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Sailing

Maine has 3,500 miles of stunning coastline, at least 6,000 lakes and ponds, countless islands and breezes that won’t stop blowing. If you’re a sailor, what’s not to like?

Inland Maine provides plenty of opportunities, especially for small-boat sailors. Getting your boat onto the water is easy; just consult the State’s comprehensive list of boat launches. Didn’t bring your boat? An outfitter like Sebago Sailing, Inc. provides rentals and lessons as well. Sailors towing larger boats can dip into freshwater in Maine’s big lakes including Sebago in the south and Moosehead in the north.

Maine’s long and varied coastline has long been a magnet for sailors internationally. In the south, The Maine Beaches regionprovides long, sandy bays and classic beach towns. Moving north, Casco Bay is a compact sailing ground with a constellation of islands anchored by the state’s largest city, Portland. The shoreline of Maine’s MidCoast & Islands region is wrinkled and folded with outcroppings and peninsulas and peppered with islands. In the DownEast & Acadia region, Maine’s coast becomes rockier and wild, incorporating the popular Acadia National Park and the remote ‘bold coast’ of northeastern Maine. To help sail successfully throughout Maine’s maritime regions, sailors often turn to the Cruising Guide to the Maine Coast.

Summer Regattas

Summertime in Maine means the coast is teeming with sailboats, many of which are classics built for speed! Classic regattas featuring vintage, wooden and Spirit of Tradition sailboats are very exciting to watch and participate in – a wonderful celebration of Maine’s boatbuilding heritage.

The Camden Classics Cup begins the season and is a regatta beautifully framed by the mountains of MidCoast Maine. Presented by Lyman-Morse, the Camden Classics Cup has two days of racing classic sailboats with an unforgettable panoramic backdrop. Participants have access to Lyman-Morse's facilities, and a full weekend of events in the lovely town of Camden, including a boat parade to view nearly 100 sailboats. There is also a one-day, free regatta for sailors ages 12-18 sailing in C420s and Optimists.

The annual Boothbay Harbor Yacht Club Regatta is the oldest in Maine with classic and modern boats competing. The event also includes the Shipyard Cup Classics Challenge, featuring a slew of classic yachts.

‘Round Southport Race is an annual reserve handicap pursuit race sponsored by the Southport Yacht Club and the Boothbay Harbor Yacht Club, with a cruising class and a racing class. The top three finishing boats from the yacht clubs determine the club that wins the coveted Trash Can Trophy.

In August, in the SailMaine Festival and Regatta, you can compete in the race or register for the non-racing division and still enjoy a day out on Casco Bay. The race is a fundraiser for SailMaine’s scholarship and community sailing programs. Everyone can enjoy watching the Windward Exhibition which celebrates Portland’s local artists with a parade of painted sails.

For a trio of races, head to Castine in August for the Castine Classic Yacht Race which is followed by the Camden to Brooklin race and the Eggemoggin Reach Regatta.

Youth Regattas

There are many youth regattas throughout the season, including the Battle of the Bay, which is hosted by Boothbay Harbor Yacht Club for centerboard dinghies under 20’ and the HYC Junior Regatta, hosted by the Harraseeket Yacht Club in Freeport. The annual Red Jacket Regatta in Rockland is free for youth with sailing experience aged 8-17. Hosted by The Apprenticeshop, it is a great time to tour the boatbuilding school’s campus.

Want to learn to sail? Go to class in Maine, either as a beginner or to brush up on skills. The Abbot Fletcher Sailing School on Orr’s Island and MDI Community Sailing Centercan provide those lessons.

Many sailors don’t bother bringing a boat. One of the most popular sailing activities in the state is voyaging aboard Maine’s fleet of windjammers - large, historically rigged vessels. Visitors can also sign up for shorter trips on historical ships such as the Anna R. and Buffleheadin Rockland, the Frances in Portland, the Olad and Owlin Camden, the Sarah Meadin Boothbay Harbor and the Surprisein Southwest Harbor.