Chatham Sailboat Rentals

Rentals from Chatham Sailboat Rentals include life jackets, safety equipment, fuel, onboard storage and a sunshade. Amenities vary by boat and by season, so confirm what comes with the boat you book.

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)

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)

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)

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)