Sail Charters on Surprise, 

our flagship yacht


Surprise is a classic, wooden yacht built in 1967 that offers some of the finest charters in Eastern Long Island.

She is a perfect platform for small parties, family and friend outings, engagements, weddings, photo shoots, or even a special "Surprise"!

Sailing daily from Greenport (other ports upon request)

Maximum Guests:

Day charters - up to 6

Overnight charters - up to 4

BYOB for all charters. 

Some charters include breakfast and/or lunch (see descriptions below).

Prices listed do not include crew gratuity (customarily 20%).

Read more about Surprise's history and amenities 

and what to bring on your charter.


Please contact us with any questions!

  • 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

  • 6:30 pm - 11:30 am (*time varies according to season) Call to Book

    Starting at $2050
  • 2-3 days / Call to Book

    Starting at $5050
  • Call to Book

    Contact us for quote

You can also contact us directly to make a booking,

or to arrange a departure from other ports.


Gift certificates available!

Looking for a different vessel?  Check out our Partner Fleet.