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.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for all fitness levels, no physical exertion required
Wildlife
History
This coast has a rich maritime history dating back to the 1800s, with many stories of exploration and trade.
Conservation
The cruise company emphasizes eco-friendly practices, including fuel-efficient sailing and waste reduction, to preserve local waters.
Surprise Sailing Yacht Charters
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.
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.
Arrive early
Get there a bit before departure to settle in and enjoy the views.
Dress for the weather
Layers and sun protection are recommended for comfort onboard.
Bring a camera
Capture the stunning sunset and water views during your cruise.
Sip responsibly
Enjoy the wines at your own pace and remember to plan your transportation home.
Sunscreen
Protect your skin during the midday and sunset hours.
summer
Light jacket or sweater
Keep warm if the evening gets breezy.
summer
Camera or smartphone
Capture the scenic beauty and memorable moments.
Sunglasses
Shield your eyes from the sun glare on open water.
summer