Sunset Sail on Long Island Sound: Help Raise the Sails

Take the helm of a tall ship as the sun drops over the water

Sail the Liberty Clipper, a 125-foot traditional schooner, for a two-hour sunset voyage on Long Island Sound from Port Jefferson Harbor. After boarding, you help raise the sails and steer the vessel while the captain and crew manage the rigging. The ship glides through the channel into open water, where you watch the harbor and local wildlife from the spacious deck.

Step-by-step itinerary

Sunset sailing on Liberty Clipper

• Board the Liberty Clipper
• Grab a drink at onboard bar
• Set sail into Port Jefferson Harbor
• Help raise the sails
• Take a turn at the helm
• Sail out into Long Island Sound

The experience

The Liberty Clipper leaves the dock and heads into Port Jefferson Harbor with a drink from the onboard bar in hand. Once clear of the channel, the crew invites you to help raise the sails. You're not watching from the rail, you're pulling the lines. If you want, you take a turn at the helm steering the vessel into Long Island Sound. The whole sail runs two hours, timed to catch the sunset over the water.

The schooner itself is the draw: a 125-foot tall ship built and rigged the way ships were built for centuries, with the traditional craftsmanship visible in every line. You're on a spacious deck with room to move, and the captain and crew stay aboard to manage the sails and keep the vessel safe. Bring any snacks or food you want. Drinks come from the onboard bar. The minimum age is 12, and the voyage suits all fitness levels.

What’s included

• The two-hour sail on the 125-foot schooner.
• captain and crew.
• a USCG certified vessel.
• access to the onboard bar for drinks.

Information

Lasts 2h, from US$ 89 per person, with a live guide in English and with free cancellation up to 24 h before.

Days and timesNext departure: 18 Aug 2027

GroupUp to 75

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Book up to2h before

AgesAdult (12 to 90 years) · Under 12: can't be booked

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated yesterday

Good to know

Low physical effortStroller-friendlyPets welcomePublic transport nearbyInfants must sit on laps

Operated by The Liberty Clipper

Is this one for you?This is a shared sail where you actively participate (you help raise the sails and take a turn at the helm), so it suits anyone who wants hands-on time on a real tall ship, not just a seat on the deck. If you prefer to sit back and watch the crew work, you can do that too, but the appeal here is doing the work yourself.

Traveler reviews

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Top questions

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

Can I steer the boat on this sail?

Yes. The crew invites everyone aboard to take a turn at the helm, so you get hands-on time steering the Liberty Clipper as it moves through Long Island Sound.

What happens if I don't want to help raise the sails?

You don't have to. The invitation is there, but you can sit back on the deck, watch the harbor, and let the crew handle the rigging while you enjoy the sunset.

Is this a shared sail or a private charter?

This is a shared sail. Other guests will be aboard with you. The schooner has a spacious deck, so there's room to move around and find your own spot.

What's included in the price?

The two-hour sail on the Liberty Clipper, the captain and crew, and use of the vessel are included. You bring your own food. Drinks are available for purchase at the onboard bar.