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.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
6–8 hours
Fitness Level
No special fitness required, but participants should be comfortable on a boat for several hours.
Wildlife
History
The coastline has long been an important site for local fishing communities, with maritime traditions dating back centuries.
Conservation
The area actively supports marine conservation efforts to protect coastal habitats and marine species.
Surprise Sailing Yacht Charters
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.
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.
Sun Protection Is Essential
Wear sunscreen, a hat, and sunglasses to stay comfortable during the open sea voyage.
Bring a Camera or Binoculars
Capture scenic views or spot wildlife like dolphins and seabirds with ease.
Stay Hydrated
Carry water and sip frequently to combat the sun and sea breeze.
Dress in Layers
Weather can change swiftly; bring layers for comfort.
Sunscreen
Important for sun protection during daytime hours.
summer
Hat and Sunglasses
Help shield your face and eyes from direct sunlight.
summer
Light Jacket or Layered Clothing
Prepare for changing weather conditions aboard.
spring;fall
Camera or Smartphone
Capture the scenic views and wildlife sightings.