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.
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Difficulty
easy
Duration
2 hours
Fitness Level
Ideal for most fitness levels; no strenuous activity required
Wildlife
History
Greenport has been a vital maritime hub since the 1800s, supporting local fishing and shipping industries.
Conservation
Surprise Sailing emphasizes eco-friendly practices by minimizing engine use and respecting marine habitats.
Surprise Sailing Yacht Charters
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.
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 layers for comfort
Evening breezes can cool the air, so dress in layers to stay comfortable throughout the sail.
Arrive early
Getting to the dock 15-20 minutes early ensures a smooth boarding process and plenty of time to settle in.
Bring a camera
Capture the stunning sunset and scenic views, but keep your camera protected from the wind and salt spray.
Wear sunscreen
UV rays can be strong, especially during the late afternoon, so apply sun protection even on cloudy days.
Sunscreen
Protect your skin from UV rays during the late afternoon cruise.
summer
Hat and sunglasses
Shield yourself from the sun and glare while enjoying the views.
summer
Water bottle
Stay hydrated during the trip, especially on warm days.
Light jacket or sweater
Bring an extra layer in case the breeze picks up or late-season chills set in.
spring;fall;winter