Boscola Yacht Sales, LLC

New York's only statutory rental age is for personal watercraft and specialty prop-craft: Navigation Law §73-a bars a livery from renting one to anyone under sixteen, and in the same clause requires genuine proof of identification and age plus compliance with the boating safety certificate rule in section 49. A personal watercraft renter over eighteen may skip that certificate only where the livery keeps them within five hundred feet of the agent assigned to supervise, on a clearly marked craft.

Operating age is separate. Section 49 sets ten years for a mechanically propelled vessel and fourteen for a personal watercraft, each with a certificate; a personal watercraft operator may instead be accompanied by a certificate holder over eighteen. Rental companies set their own minimum age.

Source: New York State Office of Parks, Recreation and Historic Preservation (nysenate.gov)

Yes, but New York calls it a Safe Boating Certificate rather than a boating license. The state generally requires recreational operators of motorized vessels to complete a state-approved course and carry the original certificate, including for personal watercraft. Operators of other motorboats must be at least 10, while PWC operators must be at least 14. Renters age 18 or older may operate a livery motorboat without a certificate after receiving basic instruction and safety information; a rented PWC may be operated without one only within a marked area near the livery. Renters under 18 need a certificate, and no one under 16 may rent a PWC at all. Course graduates receive a temporary certificate valid for 90 days. Valid U.S. Coast Guard operator licensees are exempt. New York State Parks administers the program.

Source: New York State Office of Parks, Recreation and Historic Preservation (parks.ny.gov)

From Greenport, you can cruise from Greenport Harbor into Shelter Island Sound and continue to Gardiners Bay. Greenport Harbor is protected by a breakwater, while adjoining Stirling Basin provides anchorage and has a 5 mph speed limit. Dering Harbor on Shelter Island is another popular anchorage with a 5 mph limit, but its entrance has shoal areas. Shelter Island Sound and Gardiners Bay form connected cruising water; NOAA describes the local bay system as well protected but generally shallow. Trailer boats can launch at Sandy Beach Road on Stirling Basin or at the Mill Creek ramp on Bayview Avenue South.

Source: NOAA Office of Coast Survey (nauticalcharts.noaa.gov)

From Greenport, boaters can make local day trips to Dering Harbor, Coecles Harbor and Taylor’s Island, Smith Cove, and Sag Harbor. Dering Harbor is a favorite anchorage for yachts and motorboats; the Coecles Harbor Marine Water Trail permits shore access at Taylor’s Island; Smith Cove offers a good small-craft anchorage plus marina services; and Sag Harbor has transient dockage and moorings, with shops and restaurants a short walk from its village marine facilities.

Source: NOAA Office of Coast Survey (nauticalcharts.noaa.gov)