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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
Friends outings
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!

Check out our weather cancellation policy

Scroll down for more important details

Morning Sail

2-3 hours

Breakfast option available

Starting at $750


Full Day Sail


9:30 am - 4:30 pm

Starting at $1,750


Afternoon Sail

3-4 hours

Times vary

Starting at $1,150

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Afternoon & Sunset
Combo Sail

6 hours

Times vary

Starting at $1,900


Sunset Sail

2 hours

Times vary

Starting at $750

genoa sunny.jpg

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

Weather Policy
Stormy Skies
Weather Cancellation Policy

Don't let the weather forecast scare you!

Check out our "no-risk" weather cancellation policy:

East End Charters withholds the right to cancel any charter due to unsafe weather conditions, including a high chance of thunderstorms, high winds (over 25kts), or steady rain.  We will make this decision at least 2 hours prior to your scheduled charter.  We do not cancel for cloudy weather. 

If your charter is cancelled by East End Charters, you may choose to reschedule or be refunded your deposit in full.

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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