Caribbean Sailing Vacations

Sail the beautiful waters of the Virgin Islands as we hop from island to island. Sailing, snorkeling, hiking by day, cocktails at sunset, and dinner under the stars. Your week will be full of exciting activities.  We will depart from Tortola and sail to a new island paradise each day, stopping along the way at secluded islands and attractions. In the evenings we will anchor or stay on a designated mooring. We'll grill aboard or dinghy ashore to grab local cuisine at some of the most famous establishments in the Caribbean. 

Call us at 631-522-5183 or email to discuss your vacation.

Sailing in the Caribbean November-April

Included in your trip:

  • Captain and Crew/Cook

  • Sailing yacht with luxury accommodations and private bathroom

  • Onboard family style meals with 7 breakfasts, 5 lunches, 3 dinners and snacks

  • Boat incidentals including fuel, water, bedding, towels, etc.

  • Mooring Fees

  • Jealous friends back home in the cold

Interested in learning while aboard?

Optional Classes during your vacation:

  • ASA 103 Basic Coastal Cruising

      Prerequisite ASA 101

  • ASA 104 Bareboat Cruising  Prerequisite ASA 101 & 103



Virgin Islands

Sail Montauk cruises through out the British Virgin Islands(BVI) and US Virgin Islands(USVI). All vacations start in Tortola BVI, with the option to end on St. John, USVI or back on Tortola. 

How it Works

1: Get a group of 4-6 adventurous friends. 

  • Make sure everyone's passports are up to date.

2. Pick a week that works for you.

  • We sail in the Caribbean November to April. 

  • Most vacations are from Saturday to Saturday, but can be tailored to your needs.

3: Next decide if you want a Monohull or a Catamaran sailboat. 

Sample Monohull

Sample Catamaran

4: Once your dates and sailboat are confirmed, book your flights to paradise.

  • ​Your sailing vacation starts in Road Town, Tortola.

  • You can fly into St. Thomas USVI and take a ferry over, or you can fly directly into Tortola via Beef Island.

5: Fill out Sail Montauk's questionnaire for food preferences, medical conditions, ect.

  • We dine family style. Sail Montauk will provision the boat with 7 breakfasts, 5 lunches, 3 dinners, and snacks.

  • Start making your epic music playlist. 

6: Don't miss your flight! 

  • It's winter, the last thing you want to do is miss out on a chance to make your friends jealous!

  • Meet your captain and crew poolside to get your sailing vacation started.

Contact Info


© 2011 by Sail Montauk

Open 7 days a week:

Monday-Sunday  8am-8pm

Sailing in Montauk May-September

Sail Montauk

Located at Gurney's Star Island (formerly the Montauk Yacht Club)

32 Star Island Road, Slip 412

Montauk, NY 11954


  • Instagram Social Icon
  • Facebook Social Icon
  • Google+ Social Icon
  • YouTube Social  Icon