Sailing with Downeast Friendship Sloop Charters

Book Southwest Harbor! Book Northeast Harbor!


2 or 3 hour Sail

Depart our pier in Southwest Harbor and cruise past Beal's Lobster Pound and the U.S. Coast Guard station as the captain raises the sails and turns off the engine. If the wind is fair you will make your way up into Somes Sound; the only natural Fjord in North America. Continue past Greening Island and past the lighthouse on Bear Island. Visit a huge Osprey nest on Sutton Island and continue on to East Bunker Ledge* to see seals sunning themselves on the rocks. Take a turn at the wheel or just sit back, relax and enjoy the most beautiful scenery in North America. Available as a private or shared charter.

* Due to its distance, East Bunker Ledge is visited only on 3 hour cruises.

Half-Day Sail

Our most popular trip is the half-day sail, which runs approximately three (3) hours. During a typical half-day trip you will sail past Bear Island Lighthouse, around the Cranberry Islands, and possibly to East Bunker Ledge! This trip provides the perfect amount of time to get the feel of sailing a traditional boat on the coast of Maine.  Wildlife is easily spotted and there is plenty of opportunity to haul the sails and take a turn at the wheel. Available only as a private charter.

Sunset Sail

There is nothing like a sunset as seen from the sea. Witness the most famous sunset over Mount Desert Island while we sail past the rock-bound coast of Bear Island, where a lighthouse originally built in 1838 towers above.  Enjoy appetizers while the sun slips behind the Western Mountains of Acadia. Sunset sails are available as a private or shared charter and are 2 or 3 hours in length.


Lighthouse Tour

The perfect trip for families with young children--or simply those looking for a relaxing morning on the water. This trip will take you out around Bear Island Lighthouse and through the mouth of Somes Sound. A perfect way to enjoy Acadia! This is a specialized trip and is only available as a private charter.

Cranberry Island Tour

This trip will leave you captivated by the maritime history of the Acadia region.  Take a step back in time and sail to the Cranberry Islands, which were first settled around the time of the American Revolution.  Observe a scenic lighthouse on Bear Island and an inhabited 100 year-old osprey nest as we sail past Sutton Island, which was purchased from the Abenaki Indians in 1755 by Eben Sutton for just two quarts of rum!  Once ashore Little Cranberry Island explore local museums and learn about island life during a time when commerce depended on islands and sailing vessels, not roads and autos. Witness a busy working pier where fishermen unload their lobster catch, artists display their pottery craft and watercolors, and a local restaurant welcomes you for an incredible lunch or dinner.  Narrow roads, a working waterfront, and an intimate community offers a unique respite away from the crowds.  A great trip even without ideal sailing conditions; if the wind is slack, the fog rolls in, or the kids are restless, the Cranberry Islands tour offers a flexible full-day combination of an ocean and island experience. This is a specialized trip and is only available as a private charter.

Fjord Explorer Tour

Somes Sound is the only fjord on the East Coast of the United States and is only a short sail from Southwest or Northeast Harbor.  Carved by a glacier some ten thousand years ago this deep, narrow channel is bound by granite cliffs and makes for a dramatic geological canvas.  It is also an excellent habitat for birds and marine mammals as well, making this sail a favorite among naturalists. This is a specialized trip and is only available as a private charter.


Learning to sail is not as hard as you think! Our instructional trips teach the basics of sailing, covering vocabulary, techniques, and good seamanship.  Have a unique experience learning the ropes of a traditional vessel and sail the boat in your first lesson.  Couples and families are encouraged to learn together. Navigation and charts of Bar Harbor and Southwest Harbor will be covered if you wish. This is a specialized trip and is only available as a private charter.