Maine

Hugh Stewart
Local Experts: Maine, Brian Kevin

By Local Expert Brian Kevin

Best Sailing Day Trips on the Maine Coast

1
Bufflehead Sailing Charters

Bufflehead Sailing Charters

Bufflehead is a 32-foot wooden sloop tied up in the harbor in downtown Rockland. Captain Daniel Bennett takes groups of one to six on custom-length trips into and around Penobscot Bay, exploring the islands and sailing past the six different lighthouses visible from Rockland Bay. The lobster bake trips anchor up at an uninhabited island for a one-of-a-kind picnic.

2
Portland Schooner Company

Portland Schooner Company

Two-hour sailing trips aboard either the Begheera or the Wendameen—with more than 180 years between them—show off the coastline around Portland and the islands of Casco Bay. Expect to see lighthouses, yes, but also seals, osprey, and various sea ducks. Pack a picnic and a bottle of wine.

3
Schooner Eleanor

Schooner Eleanor

The tall masts of the Eleanor loom over the docks in downtown Kennebunkport, and Captain Rich Woodman (who also built the boat) leads three two-hour trips each day in the summertime. The excursions follow the coastline between Cape Arundel and Cape Porpoise, passing, among other things, the Bush family compound on Walker’s Point, plus some similarly grand, less fortified coastal homes.

4
Mansell Boat Rental Company

Mansell Boat Rental Company

Able-bodied seamen (with a captain’s license) can rent a sailboat or a powerboat from this outfit in Southwest Harbor on Mount Desert Island, and for a fee, you can rent the captain too. Captain Robert Wellborn pilots narrated, five-hour sailing trips in the summer. Hear tales of the island’s nautical history and the founding of Acadia National Park while keeping an eye out for harbor seals and cormorants.

5
Isaac H. Evans

Isaac H. Evans

Captain Brenda Thomas of Rockland leads week-long adventures in her 1886 windjammer, Isaac H. Evans (since rebuilt, of course).  She also runs two-to-three-hour sunset dinner sails and lunchtime sails, both featuring what else but a plate of Maine lobster. Ready your cameras for shots of the quaint, squat Rockland Breakwater Lighthouse as you sail in and out of the harbor.


Visit the Best Sailing Day Trips on the Coast Maine

Isaac H. Evans
Maine, United States
0/10

People like this place

Harbor / Marina
0
Mansell Boat Rental Company
135 Shore Road (Mansell Lane), Southwest Harbor, ME 04679, United States
0/10

People like this place

Other Great Outdoors
0
Schooner Eleanor
Maine, United States
0/10

People like this place

Boat or Ferry
0
Portland Schooner Company
Maine State Pier (56 Commercial St.), Portland, ME 04112, United States
0/10

People like this place

Boat or Ferry
0
Bufflehead Sailing Charters
Captain Spear Dr. (Tillson Ave), Rockland, ME 04841, United States
0/10

People like this place

Boat or Ferry
0
Advertisement
Advertisement