On the border of northern New York State and Canada, a cluster of 1,864 islands create a region of endless shorelines, epic sunsets, and a unique maritime history. Fifty miles of river islands give this region its name: the Thousand Islands.

Stretching downstream from Lake Ontario into the St. Lawrence River, the scenery and seclusion from the mainland have made 1000 Islands a popular getaway for generations. Hot summers in the city have always been “escapable” for visitors from New York City, Syracuse, Chicago, Cleveland and Pittsburgh. In its heyday–approximately 1874 through 1912–grandiose resorts were built for wealthy visitors, and filled with people. (By the way, much of those structures have been restored and still stand.) These days, as the region sees a rebirth in tourism, the Taste 1000 Islands offers yet another reason to visit: a craft beverage trail with seven wineries, three distilleries, and a brewery. Their locations range from mainland, to shoreline to private island; all are unique experiences.

Save for a few rocky ones, most of the islands are heavily wooded, spattered with cabins and cottages, exuding a campy mysteriousness. Many of them are small and privately owned–although others, such as Grindstone Island, are larger with paved roads. For locals, boats are the main mode of transportation, and on any given summer day the river is highly trafficked. Visitors to the area can get around without a boat, taking advantage of boat tours and water taxis.

Where To Stay: Airbnb Cabins on Islands & Motels on Land

Our home base to the 1000 Islands was in Clayton, NY at the Islander Marina Lodge. Most of the hotels and motels are similar, so it’s all about location here, which is right on the water. To really make the most of a trip, though, visitors should consider renting a boat or arranging a water taxi–because renting a cottage on a private island begins around $100. Our favorites were Wintergreen IslandIsland Boat House B&B, Buck Bay Cottage, Whiskey Island Lodge, and Jolly Island. All are within a reasonable distance to Clayton.

Where To Eat & Drink: Taste 1000 Islands, The Best Sunset Spots

Thousand Islands’ unique maritime culture and scenery aside, another reason to visit is its great food and craft drink scene. Seven wineries, three distilleries, and a brewery make up the Taste 1000 Islands Beverage Trail. See our list below for some combination drinking/exploring ideas.

  • Head into downtown Clayton in the evening, exploring the shops and waterfront, then grab a glass of Frontenac at Coyote Moon. It’s a perfect sunset spot. Though the tasting room is located downtown, the vineyard is one of the biggest in Northern New York, boasting 18 acres of grape vines.
  • Twenty minutes from Clayton, Cape Winery is a small family-run operation who treats visitors like one of their own. Try the rosé! Afterward, take a walk down to the Tibbets Point Lighthouse, dating back to 1854.
  • Northern Flow Vineyards has the most brilliant business strategy ever: wine and flowers. The tasting room is connected to a gardening center, so if you’re heading in for both, best to get the shopping part done first. On a hot day, grab a glass of Summerland, with major notes of pineapple—and if you’re feeling really indulgent, give the wine slushies a go.
  • Grindstone Island Winery is the definition of “off the beaten path”—you’ll need a boat to get here, and hours are by chance. Still, it’s worth the effort in getting there, because its wines and location are pretty exquisite. An outdoor tasting room overlooks the vineyards where Baco Noir and Pinot Noir grown, aged and bottled on the island estate.
  • Grab a glass of wine, some NY state maple syrup, or craft soda at Otter Creek Winery. Named after the creek it overlooks, Otter Creek produces over 7000 gallons of 13 different varieties of wine. Wine slushes are served here, too!
  •  Clayton Distillery is just down the road from Northern Flow, housed in a big beautiful barn. It’s the region’s first micro-distillery. Clayton Distillery produces premium grade vodka, gin, whiskey, moonshine, limoncello, liqueurs, bourbon, and more; tastings and tours are available daily.
  • Its stunning location in a nearly 100-year old stone mansion makes St. Lawrence Spirits a must-see. The building was a private home called Fairview Manor for years before turning into a nunnery, eventually turning into a restaurant. These days, the building is a farm-to-table restaurant called Château, and the perfect spot to try St. Lawrence Spirits, which are made next door.
  • Beer enthusiasts will enjoy Wood Boat Brewery, who’s serving up great beer in their marina-side brewery. Grab a flight and enjoy on their patio, which overlooks the Antique Boat Museum.
  • Though not a part of the craft trail, honorable mentions go to River Bottom Bar, O’Briens and Lost Navigator. River Bottom and O’Briens are both your standard pubs with pub fare; Lost Navigator is an awesome dive bar with a jukebox and pool table.
What To Do: Boat Tours & Antique Boats, Daytrip to Canada

Boat tours have long been the most popular activity in Thousand Islands. On an easy day, visitors can easily see 100+ islands , but also hear stories about them–including bootleggers, the Gilded Age rich-and-famous, as well as the the more recent history of the islands and their wealthy owners. Cruises vary in length from one-hour tours to upward of five hours; many include lunch or dinner. We were recommended the Uncle Sam Boat Tours, whose excursions include a shuttle to Boldt Castle, which is an incredible piece of architecture and piece of 1000 Islands history.

Back on land, The Antique Boat Museum is really cool and features over 300 classic boats in 33,000 square feet of exhibit space. The collection ranges from massive yachts to luxury speed boats to wooden Adirondack canoes. Set aside about two hours to peruse the multi-building space, which is connected by meandering paths.

From Clayton, it’s a thirty minute drive over the Canadian border to the small town of Gananoque. (Just make sure to bring your passport!) Stop into The Socialist Pig for breakfast, lunch, or coffee. The multi-use space houses both a coffee shop and a restaurant; the food is the best meal we had during our time in the region. After eating, check out Steel, a cute boutique with mens and womens clothing, through the door in the coffee shop. Other points of interest in Gananoque are the flea market/antique mall, downstairs from Gananoque Brewing Company; several antique shops; and last, the Purple House Cafe, another great spot for a meal.

This post was created in collaboration with Taste 1000 Islands. All views and recommendations are our own. Special thanks to the Taste 1000 Islands team for contributing photography.