A NORTH FORK SAILING ADVENTURE TO AWAKEN YOUR SENSES

Sailboat Charters in Greenport, NY - Choose from adventurous day cruises, local harbor jaunts, or various overnight voyaging options within and around the North Fork and Southern New England.

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VOYAGES

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Day Sails

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Overnight Sails

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  • DAY SAILS: Come aboard Friday through Sunday and enjoy an afternoon or sunset cruise in and around Greenport/Shelter Island. Click the heading above for details, destinations and times.
  • OVERNIGHT SAILS: Join us for unique learning experiences on overnight voyages Monday through Thursday. Destinations are determined by tides, weather, sea conditions, Guest desires and experience, and include Peconic Bay, Montauk, Block Island, Fisher Island, Stonington, CT, Newport, RI and surrounding anchorages. Click the heading above for details.
  • Follow us on @SailNoFo to learn about unique sailing events and opportunities throughout the season, such as Under the Fireworks Cruises!
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From Sunset Sails in the Harbor to learning to navigate the seas on your own adventure away from land, a memorable Sailboat Charter experience is awaiting you.

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Celebrate Special Moments with Sail Nofo

Make your special moments unforgettable on the open water. Whether it’s a romantic proposal, a fun-filled bachelorette party, a heartwarming family reunion, or a joyous birthday celebration, Sail Nofo offers the perfect setting. Enjoy breathtaking views, serene sunsets, and personalized sailing experiences that will make your event truly unique.

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Experience Open Ocean Sunsets

After a day of sailing, settle in for a meditative experience as stars, planets and constellations develop into evening’s guiding “Heavenly Bodies”

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Exhilarating Sunrises

Early morning “watches” present a star-filled sky morphing into vibrant sunrays of the new day’s beginning.

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Or, Simply Glide Around the Local Harbor and Bays to Absorb the North Fork’s Magic

On any of our afternoon sailing charters, experience a peaceful sunset, local maritime sites from a unique seaward perspective, jump in for a swim off the beaten path, or just admire the beauty of local shoreside vistas

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Follow on Facebook and Instagram for Voyage Updates, or sign-up for latest update below.

    Google Reviews

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    We want to extend a heartfelt shout-out to Captain Dan and his wonderful wife Nancy for the incredible experience aboard the SV RHAPSODY.

    Thank you for the exceptional, personalized care. Thank you for the delicious refreshments. You made our 4th of July celebration truly unforgettable! It was a bucket list experience we didn’t even know we had!

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    Liz M.E - 2 days ago
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    Captain Dan showed us such a lovely time on the water, and SV Rhapsody is not only a stunning vessel but also extremely comfortable to sail. Dan is a very accomplished sailor and it shows, we thoroughly enjoyed our afternoon cruising knowing we were in good hands with his expertise.

    His vast knowledge of the North Fork, his passion for sailing, and his welcoming personality really set SailNofo charters apart from the rest. If you want the real deal while also sailing in comfort and style Dan is your guy, can’t wait to come sail again when I’m back in August!

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    Michela Torchio - 3 weeks ago
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    Captain Dan gave us a magical afternoon on the water. He is a skilled sailer and his boat is just beautiful . He knew so much about the landscape and pointed out the sights and taught us their stories. We brought sandwiches and snacks and it seems everything taste better with the wind in your hair. it was such a nice memory as a family would highly recommend

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    michele mizrahi - 3 weeks ago
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    Sailnofo brings such a unique experience of the North Fork waters on board the beautiful Rhapsody. Captain Dan is an experienced sailor who puts you at ease with both safety and nautical aspects. The result is the making of a lifetime memory with friends. Dan goes above and beyond with hospitality and luxury sailing. He truly exceeds your expectations in the most wonderful way.

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    Lesaya Kelly - 4 days ago