Excursions
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Vineyard Sound & Cuttyhunk Loop
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.
6 hours from Vineyard Haven: $1,475
Elizabeth Islands & Cuttyhunk
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. Take a swim break to finish your trip!
4 hours from VINEYARD HAVEN TO SEAL COLONY (NO CUTTYHUNK): $995
5 HOURS FROM VINEYARD HAVEN TO CUTTYHUNK: $1,275
The Elizabeth Islands & Cuttyhunk trip is also available to book by the person ($300 pp) on Tuesdays, September 10-October 15. Trips run 10:00-4:00 to/from Vineyard Haven. Please scroll down to book!
Tarpaulin Cove Treasures
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!
4 hours from Vineyard Haven: $965
North Shore & Gay Head Cliffs
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. Snorkel among the boulders and sandy beach. Learn about the history and geology of this unique part of the island.
4 hours from Vineyard Haven: $995
Taste of Tashmoo
Looking for a shorter daytime trip? Leaving Vineyard Haven Harbor, round West Chop and cruise the Vineyard’s North Shore to Lambert’s Cove. Enter the world of Lake Tashmoo, view an Osprey nest and other bird life up close and explore the flats. Take a refreshing swim at either Tashmoo or Lambert’s Cove Beach.
3 hours from Vineyard Haven: $825
Edgartown Cape Pogue Adventure
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.
3 Hours from Edgartown: $895
Sunset Cruises
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, grab seafood or ice cream in Menemsha, or head to the Gay Head Cliffs if weather allows. We are also happy to supply food and beverages for an additional fee.
2.5 hours, Vineyard Haven to Lambert’s cove: $725
3 hours, vineyard haven to gay head cliffs: $795
2 HOURS, EDGARTOWN: $775
Nantucket Day Out
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!
7.5 hours from Edgartown: $1,875
Two Boat Float (for groups of 7-12 passengers)
Two boats are better than one! Perfect for wedding parties, large families, or other groups over 6 people. For these trips, we partner with one of our colleagues to get you all out on the water! These trips are best done during the day time. Leaving from Owen Park, Vineyard Haven, your group boards the two boats, motors to either the Tashmoo/Lambert’s Cove area, Tarpaulin Cove, or off of Oak Bluffs. We then anchor and raft the boats together for you to enjoy the time together as a whole group. Please call or submit a booking request form. Cannot be booked through online booking at this time.
3 Hours: $1,750
4 hours: $1,995
Extras:
Water Carpet: $50
Charcuterie: $85-$105
Masks and Snorkels: $5 per person
Food or Beverage Order Pick-Up: $45
Children’s Explorer Pack: $35 each (includes net, bucket, critter viewer, juice box and Pirate Booty)
All charters include bottled water, and a variety of non-alcoholic beverages. Please feel free to BYOB and food.
Design Your Own Charter
Create an itinerary with any of the activities or locations above, or design your day around a special event.
Bachelorette/Bachelor Parties
Private shuttles
Edgartown, Cuttyhunk, or Oak Bluffs Fireworks
Vineyard Cup, Vineyard Haven, and Edgartown Regattas
Nantucket Regatta and Opera House Cup
Wedding Services, Birthday Parties, and Ashes Ceremonies
CUSTOM 3 HOUR: $825
CUSTOM 4 HOUR: $965
custom 5 hour: $1250
CUSTOM 6 HOUR: $1495
** prices may be adjusted due to pick-up location and trip route **
if you are looking for a shuttle or shorter trip, please call BECCA AT (774)563-8323,
as we may be able to do this before or after another scheduled trip