From Shelter Island to Shinnecock: The Boating Life Returns

It’s that time of year again—boats are being prepped for launch. Shrink-wrap is being peeled off, boat bottoms are being painted, decks are being cleaned and polished, and teak is being spruced up for the upcoming 2025 boating season. In recent years, East End boating has seen a major resurgence. On summer days, you’ll spot majestic sailboats, sleek powerboats, and multi-million-dollar yachts cruising through Gardiner’s Bay or slipping in and out of Shelter Island, Sag Harbor, the Shinnecock Canal, Montauk Harbor, Hampton Bays, and Three Mile Harbor.

For some, getting a boat ready is a labor of love. Others hire professionals to handle the labor-intensive job of making a boat seaworthy after months out of the water. Each year brings new developments, and in 2025, one notable addition is the creation of “Swans Marina,” located at 10 Boatyard Road, East Hampton. Local resident Dane Riva has leased the property formerly known as Vanderveer’s Boat Yard and is now actively offering summer slips at $170 per foot. Additional services include haul-outs, launchings, and winter storage. 

For many, the waters surrounding the Hamptons remain unfamiliar territory. Homeowners and renters typically enjoy the beaches and parks and revel in the magic of a Hamptons summer. But another layer of the experience lies offshore—aboard a recreational vessel. The idea of being free at sea holds a unique appeal for those who spend too many days under the pressure of pursuing career success. For example, while sailing, it’s the pure pleasure of catching and harnessing the power of the wind that frees the mind from its usual mental clutter.

Albert Einstein found relief and joy sailing around Long Island in a modest 17-footer. He once said, “A ship is always safe at the shore, but that is not what it is built for,” and described his sailing approach as, “Set sail, make it fast, no thoughts of energy or velocity, loll back, let the boat drift.” Billionaire Paul McCartney has often been seen sailing a Sunfish near Albert’s Landing in the Springs—sometimes with a daughter or his wife, Nancy. He says it relaxes him. Meanwhile, billionaire David Geffen has anchored his 453-foot yacht Rising Sun in Gardiner’s Bay for weeks at a time. The message is clear: no matter your wealth, the waters of the Hamptons can be enjoyed both simply and extravagantly.

Of course, any discussion of East End boating must include fishing. It’s a time-honored tradition in the region. Every fisherman has a system, a favorite spot, and a deep connection to his boat—often considered a true fishing partner. Recreational fishing boats range from multi-million-dollar vessels to modest setups costing just a few hundred dollars. Fishermen are a special breed, marked by patience and a unique bond with nature—something only countless peaceful hours at sea can foster. It touches the soul.

That said, boating isn’t for everyone. For some, it feels like being trapped in someone else’s floating sandbox. This author felt that way too—until sailing solo changed everything. Out on the water off East Hampton, with only the sound of wind in the sails, came the discovery of something beautiful. Offshore, the cool breeze, the vast sky, the sun, and the fast-moving clouds offer a slice of heaven. The nightly Hamptons sunsets are breathtaking, the salt air is rejuvenating, and the views—of bluffs, beaches, homes, and lighthouses—never get old. They keep the soul feeling young.