Skipper Fishing Charters | Top Boat Rental in Oak Bluffs, MA Skip to content

Skipper Fishing Charters

2 Circuit Avenue Extension, Oak Bluffs, MA 02557

About

Oak Bluffs, Massachusetts, is the departure point for Skipper Fishing Charters, a Vineyard Sound charter operator centered on ocean fishing trips. The Skipper runs daily fishing trips, sunset cruises, and private charters from Slip 74 near the Island Queen, with protected, calm Vineyard Sound waters close to the fishing grounds. Guests can join morning or afternoon outings according to season, or arrange private trips for company, bachelor or bachelorette, and birthday groups.

Each outing includes rods, reels, bait and a bag for the catch, while crew members help anglers learn the tackle and fishing process. Free nearby parking and fish-cleaning access support a practical day on the water. Contact Skipper Fishing Charters to plan a fishing charter from Oak Bluffs.

Features

  • Daily fishing trips
  • Private group charters
  • Fishing instruction
  • Family fishing outings

Amenities

  • Fishing
  • Parking
  • Restrooms & Showers
  • Navigation & Electronics
  • Audio & Entertainment

Why book with us

  • Fish protected calm waters of Vineyard Sound
  • Bring your catch home after the trip
  • Learn to use the onboard tackle
  • Arrange a charter for group celebrations
  • Enjoy a variety of music onboard

Frequently Asked Questions

What's included with a rental at Skipper Fishing Charters?

Rentals from Skipper Fishing Charters include safety equipment, fishing gear, comfortable seating, GPS navigation and an onboard restroom. Amenities vary by boat and by season, so confirm what comes with the boat you book.

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

2 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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