PRIVATE SAILING CHARTERS

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 tiller and trim the sails for a hands on experience. Do as much or as little as you like! No experience necessary. 

All trips include:

  • A licensed captain

  • Cooler with ice & waters

  • Cups & bottle opener

  • Bluetooth speaker for a custom playlist

  • Pool noodles & water guns for epic water fights

  • Feel free to BYOB or bring snacks to enjoy!

Offering 2 and 3 hour charters. Swimming, family outings and sunset sails, we have something for everyone!

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TASTE OF SAILING

Your Taste of Sailing experience is a 2 hour private sailing trip with a US Coast Guard licensed captain. Sailing area includes: Montauk harbor, Lake Montauk, Block Island Sound and Fort Pond Bay. Your captain can show you how to steer the boat, or just sit back enjoy the beautiful scenery.

All trips include:

  • A licensed captain

  • Cooler with ice & waters

  • Cups & bottle opener

  • Bluetooth speaker for a custom playlist

  • Feel free to BYOB or bring snacks to enjoy!

 

$250 base price (includes first 2 passengers)
$60 for each additional person
$40 for each child under 12 years old


5 guests maximum per boat. Our Flotilla Boat Parties are perfect for larger groups.


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

 
SAIL & SWIM

Get a Taste of Sailing with some swim time. Pack a picnic or snacks to have  aboard. Sailing participation is optional, do as much or as little as you like. Pool noodles are kept on board, and we encourage cannonballs, so make a splash!

All trips include:

  • A licensed captain

  • Cooler with ice & waters

  • Cups & bottle opener

  • Bluetooth speaker for a custom playlist

  • Pool noodles & water guns for epic water fights

  • Feel free to BYOB or bring snacks to enjoy!

$320 base price (includes first 2 passengers)
$70 for each additional person
$50 for each child under 12 years old

5 guests maximum per boat. Our Flotilla Boat Parties are perfect for larger groups.


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

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SUNSET SAIL

Enjoy a beautiful Montauk sunset aboard a private sailboat. Sit back to relax and unwind, or take the tiller and trim the sails for a hands on experience.  

 

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

All trips include:

  • A licensed captain

  • Cooler with ice & waters

  • Cups & bottle opener

  • Bluetooth speaker for a custom playlist

  • Feel free to BYOB or bring snacks to enjoy!

$250 base price (includes first 2 passengers)
$60 for each additional person
$40 for each child under 12 years old

5 guests maximum per boat. Our Flotilla Boat Parties are perfect for larger groups.


6 pm - 8 pm


Reservations required.

 
FLOTILLA BOAT PARTY

For larger groups, book multiple boats and sail along side each other flotilla style. Raft up for picnic parties and swimming, shoot your friends with waterguns to gain bragging rights for the season. All of our sails are hands on, so do as much or as little as you like. Perfect for bachelor/bachelorette parties, corporate events, and family reunions.

All trips include:

  • A licensed captain

  • Cooler with ice & waters

  • Cups & bottle opener

  • Bluetooth speaker for a custom playlist

  • Pool noodles & water guns for epic water fights

  • Feel free to BYOB or bring snacks to enjoy!

$320 per boat base price (includes first 2 passengers)
$70 for each additional person
$50 for each child under 12 years old

5 guests maximum per boat. Our Flotilla Boat Parties are perfect for larger groups. 20 guests maximum.

18% gratuity for your captains will be added to your total for Flotilla Sails.


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

Contact us for groups larger that 20.

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