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Already know how to sail? Rent a Catalina 22 sailboat for some day sailing. Create everlasting memories when you Sail Montauk. Your rental includes one tank of fuel, cooler stocked with ice & water, required safety equipment including life jackets (children under 12 must wear life jackets at all times) and VHF radio.

Rent a sailboat in Montauk

Previous sailing experience required. Knowledge of boating safety and operating an outboard engine a must.


First time Sail Montauk Bareboat charter skippers will be required to pass an on the water evaluation prior to their rental. They must demonstrate a man overboard drill or ability to pick up mooring under sail, and must be able to anchor and dock the boat without assistance. There is a one time, non refundable fee of $125 for the checkout sail.

Please note, if you schedule your checkout sail right before your rental, you will be responsible for the cost of both the checkout sail and your rental fee even if you do not pass your checkout sail.

View the Sailing Area and Sample Day Trips


Rental rates:

$390* per session                                         


Morning:   9:30am -12:30pm

Afternoon: 1:30pm - 4:30pm                                          

Evening: 5:00pm - 8:00pm


Please note: If you do not see availability on our booking calendar, reach out to us, we can likely find a time that works for you!

Book consecutive sessions for longer sail time.

Bareboat Packages

Book 5 sessions and get $50 off

Book 10 sessions and get $150 off

*Plus tax, additional credit card deposit will be required. 

For safety, there is a 2 occupant minimum and a

6 occupant maximum on all bareboat rentals.

Have some sailing experience but unsure if you're ready to bareboat? Try one (or more) of our Fleet Skipper Workshops!

Boat rental in Montauk
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