Albertson Marine, Inc.

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 Southold, you can boat Southold Bay and Shelter Island Sound, explore the shallow town creeks, or use nearby ramps for Hallock Bay and Long Island Sound. Southold Bay is a bight of Shelter Island Sound, with nearshore shoals and an anchorage area off the entrance jetty. Town Creek and Jockey Creek have shallow, seasonally buoyed channels; put in at Pine Neck Road or Terry Lane. Dering Harbor offers a popular small-craft anchorage with a 5 mph limit. Hallock Bay is shallow and shoal-prone, so NOAA advises local knowledge. Cedar Beach, Hashamomuck, Narrow River Road and Truman’s Beach are additional launch points.

Source: Town of Southold (southoldtownny.gov)

Good day-trip choices from Southold are Greenport, Coecles Harbor on Shelter Island, and Sag Harbor. Greenport’s Mitchell Park Marina gives boaters transient dockage beside the harbor walk, carousel and village waterfront. Coecles Harbor offers a designated transient anchorage for a quieter stop in Shelter Island waters. Sag Harbor has transient docks and moorings, with shops and restaurants a short walk from the village marina facilities.

Source: Village of Greenport (villageofgreenport.org)