Best Sailing Day Trips in Maine
Credit: Blaine Harrington III / Alamy

"If a man must be obsessed by something," adopted Mainer E.B. White once wrote. "I suppose a boat is as good as anything, perhaps a bit better than most." Mainers have been obsessed with boats at least since the first settlers landed at Popham in 1607 and arguably for a good while before that. Maritime heritage runs deep here. The state is still today home to some of the finest boat builders in the world, from the artisans of the WoodenBoat School in Brooklin to the manufacturers of immense naval vessels at Bath Iron works. Somewhere in between are the elegant sailboats found up and down the coast and the many schooners and windjammers that crowd the harbor in the summer months in towns like Camden and Rockland. Multi-day trips are the norm, but some captains offer day trips to watch wildlife or peep nearby lighthouses. Shove off with one of the five sailing companies below.

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.

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.

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.

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.

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.