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27ft Daysailer Boat Rental in Montauk27ft Daysailer Boat Rental in Montauk27ft Daysailer Boat Rental in Montauk27ft Daysailer Boat Rental in Montauk

27ft Daysailer Boat Rental in Montauk

Step aboard a private sailboat and sail with one of our US Coast Guard licensed captains. Sit back and relax with a cool beverage in hand, while exploring the waters of Montauk. Groove to your own soundtrack on our bluetooth speakers, or take the wheel and trim the sails for a hands on experience. Do as much or as little as you like! No experience necessary.  Offering 2-3 hour private charters in Montauk. 2 hour Taste of Sailing, 3 hour Sail & Swim, and 2 hour Sunset Sails. Up to 6 guests max. Our Performance Sailer is a Catalina 270 sailboat with wheel steering, inboard diesel engine, and self tailing winches. It comes fully equipped with: ​-All Coast Guard Required Safety Equipment -Cockpit Cushions  -Bluetooth stereo  -Cooler with Ice and Waters  -Cups & Bottle Opener -Pool Noodles -Electric Marine Toilet -Enclosed Cabin with Table & Seating -Swim Platform & Easy Board Ladder

Starting from

Base Cost
  • $400/hr
    2 hrs min
Captain Included
The base cost includes the Captain.


2 total bookings
6 guests

Check Availability



2 total bookings

Captain Darius learned to sail on the waters of Lake Montauk. He holds his US Coast Guard Masters Captains license, is Red Cross certified in CPR, AED and first aid and is an ASA instructor. He has taught adults and teens in Montauk, New York Harbor, Biscayne Bay and the Caribbean.

Features & Details


Approximate Location

You’ll get directions to the departure location when you make a booking.

The boat's approximate location on a map

Cancellation Policy

Full refund up to 7 days prior.

Additional Terms & Information

-Adult beverages are BYOB and are allowed on our Private Charters. We keep a cooler on board with complimentary water and ice, along with cups and a bottle opener. If you are enjoying wine on board, please make it white, as red wine can cause stains. -Children of all ages are welcome. Children under 12 must wear life jackets at all times, which we will provide. -Most people have all the necessary clothing in their wardrobe for sailing. A windbreaker or sweatshirt, t-shirt, and jeans or shorts are generally the most comfortable sailing gear. We recommend sailing barefoot, but if you prefer to wear shoes you should also have some type of non-marking boat shoe or a sneaker with light-soles which will not scuff the boat. -We reserve the right to determine if the weather will prevent sailing on any given day. Sailing is a water sport and it’s natural to get a little wet. A full refund or rescheduling will be made in the event of small craft warnings on inland waters, heavy rain or high winds. Cloudy conditions, light winds or rain showers will not result in a refund or a rescheduling. ​We do not accept cancellations based on forecasted weather. The charter is rescheduled based on marine weather forecast no earlier than 1 hour before scheduled departure. -Cancellations made 7+ days prior to a trip will be refunded 100%. Cancellations or changes made less than 7 days before a trip and no shows will not receive any refund. Cancellations are confirmed only when acknowledged by a managing member.  ​-We reserve the right to cancel a trip due to severe weather. Every attempt will be made to reschedule weather-canceled outings. Trips which we cancel due to weather which cannot be rescheduled will be refunded 100%. If unexpected heavy rain or winds cause us to terminate a sail early (within the first half of your time), a 50% refund OR your sail can be rescheduled for no fee. If we terminate a sail during the last half of your time, your sail may be rescheduled at half price.

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