Day Charters 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!

Don't see an option that's right for you? Contact us to customize your perfect day on the water.

View more important details below


A few more details...

All charters are BYO food and beverage (except Breakfast on Board)

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

  • Sunscreen (NON-AEROSOL please)

  • Extra layer for wind

  • Barefeet OR 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

Please ​contact us with any questions! 

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

Gift certificates available!