Day Sails and Private Charters

The Friendship Sloop Surprise is now available for Day Sailing and Private Charter for up to 6 passengers.  She was designed with a huge cockpit giving plenty of space for hauling lobster traps. The Friendship Sloop Surprise has been continuously sailing Maine waters since 1964. She was built in Round Pond, Maine using local oak and cedar trees. She was first employed as a lobster boat fishing from Monhegan Island and also carried firewood. She first entered passenger service in 1979 sailing from the East Wind Inn at Tenants Harbor, Maine.

The Friendship Sloop Surprise now sails daily from the Cranberry Island Dock on Shore Road in Southwest Harbor, Maine.


10 am ~ 12 pm ~ 2 pm ~ 4 pm ~ Sunset Sail*

* Ask about our Sunset Dinner Sail or Lunch Cruise to the Islesford Dock Restaurant on Little Cranberry Island.


2-hour day sail ~ $50 per person

Private Charter for up to 6 people $125/hour ~ Good Dogs Free!


Bear Island Light

Reserve Now...

Call us now   207-288-2216 ~ 888-405 SAIL