Thousand Islands Weekend Itinerary

thousand island weekend itinerary

A few weeks ago, my husband and I took a weekend trip to the Thousand Islands for our one year anniversary, It was the perfect getaway, just close enough so we weren’t spending too much time in the car but far enough away to feel like we were somewhere completely new.

We learned about the Thousand Islands a few months back through a random brochure and were intrigued by the laid back vibe and beautiful scenery, so we booked the trip without a second thought. As our trip grew closer, we had so many friends come to us to share their love of the islands. It built up so much anticipation for the trip to hear about all these great stories from people we knew!

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The drive up was gorgeous. We wound threw tiny New York towns, bursting at the seams with fall foliage. The deep oranges and yellows that speckled the trees made for the perfect fall background for our weekend trip.

Clayton vs. Alexandria Bay

We opted to stay outside of the main town, Alexandria Bay, and instead stayed in the neighboring village of Clayton. Looking back, this was one of the best choices we could have made. Alex Bay, while beautiful, seemed outdated, loud, and touristy, whereas Clayton was this adorable quiet town perfectly perched on the edge of the St. Lawrence River. All of the shops and restaurants were within a half mile walk from our hotel and we took advantage of the beautiful riverside walking paths to get around.

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We stayed at the brand new Harbor Hotel, and my my, was it a treat. Since it was the off-season (most people visit the islands during the summer, but we went late fall), we got a great deal on our room. The room itself was very nice, but the bathroom was like a spa. It had a beautiful floor to ceiling glass shower and velvety-soft robes to wrap yourself in. Good choice #2 of the trip was booking a room with a view of the river. Every evening, we would watch the sunset over the river from our bay window. It was breathtaking.

We took it easy our first night and walked around outside to enjoy the fall sunset and get a feel for where we were. No matter the destination, I always like to do a little walking when I first arrive to get my bearings for the rest of the trip. The hotel had a great outdoor space with lots of chairs, benches, and even fire pits that guests could relax in.


Next up was dinner, and we had made reservations at the fancy and new St. Lawrence Chateau. The restaurant sits right on the river in a grandiose historic castle-like building (like most of the historic houses in the area). Dinner was excellent, but it was really neat to be in such a well-preserved historic home.

Day Two

Before even leaving, we had made a point to relax during our trip. I always end up overstuffing an itinerary beforehand and need a day of vacation after vacation to recover. But this trip was different – we needed some down time. Day two, we woke up early, and coffee in hand, took a sunrise walk outside. Breakfast was served at Bellas, one of Clayton’s most highly recommended restaurants and it did not disappoint! My breakfast burrito was delicious, but Jordan’s bagel breakfast sandwich with a homemade mustard sauce was unbelievable. Who would have thought that a mustard sauce would be so good with a bagel, eggs, and bacon? Bellas sits right on the river, so we got to enjoy a beautiful view of the St. Lawrence between bites.

Boat Tour

We had nothing planned for the day, so we consulted our hotel concierge and settled on the Uncle Sam boat tour of the Thousand Islands – the only boat touring still operating this time of year. The boat tour takes 2.5 hours and travels 12 miles around some of the most famous islands in the region. It was incredible. We were blessed with mostly sunny and warm weather, even though the wind on the top deck was a bit chilly. After breakfast, we wandered around the quaint town of Clayton for an hour or so, popping into fun shops and getting a taste of the local flavor.

The tour started with a history of Boldt Castle, one of the most famous tourist destinations in the area. During the summer, you can take a tour of the grounds, something we would love to go back for someday. Boldt Castle and many of the other houses in the area were summer homes to some of the nation’s wealthiest who fell in love with the area in the early to mid 1900’s. Stories of pirates, love, riches, and old folk-lore dotted our journey weaving between US and Canadian waters. One of the mansions was for sale if you were able to shell out a mere 5 million.

thousand island weekend itinerary
For Sale – for 5 million $$$
thousand island weekend itinerary
Boldt Castle

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Dinner #2

After our tour, we headed back to the hotel and got ready for dinner. We wanted something laid back and casual, so we went to the Wooden Boat Brewery. We ordered a buffalo chicken pizza and open faced reuben, both of which were incredible. I have had many a reubens in my day, but none as good as this. Perhaps because we were having true Thousand Island dressing? I really have to say that I was surprised with how good all the food we had in Clayton was. For such a small town, they really know how to cook!

Day Three

Our final day in the Thousand Islands started with breakfast at the Koffee Kove (yet another delicious restaurant, surprise surprise) and then made our way to the Antique Boat Museum. The only way to get around the Thousand Islands is by boat, so every grand and beautiful home in the area had a grand and beautiful boat.

Antique Boat Museum

I’ve never considered myself much of an antique boat person, but this museum opened my eyes. Both big and small, these wooden antique boats were the pinnacle of luxury. Beautiful inlaid wood, leather seats, and vintage touches gave these boats an incredible classic look. We wandered around the campus for an hour or so enjoying the history, the opulence, and a newfound appreciation for antique boats.

thousand island weekend itinerary thousand island weekend itinerary thousand island weekend itinerary thousand island weekend itinerary thousand island weekend itineraryTakeaways from our Thousand Islands Trip

We had such an amazing time at the Thousand Islands. The history there is so neat, the area is gorgeous, and the food is incredible.

We went the last weekend of October, which ended up being a really good time to visit. The trees were at their peak in color and the weather was still nice enough to walk around in. Most everything in the Thousand Islands, including restaurants, closes for the winter. Had we gone a week or two later, we wouldn’t have been able to visit the Antique Boat Museum, go on the Uncle Sam Boat Tour, or eat at Bellas. I have no doubt the Thousand Islands would be absolutely gorgeous and alive in the summer, but it’s also probably really crowded and really expensive. Since we visited during the off-season, our hotel was 1/3 of the price it would be mid-summer.

All in all, we can see why so many people love the area and go back year after year. It was the perfect relaxing weekend getaway.

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