Day Sails


$200 pp.
2-6 People

Sunset Sails


$175 pp.
2-6 people

Full Day Sails


$250 pp./$275 pp.
2-6 people.


Spend the Night On Board $1,150.00pp. Includes all meals.

Contact us for details!

What better way to see scenic vistas, breathtaking sunrises and sunsets and visit isolated beaches
and quaint coastal villages than as part of a sailing vacation?

From Memorial Day weekend through October, Little Dutch Sailing Charters will traverse the waters of the Long Island Sound. Day trips, sunset sails, weekend and week-long adventures are available, and all charters can be customized.

We sail out of Three Mile Harbor in East Hampton, NY through its charming inlet, filled with local marshes, islands and indigenous coastal wildlife, and into Gardiners Bay and Long Island Sound. A typical charter may begin with a sweet sail over to Coecles Harbor on Shelter Island for a swim. We could then sail back to Three Mile Harbor in time for your beach chair for the afternoon, and dinner at one of East Hampton’s wonderful restaurants conveniently located just up the road from Little Dutch.

Pick-ups can also be made from Sag Harbor, Greenport, Shelter Island and Montauk for an additional pick-up fee.

Our overnight or week-long adventures includes hearty meals and snacks. We could take you to magical Block Island or Martha’s Vineyard. We will accommodate you to make your sailing adventures ideal. Special event charters are available for weddings, commitment ceremonies, memorial services, birthdays, anniversaries and other celebrations.

Week-long charters available. All charters can be customized.
Alcoholic beverages welcome on all charters.

“Captain Missy and Little Dutch were beyond our expectations. We wanted to do something special for our first year wedding anniversary and this was perfect! The Whitby 42 sailboat was super comfortable and seaworthy – and pretty as a picture. Our stay aboard was relaxing and fun with just the right amount of activities mixed with solitary time. The meals were perfect – simple and absolutely satisfying. Her crew and galley mate Kendall was the perfect addition. Captain Missy is a knowledgeable, capable and responsible skipper as well as fun and a wonderful host – full of endless stories from her sailing adventures like crossing the Atlantic Ocean! We also LOVED that she is a female captain. We hope future guests heed our advice and get aboard because I know it will an incredible experience that they will love! We highly recommend Little Dutch Sailing Charters.”
- Kyle & Ali Egan June 2015

“Captain Missy provided for everything we needed for a wonderful and peaceful sunset sail on Little Dutch. Highly recommended!”
- Kevin H. September 2014

“Two thumbs up for Little Dutch Sailing Charters! The boat is beautiful, clean, and spacious. Captain Missy is also gracious and great fun, as well as being an excellent captain and knowledgeable about Long Island’s history and eco system. Spacious and gracious – the perfect combo for a perfect day, sailing out of the harbor and into Gardiners Bay, then over to Shelter Island for a swim and picnic. We were happy to bring our own food as everyone got what they wanted and it just made it easier all around. Really great value and better than waiting for a table in town for lunch after the beach. We had a marvelous time and look forward to doing it annually!”
- Jennifer Dwyer July 2017