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.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most people in reasonable health; no prior sailing experience necessary
Wildlife
History
The area has a rich maritime history, once serving as a hub for local fishing fleets and trade routes.
Conservation
Surprise Sailing emphasizes eco-friendly practices, including waste reduction and respectful wildlife viewing.
Surprise Sailing Yacht Charters
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.
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.
Check the weather forecast
Always review local weather conditions before heading out to ensure a safe and enjoyable sail.
Bring sun protection
Wear sunscreen, hats, and sunglasses to stay comfortable in the sun during your trip.
Book in advance
Reserve your spot ahead of time, especially during peak season, to secure availability.
Wear comfortable clothing
Dress in lightweight, quick-drying clothes suitable for water activity.
Sunscreen
Protect your skin from UV rays during the sunny sail.
summer
Hat and sunglasses
Shield your eyes and face while enjoying the open water.
summer
Light waterproof jacket
Bring a jacket in case of wind or unexpected weather.
spring; fall; winter
Comfortable shoes or sandals
Wear non-slip shoes suitable for being on a boat.