Cruise the Virgin Islands this Winter!

Spend a week living aboard a 40-50ft sailing yacht in the VI, enjoying sailing, sun, and sand. We are offering:

  • Instructional weeks offering ASA cruising and bareboat charter courses
  • Captained charters offering an incredible guided tour of the best of the islands
  • Flotilla charters providing support and guidance during your week afloat

No matter what option you select, this is an amazing vacation that will prepare you to return on your own again and again, while escaping from your daily grind and creating life-long memories.

The Boats

Our lead boats include a new Hunter 49, 2008 Hunter 41DS and a Beneteau 505. Both boats are well-equipped and provide everything you need for an enjoyable week on the water. Chartplotters, electronics, VHF, bimini, fans, stereo, and roller-furling headsails are standard.

"SunShine", a new Hunter 49, is a beautiful cruising vessel. She sports twin helms, electric winches, and full electronics. Three cabins and two heads provide plenty of living space. Air conditioning, generator, inverter, multiple fridge/freezers, microwave, TV/DVD, stereos, and more offer complete confort for your week at sea.

The Hunter 41DS offers two cabins, two heads along with a long list of optional gear. In addition to the Raymarine C90W chartplotter, "Island Girl" sports radar, autopilot, in-mast furling mainsail, inverter, generator, air conditioning, and three LCD TVs with DVD players! You simply won't find another charter boat so incredibly outfitted.

Beneteau 505 Layout The Beneteau 505 is complete with four private staterooms, each with its own head. This huge vessel provides a great platform for families with kids.

These yachts will be available for double or single occupancy per cabin. Additional yachts can be chartered, with a captain or on your own, depending on registrations. We will circle the entire island chain, and possibly visit Anegada, an island off-limits to most! Enjoy eating ashore every evening and likely visit some famous bars too (alcohol and dinner are not included in pricing).

Instructional Trips

Cruise the VI while you earn internationally recognized ASA Cruising or Bareboat Charter Sailing Certification. Each day offers world class sailing instruction in a premier sailing destination, with plenty of time for sight-seeing, beach-combing, snorkeling, hiking, and shopping. All ASA practical skills and written exams will be completed by week's end.

Our instructional vacations are for adults only, but if you can muster up your own crew of four to six, you can fill the boat with whomever you want and have your own private charter! This is a fantastic way to get your family and friends involved in sailing and adventuring.

Captained Charters and Flotilla Vacations

Spend a fabulous vacation cruising the VI under the watchful eye of former VI resident, Captain, and instructor Brenton Lochridge. With our 50ft Beneteau as lead vessel, and additonal boats as needed, we'll enjoy everything the Islands have to offer and bring our own party wherever we go. Brenton's extensive experience and local knowledge of these gorgeous islands will provide you with unique adventures both afloat and ashore. Learn how to plan your trip, where to provision, how to find the best parties, sites that cannot be missed, local secrets, and more. By the end of the week, you will not only have had a memorable vacation, you'll also be well-prepared to do it on your own next trip!


Instructional and Captained Charters from $2150/week

Flotilla Weeks from $1995/week

Minimum of four participants required each week. We'll help you match-up.

Rates include charter boat for 7 days/7 nights, breakfast and lunch provisions, boat fuel, and cruising taxes. Airfare, island airport transportation, alcohol, dinners, and VI departure tax are not included. Instructional Trips include one ASA course fee, book, and certification per person; additional ASA courses for $350/person or ask about ASA 101 (Basic Keelboat) pricing. Flotilla Weeks include flotilla fee, on-water support, daily briefings, and special events. Captained Charters include captain fee, and daily briefings.

Choosing a Week

Courses/Charters can be created during any winter week (November 1 - April 20) depending on boat and instructor availability. You would be required to muster a crew of at least four student/guests, OR join up with other participants looking for the same weeks. There is a lot of interest in these trips, and we can usually pair people up who have similar scheduling needs. Note: There are a limited number of weeks and a limited number of cabins, so space will fill quickly!

Flotilla Weeks:
Dates TBD
Create your own!

Instructional Trips:
Dates TBD
Create your own!

Captained Charters:
1/15 - 1/22 on SunShine BOOKED!
2/25 - 3/3 on SunShine BOOKED!
Create your own!

Travel Rates

There are many options and deals out there if you look hard enough. We generally fly Jet Blue from Boston to San Juan and then Cape Air to Beef Island, Tortola, although American Airlines and American Eagle service this same route.

Flying into St. Thomas, USVI is another good option, and many airlines offer fantastic pricing into this larger airport. There are inter-island ferries from Red Hook, St. Thomas to Road Town, Tortola. Once on Tortola, the boat is a short cab ride away.

Travel rates usually range between $400-$800, although deals are frequently available. Or use your frequent flyer miles! We would be happy to discuss all travel options. We can purchase bulk tickets to save you approximately $60+ roundtrip on Cape Air between San Juan, PR and Beef Island, Tortola if you choose that route.

Payment Schedule

- A $500.00 non-refundable deposit per person is required to hold the boat, with full payment due eight weeks prior to trip (or immediately if trip scheduled within eight weeks).
- We will accept full payment only after a minimum of four students have confirmed. DO NOT book flights or send us full payment until trip is officially confirmed! It is best for everyone to coordinate flights and arrival times with Brenton!

If you are interested in more details or want to confirm interest, please contact Brenton at 617-639-3061 or brenton@blackrocksailingschool.com.