept Our Packing Manageable for Four Nights

    We made a point of not overpacking, and I was happy with that decision.

    Our luggage was manageable for the three of us, and carrying it off at the end of the trip felt straightforward. That was a good reminder that everything you pack eventually needs to make its way home!

    For our next four-night cruise, I would use the same approach:

    ● Start with the clothing and everyday essentials our family needs.

    ● Use packing cubes to organize the suitcase.

    ● Add the small room extras we found helpful.

    ● Question anything we’re bringing only because someone else calls it a must-have.

    ● Check whether we can comfortably move all our luggage ourselves.

    Our final packing list will always depend on the trip, but I don’t feel the need to bring every cruise accessory available.

    Our Original Packing Plan vs. What We Actually Did

    If you read my first Disney cruise packing list, this is the follow-up with our actual experience.

    One thing changed beyond the suitcase: we had discussed staying overnight before the cruise, but ultimately did not. We arrived at Port Canaveral on embarkation day, and our assigned port arrival time was 2 p.m.

    That’s why I like coming back to share what happened after a trip. The plan is helpful, but the things we actually used—and the decisions we changed—are what I want to remember for next time.

    What I’d Bring on Our Next Disney Cruise

    Packing cubes, a pop-up hamper, magnetic hooks, a night-light, and reusable cups all earned their space. The stroller was helpful for our family, too.

    The over-the-door organizer can stay home.

    Our first cruise was fantastic, and Mila is already asking to go again. When that next sailing comes around, I’ll be starting with a shorter, more personal packing list based on what worked for us.

    What’s one thing you always pack for a cruise—and one thing you wish you’d left at home? Tell me in the comments!

  • Honest Halloween on the High Seas: Disney Cruise Review

    Honest Halloween on the High Seas: Disney Cruise Review

    Disney Cruise Experience

    Our first Disney Cruise is officially in the books, and I already understand why families keep going back.

    Additionally, between the beautiful ship, amazing food, and friendly staff, we had a fantastic experience.

    Mila could spend swimming, and the voyage aboard the Disney Fantasy was memorable.

    Disney Cruise Family Halloween Sailing

    We sailed on a four-night Halloween on the High Seas Disney Cruise.

    Additionally, it had stops at Castaway Cay and Disney Lookout Cay at Lighthouse Point.

    It was just my husband, our daughter Mila, and me.

    Mila is already asking when we can book the next one.

    Additionally, there were a few things I would change, especially regarding Halloween theming.

    The crowded pool on our sea day stood out. But would we do another Disney Cruise? Absolutely.

    Our Cruise at a Glance

    • Ship: Disney Fantasy
    • Sailing: Four-night Halloween on the High Seas cruise
    • Departure port: Port Canaveral, Florida
    • Stops: Castaway Cay and Disney Lookout Cay at Lighthouse Point
    • Travelers: Two adults and our daughter Mila
    • Stateroom: Originally an oceanview on Deck 2; upgraded onboard to a veranda on Deck 10
    • Dining: Late seating, which worked perfectly for our family

    Boarding the Disney Fantasy for the First Time

    We did not stay overnight before our cruise. We headed to Port Canaveral on embarkation day and arrived a couple of hours early, although our assigned port arrival time was 2 p.m.

    My takeaway for first-time cruisers: pay attention to the port arrival time on your reservation when planning your day. Arriving early does not mean you should count on getting onboard early.

    Once we stepped onto the ship, I was amazed. I loved how they announced each family as they entered. It was such a sweet way to start our first cruise and made boarding feel like an occasion all on its own.

    Then there was the main atrium. The Halloween decorations were beautiful, and I loved walking into that festive atmosphere.

    Our $250 Stateroom Upgrade Was Worth Every Penny

    We originally booked an oceanview stateroom on Deck 2. Once onboard, we asked about upgrading and moved to a veranda stateroom on Deck 10.

    The extra cost was $250 total for our whole family for the cruise, and for us, it was worth every penny. The process was easy, and the veranda space felt huge.

    Our room was toward the back of the ship on the starboard side. The location worked really well for getting to the pool, which was a big part of our trip.

    As first-time cruisers, we had been worried about seasickness. Thankfully, none of us experienced it on this sailing. That was our personal experience with this room, rather than a guarantee about staying on a particular deck.

    The exhaust from the ship’s funnel could be a lot near our balcony at times.

    Additionally, we had an incredible view of the fireworks from our veranda.

    Watching them from our own space was one of my favorite moments on the Disney Cruise.

    This was the upgrade price we were offered on our Disney Cruise.

    Additionally, I would not plan a future trip around getting the same room or price.

    The Food Was Amazing—and Enchanted Garden Was My Favorite

    One thing is certain: we did not go hungry on this cruise!

    The food was amazing, and my favorite restaurant was Enchanted Garden. It was beautiful and, to me, felt like stepping into Alice in Wonderland.

    As the evening progressed, the flower-shaped light fixtures opened and bloomed. It was such a lovely detail, and the setting made dinner feel special before we even got to the food.

    Everything we enjoyed there felt fresh and was beautifully plated. The restaurant staff were friendly and went above and beyond for our family. Their service was a big part of what made our dinners so memorable.

    Why Late Dining Worked for Us

    We loved our late dining time. We had a late lunch, and with so much food available around the ship, we never felt like we were waiting around hungry for dinner.

    For our family, the later seating fit comfortably into our days. I would choose it again based on this experience.

    What Mila Loved Most on the Disney Fantasy

    If you asked Mila to plan the entire cruise, I think we would have spent almost all of it at the pool.

    She loved swimming and the slide and could happily have stayed there all day. We spent our last day, which was our sea day, enjoying the pool—but it was packed.

    That was one of the biggest drawbacks of our sailing. We still had fun, but the pool experience on that day was definitely busy.

    Another favorite was the nine-hole mini golf area. Mila loved it, and it gave us another fun activity to enjoy together between swimming and everything else happening onboard.

    Our Experience With the Onboard Kids’ Club

    Mila tried the kids’ club onboard the ship, but it was not her favorite. She preferred swimming to playing games there.

    I am glad we let her try it, but we followed her lead about how she wanted to spend the trip. For our family, the pool and mini golf were the bigger hits.

    Castaway Cay vs. Lookout Cay: Which Did We Prefer?

    We enjoyed visiting both islands, but I preferred the smaller layout at Castaway Cay.

    The walk from the ship was much shorter than at Lookout Cay, and the more compact layout felt easier for our family.

    The smaller water play area we liked at Castaway Cay was part of the island’s supervised kids’ club. It felt perfect for a little one like Mila.

    This was a drop-off area for children. We checked Mila in, and at pickup we used her kids’ club wristband and our secret word. That is a helpful detail to know when planning your island day!

    Lookout Cay’s water play area was nice too, but it became very full during our visit. Between the longer walk and the busier water play area, Castaway Cay was the better fit for us on this trip.

    That does not mean we did not enjoy Lookout Cay. Castaway simply matched what we wanted from a beach day with Mila.

    Halloween on the High Seas: What We Loved

    I loved the Halloween activities and the chance to see the characters in their costumes. They were so cute, and the character lines did not feel too long during our sailing.

    We also went trick-or-treating in the buffet area. It was fun and perfect for little ones.

    Our trick-or-treat session lasted only 30 minutes, so getting there on time mattered. Check the schedule for your own sailing so you do not miss the window.

    What I Wish Disney Had Added

    The Halloween decorations in the main atrium were gorgeous. I just wished that level of decorating continued throughout more of the ship.

    I also would have loved more Halloween-themed food in the restaurants to match the activities and decorations. The food itself was excellent, but some seasonal touches would have made the experience feel even more festive.

    For me, that felt like a missed opportunity on an otherwise beautiful Halloween cruise.

    Pirate Night, Fireworks, and Frozen

    We watched the Pirate Night show, which was a lot of fun. The fireworks were another highlight, especially because we had such a great view from our veranda.

    We missed the Aladdin show, but we did see Frozen, A Musical Spectacular, and it was amazing.

    The “snow” at the end was such a fun touch! It was one of those moments that made the show feel extra special.

    We did not fit in everything, and I was happy with that. We enjoyed the entertainment we saw while still leaving plenty of time for swimming and relaxing together.

    What We Packed—and Actually Used

    We made a point of keeping our luggage manageable. For the three of us, we brought one large suitcase and a couple of smaller tote bags.

    These were the items that earned their space:

    The item we did not need was the over-the-door organizer. We brought it but never used it, so I would leave it out next time.

    Keeping our packing simple also helped at the end of the cruise.

    Leaving the Ship Was Easy

    We chose to carry our luggage off the ship ourselves instead of having it collected and picking it up in the terminal.

    With one large suitcase, our tote bags, and the stroller, this worked well for our family. Leaving the ship was easy, and I was glad we had not overpacked.

    If you are considering doing the same, think about whether your family can comfortably manage everything you bring.

    Was a Four-Night Disney Fantasy Cruise Worth It?

    For us, absolutely.

    Four nights went by quickly, but it felt like the perfect length for our first cruise. We got to experience the ship, visit both islands, enjoy the Halloween activities, and figure out what our family likes about cruising.

    The food and restaurant service were highlights. Mila loved the pool, slide, and mini golf. And that $250 veranda upgrade gave us a space we loved, plus an unforgettable fireworks view.

    I would have enjoyed more Halloween decor throughout the ship and themed food in the restaurants, and the crowded sea-day pool is something I would keep in mind for another sailing.

    But we left happy, and Mila is already asking to go again. I think that tells you exactly how our first Disney cruise went!

    Have you sailed on the Disney Fantasy—or are you planning your first Disney cruise? Let me know in the comments!

  • Mickey’s Not-So-Scary Halloween Party With a 5-Year-Old: Was It Worth It for Us?

    Mickey’s Not-So-Scary Halloween Party With a 5-Year-Old: Was It Worth It for Us?

    Our night at Mickey’s Not-So-Scary Halloween Party came with rain, character sightings, plenty of rides, and loads of candy. Mila is already asking when we can go back, which tells you how she felt about it!

    Where we stayed

    We stayed at Disney’s All-Star Movies Resort. The movie theme was such a cute part of our stay and kept the Disney fun going even when we left the park.

    Perfect for my puppy loving girl 💕

    We took Disney’s bus transportation to and from the party. It was convenient for us, especially after a long evening at Magic Kingdom. The bus back was full at the end of our night, though, so I’d allow a little extra time and patience for that last trip with tired kids.

    Yes, it rained

    The rain didn’t stop us from enjoying the party. We came prepared with ponchos and kept going. If rain is in your forecast, I’d pack ponchos before leaving for the park so you’re ready when it starts.

    Prepare for Rain 🌧️

    I’ve gathered more of my park and party finds in my storefront if you’re putting together your own bag.

    Our favorite parts of the party

    We got to see characters, and the ride waits were low during our visit. That gave us time to enjoy the Halloween atmosphere without feeling like we had to rush from one thing to the next.

    And then there was the candy! We brought home loads of it. Trick-or-treating was a huge part of the fun for Mila, and seeing her excitement made the night feel special even with the rain.

    Puppy Pals

    Would we go again?

    Absolutely. Our night wasn’t picture-perfect weather, but we were prepared, had fun together, and made memories Mila is still talking about. If you’re considering Mickey’s Not-So-Scary Halloween Party with a young child, I’d plan for the weather, bring a roomy candy bag, and save some energy for the trip back to your resort.

    Mila’s verdict is simple: she wants to go back again. 🎃

  • St. Augustine and Mount Dora: Top Florida Christmas Picks

    St. Augustine and Mount Dora: Top Florida Christmas Picks

    Two festive Florida Travel towns for a family holiday getaway in 2026

    If you live in Florida and want a Christmas outing, consider Florida Travel. It offers a touch more charm than driving around your neighborhood to view lights. Put St. Augustine and Mount Dora on your list; they each have a different feel. That’s why I like recommending both.

    “Snowing” around St.Augustine

    St. Augustine is the trip I’d choose for a full holiday weekend: historic streets, waterfront views, and lights everywhere you turn. Mount Dora is perfect for a slower downtown holiday trip with shops, food, and lights after dark. I usually book a hotel for convenience, especially during the holidays. Having a place to settle in makes each trip feel like a little Christmas getaway, even when we spend most of our time out exploring.

    In a Rush? Here Are Our Favorite Hotels in St.Augustine

    Bayfront Marin House – Click here for rates & availability
    We loved our beach cottage stay! Choose the downtown property if you want to stay close to Nights of Lights.

    Hilton St. Augustine Historic Bayfront – Click here for rates & availability
    A convenient bayfront option for exploring downtown with the family.

    Bayfront Inn – Click here for rates & availability
    A downtown waterfront stay with complimentary breakfast and parking.

    Here is how I’d plan each one with a child, plus the 2026 dates you’ll want to know before you go.

    St. Augustine: Make a weekend out of the lights

    The big draw is Nights of Lights. The historic district glows with millions of white lights, and you can enjoy the display just by walking around—there is no ticket required to see the lights. For 2026, the season runs November 21, 2026, through January 18, 2027. Check the official Nights of Lights guide as you plan.

    I love the idea of arriving before sunset, exploring the historic streets while everyone still has energy, and then watching downtown change as the lights come on. Walk through the Plaza de la Constitución, see the Christmas tree, and make your way toward the Bridge of Lions for a view of the lights along the water. That is plenty for a memorable evening without booking a tour.

    If your family would rather sit for part of the evening, you can look into a holiday trolley, electric cart, or boat tour. Those are optional extras; walking downtown is the simplest way to experience it. I’d choose one tour at most with a young child and leave time for an unhurried dinner or dessert.

    My family tips for St. Augustine

    • Make the overnight part of the fun. I usually stay in a VRBO here during the holidays. I look for a location that works for our downtown plans and check parking, fees, and the cancellation policy before booking. Staying over takes the pressure off dinner, lights, and a late drive home.
    • Wear comfortable shoes. This is a walking evening, especially if you want to see several parts of the historic district.
    • Bring a layer. Even in Florida, standing near the water after dark can feel chilly.
    • Plan parking before you leave. Free Park & Ride shuttles are expected on select dates, but 2026–27 routes and schedules have not been posted yet.
    • Keep the evening flexible. With a child, lights, a treat, and a little exploring can be a complete night. You do not have to fit every attraction into one visit.

    Who I’d recommend it for: Families who want a true holiday getaway, couples looking for a festive overnight trip, and anyone who loves historic towns after dark.

    Mount Dora: A cozy downtown Christmas outing

    Mount Dora feels like the town to visit when you want to slow down. I would plan an afternoon downtown, browse the shops, get something to eat, and stay to see the lights after sunset. It’s a sweet choice for a family holiday outing because the town itself is part of the fun; you don’t need an attraction booked for every hour.

    If you can pick your date, Light Up Mount Dora is scheduled for Saturday, November 21, 2026. The Chamber’s 2026 guide says the downtown celebration includes lights at Elizabeth Evans, Sunset, and Donnelly parks, along with entertainment, food vendors, Santa, a drone show, and fireworks. See the Mount Dora Chamber’s 2026 festival guide for updates.

    Another great date is the Christmas Walk on Friday, December 4, 2026, from 6 to 9 p.m. The event listing describes a free downtown evening with lights, shopping, carolers, Santa, and family entertainment. If your child loves a parade, the Chamber also lists the Christmas Parade for the following morning, December 5.

    My family tips for Mount Dora

    • Go before dark. You’ll have time to explore downtown and eat before the main holiday crowds arrive.
    • Consider staying the night. I usually book a VRBO in Mount Dora during the holidays, too. It’s nice to enjoy the lights and dinner without rushing back to the car for a long drive. Check the distance to downtown and parking details when comparing places.
    • Choose your event date intentionally. Light Up Mount Dora and Christmas Walk are different events, so check which atmosphere and schedule fit your family.
    • Leave space for spontaneous stops. This is the kind of outing where a shop window, a snack, or a photo by the lights can become your favorite part.
    • Check the event page right before you go. Entertainment, weather plans, and parking details can change.

    Who I’d recommend it for: Families who enjoy small-town holiday charm, shopping, and a festive evening they can make as short or as long as they like.

    Which Florida Christmas town should you choose?

    If you want…I’d choose…
    An overnight holiday getaway with a big light displaySt. Augustine
    A slower overnight trip with shops and seasonal eventsMount Dora
    A flexible evening focused on seeing lights on footSt. Augustine
    A Christmas Walk or a parade dayMount Dora

    Honestly, you don’t have to choose just one. For Florida Travel, I like booking a VRBO for each trip and allowing time to enjoy the town after dark. St. Augustine makes a wonderful full weekend, while Mount Dora is lovely for a slower overnight escape. Both give us a reason to step away from the usual December rush and make a memory together.

    Have you been to either town at Christmas? Tell me which one you’d visit first!

  • Ultimate Fall Family Weekend in Maine: Portland, Ogunquit, Kennebunkport

    Ultimate Fall Family Weekend in Maine: Portland, Ogunquit, Kennebunkport

    Our family is planning a Maine Fall Trip in October.

    We’ll then continue to Salem, and I keep asking where we should stay for a short fall weekend with Mila.

    Portland, Kennebunkport, and Ogunquit all sound appealing, but they would form one Maine Fall Trip rather than three separate trips.

    This is my pre-trip planning guide, based on the locations and hotels I’m comparing for our family. I haven’t stayed at these Maine properties yet during our Maine Fall Trip. After our trip, I’ll share where we chose, my own photos, and what actually worked for us.

    Affiliate disclosure: This post may contain affiliate links. If you book through one of my links, I may earn a commission at no extra cost to you. The hotel ideas below are places I’m researching, not hotels I’ve personally reviewed.

    The quick comparison

    Stay inBest if your family wantsWhat I’d think about first
    PortlandA city base with restaurants, waterfront walks, and indoor optionsDowntown parking and whether you want a kitchen or extra room
    KennebunkportA slower coastal getaway and charming villageThe specific hotel’s October activities and what is included
    OgunquitBeach scenery and a festive October weekendFestival crowds, walking distance, and seasonal hotel amenities

    If I were booking specifically for October 24–25, 2026, Ogunquit would get an extra look: OgunquitFest is scheduled for October 23–25 and lists children’s trick-or-treating, a craft fair, and other events. I’d check the latest event schedule again before we leave, since times and details can change. This would fit a Maine Fall Trip, and I’d verify updates before travel.

    Portland: the easiest base for variety

    Portland is the option I’d lean toward if I wanted to keep our plans flexible. A waterfront stroll and a good meal sound lovely, but with a child on a short October trip, I also want choices if it rains or everyone needs a slower afternoon. Visit Portland’s family guide lists activities across the region, so I wouldn’t have to build the whole weekend around one outdoor stop.

    A Portland hotel I’d compare: Residence Inn Portland Downtown/Waterfront

    The Residence Inn Portland Downtown/Waterfront stands out to me for a family stay because it lists suites with kitchens, complimentary breakfast, and an indoor pool. Having breakfast handled and space to keep snacks in the room could make mornings with Mila easier. It’s also near the Old Port waterfront area.

    The detail I’d price carefully is parking. The hotel currently lists a daily self-parking charge, so I’d compare the full stay cost, not only the nightly room rate. I’d also choose the exact suite layout before booking; a studio and a two-bedroom suite would feel very different for a family weekend.

    I’d pick Portland if: we want a comfortable hotel base, easy food options, and a backup plan for less-than-perfect weather.

    Kennebunkport: the classic coastal Maine stay

    Kennebunkport is the picture that comes to mind when I imagine a cozy Maine fall trip: waterfront views, village shops, and time to slow down. Visit Maine’s Kennebunk and Kennebunkport guide highlights the area’s beaches, historic streets, shops, and places to stay.

    A Kennebunkport hotel I’d compare: The Nonantum Resort

    The Nonantum Resort is on the Kennebunk River and has family-oriented rooms and activities. I like the idea of having a resort as our home base instead of treating the hotel as just a place to sleep. Its waterfront setting would make even a quieter morning feel like part of the trip.

    One thing I’d confirm before reserving an October stay: which activities, dining options, pool facilities, and transportation services will be running on our dates? Some resort features are seasonal. I’d ask about the best room arrangement for two adults and a child, too, rather than assuming every room has the same setup.

    I’d pick Kennebunkport if: our priority is the coastal atmosphere and we want time to enjoy the hotel and town at a relaxed pace.

    Ogunquit: beach scenery and a fall festival

    Ogunquit may be the most tempting choice for our particular weekend. OgunquitFest is scheduled for October 23–25, 2026, which lines up with our Maine dates. The Chamber of Commerce lists children’s trick-or-treating downtown and in Perkins Cove, an artisan craft fair, live music, and other festivities. Mila would probably have fun with the Halloween atmosphere, and we’d still get a coastal Maine setting.

    I wouldn’t count on beach weather in late October. For us, this would be about walking by the water, enjoying the town, and building an easy day around the festival. I’d check the updated schedule before promising Mila any particular activity.

    An Ogunquit hotel I’d compare: The Meadowmere Resort

    The Meadowmere Resort describes itself as a family-friendly Ogunquit stay near the village and beach. Its hotel FAQ currently estimates a 10-minute walk to Ogunquit Beach and lists parking with the stay. That walk could be useful on a busy festival weekend, although I’d map our specific festival stops from the hotel before booking.

    I’d check the total price carefully here, too: the property currently lists a daily resort fee. I’d confirm which pool areas and other amenities are open in late October, the room’s sleeping arrangement, and the cancellation terms.

    I’d pick Ogunquit if: we want a fall event that Mila can enjoy and would rather explore a coastal town than spend most of the weekend driving between stops.

    How I’m deciding for our family

    Because we’re flying into Boston, spending the weekend in Maine, and then heading to Salem on Monday, I don’t want to overfill our time. My plan is to choose one base for the Maine portion and make any other town a stop only if it fits naturally into the drive. Changing hotels every night would use up too much of a short family trip.

    These are the questions on my booking checklist:

    1. What will Mila enjoy nearby? For our dates, OgunquitFest makes Ogunquit especially appealing.
    2. What happens if it rains? Portland’s variety and a hotel with an indoor pool could make a weather change easier.
    3. What is the complete price? I’m adding parking, resort fees, breakfast, and any extra room costs before comparing hotels.
    4. Will the hotel work for our actual dates? I’ll verify fall operating hours and amenities directly with the property.
    5. How easy is the move to Salem? On Monday, I’d rather enjoy the morning than rush through checkout and another packed itinerary.

    Right now, Ogunquit has the edge for our October 24–25 weekend because of OgunquitFest, while Portland feels like the most flexible family base. Kennebunkport is the one I’d choose for a quieter coastal stay where the hotel itself is part of the experience. My final choice will depend on availability, the full price, and what kind of weekend we decide to have.

    Before we go

    I’ll update this guide after our trip with the hotel we actually booked, original photos, and my honest take on traveling through Maine with Mila. In the meantime, if you’re putting together a similar fall trip, you can read what I’m packing for Salem and Maine in October and my Salem hotel planning guide.

    Which would you choose for a family fall weekend: Portland, Kennebunkport, or Ogunquit?

  • Where to Stay Near Disneyland: 4 Places I’ve Personally Tried

    Where to Stay Near Disneyland: 4 Places I’ve Personally Tried

    Choosing where to stay near Disneyland can be almost as overwhelming as planning the park days themselves. Do you pay more to stay on Disney property? Choose a hotel within walking distance? Book a larger rental for the whole family? Or stay a little farther away to save money?

    I’ve tried all four approaches. I’ve stayed club level at the Disneyland Hotel, shared an Airbnb across from Disneyland with my family and parents, booked club level at the Anaheim Marriott, and stayed at Hotel Indigo Anaheim.

    Each option worked for a different reason. One gave us maximum convenience, one gave our multigenerational family the space we needed, and the others offered a more affordable hotel stay near the parks.

    If you’re deciding where to stay for your own Disneyland vacation, here is my honest comparison of all four.

    Affiliate disclosure: This post may contain affiliate links. I may earn a commission from qualifying bookings made through these links at no extra cost to you. I only share places I have personally stayed or options I genuinely think may help you plan your trip.

    The quick comparison

    PlaceBest forWhat I liked mostMain Tradeoff
    Disneyland Hotel Club LevelConvenience and a special Disney splurgeStaying in the Disney bubble with lounge accessThe highest-priced option
    Airbnb near DisneylandFamilies and multigenerational tripsMore bedrooms, bathrooms and shared living spaceA vacation rental requires more self-service
    Anaheim Marriott club levelComfort, Marriott benefits and valueA comfortable room plus lounge accessFarther from the park entrances
    Hotel Indigo AnaheimA closer off-site hotelA manageable walk and comfortable stayBreakfast was not included with our rate

    Hotel rates, lounge access and included benefits can change, so compare the total cost for your dates—including parking, breakfast, transportation and any resort fees—before booking.

    1. Disneyland Hotel club level: best for convenience and a splurge

    Our club-level stay at the Disneyland Hotel was the most convenient option of the four, and I felt it was worth the price for that trip.

    There is something special about staying on Disney property. We could remain in the Disney atmosphere even after leaving the parks, and being close to Downtown Disney made it easy to find shopping, food and entertainment without adding another drive to the day.

    Club-level access also made the stay easier. Disney currently lists continental breakfast, daytime snacks, a wine-and-cheese reception, evening desserts and access to the High Key Club among its club-level benefits. Offerings can change, so check the current details for your dates.

    The lounge was especially useful in the morning. Starting the day with breakfast already available removed one decision before heading to the parks. Snacks and drinks also gave us a convenient place to recharge.

    Why I would choose it again

    • I wanted the easiest, most immersive Disney stay.
    • The lounge made mornings and breaks more convenient.
    • It felt like part of the vacation rather than simply a place to sleep.
    • The extra cost made sense for a special trip.

    What to consider

    The Disneyland Hotel will usually be the splurge option. I would compare the price difference with nearby hotels and think honestly about how much time you will spend enjoying the resort and lounge. If you plan to leave early, stay in the parks until closing and barely use the hotel, the upgrade may not offer the same value.

    Best for: travelers who prioritize convenience, Disney atmosphere and club-level amenities over the lowest price.

    2. Our Airbnb near Disneyland: best for a multigenerational family

    When we traveled with my parents, having more room mattered more than having traditional hotel service. This Anaheim Airbnb near Disneyland was perfect for our family setup.

    The listing accommodates up to seven guests and has two bedrooms, six beds and two-and-a-half bathrooms. That gave us shared space to spend time together without expecting everyone to stay in one hotel room. The kitchen, dining area and living room also made the trip feel more relaxed.

    The listing currently describes the walk to Disneyland Park as about 15 minutes, with Downtown Disney along the way. Walking time can vary based on your pace, route and security lines, so I would still map it before your visit—especially if you are traveling with children, grandparents or a stroller.

    The property also lists three pools, a hot tub and a private patio with a grill. Those extras can be helpful when you want a slower evening away from the parks.

    Why it worked for our family

    • My parents could travel with us while still having more personal space.
    • Multiple bathrooms made mornings easier.
    • The kitchen gave us the option to keep food and drinks at the rental.
    • We had a living area where everyone could gather.
    • The location allowed us to walk rather than coordinate multiple cars.

    What to consider

    Vacation rentals come with a different rhythm than hotels. You may need to handle more of your own meals, tidying and transportation planning. This listing also notes a three-night minimum, so it may not fit a very short trip. Review the current rules, fees, cancellation policy and sleeping arrangement before booking, since listing details can change.

    Best for: larger families, grandparents traveling with adult children, or anyone who values bedrooms and shared space more than hotel services.

    3. Anaheim Marriott club level: best for comfort and Marriott value

    The Anaheim Marriott was a comfortable option that helped us save compared with our Disney-owned hotel stay. We stayed with club-level access, which added convenience without paying Disneyland Hotel prices.

    The hotel is by the Anaheim Convention Center, so it is farther from the park entrances than Hotel Indigo or the Airbnb we used. For me, that was the biggest tradeoff. You will want to plan whether you are comfortable walking, using a rideshare or checking the transportation options available during your visit.

    The lounge helped balance that distance. The Anaheim Marriott currently lists complimentary weekday breakfast, snacks and evening appetizers for qualifying lounge guests, with breakfast served at nFuse on weekends. Access rules depend on room type and Marriott Bonvoy status, so confirm that your reservation includes it rather than assuming it will be available.

    Why I liked it

    • The room was comfortable after long park days.
    • Club-level access added food and drinks to the stay.
    • It offered a better price for us than staying on Disney property.
    • It can be a smart choice for travelers using Marriott Bonvoy benefits.

    What to consider

    This was not my closest stay to Disneyland. When comparing prices, include the possible cost and time of transportation. A lower nightly rate can still be an excellent value, but only if the location works for the way your family wants to visit the parks.

    Best for: Marriott loyalists, convention-center visitors and families who want a full-service hotel with lounge access at a potentially lower price than a Disney-owned resort.

    4. Hotel Indigo Anaheim: best for a closer off-site hotel

    Hotel Indigo Anaheim gave us a closer off-site location in a smaller, more boutique-style hotel. The hotel currently describes itself as approximately a 10-minute walk from the Disneyland Main Gate, although your actual time will depend on pace and conditions.

    The location was the biggest benefit for us. After a long day in the parks, a shorter return walk can matter more than it seems when you are comparing hotels from home.

    Our rate did not include breakfast, which is important to include in the budget. The hotel does have on-site dining, but I would check current breakfast prices and hours or plan another morning option before your trip.

    Why I would consider it again

    • It was closer to the parks than the Anaheim Marriott.
    • The room was comfortable.
    • The location made it easier to reach Disneyland on foot.
    • It can offer a middle ground between a Disney resort and a farther hotel.

    What to consider

    Because breakfast was not included with our stay, we had to account for that separately. Always compare the complete trip cost instead of looking only at the room rate. Parking, resort fees, breakfast and transportation can change which hotel is actually the best value.

    Best for: travelers who want a comfortable hotel within a manageable walk of Disneyland without paying for an on-property stay.

    Which place near Disneyland would I choose?

    I would choose based on the group and the purpose of the trip:

    • For the easiest and most special stay: Disneyland Hotel club level.
    • For a trip with parents or a larger family: the Airbnb near Disneyland.
    • For club-level comfort at a lower price: Anaheim Marriott.
    • For a closer off-site hotel: Hotel Indigo Anaheim.

    There is not one perfect Disneyland hotel for every trip. The Disneyland Hotel was worth the splurge when convenience was the priority. The Airbnb was the best fit when we traveled with my parents and needed more space. Anaheim Marriott gave us a comfortable club-level experience at a better price, while Hotel Indigo offered a closer location without the cost of staying on Disney property.

    How to compare Disneyland-area stays before booking

    Before choosing, I recommend checking these five things:

    1. Total price: Include taxes, parking, resort fees, breakfast and transportation.
    2. Realistic walking distance: Think about the walk after a full park day, not only in the morning.
    3. Sleeping space: A less expensive room is not a bargain if your family cannot rest comfortably.
    4. Food access: Club lounges and kitchens may reduce what you spend elsewhere.
    5. Cancellation terms: Plans and prices change, so understand the policy before paying.

    If you are traveling with a larger group, you can also check the exact Airbnb we stayed in and compare its full price with booking multiple hotel rooms.

    My final take

    Where you stay can shape the entire Disneyland trip. A convenient room can make early mornings easier, a lounge can simplify meals, and extra living space can help a multigenerational family enjoy the vacation together.

    For us, each of these stays solved a different travel need. I would happily choose any of them again when it fits the group, budget and style of the trip.

    Hotel amenities, lounge offerings, walking estimates, fees and vacation-rental details can change. Verify the current information directly with the property or listing before booking.

  • What I’m Packing for Salem and Maine in October: A Family Fall Weekend Packing List

    What I’m Packing for Salem and Maine in October: A Family Fall Weekend Packing List

    There is something especially exciting about planning a New England trip in October. I’m picturing colorful leaves, cozy sweaters, historic streets, coastal views and plenty of fall atmosphere—but I’m also trying to be realistic about changing weather and long days of walking.

    For our family trip, we’re planning to visit Maine first and then spend time in Salem before flying home. That means I need clothes that can work for coastal sightseeing, a road-trip day, Hocus Pocus filming locations and a full day exploring Salem with Mila.

    This is my packing plan before our first trip, rather than a recap of what I wore. I’ll update the post afterward with our actual weather, photographs and anything I wish I had packed differently.

    Affiliate disclosure: This post may contain affiliate links. I may earn a commission from qualifying purchases through these links at no extra cost to you.

    Before You Start Packing

    If you’re also planning an October visit, these related guides may help:

    ● Salem in October: 7 Things to Know Before You Go

    ● 6 Hocus Pocus Filming Locations to Visit in Salem, Massachusetts

    ● Shop My Fall Outfits for Salem and New England

    ● Shop My Fall Travel Outfits on LTK

    Why Packing for New England in October Takes a Little Planning

    The hardest part of packing for this trip is preparing for several types of weather without bringing an oversized suitcase. A sunny afternoon may feel comfortable while an early morning, breezy coastal stop or evening in Salem could call for another layer. Rain is another possibility, so I don’t want every outfit to depend on perfect weather.

    My goal is to pack pieces that can be layered, reworn and mixed together. I’m keeping most of the wardrobe neutral—cream, black, denim, olive and brown—with a little rust and plaid for a fall feel.

    I’ll check the National Weather Service forecast close to departure and make final adjustments then. For Salem events, closures and current visitor information, I’ll also recheck the official Salem Haunted Happenings website.

    My Carry-On Fall Capsule Wardrobe

    I don’t need a completely different outfit for every day. Instead, I’m planning a small capsule wardrobe with pieces that can create several combinations.

    Tops and Sweaters

    I’m planning to bring:

    ● One cream cable-knit sweater

    ● One striped or rust-colored sweater

    ● One fitted black turtleneck or long-sleeve top

    ● One neutral long-sleeve layering shirt

    ● One cardigan, flannel or quarter-zip pullover

    The thinner tops can be worn alone if the afternoon is mild or layered under a sweater or jacket when it gets colder. I’m avoiding several bulky sweaters because they take up too much carry-on space and are harder to layer comfortably.

    Shop sweaters and layering tops

    Bottoms

    My basic bottoms will be:

    ● One pair of comfortable straight-leg jeans

    ● One pair of black leggings

    ● One optional plaid midi skirt

    ● One pair of tights or fleece-lined tights if the forecast is cold

    Jeans work for sightseeing, restaurants and most of our planned stops. Leggings give me a comfortable option for the flight, drive and a casual day. The plaid skirt is my fun fall piece, but I’ll only pack it if the forecast makes sense.

    Shop jeans, leggings and fall skirts

    Jackets and Rain Layers

    Rather than packing one very heavy coat, I’m planning to use layers. My outerwear options include:

    ● One olive or neutral quilted jacket

    ● One lightweight waterproof rain jacket

    ● One packable puffer if colder weather is expected

    I probably won’t bring all three. I’ll choose the quilted jacket for a milder forecast or swap it for a packable puffer if temperatures look colder. A lightweight rain shell can fit over either outfit without taking up much space.

    Shop packable jackets and rain layers

    Comfortable Shoes for Maine and Salem

    Shoes may be the most important part of this packing list. We’ll likely spend a lot of time walking on sidewalks, brick paths and uneven historic areas, so this is not the trip for shoes I haven’t already tested.

    I’m limiting myself to two pairs:

    ● Comfortable walking sneakers for travel and longer sightseeing days

    ● Flat waterproof Chelsea or ankle boots for cooler or rainy days

    I love the look of heeled boots with a fall outfit, but I’d rather have a pair I can comfortably wear for hours. If space is tight, I’ll wear the bulkier pair during the flight and pack the lighter pair.

    For more walking-shoe ideas, read my guide to the most comfortable shoes for Disney. The same qualities—support, cushioning and shoes that are already broken in—matter for a busy sightseeing trip.

    Shop comfortable fall walking shoes

    Fall Accessories I’m Packing

    Accessories make a simple capsule wardrobe feel more seasonal without filling the suitcase. I’m considering:

    ● One plaid scarf

    ● One neutral or olive beanie

    ● Lightweight gloves if colder weather is expected

    ● A compact umbrella

    ● A small crossbody bag

    ● Sunglasses

    A scarf and beanie can change the look of a neutral sweater, and they’re easier to remove if the afternoon warms up. I’m choosing a crossbody that leaves my hands free while walking with Mila and taking photographs.

    Before using any day bag, I’ll check the bag rules for our reserved attractions.

    Shop fall accessories and travel bags

    What I’m Packing in My Day Bag

    I want our daytime bag to be useful without becoming heavy. My current list includes:

    ● Portable phone charger and charging cable

    ● Wallet and identification

    ● Reservation confirmations saved on my phone

    ● Compact umbrella or packable rain layer

    ● Water bottle, where permitted

    ● A few kid-friendly snacks, where permitted

    ● Hand wipes and sanitizer

    ● Tissues

    ● Lip balm and a small hand lotion

    ● Bandages and blister protection

    ● A foldable reusable shopping bag

    ● A small plastic bag for wet items

    I’ll download or screenshot important directions and reservations before leaving the hotel so I’m not depending entirely on cell service or a fully charged battery.

    What I’m Packing for Mila

    Packing for a child means having a little more flexibility. I’m planning comfortable pieces that can handle walking, snack breaks and changing temperatures.

    For Mila, I’m packing:

    ● Comfortable sneakers she has already worn

    ● Two pairs of leggings or soft pants

    ● Long-sleeve tops

    ● Cozy sweatshirts or sweaters

    ● A lightweight jacket

    ● A rain layer

    ● Extra socks

    ● Pajamas

    ● A warm hat if needed

    ● One complete change of clothes in our day bag

    I’ll also bring a small activity for travel time and any familiar snack that makes a long day easier. Her cutest outfit won’t be useful if she is uncomfortable, so shoes and layers come first.

    Four Easy Outfit Formulas for the Trip

    1. Travel Day

    Black leggings, a neutral long-sleeve shirt, a cardigan or quarter-zip and comfortable sneakers. I can add the quilted jacket after landing if needed.

    2. Maine Sightseeing

    A striped sweater, straight-leg jeans, waterproof ankle boots and a crossbody bag. Add the quilted jacket and scarf for a breezy coastal stop.

    3. Salem and Hocus Pocus Locations

    A fitted black turtleneck, plaid midi skirt, tights and comfortable black ankle boots. If the skirt doesn’t suit the forecast, I can switch to jeans without changing the rest of the outfit.

    4. Chilly or Rainy Day

    A cream sweater, black leggings, rain jacket or packable puffer, waterproof boots and a beanie.

    These formulas use the same small group of pieces, which makes it easier to pack light while still having outfits that feel different in photographs.

    How I’m Fitting Everything Into a Carry-On

    Wear the Bulkiest Pieces

    I’ll wear my largest shoes and jacket on the plane instead of using valuable suitcase space.

    Use One Color Palette

    Cream, black, denim, olive, rust and brown all work together. Every top should coordinate with at least two bottoms.

    Pack Only Two Pairs of Shoes

    Shoes quickly take over a carry-on. One walking pair and one weather-friendly pair should cover the trip.

    Use Packing Cubes

    I’ll separate adult clothing, Mila’s clothes and smaller accessories so we can find what we need without unpacking everything.

    Rewear Outer Layers

    Jackets, jeans, scarves and sweaters can usually be worn more than once during a short trip. I’ll pack enough base layers and undergarments without duplicating every complete outfit.

    Leave a Little Extra Space

    I don’t want to begin the trip with an overfilled bag. Leaving a little room makes repacking easier and gives us space for a small souvenir.

    Complete Salem and Maine Fall Packing Checklist

    Clothing

    One cardigan, flannel or quarter-zip

    One pair of jeans

    One pair of leggings

    Optional skirt and tights

    One quilted jacket or packable puffer

    One lightweight rain layer

    Pajamas

    Undergarments

    Comfortable socks

    Shoes and Accessories

    Walking sneakers

    Waterproof ankle boots

    Scarf

    Beanie

    Optional gloves

    Crossbody bag

    Sunglasses

    Compact umbrella

    Travel Essentials

    Identification and payment cards

    Reservation details

    Phone and charging cable

    Portable charger

    Toiletries and medications

    Packing cubes

    Reusable water bottle

    Reusable shopping bag

    Snacks

    Blister care and small first-aid items

    Mila’s Essentials

    Comfortable outfits and layers

    Walking shoes

    Jacket and rain layer

    Extra socks

    Pajamas

    Change of clothes for the day bag

    Snacks and travel activity

    Any daily medication or comfort item

    What I’m Leaving at Home

    To keep the suitcase manageable, I’m skipping:

    ● Shoes that haven’t been broken in

    ● Several heavy sweaters

    ● More than one dressy outfit

    ● A large handbag

    ● Clothing that only works with one specific outfit

    ● Too many “just in case” pieces

    If the forecast changes, I’d rather make one thoughtful substitution than keep adding items.

    Final Thoughts on Packing for Salem and Maine in October

    My goal is to feel comfortable, prepared and still enjoy the fun of dressing for New England in the fall. A small capsule wardrobe, two dependable pairs of shoes and a few weather-ready accessories should give me enough options without overpacking.

    Because this is our first trip, I’ll update this guide afterward with what we actually wore, what the weather was like and anything I would change next time.

    Planning your own trip? Save this packing list for later, browse my Fall Outfits for Salem and New England, and read my guide to seven things to know before visiting Salem in October.