Mid-May through September we sail from Greenport Harbor, situated in the heart of Long Island’s North Fork. Our sailing grounds include Peconic and Gardiners Bays, Long Island/Block Island/Fisher Island Sounds, Narragansett and Buzzards Bays and beyond, as well as afternoon and sunset sails in and around the Greenport/Shelter Island waterways.
Experience the charm of Greenport, Gardiners Bay, Peconic Bay and Shelter Island with our delightful day sails. Available Friday through Sunday, choose from afternoon or sunset cruises and immerse yourself in the stunning local waters. For more details, destinations, and times, click the heading above.
All Day Sails are limited to 6 Charter Guests (children under 16 years of age must bring proper life vest and be properly supervised).
| Charters | Time | Fee |
|---|---|---|
| Afternoon Charters: | 12:30-4:30 | $1050.00 |
| 1:30-4:30 | $950.00 | |
| Sunset Cruise Charters: | 5:30-7:30 | $850.00 |
Join us for unforgettable overnight voyages from Monday through Thursday. Learn and explore as we sail to scenic anchorages throughout the East End and Southern New England. Destinations are tailored to tides, weather, sea conditions, and guest preferences. Click the heading above for more details.
Stay updated with unique sailing events and opportunities throughout the season by following us on Instagram @SailNoFo. Don’t miss out on special adventures like our Under the Fireworks Cruises!
Join us for “Hands-On” cruising and open water sailing from Mid-May to Mid-June on overnight voyages specifically tailored to reach your next level experience. Our programs provide an opportunity to improve confidence and skill in sailing “Beyond The Bay,” while enjoying beautiful and challenging cruising grounds. With an experienced Captain and crew by your side, develop confidence and understanding in an open water sailing adventure by direct participation in voyage planning, boat handling, sail trim, navigating, watch standing, galley operations, anchoring, etc.
From a simple overnight to and from Block Island, or multiple nights beyond in the Southern New England cruising grounds, we can design a plan to suit your desired goals. These trips are also a way to qualify for extended Offshore crewing opportunities with us in October on various legs to Bermuda and then to the Eastern Caribbean.
Intended for persons having some “boating” knowledge, from beginners to sailors desiring to up their game, and who want to participate in the operation and management of a cruising sailboat. All provisioning and safety equipment provided (except alcohol and off-boat meals). All trips limited to a minimum of 2 persons and a maximum of 4 persons.
A portion of all our Charter Fees are contributed to Greenport’s “Glory Going Green,” Not-For-Profit, College Scholarship Program: $25 from each Day Sail and 3% of Overnight Charter Fees.
| Info | Fee |
|---|---|
| Charter Experience | |
| Per person/per night
Includes all provisioning (not including onshore meals), equipment, and fees ( minimum 2 persons/maximum 4 persons) |
$1,250.00 |
| Hands-on Overnight Cruising | |
| Single Night Voyages per person | $1,500.00 |
| Multiple Nights per person/per night | $1,250.00 |
| Includes all provisioning (not including onshore meals), equipment, and fees | |
**All trip times are approximate, and are subject to rescheduling based on weather & sea conditions (wind gusts in excess of 30kts/excessive seas), but are not cancelable because of inclement weather not otherwise a hazard to safe operations. Arrival and boarding at least 15 minutes before scheduled departure is encouraged. BYOB is permitted. Maritime law prohibits use of recreational drugs as defined under federal law, and are not permitted on-board. All voyages and crew participation are subject to the exclusive discretion of the Vessel’s Captain, at all times, to limit, cancel, or extend the same.
A $100.00 Deposit is required on Booking and is non-refundable unless trip is cancelled no less than 7 days in advance, or at the discretion of the Captain in the event of inclement weather or unexpected mechanical issues (25% of total Charter Fee required as deposit on Overnight Voyage Bookings). Payment in full required at dock prior to departure. Cash, Venmo or Zelle accepted.
For more information on how to book a voyage, please visit the Book a Voyage page.