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Working in unison to create a fun, safe and unique sailing experience.


Your captains Toby & Will are partners, who have sailed together for many years between New England and the Caribbean.


Each are passionate about sailing and have over 20-years combined charter experience.


They pride themselves on tailoring every charter to suit each guest’s desires. Whether onboard for a day in Sag Harbor or for two weeks in the Caribbean, Will and Toby truly believe their first mission is to make your sailing dreams come true.

Captain Toby Stull

Captain Toby Stull has sailed his entire life. He holds a USCG Master Captain License and several American Sailing Association Instructor certifications. He was on boats before he could walk. Toby has an intricate knowledge of waters surrounding Sag Harbor, as well as the Virgin Islands, allowing him to know exactly where the action is, where the activities are, and exactly where to bring guests who want to stay “off the track.” Captain Toby has also served on the board of directors for “Sailing Heals,” a 501(c)(3) non-profit that provides cancer patients with a day of respite under sail and loves to share sailing with all.

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Captain Will Bishop

Captain Will Bishop is also a life-long sailor. Since the age of 19, he has captained several luxury mono-hull charter yachts of many sizes in the Caribbean and New England. He has worked as a yacht manager, captain and engineer aboard some of the worlds finest vessels. Beyond his sailing acumen, Will is an excellent cook who’s onboard prepared meals (Caribbean) and catering (Hamptons) are focused on balanced and healthy appeasing combinations. He enjoys a varied cooking style incorporating every type of foods from latin to Asian, and everything in between. He has an acute understanding and love of local grown fare.

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Boat Dog Bamboo

Bamboo is a St. John ‘Coconut Retriever’ who was originally a Puerto Rican street dog (Sato). She is 6-years old and has been aboard for nearly two years.

She is friendly, yet unobtrusive, and is the favorite part of the vacation to guests.