Travel With Kids: Looking Back on Our 2025 Family Adventures

Join us for a special 2025 year-end review including travel with kids to 10+ destinations! Family travel expert Melissa shares her year-in-review adventures including Maui family vacation tips, Italy with teenagers, Costa Rica with kids, and budget-friendly family trips using points. Discover family travel planning strategies, traveling with kids who have Celiac disease, multi-generational family vacation ideas, and underrated destinations for families. Learn how to balance adventure travel with kids and resort relaxation for the perfect family getaway!

Episode Highlights:

• Family travel to Maui: Andaz Wailea resort review & sea turtle snorkeling with kids
• Travel with kids to Costa Rica: Best Celiac-friendly family destination
• Italy family travel: Rome with teenagers & Dolomites hiking with kids
• Budget family travel tips: Miami, St. Louis & Colonial Williamsburg with kids
• Family vacation planning: Balancing adventure and relaxation when traveling with children
• Multi-generational family travel
  
  

00:00 Welcome and Introduction

00:25 Reflecting on a Year of Travel

00:49 Winter in Maui

02:13 A Weekend in Miami

03:30 Spring Break in Costa Rica

04:19 Summer in Wisconsin and St. Louis

05:46 Italian Adventures

07:13 Quick Trips to Chicago and Boston

08:00 Colonial Williamsburg and Virginia

08:47 Family Time in Los Angeles

10:25 Year-End Reflections and Future Plans

Don't miss this inspiring, practical travel with kids podcast hosted by family travel expert Melissa Conn, founder of The Family Voyage, certified Child Passenger Safety Technician, and mom of two who proves family travel is achievable for everyone.

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Transcript

0:02

Hey there, and welcome back to Family Travel Unpacked. I'm Melissa, and in case you're new here, you can always find tons of detailed destination guides, travel tips, hacks, and more on my website, thefamilyvoyage.com. First off, happy holidays everyone. I hope this season has been filled with joy and warmth and light for your family. This episode's gonna be a little different from our usual format. I'm recording just before we head out on our winter break Cruise. And I wanna take a moment to look back at what turned out to be a pretty incredible year of travel for our family. Instead of diving deep into strategies and tips, I'm just gonna walk you through where we went this year, what we loved, and some of the memories that really stuck with us. Think of it as sitting down with a friend over coffee and catching up on the year. So grab your hot chocolate or eggnog, get cozy, and let's reflect on 2025 together. We kicked off the year in one of our absolute favorite places: Maui. This was actually our third visit with kids, and we brought our extended family along to ring in the new year together. If you missed last week's episode, I answered a lot of the most common questions about planning a family trip to Hawaii, so definitely go back and give that a listen. One of the highlights for us is that we fell completely head over heels for the Andaz Wailea. I know I've mentioned it before, but this hotel just hits that sweet spot for our family. It has high-end touches that make you feel like you're somewhere special, but without any of the stuffiness that makes you worry your kids are gonna break something expensive. The beach there is perfect for us too. We can snorkel right off the shore, the kids can splash around or boogie board, and we've gotten pretty good at spotting sea turtles gliding by also. Also, the sunsets here are incredible. There's something so magical about those moments. One of my favorite experiences from that trip was the complimentary outrigger canoe excursion the hotel offers. I wasn't sure what to expect, but it ended up being this really memorable time with my husband, my son, brother-in-law, and my nephew. We were out on the water in a traditional Hawaiian canoe, and it just feels different from your typical tourist activity. We also went to the Old Lahaina Luau, which I know can sound touristy, but it's genuinely really well done, and we all loved it. It's especially nice to see the business back on its feet after the terrible Lahaina fire in 2023. Since it was a winter trip, we made sure to get out for a whale watching excursion, which was fantastic too. Maui in January is just... it's hard to beat. In February, we snuck down to Miami for a long weekend. This was actually our second time staying at the Hyatt Regency Coral Gables, and I have to say, I really love that hotel. It's in a beautiful, walkable neighborhood that feels safe and has so many family friendly restaurants that you can get to on foot. The pool is heated and there's a hot tub too. And here's my favorite part: complimentary Cuban coffee and pastelitos in the lobby. As a coffee person, it makes me so happy that I can grab a little shot every time I'm down there. We did a great food, culture and history tour in Little Havana. That was fantastic for all of us. It's one of those experiences where you're eating amazing food, but also learning so much about the Cuban American community and their history. And then we took a day trip out to Shark Valley in Everglades National Park, which is a completely different experience from the city even though it's only an hour away. Of course, since it's Miami, we also hit up a great local beach to meet up with some friends. You know, I hear people say all the time that Miami isn't kid friendly, and as I was putting together my notes for this episode, I asked my son about it since he was sitting next to me. He was genuinely surprised by the question. My kids love Miami. There's so much to see and do beyond South Beach, which I grant is much more adult oriented. In fact, we're heading back as I record this, we're gonna spend a few days in the city before getting on a cruise ship for our winter break trip, and we're all pretty excited to check out some new stuff. More on that in a few minutes though. Spring break took us to Costa Rica, and if you listen to episode five, you heard the full story about the strangest most disrupted flight we've ever experienced. I mean, it was wild; it required completely rearranging several days worth of plans. But even with all the chaos, Costa Rica was an excellent family destination. We balanced adventure and wildlife experiences with plenty of time to decompress and relax too. Seeing sloths in La Fortuna was definitely a highlight. I just love watching them do their slow, slothy thing. After La Fortuna, we spent time at the Andaz Papagayo, which gave us a beautiful beach and resort experience to recover from all the excitement. One thing worth mentioning: Costa Rica's fantastic if you're traveling with someone who has celiac disease, our daughter could eat so easily there because most of the food is based on corn and casava rather than wheat. That alone made the trip much more relaxing for us because we didn't have to stress about her food all the time. In May, we did something completely different and totally Midwestern. We went up to a lake house in Wisconsin with extended family. Honestly, it was a great low-key relaxing time. There was fishing, we went horseback riding, we all sat around the fire pit at night, and the kids just ran around outside doing kid things. I totally get why people do it year after year. Sometimes the trips where you're not checking off major sites or having big adventures are exactly what you need to decompress. It was just quality time hanging out together in a beautiful setting. June brought us a quick weekend in St. Louis, which we've visited several times before to see family. It's a great little getaway city for families, and I think people really underestimate it. The highlight for us was seeing our Los Angeles Dodgers play at Bus Stadium. If you listen to the last episode, you might be catching a pattern here, which is that we always look for a weekend swing through the Midwest on the Dodgers schedule. It's a great excuse to check out a different part of our region and make my teenage son and husband really happy. Of course, I like the Dodgers too, and I really enjoy seeing all the different stadium designs. It's just a weird thing for me. Busch is a neat one because it has a perfect view of the gateway arch, which is just iconic. We didn't go up the arch this time because we've done it before, but it's definitely worth doing if you're new to St. Louis. We also went to the City museum one night. We've gone before during the day, but man, the evening is so much better because it's way less crowded and cheaper. And here's a fun story. We actually saw some of the Dodgers players there with their own kids. It was a cool reminder that even professional athletes are just parents trying to entertain their children on a long road trip. July was definitely our busiest month of travel. We went to Italy and we did something we've never done before. My son and I went first, just the two of us, to spend time in Rome. He really wanted to see the Colosseum and I wanted to visit Pompeii. Then my husband and daughter joined us and we continued on to Bologna, the Dolomites and Venice together. Going to Rome alone with my son was such a special experience. We're really similar as travelers. We like the same pace, the same kind of activities. And since he's about to start high school, I know these opportunities are only gonna get harder to come by. We crammed in so many tours and experiences, and I feel like I understand Rome in a way that I didn't after my previous visits. But more than that, it was just the time we had together one-on-one chatting, walking, seeing new stuff. It was really amazing. The Dolomites, which are those picturesque mountains in the northern Italy you've probably been seeing all over social media, they completely lived up to the hype. I get it now. I understand why people rave about this area. It's truly spectacular. The mountains, the hiking, the little huts where you can stop for lunch or coffee. I think all in it's one of the world's best hiking destinations for kids. We'd definitely go back, especially to explore the western side more. Venice was about as crowded as we expected, but we stayed on the island of Murano, which is nearby and famous for glass making. It was so much quieter and we really appreciated that. We did some great craft workshops in Venice that our daughter absolutely loved. She's 11 and at an age where those hands-on experiences are perfect way to engage her on a trip. Right after we got back from Italy, Ronnie and I snuck up to Chicago for a few days without the kids. We go to Chicago pretty often to see family, but we actually hadn't been there as a couple before. It was great. We ate amazing food, we checked out the Art Institute, took an architecture boat tour. It was really nice just to have that time together. August was busy with a capital B. We spent the night in Boston with our daughter before picking up our son from his sleepaway camp. During our very brief window, we went to the Boston Tea Party Ships and Museum, which is so well done. It's one of those places that could easily be cheesy, but instead it's incredibly engaging with costumed interpreters and really slick multimedia presentations. But it was nice to show the kids someplace new and I'd been to Maine many times as a child and something, there's something amazing about Maine in the summer. It's just glorious. The next weekend, which was the last weekend before school started, we did a quick trip to Colonial Williamsburg, Jamestown and Yorktown in Virginia. I visited Colonial Williamsburg a bunch of times as a kid and when my brother was in college there. But taking my own kids, now that they're old enough to really appreciate the history was wonderful. We had dinner at the King's Arms Tavern, and it felt like stepping back in time and they have this cool nighttime pirate trial reenactment that was a huge hit. I still remember going to it when I was a kid, and it was just as memorable for my own kids. Jamestown and Yorktown have so much more to offer than they did when I was growing up. So if you're thinking about getting down there, definitely add those on. If we'd had more time, I also would've added Richmond on one end and Virginia Beach on the other. There's a ton to explore in that part of Virginia, so keep it in mind if you're looking for a getaway that has a huge range of things to check out. September took us back to LA mostly to visit family and friends. But we always try to do some tourist activities while we're there. In case you missed this part of my background, I lived in LA for 20 years and that's where my kids were born and my husband was born and spent almost his entire life there. So we're really familiar with LA and we've done almost everything there is to do, but we love finding new stuff whenever we go back to visit. The kids really wanted to revisit Warner Brothers Studios. They'd been there before, but now that they're older, they got so much more out of it. And we took our son and his older cousin to tour SoFi Stadium, which is an incredible feat of architecture and engineering. Even if you're not a huge sports fan, it's totally worth seeing. While the rest of the family flew back to Ohio, I actually went straight from LA up to Seattle for a work trip and managed to squeeze in a visit to Snoqualmie Falls, which is a gorgeous, easy day trip from the city. Between holidays and a long work trip for my husband. I was pretty much grounded for October and November, and you know what? It was okay. Sometimes you need those months where you're just home, getting back into routine and letting the travel memories settle. plus it was a great time to catch up on content creation and launch this podcast. But don't worry, our schedule's picking up again now that we're in December. We just got back from a ski weekend in Pennsylvania with friends. Most of us are pretty new to skiing, but it's been really fun learning together and trying something different. If you missed episode 11, my friend Jess, who's a total skiing expert, was on talking all about planning family ski trips. So definitely check that out if you're considering it. And now we're getting ready to head back to Miami tomorrow and hop on a cruise with our extended family. We really love doing these winter break trips together. There's something special about gathering the whole family and just having that time to bond with no other responsibilities. Looking back at this list, I'm kind of amazed at how much we managed to fit in in 2025. We had international trips, domestic weekend getaways, city experiences, beach time, mountains history, and everything in between. Some trips were big adventures we'd been planning for months and others were spontaneous weekend getaways that were thankfully easy for me to plan. But here's what strikes me most. It wasn't about checking off a certain number of countries or destinations. There were plenty of places that we'd been to before. The best moments weren't necessarily at the most famous sites. They were things like Jacob and me wandering around Rome at night together. Watching sea turtles in Maui with my daughter sitting around a fire pit in Wisconsin, spotting baseball players at a children's museum in St. Louis. This year really enforced for me that family travel is about so much more than where you go. It's about the time together, the shared experiences, trying new things, and yes, sometimes dealing with major flight delays and connections, but still finding a way to make it work and have fun Anyway. I'm not gonna give away all of our plans for 2026 yet, you'll have to tune into the next episode for that. So be sure to hit follow. But I'll tease that we've got some exciting trips on the horizon, and I'm looking forward to sharing those adventures with you throughout the next year. Thank you so much for being part of the Family Travel unpacked community this year. Whether you've been listening since episode one, or you just found us recently, I'm really grateful that you're here. I love hearing from you your- questions, your own travel stories, your tips and tricks. If you haven't already, be sure you subscribe so you don't miss any episodes. And as always, you can find detailed destination guides, articles, and resources on my website, thefamilyvoyage.com. Have a wonderful holiday season, whatever you're celebrating and wherever you are, I hope you get to spend quality time with the people you love and maybe even sneak in a little travel planning for the year ahead. I'll be back soon with a sneak peek at what 2026 has in store. Until then, happy travels.