Wide angle shot of sailboats anchored in a harbor

Sailing Cruises in Kennebunkport

Kennebunkport, located on the Kennebunk River, is a great place to sail. With tons of coves, islands, and harbors to explore, you'll love taking in a sailing cruise in Kennebunkport. The area has a rich history of sailing, from the sea captains who once lived in our boutique Kennebunkport hotel Captain Fairfield Inn to the shipbuilding industry that developed in Southern Maine. Take in some of this local history with our two recommendations for sailing cruises in Kennebunkport. Next time you're on a lark to KPT, get a different look at the Maine coast by setting sail with one of these sailing cruises in Kennebunkport.

Pineapple Ketch | 95 Ocean Ave, Kennebunkport | (207) 468-7262

Both sailing cruises in Kennebunkport are a short walk from the Captain Fairfield Inn (there is also free parking at the Nonantum Resort, where the boat leaves from). Docking in the Kennebunk River, the Pineapple Ketch is a two-masted sailboat with tanbark sails—a reddish material that makes for a unique sight as she sails by the beaches. Enjoy a one- or two-hour afternoon cruise or a two-hour sunset sail. Help to set the many sails, learn some local history, or just kick back and take in the sights (keep an eye out for seals and whales!). Soda and water are provided, but you are welcome to bring adult beverages on board as well.

Schooner Eleanor | 43 Ocean Ave, Kennebunkport | (207) 967-8809

The Schooner Eleanor is another great option for a sailing cruise in Kennebunkport. Docked at the Arundel Wharf restaurant, the Schooner Eleanor is also a short walk or drive from the Captain Fairfield Inn. Enjoy a 2-hour morning or afternoon sail with Captain Rich and crew or a sunset sail. The morning sail will typically take you closer to the coastline, while the afternoon, when the winds pick up, will see the schooner sailing further out into the Gulf of Maine. No matter which way the winds take you, you are sure to enjoy this unique way to see the coast of Maine.