Where does the charter depart?

The cruise departs from Montauk; specific check-in details are provided at booking and guests can use Montauk Yacht Club facilities prior to boarding.

How many people fit on the boat?

The Catalina 36 MkII accommodates a maximum of six passengers for private charters.

Yes—white or rosé only. Red wine is not permitted to avoid staining the boat.

Is swimming included?

Yes—charter includes anchor stops for swimming with pool noodles and floating toys provided.

What is the cancellation policy?

Cancellation details are provided at booking; confirm terms with the operator when you reserve.

Are children allowed?

Children are welcome, but parents should assess swimming ability; life jackets are provided and required when requested or in choppy conditions.

Sail & Swim Montauk: Private 3-Hour Cruise to Gardiners Island and Montauk Point

Montauk's Sail & Swim is a three-hour private cruise that launches from Montauk on Long Island’s eastern tip, sending you across Lake Montauk and Block Island Sound past Navy Beach, Fort Pond Bay, Gardiners Island, and the Montauk Point Lighthouse. Onboard the roomy Catalina 36 MkII—known as the Barbara Bell—guests relax in shaded seating, take in wide ocean views, and anchor for a swim with pool noodles and toys.

This trip reads like a seaside postcard: low, drumbeat surf against rocky bluffs, the salt-stung scent of bay grass, and an unpressured line of horizon where birds wheel overhead. Key features include Navy Beach’s exposed shoreline, the broad bowl of Fort Pond Bay, the privately owned Gardiners Island with its windswept bluffs, and the white cone of Montauk Point Lighthouse, first lit in 1796 and a navigational landmark for two centuries. Geologically, the route crosses glacial-age deposits and exposed Cretaceous cliffs on Gardiners; you’ll notice reddish glacial till and the flat, exposed bedrock that shapes Montauk’s headlands.

Why book this over a crowded ferry? It’s the private tempo: a maximum six passengers, a knowledgeable local skipper, and a small sailboat that moves quietly enough to feel part of the water. The Barbara Bell also includes a head for comfort and easy access to the Montauk Yacht Club facilities before boarding. Swim stops are the real reward—clear bays, gentle beaches, and floating toys for families or a couples’ escape.

Practical notes: dress for cooler sea air even on warm days, and adhere to the operator’s footwear rules—soft soles or bare feet for safety. The captain can recommend sheltered anchorages if winds pick up; the vessel’s size makes it nimbler than larger charters, perfect for exploring the coves near Fort Pond Bay or drifting off Gardiners.

This experience is a strong match for visitors who want short, rejuvenating time on the water without committing to a full-day charter. It’s family-friendly, lower-impact on the local shoreline than beach driving, and a vivid way to see Montauk’s maritime landscape from sea level. Whether you want to cool off with a swim, watch the lighthouse slide past the rail, or sip something chilled under sail, Sail & Swim delivers a straightforward, small-boat outing that highlights the unique shores and seascapes of eastern Long Island. Bookings are private and capped at six passengers, keeping the outing intimate—ideal for families or couples. The operator asks that guests serve only white or rosé wine to avoid stains and requires barefoot or soft-soled footwear aboard the Barbara Bell. Pack a light jacket, sunglasses, and a waterproof phone case; the captain will adjust the plan based on wind and tide, offering local knowledge through the three-hour trip with safe, friendly service.

Sail & Swim Montauk: Private 3-Hour Cruise to Gardiners Island and Montauk Point

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