We Found These Experiences For You (87)
Boat Tour and Maine
Penobscot Bay Sunset Charter
2.5 hours • All ages • Golden hour sailing through Penobscot Bay’s islands and lighthouses.
There are a lot of ways to get out on the water in Maine, but at Sailing Sasa, we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and ...
Georgetown
2.5 Hours
Boat Tour
Sailing Sasa
Copy to Clipboard to Share
Casco Bay Escape, Half-day Charter
4 hours • All ages • Fully custom • Sail, relax, swim, and take the helm!
There are a lot of ways to get out on the water in Maine, but at Sailing Sasa, we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and ...
Portland
4 Hours
Private Tours
Boat Tour, Sailing
Sailing Sasa
Copy to Clipboard to Share
Private Penobscot Bay Sailing Experience
All ages • 56 feet of sailing paradise, entirely yours for the half or full day adventure.
There are a lot of ways to get out on the water in Maine, but at Sailing Sasa, we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and ...
Georgetown
4 or 7.5 Hours
Private Tours
Boat Tour
Sailing Sasa
Copy to Clipboard to Share
The Maine Coast Experience, Portland Full Day Charter
7.5 hours. All ages. Explore Maine’s Islands, sail, swim, and enjoy your perfect day in Casco Bay!
There are a lot of ways to get out on the water in Maine, but at Sailing Sasa, we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and ...
Portland
7.5 Hours
Boat Tour
Sailing Sasa
Copy to Clipboard to Share
Casco Bay Golden Hour Sail, Sunset Charter
2.5 hours • All ages • Golden hour sailing through Casco Bay’s islands and lighthouses.
There are a lot of ways to get out on the water in Maine, but at Sailing Sasa, we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and ...
Portland
2.5 Hours
Boat Tour
Sailing Sasa
Copy to Clipboard to Share
Private Casco Bay Sailing Experience
All ages • 56 feet of sailing paradise • Entirely yours for the half or full day adventure.
There are a lot of ways to get out on the water in Maine, but at Sailing Sasa, we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and ...
Portland
4 or 7.5 Hours
Private Tours
Boat Tour
Sailing Sasa
Copy to Clipboard to Share
Coastal Escape, Penobscot Bay Half-day Charter
4 Hours • All ages • Fully Custom • Sail, relax, swim, and take the helm in iconic Penobscot Bay!
There are a lot of ways to get out on the water in Maine, but at Sailing Sasa, we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and ...
Georgetown
4 Hours
Private Tours
Boat Tour
Sailing Sasa
Copy to Clipboard to Share
Ultimate Maine Island Adventure, Full-day Penobscot Bay Charter
7.5 hours. All ages. Explore Maine’s Islands, sail, swim, and enjoy the perfect day in Penobscot Bay
There are a lot of ways to get out on the water in Maine, but at Sailing Sasa, we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and ...
Georgetown
7.5 Hours
Boat Tour
Sailing Sasa
Copy to Clipboard to Share
Lobsters, Sailing & Music - June 22, 2027
4-night • Starting at $1,525.00 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 June 22, 2027 at 5pm · Disembark on Ju
Kid-Friendly
Boat Tour
Schooner Heritage
Copy to Clipboard to Share
WoodenBoat Rendez-vous - September 11, 2027
6-night trip • Starting at $1,850 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 11th, 2027 at 5pm · Disembar
Boat Tour
Schooner Heritage
Copy to Clipboard to Share
Perseid Meteor Showers - August 1, 2027
4 nights • $1,725 per person based on double occupancy • Ages 12+
Duration Board August 1, 2027 at 5pm Disembark August 5, 2027 at 11am. Trip Description We’ll sail through the days in search of remote anchorages sheltered from lights, the perfect backdrop for the show. Stay up late enjoying quiet conversation with all eyes turned to the sky as the Perseid Meteor ...
Rockland
Boat Tour
Schooner Heritage
Copy to Clipboard to Share
Lobsters, Sailing, & Music - June 27, 2027
3-night trip • Starting at $1,325 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 June 27, 2027at 5pm · Disembark on Jun
Boat Tour
Schooner Heritage
Copy to Clipboard to Share
Lobsters, Sailing & Music - September 18, 2027
4-night trip • Starting at $1,525 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 September 18, 2027 at 5pm · Disembark
Boat Tour
Schooner Heritage
Copy to Clipboard to Share
Lobsters, Sailing & Music - August 11, 2027
4-night trip • Starting at $1,525 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 August 11, 2027 at 5pm · Disembark on
Boat Tour
Schooner Heritage
Copy to Clipboard to Share
Lobsters, Sailing & Music - Celebrate July 4th - July 1, 2027
4-night trip • Starting at $1,525 Per Person based on double occupancy • Ages 12+
Duration Board Sunday, July 1st, 2027 at 5pm Disembark Saturday, July 5th, 2025 at 11am Trip Description Celebrate the 4th of July aboard the Schooner Heritage as we head out in search of the perfect island to indulge our lobster cravings on the beach, brisk breezes to fill the sails and festive music ...
Rockland
Boat Tour
Schooner Heritage
Copy to Clipboard to Share
Fall Foliage - September 24, 2027
4-night trip • Starting at $1,525 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 September 24th, 2027 at 5pm · Disembar
Boat Tour
Schooner Heritage
Copy to Clipboard to Share
Lobsters, Sailing, & Music - June 2, 2027
3-night trip • Starting at $1,325 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 June 2, 2027 at 5pm · Disembark on Jun
Boat Tour
Schooner Heritage
Copy to Clipboard to Share
Lighthouses and Shore Trips - August 16, 2027
5-night trip • Starting at $1,725 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 August 16th, 2027 at 5pm · Disembark o
Boat Tour
Schooner Heritage
Copy to Clipboard to Share
Great Schooner Race--Gathering of the Fleet July 6, 2027
4-night trip • Starting at $1,525 per person based on double occupancy • Ages 12+
Duration Board Saturday, July 6, 2027 at 5pm Disembark July 10th, 2027 at 11am. Trip Description Join us as we set off from Rockland in search of fine sailing, a pristine island to explore enjoying an all-you-can-eat lobster bake, and beautiful sunsets. Later in the trip we’ll meet up with a dozen ...
Rockland
Boat Tour
Schooner Heritage
Copy to Clipboard to Share
Fall Foliage - September 29, 2027
4-night trip • Starting at $1,525 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 September 29th, 2027 at 5pm · Disembar
Boat Tour
Schooner Heritage
Copy to Clipboard to Share
Viewing 41 to 60 of 87 Experiences