Voyages

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.

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DAY SAILS

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.

  • Schedule: Available Friday through Sunday.
  • Experience: Hands-on sailing adventure in the scenic Bays and Sounds of the East End.
  • Historic Routes: Sail in the wake of classic vessels that have navigated these waters for centuries.

Charter Options:

  • 2-Hour Charters:
    • Tour Greenport Harbor/Pipe’s Cove
    • Explore Little Peconic Bay
    • Venture past Bug Light into Gardiners Bay
  • Longer Sails:
    • Enjoy swimming sessions
    • Take lighthouse tours
    • Relax on coastal cruises along historic shores

Amenities Included:

  • Complimentary bottled water and sparkling water
  • Ice, glassware, plates, utensils, and refrigeration
  • Service for food and beverages you bring

Customizable Experience:

  • Hands-on sailing or a relaxing cruise
  • Tailored to meet your goals and interests

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 $950.00
1:30-4:30 $850.00
Sunset Cruise Charters: 5:30-7:30 $750.00
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OVERNIGHT SAILS

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!

  • Voyaging Plans:
    • Multiple-day, overnight charters available from one to three nights
    • Scheduled from Monday through Wednesday
    • Explore unique shore-side destinations within our local cruising grounds

Destinations:

  • Montauk, NY
  • Stonington, CT
  • Mystic, CT
  • Fisher Island, NY
  • Block Island, RI
  • Newport, RI
  • Surrounding anchorages (dependent on voyage length, tides, and weather)

On-Board Provisioning:

  • Emphasis on whole food products
  • Sourced from North Fork, Long Island community
  • Based on seasonal availability

Learning Environment:

  • Hands-on experience in:
    • Boat and sail handling
    • Navigation
    • Standing watch
    • Provisioning/galley operations
    • Anchoring and mooring
  • Customized voyages to meet guest preferences and abilities

Guest Requirements:

  • Sailing experience not required (familiarity with being “on the water” advised)
  • Minimum of 2 and maximum of 4 charter guests (2 per shared cabin)

Charter Details:

  • Departure:
    • Early to mid-morning on the first voyage day (based on tides & weather)
  • Return:
    • Mid to late afternoon following the last night

Alcoholic Beverages:

  • Alcohol not included
  • Guests welcome to bring their own favorite local wines or other alcoholic beverages

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
Per person/per night
Includes all provisioning, equipment, and fees 		1,000.00

**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 $200.00 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.