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.

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.

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.

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. Cost: $1,195-$1,425

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!

Looking for a shorter daytime trip? Leaving Vineyard Haven Harbor, either head to Tarpaulin Cove, round West Chop and cruise the Vineyard’s North Shore to Lambert’s Cove, or hang off of Oak Bluffs and State Beach (depending on wind direction). All locations offer great spots to swim and relax!

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! Great for adults groups and kids too!

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

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! Note: If wind conditions do not allow travel to the cliffs, the captain may choose an alternate route.

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.

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 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!

Cost: $2195-$2595

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

Design your perfect boat day: Swim, Sun and Unwind; Celebrate a Bachelor/Bachelorette, Proposal, Wedding, Birthday; or a Celebration of Life. Price is based on Vineyard Haven pick-up and drop-off.

Design your perfect boat day: Swim, Sun and Unwind; Celebrate a Bachelor/Bachelorette, Proposal, Wedding, Birthday; or a Celebration of Life. Price is based on Vineyard Haven pick-up and drop-off.

Design your perfect boat day: Swim, Sun and Unwind; Celebrate a Bachelor/Bachelorette, Proposal, Wedding, Birthday; or a Celebration of Life. Price is based on Vineyard Haven pick-up/drop off.

Design your perfect boat day: Swim, Sun and Unwind;  Celebrate a Bachelor/Bachelorette, Proposal, Wedding, Birthday; or a Celebration of Life.