Captained Charters

Virgin Islands Sailing Academy

If you want to charter a sailboat with an experienced captain for 3-9 days in the Virgin Islands you may want to consider a captained charter. We offer 3-9 day captained charters on our 39 foot Pearson sloop sailboat, operating out of Red Hook, in the US Virgin Islands, during December- April. A captained charter is of interest to sailors or would be sailors who don't want to captain their own boat yet or who just want to see what sailing is all about. You can just sit back and let the captain sail the boat, or get involved at whatever level you want, including getting certified to ASA standards. Each charter includes a USCG licensed captain and ASA certified sailing instructor. Boat can accommodate up to five plus the captain.

Destinations in the Virgin Islands include Saint Thomas, Saint John, Jost van Dyke, Tortola, Anegada, Virgin Gorda, the Spanish Virgin Islands, and more.

You can work with your captain to design the trip of your dreams. Captained charters are of interest to families, newlyweds, small groups of friends, small corporate groups, and others. A captained charter combines a carefree time away from it all with sailing in an exotic location.

Rates are very competitive. Prices are as follows with or without ASA certification, including all on board food and beverages (other than alcohol). Pricing also includes all boat related fees and clearance fees.

$3499 for a three day cruise.

$4665 for a four day cruise.

$5832 for a five day cruise.

$6299 for a six day cruise.

$7349 for a seven day cruise.

$8399 for an eight day cruise.

$8999 for a nine day cruise.

Contact Captain Mike to discuss availability.

Contact us today to create the custom cruise of your dreams. In addition to visiting the US Virgin Islands, British Virgin Islands, visit many other places including St. Croix, or Vieques and Culebra in the Spanish Virgin Islands.
No hotels are required since you can stay on board the yacht all nights. Please contact to learn more and start planning your exciting trip today.
Captained Charters
Sopers Hole on West End, Tortolla, BVI
Cane Garden Bay, Tortolla, BVI
Sunset at Cane Garden Bay, Tortolla, BVI
Sailing in Pillsbury Sound between
    St. Thomas and St. John, USVI
Coral Heads at Loblolly Bay, Anegada, BVI
Captain Mike enjoying the pristine beach at Loblolly Bay, Anegada, BVI
Veterans Discount Program
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Virgin Islands Location, Classes, and Prices
Common Questions
Captained Charters
Our Teaching Vessel
Schedule and
How to Sign Up?
Captain In You Sailing Schools, Inc.