Sometimes the best family trips are the ones that completely surprise you, and that’s exactly what happened during our recent getaway to New York’s Thousand Islands.
Where To Stay
Nestled along the St. Lawrence River between New York and Canada, the Thousand Islands is one of those destinations that feels like a hidden gem. The scenery is stunning, the pace is slower, and there’s something magical about being surrounded by water in every direction. We checked into Capt. Thomson’s Resort, which quickly became the perfect home base for our adventure. The location couldn’t have been better—right on the waterfront and within walking distance of restaurants, shops, and boat tours.
Uncle Sam Boat Tour
One of the highlights of our trip was spending the day on the river with Uncle Sam Boat Tours. Before visiting, I had no idea there are actually more than 1,800 islands scattered throughout this region. Cruising through the St. Lawrence River felt like stepping into another world. One moment we’d pass a tiny island with a single cottage, and the next we’d be admiring sprawling waterfront estates that looked straight out of a movie. The girls were fascinated trying to count islands and spot the most unique homes along the way. Seeing just how closely intertwined the United States and Canada are throughout the river was incredible. Uncle Sam Boat Tour is celebrating 100 years of being on the river this year, so happy birthday to them. It’s pretty incredible!
Boldt Castle
The absolute highlight of the trip, though, was visiting Boldt Castle. Even after seeing photos beforehand, nothing prepares you for the moment it comes into view from the water. Rising from Heart Island, the castle feels like something you’d expect to find in Europe rather than Upstate New York.
As we explored the property, we learned the incredible story behind it. Hotel magnate George C. Boldt began building the castle in 1900 as a grand expression of love for his wife, Louise Boldt. The six-story castle was meant to be their summer dream home, but when Louise unexpectedly passed away before it was completed, construction stopped immediately. For decades the castle sat unfinished, a lasting tribute to a love story that never got its ending.
Walking through the beautifully restored rooms, grand staircases, and sprawling grounds was fascinating. The girls loved exploring every corner and imagining what life would have been like over a century ago. I found myself constantly stopping to admire the architecture, stained-glass details, and sweeping river views visible from nearly every angle. The grounds are just as impressive as the castle itself, with gardens, pathways, and waterfront vistas that make you want to stay all afternoon.
We also visited the Boldt Yacht House, which ended up being one of the most unexpected highlights of our visit. Located just across from Heart Island, the Yacht House was originally built to house George Boldt’s impressive fleet of luxury boats. Today, it offers a fascinating glimpse into the Gilded Age, showcasing beautifully restored antique vessels, vintage engines, and original boathouse slips. The kids loved seeing the historic boats up close, while I was amazed by the craftsmanship and attention to detail throughout the building. Together, the Yacht House and Boldt Castle tell the full story of George and Louise Boldt’s vision for their summer retreat.
Vineyards
One thing I wasn’t expecting was how much I would love the vineyard scene in the area. The Thousand Islands region is home to several beautiful vineyards and wineries, many offering stunning views of the river and surrounding countryside. We spent an afternoon enjoying the peaceful scenery, sipping local wines, and taking in a completely different side of the region. It was the perfect balance to our days spent exploring castles and cruising the river.
Where To Dine
Speaking of memorable experiences, the food scene was another pleasant surprise. We enjoyed a fantastic meal at Blu Anchor Bar & Grill, where waterfront views paired perfectly with fresh, flavorful dishes. Another favorite was Cavallario’s Steak & Seafood, a longtime local institution known for its welcoming atmosphere and delicious menu. These are the kinds of places that make you want to linger a little longer and order dessert even when you’re completely full.
And here’s a fun fact I learned while visiting: the famous Thousand Island dressing actually originated right here in the Thousand Islands region. Somehow it tastes even better knowing you’re enjoying it where it all began.
What I loved most about this trip was how easy it was for everyone in our family to enjoy. The kids loved the boats, castles, and endless time outdoors. The adults appreciated the history, incredible scenery, wineries, and relaxed atmosphere. It’s one of those rare destinations that truly offers something for every age.
As we packed up to head home, I found myself already thinking about a return visit. Between the river views, charming towns, family-friendly activities, vineyard afternoons, memorable meals, and the unforgettable experience of exploring both Boldt Castle and the Boldt Yacht House, the Thousand Islands delivered the perfect summer escape.
If you’re looking for a destination that’s beautiful, unique, and filled with experiences the whole family will love, add the Thousand Islands to your summer travel list. We arrived expecting a weekend getaway and left with memories we’ll be talking about for years.
For more travel posts visit here!
