The 10 Best Outdoor Activities in Rockland, Maine (ME)

Join us aboard our fully restored 51-ft. WW II Liberty Launch, Rendezvous, and you’ll delight in views of picturesque islands, historic lighthouses, traditional windjammers, and stunning sunsets as you look for seals, porpoises, and seabirds. From the polished brass, comfortable seating, luxurious brightwork and professional crew, to the fully stocked copper-topped bar, you’ll simply love cruising in vintage style. Choose a 1 or 2-hour sightseeing cruise, a 3-hour lobster dinner cruise, or a dockside cocktail.

Driven only by Atlantic Ocean breezes, the Stephen Taber sets sail from Rockland Harbor, taking guests on four and six day windjammer sailing adventures on the legendary Maine coast. The Schooner Stephen Taber is the oldest sailing vessel in continuous service in the United States, and a National Historic Landmark.

Bufflehead is a 32 foot wooden gaff sloop, a classic boat, built in 1964. She is a very pretty boat, superbly swift, comfortable and safe. Captain Daniel Bennett sailed around the Pacific Ocean on a tall ship, and twice across the Atlantic (and back and forth to the Caribbean) on his own small boat.

The Rockland Sailing Company offers day sails and charters aboard the Friendship Sloop Anna R. We sail four times daily from the Rockland Public Landing, and offer longer custom charters by request. Our regular day sails are two hours in length, You can take the wheel and help set the sails if you like, or you can just sit back and enjoy the view. Upon request and with advance reservation, we will guarantee that your party will have the Anna R all to yourselves, making this a truly unique opportunity to see Maine’s beautiful coast under sail.

Gourmet sailing cruises, daily. Departing and returning from/to Rockland, Maine.

Koukla is a custom classic wooden schooner built to sail the world in comfort, safety and style. We offer day sails and overnight trips on Penobscot Bay, from Windjammer Wharf in Rockland, Maine. Departure times and duration of the trip are as per the customers desires.

Our spacious and classic fifty-eight foot Hatteras Motor Yacht offers you the “best-in-class and quality.” STELLA DI MARE is available for your private charter for up to 35 passengers. Please plan ahead for birthday parties, corporate meetings, reunions, wedding parties, family outings or special celebrations. Catering is available through our carefully selected caterers, or you may use the caterer of your choice. Wine, champagne, beer, a selection of cocktails, and non-alcoholic beverages are available on board. STELLA DI MARE also offers periodic cruises, such as a two hour Morning Harbor Cruise with brunch, a two hour afternoon Tea-on-the Sea cruise, and a 1-1/2 hour Evening Harbor with appetizers & desserts. We have also partnered with PortCity Bike, LLC to offer a combined bike and cruise tour. Reservations are required for all cruises. Cruise schedules and prices are subject to change.

The American Eagle sails on cruises of varying lengths, from 3-11 days along the Maine coast, maritime provinces and Gloucester Massachusetts. Lighthouses, wildlife and unspoiled scenery are part of every trip. Each cruise is a unique vacation: exciting sailing at a reasonable price. A National Historic Landmark, this is the real deal. Fun personalized cruises with terrific meals included.

Sail aboard a historic Oyster freighter along the Maine coast, nature will provide the beautiful scenery, your hosts will provide the food and beverage. Departing 6 days a week, we offer a variety of sailing experiences, ranging from a 4-hour sail to a 5-day cruise. We have a full liquor license onboard with a great cocktail program, so no need to rush around and provision. Selling oysters on the half shell and snacks on our day sails and oysters are included on all our 4 hour plus cruises. Serving surf and turf Friday and Saturday evenings, brunch on Sunday and Chef’s choice dinner cruises on Tuesdays. We are the only windjammer that offers an exclusive 28 hour overnight cruise. Experience everything a Windjammerhas to offer in an abbreviated time period.