We Found These Experiences For You (18)
Lobsters, Sailing, & Music - June 2, 2026
3-night trip • Starting at $1100 per person based on double occupancy • Ages 12+
Enjoy days of sailing, and evenings of relaxing conversation, music provided by the captains, or quiet reflection on your day and surroundings. No set itinerary. We'll let the winds, weather, and tides determine where we sail and where we anchor. Our favorite anchorages are in the harbors of fishing ...
Rockland
Board on Tuesday, June 2, 2026 between 6 pm and
Schooner Heritage
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Windjammer Gam (Fleet Gathering) - June 6, 2026
4-night trip • Starting at $1,300 per person based on double occupancy • Ages 12+
Enjoy a gathering of the fleet with spectacular photo opportunities of a grand sight the likes of which is unseen anywhere else in the world! We sail to a picturesque anchorage with the windjammer fleet and tie up together for an evening of food, stories, music, and laughter. Walk from boat to boat seeing ...
Rockland
Board on Saturday, June 6th, 2026 between 6 pm a
Schooner Heritage
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Lobsters, Sailing & Music - June 11, 2026
3-night • Starting at $1100 per person based on double occupancy • Ages 10+
Enjoy days of sailing, and evenings of relaxing conversation, music provided by the captains, or quiet reflection on your day and surroundings. No set itinerary. We'll let the winds, weather, and tides determine where we sail and where we anchor. Our favorite anchorages are in the harbors of fishing ...
Rockland
Board on Thursday, June 11, 2026 between 6 pm an
Kid-Friendly
Schooner Heritage
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Lighthouses and Shore Trips - June 15, 2026
5-night trip • Starting at $1,500 per person based on double occupancy • Ages 12+
Experience the Maine coastline. Count the picturesque historic lighthouses dotting the rocky shoreline and visit Maine fishing villages and coastal towns where the people rely on the sea. The summer solstice provides more time to enjoy the scenic vistas. No set itinerary. We'll let the winds, weather, ...
Rockland
Board on Monday, June 15th, 2026 between 6 pm an
Schooner Heritage
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Boothbay Harbor Windjammer Days - June 21, 2026
6-night trip • Starting at $1,700 per person based on double occupancy • Ages 12+
Join us for an exciting trip where we venture beyond our usual sailing grounds of Penobscot Bay as we sail to Boothbay Harbor for the Windjammer Days Festival. The 64th annual celebration of maritime history in the small coastal town of Boothbay will also be celebrating our nation's 250th year as ...
Rockland
Board on Sunday, June 21st, 2026 between 6 pm an
Schooner Heritage
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4th of July Celebration & Race - Fleet Gathering - June 28, 2026
6-night trip • Starting at $1,700 Per Person based on double occupancy • Ages 12+
Celebrate the 4th of July aboard the Schooner Heritage as we head out sailing for lobsters on the beach, fireworks, and festive music aboard. Later in the week we’ll meet up with a dozen other historic vessels for contests of speed and skill, culminating with a great race amongst the windjammer fleet. ...
Rockland
Board on Sunday, June 28th, 2026 between 6 pm an
Schooner Heritage
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Lobsters, Sailing & Music - July 5, 2026
3-night trip • Starting at $1,100 per person based on double occupancy • Ages 12+
Enjoy days of sailing, and evenings of relaxing conversation, music provided by the captains, or quiet reflection on your day and surroundings. No set itinerary. We'll let the winds, weather, and tides determine where we sail and where we anchor. Our favorite anchorages are in the harbors of fishing ...
Rockland
Board on Sunday, July 5, 2026 between 6 pm and 8
Schooner Heritage
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Lobsters, Sailing, & Music - July 8, 2026
3-night trip • Starting at $1,100 per person based on double occupancy • Ages 12+
Enjoy days of sailing, and evenings of relaxing conversation, music provided by the captains, or quiet reflection on your day and surroundings. No set itinerary. We'll let the winds, weather, and tides determine where we sail and where we anchor. Our favorite anchorages are in the harbors of fishing ...
Rockland
Board on Wednesday, July 8, 2026 between 6 pm an
Schooner Heritage
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Explore the Maine Coast - July 12, 2026
6-night trip • Starting at $1,700 per person based on double occupancy • Ages 12+
Come see Maine from the right side, from the water! The natural beauty of the unspoiled coastline and the seals, porpoises, and pelagic birds who call it home make this trip an adventure you’ll always remember. Lighthouses, those sentinels of our rocky coast, can be spotted throughout your time aboard. ...
Rockland
Board on Sunday, July 12, 2026 between 6 pm and
Schooner Heritage
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Explore the Maine Coast - July 19, 2026
6-night trip • $1,700 per person based on double occupancy • Ages 12+
Come see Maine from the right side, from the water! The natural beauty of the unspoiled coastline and the seals, porpoises, and pelagic birds who call it home make this trip an adventure you’ll always remember. Lighthouses, those sentinels of our rocky coast, can be spotted throughout your time aboard. ...
Rockland
Board on Sunday, July 19, 2026 between 6 pm and
Schooner Heritage
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Explore the Maine Coast - July 26, 2026
4-night trip • Starting at $1,300 based on double occupancy • Ages 12+
Come see Maine from the right side, from the water! The natural beauty of the unspoiled coastline and the seals, porpoises, and pelagic birds who call it home make this trip an adventure you’ll always remember. Lighthouses, those sentinels of our rocky coast, can be spotted throughout your time aboard. ...
Rockland
Board on Sunday, July 26, 2026 between 6 pm and
Schooner Heritage
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Lobsters, Sailing & Music - August 20, 2026
4-night trip • Starting at $1,300 per person based on double occupancy • Ages 12+
Enjoy days of sailing, and evenings of relaxing conversation, music provided by the captains, or quiet reflection on your day and surroundings. No set itinerary. We'll let the winds, weather, and tides determine where we sail and where we anchor. Our favorite anchorages are in the harbors of fishing ...
Rockland
Board on Thursday, August 20th, 2026 between 6 p
Schooner Heritage
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Explore the Maine Coast - August 25, 2026
5-night trip • Starting at $1,500 per person based on double occupancy • Ages 12+
Come see Maine from the right side, from the water! The natural beauty of the unspoiled coastline and the seals, porpoises, and pelagic birds who call it home make this trip an adventure you’ll always remember. Lighthouses, those sentinels of our rocky coast, can be spotted throughout your time aboard. ...
Rockland
Board on Tuesday, August 25th, 2026 between 6 pm
Schooner Heritage
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Camden Windjammer Festival (Fleet Gathering) - August 31, 2026
5 Nights • $1,500 per person based on double occupancy • Ages 12+
The best of both worlds. See Maine's mid-coast from the water and ashore. We'll enjoy exploring the Maine coast in search of the perfect lobster island before heading toward the beautiful town of Camden, where the mountains meet the sea. Friday afternoon and evening we'll enjoy all that ...
Rockland
Board on Monday, August 31, 2026 between 6 pm an
Schooner Heritage
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Explore the Maine Coast - September 6, 2026
5-night trip • Starting at $1,500 per person based on double occupancy • Ages 12+
Come see Maine from the right side, from the water! The natural beauty of the unspoiled coastline and the seals, porpoises, and pelagic birds who call it home make this trip an adventure you’ll always remember. Lighthouses, those sentinels of our rocky coast, can be spotted throughout your time aboard. ...
Rockland
Board on Sunday, September 6, 2026 between 6 pm
Schooner Heritage
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WoodenBoat Rendez-vous - September 12, 2026
6-night trip • Starting at $1,700 per person based on double occupancy • Ages 12+
This trip is perfect to experience what it's like sailing on a traditional Maine schooner and to see up close the fishing villages and lighthouses that dot the coastline. Come see Maine from the right side, from the water! Enjoy days of sailing and evenings of live music, great conversation, or ...
Rockland
Board on September 12th, 2026 between 6 pm and 8
Schooner Heritage
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Fall Foliage - September 26, 2026
4-night trip • Starting at $1300 per person based on double occupancy • Ages 12+
Enjoy the fall colors as we set sail in search of the perfect island for a lobster feast.
Rockland
Board on Saturday, September 26 between 6 pm and
Schooner Heritage
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Fall Foliage - October 1, 2026
4-night trip • Starting at $1300 per person based on double occupancy • Ages 12+
Enjoy the fall colors as we set sail in search of the perfect island for a lobster feast.
Rockland
Board on Thursday, October 1st between 6 pm and
Schooner Heritage
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