Where is the Best Sailing in Maine?

Sailing the Atlantic waters of coastal Maine makes the bucket list of most East Coast mariners. The world-class sailing available in the Gulf of Maine, Penobscot Bay, and Eggemoggin Reach attracts people from around the world. 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. The ports listed below all offer ways for you to experience the best sailing in Maine! For more great outdoor adventures to include in your Maine getaway itinerary, be sure to check out our free Vacation Guide!  

The Best Sailing in Maine

Sailing in Portland, Maine

Portland is a hub of activity, and the central location makes it a great starting point for 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 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. A private charter in Casco Bay, Go Sailing, offers both day sail and sunset sail opportunities. Step aboard a 30-foot sloop and watch the porpoise and harbor seals pass by while you enjoy the gentle bay breezes. You will also have the chance 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 Maine’s lighthouses!

Passage into Boothbay Harbor

Sailing is a way of life in Boothbay Harbor. This charming coastal town in Lincoln County even has its own yacht club with adult sailing instruction. The Boothbay Harbor Yacht Club began over 100 years ago and is still the perfect destination for visiting sailors. With extensive guest moorings and a full-service clubhouse, this yacht club can host individual yachts and affiliate clubs easily. The sheltered and spacious harbor features an excellent holding ground as well as a tranquil community that serves as a relaxing escape.  

Sailing in St. George

The St. George Community Sailing Foundation in Knox County 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 and is 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 for sailing enthusiasts. Choose between three sails daily from Bar Harbor, including morning, afternoon, and sunset cruises. These pet-friendly cruises last around two hours and allow guests to have a hand in hoisting the sails! Nature lovers will enjoy the 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 breathtaking views as the sun melts into the horizon.

Sailing in Maine from Deer Isle

The Old Quarry Ocean Adventures on Deer Isle offers sailing adventures as well as many other offshore activities! Enjoy the beauty of Downeast and the islands in the Stonington archipelago on a kayak, eco-cruise, or boat tour. Old Quarry offers sailing lessons, refresher lessons, 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 large boat accommodates up to six sailors at a time and is available for half-day or full-day rentals!

Where to Drop Anchor

If you plan to arrive at Deer Isle on your own boat or a charter, you will find 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 even 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.

Where to Stay in Downeast, Maine

A trip up the rocky New England coast is an experience of a lifetime! Spend your summer indulging in adventurous outdoor activities such as kayaking, hiking, and sailing in Maine. The rugged coastline boasts beautiful coves and inlets, pine-covered islands, picturesque harbors and small towns for you to explore. Pilgrim’s Inn sits on Deer Isle and allows travelers to immerse themselves in a nature lover’s dream getaway fully. Our cozy accommodations give you the perfect spot to rest your head after a long day in the great outdoors.

Ginny's Cottage 1 at Pilgrim's InnOur cottage rentals give our guests a little extra space for added privacy and comfort! If you’re traveling with children or a furry, four-legged friend, stay in Ginny’s Cottage One! Enjoy a complimentary, delicious breakfast each morning and savor the breathtaking views of our property’s millpond and beautiful landscaping. What are you waiting for? Start planning your vacation today!

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