Cape Ann Cruises

Rentals from Cape Ann Cruises include life jackets, safety equipment, fuel, fishing gear, a sunshade, a Bluetooth stereo, navigation maps and dockside assistance. 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)

From Gloucester, you can explore Gloucester Inner Harbor, follow the Annisquam River to Ipswich Bay, or tuck into Lanes Cove. Inner Harbor is a headway-speed, no-wake area, with Cripple Cove Landing available as a public boat landing. Trailer boats can put in at Dun Fudgin Landing on the Annisquam River.

The Annisquam and Blynman Canal form a narrow, marked small-craft route between Gloucester Harbor and Ipswich Bay; the river and its tributaries are no-wake. Ipswich Bay is the more exposed choice because the northern entrance bar can be difficult in a heavy sea. Lanes Cove is a small harbor protected by stone breakwaters.

Source: City of Gloucester Harbormaster (gloucester-ma.gov)

Good day-trip choices from Gloucester are Rockport Harbor, Thacher Island, Great Misery Island and the Essex River estuary. Rockport Harbor puts Bearskin Neck’s shops, galleries and restaurants close to the waterfront; Thacher Island offers views of its twin granite lighthouse towers; Great Misery Island has dinghy access, walking trails, stony beaches and former resort remains; and Essex maintains transient moorings between the back of Crane Beach and Hog Island, a popular stop for fishing and coastal scenery.

Source: Town of Rockport (rockportma.gov)