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Pirate Adventures Martha’s Vineyard

12 Circuit Avenue Extension, Oak Bluffs, MA 02557

About

Pirate Adventures Martha’s Vineyard runs family-focused pirate cruises from Oak Bluffs, Massachusetts, aboard the Sea Gypsy X. The regular adventure combines a treasure hunt along the shores of Oak Bluffs with pirate dress-up, map-making, water-cannon battles and recovered treasure. Trips include pre-departure face painting and pirate preparation, then spend about 70 minutes at sea within an approximately 90-minute experience. Reservations are required, with online booking available; walk-up tickets may be accepted before departure when space remains.

Beyond the daytime family cruise, the business offers private sunset cruises from Oak Bluffs Harbor through Nantucket Sound, along with private pirate adventures and birthday parties. Private cruises can accommodate food and drinks brought by guests, with crew-provided cleanup and a Bluetooth sound system. The custom-built vessel has covered and uncovered seating, life-saving equipment and a ship-to-shore radio. Plan a day on the water by contacting Pirate Adventures Martha’s Vineyard.

Features

  • Interactive pirate cruises
  • Family treasure hunts
  • Private sunset cruises
  • Private pirate adventures
  • Birthday party cruises

Amenities

  • Safety Equipment
  • Seating & Comfort
  • Audio & Entertainment
  • Restrooms & Showers
  • Waterfront & Access
  • Family & Play

Why book with us

  • Join a treasure hunt along Oak Bluffs shores
  • Book an interactive cruise for the whole family
  • Bring snacks and drinks aboard
  • Celebrate on a private sunset cruise
  • Make birthday parties easy with onboard entertainment

Frequently Asked Questions

How old do you have to be to rent a boat in Massachusetts?

Massachusetts sets 12 as the minimum age to operate a motorboat without direct adult supervision, if the operator satisfies the applicable boater safety certificate rule; personal watercraft operators must be at least 16. A child under 12 may operate a motorboat only while accompanied on board and directly supervised by a certificate holder at least 18. Direct supervision requires visual contact and verbal communication at all times while underway.

Certification is phased by birth date under Massachusetts General Laws chapter 90B, section 9E: people born after January 1, 1989, have been covered since April 1, 2026; those born on or before that date must comply by April 1, 2028. Rental operators set their own minimums, so confirm when booking.

Source: Massachusetts Environmental Police and Boat and Recreation Vehicle Safety Bureau (mass.gov)

Do you need a boating license in Massachusetts?

Yes. Massachusetts requires a boater safety certificate, rather than a boating license, for motorboat and personal watercraft operators born after January 1, 1989; those born on or before that date must comply by April 1, 2028. Personal watercraft operators must be at least 16. Children under 12 may operate a motorboat only under direct onboard supervision by a certified adult age 18 or older.

Rental customers are not generally exempt, and temporary rental certificates are only under consideration for lower power boats. Exemptions include direct supervision, qualifying nonresident certificates, merchant mariner credentials, certain military and commercial fishing operators, and recent boat buyers carrying a temporary certificate. Massachusetts Environmental Police administers the program.

Source: Massachusetts Environmental Police (mass.gov)

What are the best places to go boating in Massachusetts?

Some of Massachusetts’ best boating variety is found in Boston Harbor, the Connecticut River, Otis Reservoir, and the connected Knops Pond and Lost Lake. Around Boston, the harbor combines coastal boating with several islands that are accessible by private boat.

In the Connecticut River corridor, state access points serve motorboats, fishing boats, canoes, and rowing craft. Inland, Otis Reservoir in Otis and Tolland offers a large great pond with trailered and cartop access, while Groton’s Knops Pond and Lost Lake form a connected lake system used for boating, fishing, and water skiing.

Source: Massachusetts Department of Conservation and Recreation and Division of Fisheries and Wildlife (mass.gov)

What are the most popular boating destinations in Massachusetts?

Popular Massachusetts boating destinations include the Boston Harbor Islands for skyline views, swimming and historic sites; Falmouth and Woods Hole for harbor scenery and boat access to Martha’s Vineyard; Nantucket Harbor for sailing and preserved seaport character; Gloucester Harbor for fishing heritage and schooner outings; and Plymouth Harbor for waterfront views near Mayflower II, plus whale watching and fishing trips. Together, these destinations offer a mix of island stops, working harbors, maritime history and open coastal water.

Source: Massachusetts Office of Travel and Tourism (mass.gov)

Location

12 Circuit Avenue Extension, Oak Bluffs, MA 02557

Disclaimer

This listing was created using artificial intelligence and publicly available data. The information presented may be inaccurate, outdated, incomplete, or incorrect. Slipstream does not verify, endorse, or guarantee the accuracy of any listing content, including but not limited to contact information, pricing, services offered, hours of operation, or business status.

All content is provided “as is” and without warranties of any kind, express or implied. Slipstream expressly disclaims all liability for any loss, damage, or reliance arising from the use of this information. Users are solely responsible for independently verifying all details directly with the business.

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