PRIVATE SAILING CHARTERS

Sail with our Captain and experience what it's like to be crew on a sloop. Hoist the sails, trim the sheets, take the tiller, or just sit back and relax with a cool beverage in hand. Do as much or as little as you want, our sailing experiences are as hands on as you want them to be. No experience necessary. 



All boats are equipped with coolers stocked with complimentary ice and water. Feel free to bring snacks or BYOB. Connect to our Bluetooth speakers for a custom playlist.

All trips include:

  • A Licensed Captain

  • Cooler with Ice & Waters

  • Cups & Bottle Opener

  • Bluetooth Speaker

  • Pool Noodles & Waterguns

  • Feel free to BYOB or bring snacks to enjoy!

With 2 and 3 hour charters, swimming, family outings and sunset sails, we have something for everyone!

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TASTE OF SAILING

Step aboard your private sailboat and start your adventure. Your Taste of Sailing experience is an optional hands on activity. Your captain can show you how to steer the boat and trim the sails to harness the power of the wind. If you prefer to sit back and relax, your captain will sail the boat while you enjoy the beautiful scenery.

$220 base price (includes first 2 passengers)
$60 for each additional person
$40 for each child under 12 years old


Maximum 3 guests, 4 if there are children in your party

Captains will be wearing masks and we're requiring the same for participants.

See our full Covid-19 policy here.


11am - 1pm &  2pm - 4pm
Reservations required

 
SAIL & SWIM

Get a Taste of Sailing and some swim time, or pack a picnic and have lunch on board. Our sailing trips are hands on, so do as much or as little as you want. Midway through, we’ll tie off for a swim and some water games. 

Waterguns and pool noodles are kept on board, and we encourage cannonballs, so make a splash!

$290 base price (includes first 2 passengers)
$60 for each additional person
$40 for each child under 12 years old


Maximum 3 guests, 4 if there are children in your party

Captains will be wearing masks and we're requiring the same for participants.

See our full Covid-19 policy here.


10am - 1pm &  2pm - 5pm
Reservations required

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SUNSET SAIL

Enjoy a beautiful Montauk sunset on your own private sailboat. Like all of our sails, participate as much or as little as you want. Watch the sun setting over the water while sipping champagne with your sweetheart or loved ones.

 

The Sunset Sail is our most popular Montauk boat cruise, so be sure to book early!

$220 base price (includes first 2 passengers)
$60 for each additional person
$40 for each child under 12 years old


Maximum 3 guests, 4 if there are children in your party

Captains will be wearing masks and we're requiring the same for participants.

See our full Covid-19 policy here.


6pm - 8pm


Reservations required.

This is our most popular sail, book early!

 

Day 8

After breakfast we say our goodbyes. Ride the ferry to St. Thomas to catch your flights back home.  

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352 West Lake Drive, slip 80. Montauk, NY 11954 |  sailmontauk@gmail.com  |  Tel. 631-522-5183

© 2020 by Sail Montauk