Day Trips (Sailboats & Windjammers)

Anjacaa has sailed the waters of the Penobscot Bay her entire life. Along with her crew, she is ready to show you some of the most beautiful sites along the coast. Anjacaa is a comfortable cruiser with a respectable record in the local racing circuit. Anjacaa was built for speed so if you are looking for a faster sail this is the boat for you. If you are up for a more hands-on adventure, guests ar

In the summer, enjoy a sightseeing daysail on Penobscot Bay, where you can observe first-hand the wildlife, islands, lighthouses, lobster boats, and beautiful coast of Downeast Maine. In the winter months, join us during your Key West vacation on the waters of the Caribbean. Go snorkeling in North America's only living coral reef or relax on a tropical sunset sail. The Appledore also offers charter sail…

Enjoy the fresh sea breeze as it determines your course. Your experience will be unforgettable as you indulge your senses in quiet enjoyment of the ocean's beauty and the wind's power. An occasional Northwest gust adds excitement; and occasional becalming occurs when the winds shift direction.

One of Penobscot Bays only Windjammer Schooner specializing in 4-hour sunset dinner cruise's operating out of Rockland Harbor. Boyd N. Sheppard also has a rotating Sunday schedule offering either Brunch or the only one of its kind in the area, the gateway to windjamming our "One-Day wonder" a 28 hour overnight. We are the only Schooner in Rockland offering a full onboard bar and cocktail program.

Let us be your Camden Maine Sailing Experience! Join us for a two-hour day sail or custom charter to enjoy all the beauties that Penobscot Bay has to offer such as its beautiful rocky shoreline, hidden mansions, small islands, lighthouses, seals, bald eagles, lobster boats, and other magnificent ships.If you are looking for a more intimate trip join us aboard our new boat- the Cutter Owl! The Owl is the …

The original Windjammer Fleet established in 1936. Experience the wonders of the Maine Coast from the broad decks of our National Landmark Schooners. Islands to explore, lighthouses, lobster, wildlife, mouth-watering meals and great company. Lend a hand or just sit back & relax. Four overnight cruise options weekly. Affordable & All Inclusive.Lobster Lunch & Dinner Cruises

Sail the Maine Coast aboard Schooner Yacht HERON - a Maine built (by the captains/owners) 65’ John Alden designed Classic Schooner Yacht. Join us for a unique sailing experience on our Private morning charter, educational eco-wildlife sail or Happy Hour Sunset sail. If you are looking for something special, a sail on the Heron is just the thing. Custom group and private charters available.

Board the elegant schooner Lazy Jack II and be transported back in time to the early 1930s. Built by Captain Sean O'Connor in 2004, her lines originate from L.F. Herreshoff's Mobjack 1935 design. Create new memories as you enjoy a romantic 2-hour sail on our 58-foot ship. We feature a cushioned cockpit and wide cabin tops for comfortable seating, the perfect place for taking in the wonders of Penobscot Bay.

Let us be your Camden Maine Sailing Experience! Join us for a two-hour day sail or custom charter to enjoy all the beauties that Penobscot Bay has to offer such as its beautiful rocky shoreline, hidden mansions, small islands, lighthouses, seals, bald eagles, lobster boats, and other magnificent ships.

Join us, on our Historic 57-foot schooner listed on the National Register. Enjoy great sea stories and cruise past islands, lighthouses, seals, and other wildlife. Limited to 18 passengers. Book your charters, weddings, corporate events, family reunions.