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Sailing Vacations & Yacht Charters Maine

Flights to Maine


Great Vacations In Maine



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Schooner Heron Eco WIldlife Tour Sailing & Yacht Charters Rockport, Maine
From USD $
50
per Trip

Schooner Heron Eco WIldlife Tour

Sailing & Yacht Charters Rockport, Maine

Sail the Schooner Heron for a fun and informative look at the history of Rockport Harbor. Sail across Penobscot Bay to see the seals and seabirds on Robinsons Rock, birthplace of Andre the Seal. Enjoy the thrill of sailing a classic wooden schooner.

Custom Sailing Charters from Rockland, Maine Sailing & Yacht Charters Rockland, Maine
From USD $
30
per Trip

Custom Sailing Charters from Rockland, Maine

Sailing & Yacht Charters Rockland, Maine

Bufflehead Sailing Charters offers a unique opportunity to experience Maine. Get on the water aboard this classic, see Rockland's working waterfront, lighthouses, panoramic vistas, seals and seabirds. More info and contact on sailrockland dot com.

Day Sailing & Custom Charters on the Schooner Olad Sailing & Yacht Charters Camden, Maine
From USD $
31
per Trip

Day Sailing & Custom Charters on the Schooner Olad

Sailing & Yacht Charters Camden, Maine

Join us for a day sail on the historic waters of Penobscot Bay. As the sails fill, be carried off into the relaxing realm of beauty that the coast of Maine has to offer. Take part in observing lighthouses and island nature preserves from our decks.

Maine Windjammer Sailing Adventures Sailing & Yacht Charters Blue Hill, Maine
From USD $
180
per Night

Maine Windjammer Sailing Adventures

Sailing & Yacht Charters Blue Hill, Maine

The Maine Windjammer Association's eight historic ships offer exciting 3- to 6-day sailing vacations along the Maine coast from May to October. Includes great food, spectacular scenery, abundant wildlife and time to explore islands and villages.

Sail the Maine Coast on the Schooner Stephen Taber Sailing & Yacht Charters Rockland, Maine
From USD $
550
per Trip
hot travel deals

Sail the Maine Coast on the Schooner Stephen Taber

Sailing & Yacht Charters Rockland, Maine

The Schooner Stephen Taber offers 3-6 day sailing trips off the coast of Maine. Built in 1871 and based in Rockland, a trip aboard the Taber is unique, authentic, personal and relaxing. The ship carries 22 passengers and is a National Landmark.

Rocks & Thrills Family Adventure Sailing & Yacht Charters Camden Hills, Maine
From USD $
1,780
per Trip

Rocks & Thrills Family Adventure

Sailing & Yacht Charters Camden Hills, Maine

Rocks & Thrills epitomizes the fun a family adventure in Maine truly is! Coastal kayaking, mountain hiking, spectacular bicycling and great seafood! All the while, enjoying every moment with your family on our fully supported tour.

Sailing aboard a Maine Windjammer Sailing & Yacht Charters Rockland, Maine
From USD $
525
per Trip

Sailing aboard a Maine Windjammer

Sailing & Yacht Charters Rockland, Maine

Experience authenic sailng on a historic Maine windjammer. See islands, wildlife, lighthouses and enjoy a traditional hearty meals cooked on a woodstove. Enjoy the rugged Maine coast from the right side...the ocean!

Twilight Charters, Maine and Bahamas Sail Charters Sailing & Yacht Charters Georgetown, Maine
From USD $
500
per Night

Twilight Charters, Maine and Bahamas Sail Charters

Sailing & Yacht Charters Georgetown, Maine

We offer 1-8 day private, crewed charters aboard a 47 ft sailboat on the midcoast of Maine and Bahamas. Summers in Maine, Winters in the Bahamas. Find out about our OVERNIGHT SPECIAL! Scroll down for more info.



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Sailing Trips & Private Charters Maine

Come sail away on our sailing trips in Maine. Enjoy sailing on your vacation and spend the day out on the water. Our sailing tours in Maine are a great activity for any traveler. You can relax and ride or learn to sail at one of our sailing schools. Our sailing adventures are a great addition to any vacation. Browse our sailing in Maine and plan your vacation today!


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