Wind's Up | Top Boat Rental in Vineyard Haven, MA Skip to content

Wind’s Up

199 Beach Rd, Vineyard Haven, MA 02568
Boat types
Sailboats
Pricing
Contact for Rates

About

On Martha’s Vineyard, Wind’s Up provides boat rentals and natural water sports equipment from its Vineyard Haven shop on Beach Road. Its rental lineup includes kayaks, canoes and sailboats, alongside windsurfers, stand-up paddle boards, surf boards and body boards. Customers can book rentals and select periods by the hour, day or week, making it possible to plan a brief outing or more time on the water.

For a boat rental near Vineyard Haven, sailors can choose Sunfish-style boats or 15-foot centerboard sloops with a main and jib. The shop also offers sailing and windsurfing lessons, wetsuit rentals, beach gear and equipment sales, giving visitors practical ways to prepare for a day on the water. The rental selection centers on paddling, sailing and wind-powered activities on Martha’s Vineyard. Contact Wind’s Up to book a rental or lesson.

Features

  • Hourly daily and weekly rentals
  • Sailing and windsurfing lessons
  • Water sports equipment sales
  • Online rental booking

Amenities

  • Rentals
  • Fleet & Boat Types
  • Water Sports Gear
  • Staff & Service

Why book with us

  • Choose rentals by the hour day or week
  • Rent kayaks canoes windsurfers and sailboats
  • Take a windsurfing or sailing lesson
  • Choose a centerboard sloop with main and jib

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

199 Beach Rd, Vineyard Haven, MA 02568

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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