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.
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Difficulty
easy
Duration
2 hours
Fitness Level
No special fitness required, suitable for all ages
Wildlife
History
Greenport has a rich maritime history dating back to the 1800s, famously known for shipbuilding and fishing industries.
Conservation
The area emphasizes sustainable boating practices to protect local marine ecosystems.
Surprise Sailing Yacht Charters
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.
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.
Location
Greenport, NY
Departures from Greenport harbor.
Trip Lengths
2-hour, half-day, full-day
Clear durations for every booking.
Vessel
Surprise
Full-day and other sails aboard Surprise.
Wine Events
Aug 17 & Sep 6
Saltbird and Chronicle tastings scheduled.
Check schedules for Two Hour Day Sails, Half Day, Full Day, Sunset, and Saltbird/Chronicle wine tasting dates.
Bring Sun Protection
Apply sunscreen, wear hats, and sunglasses to stay comfortable during the sail.
Dress for the Weather
Bring layers and windproof clothing to stay warm if breezy.
Arrive Early
Get there 15 minutes before departure for a smooth check-in.
Secure Personal Items
Hold onto valuables or keep them in dry bags to avoid loss overboard.
Hat
Protects from the sun during the sail.
summer
Sunscreen
Prevents sunburns and keeps skin protected.
summer
Layers
Optional for added warmth on brisk days.
springfall
Camera
Captures scenic views and wildlife encounters.