Where is the Best Sailing in Maine?

Sailing the Atlantic waters of coastal Maine is on the “must do” list for most East Coast mariners, and world class sailing in the Gulf of Maine, Penobscot Bay and Eggemoggin Reach, attracts people from around the world.  A trip up the rocky Maine coast is an experience of a lifetime and a great summer adventure for those looking for a unique vacation with lasting memories.  Maine’s rugged coastline is filled with beautiful coves and inlets, pine covered islands, picturesque harbors and small towns for you to explore, including Deer Isle and Stonington, where you can spend a few nights enjoying comfortable accommodations and delicious food at Pilgrim’s Inn.   Whether you own your own boat, are looking for a charter, or are just interested in a day sail, there are many ways to get out on the water.  So where is the best sailing in Maine? The ports below all offer ways for you to get out and experience sailing in Maine, so you’ll just have to find out for yourself!

Sailing in Portland, Maine

Portland is a hub of activity, and its location is a great spot for starting your sailing trip in Maine. The city is home to many sailing organizations, including Portland Schooner Company, South Portland Sailing Center, and Portland Yacht Club. In fact, the latter is the third oldest continuously operating yacht club in the United States. The Portland Yacht Club provides easy access to the water for racing, cruising, and day trips alike and offers reciprocity to members of other clubs visiting the area.  The South Portland Sailing Center hosts sailing courses and lessons using smaller boats, along with a fleet of vessels as a part of the rental program. This is ideal for vacationers who are sailing aficionados but couldn’t bring their own sailboat along for the trip.

The Calendar Islands of Casco Bay

Just north of Portland, Casco Bay is an inlet off the southern coast with prime waters for sailing in Maine. Go Sailing is a private charter in Casco Bay that offers both day sail and sunset sail opportunities. Step aboard a 30-foot sloop and watch the porpoise and harbor seals pass by while enjoying the gentle bay breezes. You will also have the opportunity to help crew the boat, including a turn at the helm as you sail into the sunset, passing several major islands off the coast. Be on the lookout for lighthouses!

Passage into Boothbay Harbor

Sailing in Maine is a way of life in Boothbay Harbor. This well known town in Lincoln County has its own yacht club with adult sailing instruction. The Boothbay Harbor Yacht Club has been celebrating yachting for over 100 years and is the perfect destination for visiting sailors. With extensive guest moorings and a full-service clubhouse, this yacht club can hosts individual yachts and affiliate clubs easily. Sailing and racing are both popular activities in this area, which is one of the best anchorages on the Maine coast and one of the most popular destinations for boaters and coastal travelers. The sheltered and spacious harbor has great holding ground, while the tranquil community is a relaxing escape.  

Sailing in St. George

St. George in Knox County is ideal for sailing in Maine. The St. George Community Sailing Foundation operates out of Tenants Harbor and teaches sailing lessons to youth at Blueberry Cove Camp. Tenants Harbor also happens to be a premier destination for sailing in Maine, known as one of the best mid-coast regions for trimming the sails and letting the wind take you into glorious waters.

Windjammers in Camden and Rockland

Perhaps one of the most famous ways to experience sailing in Maine is aboard a windjammer out of Camden or Rockland.  The  Maine Windjammer Association is a great resource for scheduling a trip on a windjammer in mid-coast Maine.  Opportunities for both day sails and week-long trips are available and are an exciting way to view the coast from the deck of these gorgeous vintage sailing vessels.

Sailing from Bar Harbor, Maine

Downeast Windjammers Cruises offers charters and group adventures while sailing in Maine. There are three sails daily from Bar Harbor, including a morning, afternoon, and sunset cruise. These pet-friendly cruises last around two hours and allow guests to have a hand in hoisting the sails! There is also an opportunity to go on a naturalist cruise with an Acadia National Park ranger. The most popular opportunity is the sunset sail, which offers live folk music onboard as well as breaktaking views as the sun melts into the horizon.

Sailing in Maine from Deer Isle

Old Quarry Ocean Adventures on Deer Isle in Stonington offers sailing in Maine and many other offshore activities. Kayaking, eco-cruises, and boat tours are just a few other ways for you to get out on the water to enjoy the beauty of Down East Maine and to enjoy the many islands in the Stonington archipelago. Old Quarry offers sailing lessons, refresher courses,rental equipment, and gear.They provide several types of sailboats, including 12 foot, 15 foot, and 19 foot boats, as well as the Freedom 21-foot sloop with a fixed keel. This boat can accommodate up to six sailors at a time and is available for half-day or full day rentals!

If you’ll be arriving on Deer Isle in your own boat or a charter, there are several places to drop anchor or moor around the island. Billings Marina in Stonington offers dockage, fuel, showers, WiFi, and other services to visiting mariners, they also have a few moorings in Burnt Cove several miles away.  Old Quarry Ocean Adventures has a few moorings for guest use on the East Side of the Island near Stonington. While planning your sailing adventures from the shores of Deer Isle, spend the night at Pilgrim’s Inn.  Quaint local charm awaits at this historic post and beam bed and breakfast with twelve rooms and three cottages, as well as a friendly and knowledgeable staff.  We are also happy to pick you up for an overnight stay from wherever you boat is on the island. Start planning your trip today by downloading our free vacation guide!