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Day Sails out of Greenport, NY

Sail in style and comfort on Surprise!

Safe and comfortable 
Surprise is a stable, seaworthy vessel. Due to her hull design, she heels over (leans) less than most sailboats, so you don't need to worry about seasickness or spilled drinks. Suitable for all ages and abilities!

Perfect for all occasions
Families
Friends outings
Celebrations
Picnics
Proposals
Weddings
Photo shoots
A special "Surprise"

Private parking at the dock
We are the only charter yacht on the North Fork with private parking right at the dock!  Avoid the hassle of finding public parking or carrying heavy coolers to the boat.

Maximum 6 guests for all charters

All charters are private (your group only) and professionally crewed.

 

Choose from the options below and book your charter today!

View more important details below

Morning Sail

2-3 hours

Breakfast option available

Starting at $750

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Full Day Sail

 

9:30 am - 4:30 pm

Starting at $1,750

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Afternoon Sail

4 hours

Times vary

Starting at $1,150

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Afternoon & Sunset
Combo Sail

6 hours

Times vary

Starting at $1,900

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Sunset Sail

2 hours

Times vary

Starting at $750

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Custom Sail

 

Call to discuss availability

Pricing varies

A few more details...

All charters are BYO food and beverage (unless you choose optional breakfast)

Pick-ups are available from other ports upon request.

Prices do not include gratuity (customarily 20%)

We suggest you bring
  • Beverages, food and/or snacks of choice

  • Swimsuit

  • Non-aerosol sunscreen

  • Extra layer for wind

  • Non-marking shoes

  • $$ Cash tip for crew (customarily 20%)

What we provide
  • Ice

  • Bottled still & sparkling water

  • Plates, utensils, wine glasses, napkins

  • Serving-ware and bar-ware

  • Swim towels & blankets

  • Bluetooth speaker

Please ​contact us with any questions! 

Ask for suggestions of local caterers and restaurants on the North Fork.

Gift cards available!

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