Sailing with Downeast Friendship Sloop Charters

Book Southwest Harbor! Book Northeast Harbor!


Our sailing tours depart from Southwest Harbor and Northeast Harbor and run three times a day. Book your charter by first choosing a harbor and then one of the following trips.

Morning Sail

Morning in Maine is generally calm and peaceful until the sea breeze begins to fill in. The morning sail begins at 10am, usually with smooth water and light wind which allows for excellent wildlife sightings like porpoise, seals, and sea birds as we gently glide through the water. We’ll work our way out of the harbor and look for wind in the Western Way, or sail to Somes Sound Fjard, Bear Island lighthouse, and the Cranberry Islands. By the end of the sail we’ll return to the harbor with a steady afternoon breeze filling the sails and heeling the boat. The morning sail is a great choice for first time sailors, young children or wildlife enthusiasts.

Afternoon Sail

The sea breeze is at its strongest between 1:30pm and 4:30pm, which makes the afternoon trip our most lively sailing experience. After motoring out of the harbor and setting sails we’ll pick a route that includes as much of the highlights as possible. We often sail to the Cranberry Islands, Bear Island Lighthouse and Somes Sound Fjard. With a fair wind we may also go to East Bunker Ledge where a colony of seals are sunbathing, swimming, and feeding. Throughout the sail your local captain will answer questions about the area history and wildlife, and share what its like to live on an island in Maine.

Sunset Sail

There is nothing like a sunset as seen from the sea. Artists and photographers will tell you the light here in Maine is amazing. The afternoon breeze gradually mellows as we sail past the rock-bound coast of Bear Island and the Cranberry Islands. Enjoy a snack on board while the sun slips behind the Western Mountains of Acadia. Feel free to bring your own favorite beverages to enjoy this calmer, beautiful sailing experience. Porpoise and seals are commonly seen in the smooth water of a sunset sail.

The above trip descriptions are based on a typical summer day in Maine but our weather varies greatly especially in early or late season. While our summer weather is generally beautiful, please keep in mind that fog, rain and thunderstorms are all part of the Maine experience. For up to date weather information and trip expectations please call the office and review our cancellation policy.

Sailing excursions are booked as Shared or Private Charters. Shared trips are enjoyed between two or more different parties and priced per person. Private charters are excursions exclusively for your party and are priced at a single rate for the whole boat. A private charter allows us to cater the cruise more to your wishes, such as sailing instruction, island picnics and a dinner cruise. For more information about private charter options please call us.

All trips have a six passenger maximum and include a snack on board and water. You are welcome to bring along your own favorite beverages or food. We have an ice box on board, wine openers and cups.

Comfort and Safety

Sailing aboard a Friendship Sloop is a safe, comfortable experience immersed in history and Maine maritime heritage. These refurbished working vessels handle very well as they were designed without an engine to navigate the rocky coast of Maine in all seasons. The deep keel and wide beam keep them steady and safe but more importantly, all our trips sail within the protected waters of the Cranberry Islands, so there’s no big ocean swell or rough waves. The boats have large cushioned cockpits, ensuring plenty of room for guests. There is a small toilet on board and blankets for cool weather.

Cancellation Policy:

  You may cancel your reservation without charge up to 48 hours prior to your scheduled departure. If you cancel within the 48 hour period or fail to show up at boarding, you will be responsible for the full amount of the charter/cruise. Weather related cancellations will be determined by the Captain. If your charter/cruise is cancelled due to weather and we are unable to reschedule the trip to your satisfaction, you will not be charged.