MONTAUK SAILING FIELD GUIDE
Sail, Swim, and Splash: A Three‑Hour Cruise Around Montauk’s Navy Beach and Gardiners Island
A 3‑hour private outing aboard a roomy Catalina 36 MkII through Lake Montauk and Block Island Sound that combines scenic cruising with an anchored swim—this guide tells you what to expect and how to prepare.
Sail, Swim, and Splash: A Three‑Hour Cruise Around Montauk’s Navy Beach and Gardiners Island.
This three‑hour private adventure threads Lake Montauk and Block Island Sound, passing Navy Beach, Fort Pond Bay, Gardiners Island and the Montauk Point Lighthouse before anchoring for a swim break with pool noodles and toys. The boat is a spacious Catalina 36 MkII with shaded seating and all the extras that make a short outing feel deliberate and relaxed.
Highlights
Outing Highlights
Roomy Catalina 36 MkII with Shaded Seating
The charter runs aboard a roomy Catalina 36 MkII that offers shaded seating and the extras you need for a comfortable three‑hour cruise.
Scenic Views from Navy Beach to Montauk Point
The route takes you through Lake Montauk and Block Island Sound with views of Navy Beach, Fort Pond Bay, Gardiners Island and the Montauk Point Lighthouse.
Anchor, Swim, and Play
After the cruise the crew anchors for swimming with pool noodles and toys. The Barbara Bell has a head for your use during the charter, and facilities at the Montauk Yacht Club are available before boarding.
What the day feels like
What the Day Feels Like
Expect a focused three‑hour rhythm: a scenic motor or sail across Lake Montauk and into Block Island Sound, slow passages past shoreline features, then a deliberate anchor to climb into the water and play with onboard swim toys. Shade on deck and roomy cockpit seating let you move between sun and shelter while the captain handles lines and navigation.
Suitability
Who it's for
Who this outing suits and what to keep in mind before you book.
Practical planner
Details to review before reserving
This is a 3‑hour private adventure.
Dress for safety and changing temperatures at sea; bring soft‑soled shoes or be prepared to go barefoot. If you bring wine, choose white or rosé to avoid stains.
The Barbara Bell has a head for passenger use during the charter, and facilities at the Montauk Yacht Club are available prior to boarding.
The boat is a roomy Catalina 36 MkII with shaded seating and swim toys such as pool noodles for the anchor‑and‑swim portion.
Review cancellation policies before reserving.
Frequently asked questions
Planning Your Outing
How long is the trip?
The outing lasts three hours.
Where will we sail and what will we see?
The cruise crosses Lake Montauk into Block Island Sound with views of Navy Beach, Fort Pond Bay, Gardiners Island and the Montauk Point Lighthouse.
Is swimming included?
Yes—after cruising the boat anchors for swimming and offers pool noodles and other toys for play.
Are there restroom facilities?
Yes. The Barbara Bell has a head for your use during the charter, and there are facilities at the Montauk Yacht Club available before you board.
What should I wear and what about footwear?
Dress for safety and the weather—the sea can be cooler than shore. Bare feet are preferred aboard; soft‑soled shoes like boat shoes or sneakers are acceptable, but you may be asked to go barefoot if you wear hard‑soled shoes or high heels.
Can I bring red wine onboard?
If you bring wine, please choose white or rosé—red wine can cause stains and is discouraged.