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 boat 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.

  • 9:30 am - noon

    850 US dollars
  • 1 pm - 5 pm

    1,000 US dollars
  • 6:30 pm - 8:30 pm *times will vary throughout the season

    700 US dollars
  • 9:30 am - 4:30 pm / Call to Book


Maximum 6 guests for all charters

Choose from the options below and book your charter today!

View more details below

A few more details...

Prices do not include gratuity (customarily 20%)

All charters are BYOB and food (except Breakfast on Board)

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 and bottled 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!