The best family vacations we’ve taken over the last few years coming at you today!
I love to travel, and I don’t get to nearly enough. But I’ve taken some excellent trips over the last few years, and most of them have been with my little family — Dave (the husband) and Brady (the nearly 8-year-old son). Today, I thought it would be fun to look back at some of our best family vacations and the top destinations we’ve been to.
Believe it or not, some of my most popular posts on this site are travel related, so I knew this one was worthy of production. Hopefully you’ll use this as inspiration to book your next family vacation …
And I’m not ranking these in any particular order …
New York, New York
A bustling non-stop urban adventure on foot.
We visited for three nights in April 2024.
This was such a great family trip, everything went right, and this was the trip that let us know Brady was ready to go to Europe.
At just 6 years old, he did amazing while walking steps-upon-steps around Manhattan for three whole days. During this short spring break long-weekend visit, we caught up family and met up with friends, we saw a show, we ate at great restaurants, we went through the park and we even visited a museum and some flagship stores. We stayed in the Chelsea neighborhood and did our best to see as much of the city on foot as we could. It was manageably chilly at this time, and we loved this little trip so much.
Here are some of the highlights from our time in NYC:
- Strolling around Central Park (Brady needed a chance to run free)
- Walking the Chelsea High Line
- Seeing a Broadway show (we saw “Aladdin”) (wouldn’t see this one again)
- Eating all the delicious food (why is it all so good?)
- Checking out the American Museum of Natural History (what a huge place)
And here’s the full recap of our family vacation in New York City.
Freeport, Portland and Bar Harbor, Maine
Some beautiful outdoor experiences and incredible scenery.
We visited for four nights in late summer 2024.
If you’ve never been to Maine, you might not know just how beautiful it is. Because of Dave, I’ve been there three times, and it’s such a lovely place. Last summer, we went to Maine for a few days, and it was a great trip (outside of one day of very bad weather).
We spent nearly all of our time outside exploring, and we ate a lot of delicious food and caught up with Dave’s family and old friends too. The coastline in Bar Harbor may have been one of the most picturesque places I’ve ever been, and that’s saying a lot. This was a stress-free, laid-back trip that also included some history, as we visited some of Dave’s schools and where he grew up in Freeport.
Here are some highlights from our time in Maine:
- Watching the Portland Seadogs baseball team play at Hadlock Field in Portland
- Visiting Portland Head Light in Portland
- Shopping at the original LL Bean and Freeport Outlets in Freeport (we did Brady’s school shopping)
- Cruising on the Margaret Todd Schooner in Bar Harbor (core memory for life)
- Driving up Cadillac Mountain in Bar Harbor (it was rainy and quite the experience)
And here’s the full recap from our family vacation in Maine.
Walt Disney World Resort in Orlando, Florida
A place for true magical family fun and entertainment.
We visited for three nights in October 2023.
Of course I had to put our Disney trip on our list of best family vacations. Although, truthfully, I had a terrible cold when we were there, and I still think I need a do-over! Yes, going to Disney is an effort, it’s expensive and it takes some major planning. But I think it’s 100 percent worth it.
We only did one park day at Magic Kingdom and one character breakfast on this trip, and that’s pretty short. If we’re able to go back again this year, I’d probably do two park days. We also fit in visiting some friends in Winter Park, Florida on our first night in Orlando, and that was another great part of our trip, in addition to seeing a Cirque du Soleil show.
Here are some highlights from our time at Disney:
- Seeing “Drawn to Life” Cirque du Soleil show at Disney Springs (loved it)
- Staying at the Grand Floridian (such a gorgeous hotel)
- Doing all the things during one day at Magic Kingdom (we paid for Lightning Lane and Genie+ to maximize our day)
- Hanging with the characters at Chef Mickey’s (my favorite experience)
And here’s the full recap from our family vacation to Disney in Orlando.
Pigeon Forge, Tennessee
Touristy and casual family fun.
We visited for four nights in July 2022.
Okay, you are just as surprised as I am that Pigeon Forge is on this list. I hadn’t even really heard of this destination until Dave suggested we meet our friends from Ohio there for a little summer cabin experience. And it ended up being such a great family fun time. Would I go back? Probably not. But it was casual, fun, full of family-stuff, and we had an awesome few days there. (Also, it was very affordable!)
Pigeon Forge is super touristy, and it has many of the same attractions that you’d see along International Drive in Orlando. We definitely did some touristy stuff, like the Ripley’s Aquarium (which does not rank as one of my favorite aquariums, but the kids in our group loved it), and we also went to Dollywood. We really only did one main activity a day, then hung out at the cabin a lot, which was nice because we had a big group and enjoyed the chill time. And as you can see, most of our vacations have zero chill, so we liked that about this one, and we liked having our friends there.
Here are the highlights from our time in Pigeon Forge:
- Having a theme park day at Dollywood (which was NOT Disney quality, but still fun)
- Renting a pontoon boat and tubing on Douglas Lake (the best activity!)
- Hanging out at our log cabin (also a great part of vacation)
And here’s the full recap from our family vacation to Pigeon Forge, Tennessee.
London, England and Edinburgh and St. Andrews, Scotland
Historical, cultural and action packed in the best way.
We visited London, Edinburgh and St. Andrews for seven nights in August 2025.
Just a few weeks ago (upon the time of writing this post) we got back from our big England and Scotland adventure, and this was our longest family trip ever. As shown above, we usually pop away for three to five days, but we were gone for eight days on this trip, and yet – it still didn’t feel long enough.
We had such a wonderful time, and I loved our trip so much. While London was busy, bustling and full of grandeur, Scotland was incredibly charming, cultural and perhaps our favorite country. It took some major planning to get this trip off the ground (thanks to Dave), and we are so grateful we made it happen. We did four nights in London and three nights in Edinburgh (with a day trip to St. Andrews). Going on this trip made me want to do many, many, more trips overseas. Brady was 7 at the time of this trip, and he held his own and was a perfect traveler.
Here are the highlights of our time in London, Edinburgh and St. Andrews:
- Riding The London Eye (the most touristy thing we did)
- Enjoying a Peter Pan afternoon tea at The Shard in London (amazing view)
- Climbing to the top of St. Paul’s Cathedral in London (a little scary, but cool)
- Staying at St. Ermin’s Hotel in Westminster (favorite hotel ever)
- Walking around Edinburgh during the Edinburgh Fringe Festival (street theater!)
- Seeing The Royal Edinburgh Military Tattoo Show (still thinking about this)
- Putting on a small course on the coast of St. Andrews
- Having an outdoor meal at Jigger Inn overlooking the St. Andrews Old Course
And here are the full recaps from our family vacation in London and Edinburgh and St. Andrews.
Honorable mention best family vacations
While the following trips didn’t make the top spots, they were still great trips …
Vancouver and Whistler, Canada
Back when we lived in the San Francisco Bay Area, we took a week-long family getaway to Canada (only a 2-hour flight), and it was a good time. Brady wasn’t even 2-years-old yet, so our trip was a bit limited (we still had him nap in the hotel room once a day), but it was a beautiful place, and I’m so happy we experienced that part of the world before moving to the East Coast. We went to The Vancouver Aquarium, we biked around Stanley Park, and we even rode a super-cool gondola on the drive between Vancouver and Whistler. It was so many years ago, I hardly remember the details, but I was very much a fan of all we saw and did in gorgeous British Columbia.
Here’s the full recap of our family vacation in Vancouver and in Whistler.
Munich, Germany
We also had an amazing time in Munich, Germany in November of 2024. We were only there for four nights, and we explored the city on foot, in between Dave going to work events. While this trip was fun and it was Brady’s first time in Europe, because so much of it was planned for us through Dave’s work, I’m leaving it off the official list. I enjoyed Munich, but I feel like now that we’ve been, we’d choose to go elsewhere if we return to Europe in the coming years.
Here’s the full recap of our family vacation in Munich.
Islamorada, in the Florida Keys
I spent many summers growing up in Islamorada, as my family took a trip there most summers (and that was always our summer trip, outside of one multi-state adventure). As a kid, I would get so bored there, but going back as an adult, I appreciated the super slow pace. There’s not much to do outside of going to the pool, laying out by the ocean or going on a boat. We took my family (including my brother, his wife and my mom) down there a few summers ago to spread my dad’s ashes, and we really did have a wonderful time hanging out. I love the Florida Keys, but because I’ve been so much, it’s not high on my list to return to anytime soon.
Here’s the full recap of our family vacation in the Keys.
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And those are our best family vacations and top destinations we’ve been to with a kid!
What’s next on our list you ask? Probably a beach destination (not in Florida), and that’s hopefully on the agenda for summer 2026. Although, we’ve said that for a few years and we keep choosing other trips.
Thanks for stopping by the blog today to chat about the best family vacations.
Come say hi on Instagram to see where we’re off to next!
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Questions of the day
What’s the best family vacation you’ve ever been on?
What’s one destination you hope to visit with your family one day?
