Two-hour sails, half-day and full-day voyages, plus seasonal wine-tasting cruises departing Greenport, New York.
Choose from Two Hour Day Sails, Sunset Sails, Half Day, Full Day, and wine-tasting events.
Outdoor activity · Greenport
Set sail on a half-day adventure with Surprise Sailing Yacht Charters, enjoying refreshing waters and breathtaking coastal views. Perfect for a quick getaway, this trip offers relaxation and fun on the open water.
Surprise Sailing Yacht Charters is a Greenport, New York-based charter company offering a range of day sails and special cruises aboard the yacht Surprise. They operate a selection of public and private sail experiences tailored for relaxation, sightseeing, swimming, and small-group celebrations. Core offerings include a Two Hour Day Sail (morning and afternoon departures), a Two Hour Sunset Sail, a Half Day Sail ideal for swimming and leisure, and a Full Day Sail for extended exploration of local waters.
Special-event cruises feature curated wine tastings on board, including the Saltbird tasting with winemaker Robin Epperson-McCarthy on August 17 and the Chronicle tasting on September 6. These themed evening sails combine sunset views with guided tastings to create a seasonal, memorable experience. Reservations depart from Greenport, Long Island, and itineraries emphasize time on the water, coastal scenery, and flexible options for families and groups. The company lists clear trip durations for guests — two-hour sails, half-day outings, and full-day voyages — allowing travelers to select the right length for their plans.
Booking pages list schedules, durations, and event dates so travelers can reserve Two Hour Day Sails, Half Day Sails, Sunset Sails, Full Day Sails, or Saltbird and Chronicle wine tasting cruises from Greenport, New York.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Departures from Greenport harbor.
Clear durations for every booking.
Full-day and other sails aboard Surprise.
Saltbird and Chronicle tastings scheduled.
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Surprise Sailing Yacht Charters listing.
Surprise Sailing Yacht Charters offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Check schedules for Two Hour Day Sails, Half Day, Full Day, Sunset, and Saltbird/Chronicle wine tasting dates.
water-activities · Greenport
Set sail on Long Island's Greenport waters with Surprise Sailing Yacht Charters. This two-hour trip offers a perfect blend of adventure and relaxation for all skill levels.
water-activities · Greenport
Sail into the sunset on a beautifully appointed yacht while sampling wines from Saltbird and Chronicle. Perfect for relaxing or celebrating with friends, this cruise offers breathtaking views and a taste of local excellence.
water-activities · Greenport
Set sail on a full-day cruise with Surprise Sailing Yacht Charters and experience the serene beauty of open waters. Discover stunning coastlines, marine wildlife, and the pure joy of sailing in this scenic adventure.
water-activities · Greenport
Set sail into the sunset along the North Fork of Long Island with Surprise Sailing Yacht Charters. Experience breathtaking views, gentle breezes, and maritime history—all in a tranquil 2-hour cruise.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.