SailHamptons - NY

SailHamptons - NY Private luxury Sailing and Motor Yacht Charters in Sag Harbor, Shelter Island, Greenport and Points

Private luxury charters in Sag Harbor, NY, Greenport, Shelter Island serving groups from 2 - 40 guests.

Waiting for your arrival back from lunch.
06/08/2026

Waiting for your arrival back from lunch.

No filter needed on last night’s glorious sunset! Welcome to the season; Luna is the reason!
05/26/2026

No filter needed on last night’s glorious sunset! Welcome to the season; Luna is the reason!

When those far away places are right around the corner. More access to beautiful destinations, bigger capacity, more fu...
05/14/2026

When those far away places are right around the corner. More access to beautiful destinations, bigger capacity, more fun. The Bermudian Schooner Luna is at SailHamptons. Perfect for all size groups … up to 41.

I don’t claim to be an artist, but sometimes a blank canvas can come in a different form giving inspiration for the ulti...
05/06/2026

I don’t claim to be an artist, but sometimes a blank canvas can come in a different form giving inspiration for the ultimate beautiful entertainment space afloat. A partially shaded mahogany day-lounge that transforms into a table seated dinner experience under the stars and string lights is in store for our wonderfully updated Vintage Lobster Yacht “Blue Sky.” I cannot wait to bring her to you. - Captain Toby

The Blizzard of 2026 aboard the SailHamptons Virgin Islands adventure. After you join us for a sail this summer, join ...
02/25/2026

The Blizzard of 2026 aboard the SailHamptons Virgin Islands adventure. After you join us for a sail this summer, join us next winter in the Virgin Islands. (Not shown, the humpback whale we hung out with sailing today 🐳☀️)

Follow our journey as Capt Toby and the team transform this iconic and classic Maine built John Williams lobster yacht i...
01/30/2026

Follow our journey as Capt Toby and the team transform this iconic and classic Maine built John Williams lobster yacht into a truly special Hamptons experience. Coast Guard inspected for over 20 guests, “Blue Sky” will offer table seated dinners under the stars with our exquisite restaurant and chef partners, swim trips with toys, restaurant outings, and so much more! Don’t worry, we have the fun coming in 2026

Thinking about that perfect summer day.
01/19/2026

Thinking about that perfect summer day.

We are working hard this winter to bring another fantastic experience to you! Our classic John Williams Lobster Yacht ...
01/05/2026

We are working hard this winter to bring another fantastic experience to you! Our classic John Williams Lobster Yacht is in for a wonderful transformation.

Join SailHamptons this winter for a Catamaran holiday in the Virgin Islands, French West Indies and other magnificent de...
10/15/2025

Join SailHamptons this winter for a Catamaran holiday in the Virgin Islands, French West Indies and other magnificent destinations. With over two decades experience sailing throughout the Eastern Caribbean, Capt Toby can guide you through your best vacation ever. PM for details.

Come aboard Luna! Harborfest sails are today at 1pm and 3pm, and tomorrow at 11:30am and 1:30pm. They are 1.5 hours a...
09/13/2025

Come aboard Luna! Harborfest sails are today at 1pm and 3pm, and tomorrow at 11:30am and 1:30pm. They are 1.5 hours and you’re welcome to bring anything you’d like for food and drink! Links to tickets in our bio and in our story.

Address

1 Bay Street
Sag Harbor, NY
11963

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