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12/23/24 — 12/25/24 12/23/24 — 12/27/24 12/23/24 — 12/29/24 or
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Elizabeth Islands and Cuttyhunk Shared Charter × × × × × × ×
Elizabeth Islands and Cuttyhunk Shared Charter

Elizabeth Islands and Cuttyhunk Shared Charter

Explore the Elizabeth Islands and Cuttyhunk Island. Perfect for fall bird watching and exploring!

Explore the Elizabeth Islands and Cuttyhunk Island. Perfect for fall bird watching and exploring! Leaving Vineyard Haven, zip across Vineyard Sound to Tarpaulin Cove. View picturesque lighthouses, Highland Cattle, and stop to enjoy swimming in secluded coves. Visit the seal colony at Gull Island, and explore Cuttyhunk Island on foot. You’ll have about 1.5 hours to explore on shore, visit Naval Lookout Point, learn about the history of the area during World War II, browse shops, and enjoy the raw bar and ice cream on the town dock. Take a swim break to finish your trip!


***If you would prefer a private charter, please contact us for discounted pricing.***

  • Duration : 6 Hours (approx.)
From USD $300.00

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North Shore & Gay Head Cliffs Half-Day: 4 Hours × × × × × × ×
North Shore & Gay Head Cliffs Half-Day: 4 Hours

North Shore & Gay Head Cliffs Half-Day: 4 Hours

Journey along the North Shore of the Vineyard, view celebrity homes, nesting Osprey, the old Brickyard, and more. Tour Menemsha for some JAWS movie lore, and view the majestic Gay Head Cliffs. Optional stops to swim or grab seafood takeout!

Journeying along the North Shore of the Vineyard, you’ll see celebrity homes, view nesting Osprey, learn about the old Brickyard, and more. Stop to swim at Tashmoo or Lambert’s Cove. Then, venture to Menemsha for some JAWS movie lore and seafood takeout (optional). Motor over Dogfish Bar to a stunning beach under the renowned Gay Head Cliffs, a national landmark. 

  • Duration : 4 Hours (approx.)
From USD $995.00

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Elizabeth Islands: 4 Hours × × × × × × ×
Elizabeth Islands: 4 Hours

Elizabeth Islands: 4 Hours

Leaving Vineyard Haven, zip across Vineyard Sound to Tarpaulin Cove. View picturesque lighthouses, Highland Cattle, swim in secluded coves, and visit the seal colony at Gull Island.

Leaving Vineyard Haven, zip across Vineyard Sound to Tarpaulin Cove. View picturesque lighthouses, Highland Cattle, swim in secluded coves, and visit the seal colony at Gull Island.

  • Duration : 4 Hours (approx.)
From USD $995.00

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Elizabeth Islands & Cuttyhunk: 5 Hours × × × × × × ×
Elizabeth Islands & Cuttyhunk: 5 Hours

Elizabeth Islands & Cuttyhunk: 5 Hours

Leaving Vineyard Haven, zip across Vineyard Sound to Tarpaulin Cove. View picturesque lighthouses, Highland Cattle, and swim in secluded coves. Visit the seal colony at Gull Island and explore Cuttyhunk Island.

Leaving Vineyard Haven, zip across Vineyard Sound to Tarpaulin Cove. View picturesque lighthouses, Highland Cattle, and stop to enjoy swimming in secluded coves. Go as far as the seal colony at Gull Island, or continue and explore Cuttyhunk Island on foot. You’ll have time to explore on shore, visit Naval Lookout Point, learn about the history of the area during World War II, browse local shops, and enjoy the raw bar and ice cream on the town dock. Return along the Elizabeth Islands.

  • Duration : 5 Hours (approx.)
From USD $1,275.00

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Vineyard Sound & Cuttyhunk Loop: 6 hours × × × × × × ×
Vineyard Sound & Cuttyhunk Loop: 6 hours

Vineyard Sound & Cuttyhunk Loop: 6 hours

Captain Eamonn’s signature trip allows you to see it all! Leaving Vineyard Haven, travel along the Elizabeth Islands chain, explore Cuttyhunk Island, and return via the Gay Head Cliffs and the Vineyard's North Shore.

Captain Eamonn’s signature trip allows you to see it all! Leaving Vineyard Haven, travel along the Elizabeth Islands chain, with a stop at Tarpaulin Cove Lighthouse. Then you’re off to the quaint, picturesque island of Cuttyhunk. You’ll have time to explore on shore, visit Naval Lookout Point, learn about the history of the area during World War II, browse local shops, and enjoy the raw bar and ice cream on the town dock. Back on the water, catch a glimpse of a seal colony, view Nashawena Island’s Highland Cattle and take a swim break. Return via the Gay Head Cliffs and the Vineyard’s North Shore.

  • Duration : 6 Hours (approx.)
From USD $1,475.00

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Tarpaulin Cove Treasures × × × × × × ×
Tarpaulin Cove Treasures

Tarpaulin Cove Treasures

Motor to a pristine beach on Naushon Island’s Tarpaulin Cove, only accessible by boat. Swim and snorkel in clear water, walk to a working lighthouse, and learn about the incredible history of the area. A scavenger hunt activity is included

Motor to a pristine beach on Naushon Island’s Tarpaulin Cove, only accessible by boat. Historically said to be Captain Kidd’s last stop before his capture, and currently known as a secluded stop for boaters, Tarpaulin Cove is truly a treasure. Swim and snorkel in clear water, walk to a working lighthouse, and learn about the incredible history of the area. A scavenger hunt activity is included for the kids, and you might even convince Captain Eamonn to pull up some special critters!


  • Duration : 4 Hours (approx.)
From USD $965.00

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Cape Pogue Edgartown Adventure: 3 hours × × × × × × ×
Cape Pogue Edgartown Adventure: 3 hours

Cape Pogue Edgartown Adventure: 3 hours

After a short tour of Edgartown Harbor, head to Chappaquiddick's Cape Pogue Bay for a remote island experience. View local shellfish and critters while snorkeling and swimming the pristine waters of this special area!

After a short tour of Edgartown Harbor, head to Chappaquiddick's Cape Pogue Bay for a remote island experience. View local shellfish and critters while snorkeling and swimming the pristine waters of this special area. Walk one of our most remote beaches! 


Edgartown pick-up and drop-off is included in the rate. 

  • Duration : 3 Hours (approx.)
From USD $895.00

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Taste of Tashmoo: 3 Hours × × × × × × ×
Taste of Tashmoo: 3 Hours

Taste of Tashmoo: 3 Hours

Looking for a shorter daytime trip? Head down the Vineyard's North Shore or over to Tarpaulin Cove for a taste of the Elizabeth Islands!

Looking for a shorter daytime trip? Leaving Vineyard Haven Harbor, round West Chop and cruise the Vineyard’s North Shore to Lake Tashmoo and Lambert’s Cove or head over to the Elizabeth Islands to Tarpaulin Cove. 

  • Duration : 3 Hours (approx.)
From USD $825.00

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Nantucket Day Out: 7.5 Hours × × × × × × ×
Nantucket Day Out: 7.5 Hours

Nantucket Day Out: 7.5 Hours

Tour Nantucket Harbor, view iconic lighthouses, learn about the island’s whaling history, and observe the seal colony. Enjoy shopping, lunch, and museums along Nantucket’s cobble stone streets. Swim and beach stops optional!

Tour Nantucket Harbor, view iconic lighthouses, learn about the island’s whaling history, and observe the seal colony. Enjoy shopping, lunch, and museums along Nantucket’s cobble stone streets. Captain Eamonn has plenty of great stories and first hand knowledge from the years he lived on Nantucket! Swim and beach stops optional!


Pick-Up and Drop Off in Edgartown at the Finger Piers next to the Edgartown Yacht Club

  • Duration : 7 Hours (approx.)
From USD $1,875.00

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Menemsha & Gay Head Cliffs Sunset Cruise: 3 Hours × × × × × × ×
Menemsha & Gay Head Cliffs Sunset Cruise: 3 Hours

Menemsha & Gay Head Cliffs Sunset Cruise: 3 Hours

Escape the crowds and experience the beauty of a Vineyard sunset by boat. Tour the Vineyard's North Shore, Menemsha Harbor, and the majestic Gay Head Cliffs. Stop for an evening swim or grab seafood takeout in Menemsha!

Escape the crowds and experience the beauty of a Vineyard sunset by boat. Tour the Vineyard's North Shore, Menemsha Harbor, and the majestic Gay Head Cliffs. Stop for an evening swim or grab seafood takeout in Menemsha!


Pick-up and drop-off at Owen Park, 19 Owen Park Way, Vineyard Haven

  • Duration : 3 Hours (approx.)
From USD $795.00

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North Shore Sunset Cruise: 2.5 Hours × × × × × × ×
North Shore Sunset Cruise: 2.5 Hours

North Shore Sunset Cruise: 2.5 Hours

Escape the crowds and experience the beauty of a Vineyard sunset by boat. Tour the harbor, view lighthouses, learn about local wildlife and aquaculture efforts. Stop for an evening swim in Lake Tashmoo or off of Lambert's Cove Beach.

Escape the crowds and experience the beauty of a Vineyard sunset by boat. Tour the harbor, view lighthouses, learn about local wildlife and aquaculture efforts. Stop for an evening swim in Lake Tashmoo or off of Lambert's Cove Beach.


Pick-up and drop-off at Owen Park, 19 Owen Park Way, Vineyard Haven

  • Duration : 150 Minutes (approx.)
From USD $725.00

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Edgartown Sunset: 2 Hours × × × × × × ×
Edgartown Sunset: 2 Hours

Edgartown Sunset: 2 Hours

Tour Edgartown Harbor, then enjoy the sunset on Vineyard Sound off of Cape Pogue. Pick-Up and Drop-Off at Edgartown Finger Piers, next to the Edgartown Yacht Club.

Tour Edgartown Harbor, then enjoy the sunset on Vineyard Sound off of Cape Pogue. 

Pick-Up and Drop-Off at Edgartown Finger Piers, next to the Edgartown Yacht Club.

  • Duration : 2 Hours (approx.)
From USD $775.00

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