Spend eight days and seven nights exploring turquoise waters, sunny skies, and stunning destinations. We will set sail from Nanny Cay, Tortola, and circle the island with stops at Norman Island, Cooper Island, Virgin Gorda, and Jost Van Dyke. Each day offers the chance to learn new sailing skills, meet new friends, and enjoy fresh adventures. Relax on pristine beaches, snorkel in crystal-clear coves, and share stories over dinner on deck. With spectacular scenery, perfect sailing conditions, and a warm, welcoming crew, this trip promises memories that will last a lifetime. Sailing truly does not get any better than this.
John is the owner of SailNashville, an ASA Sailing School in Nashville, sailing on Percy Priest Lake. John has over 40 years sailing experience and has chartered numerous times in the Caribbean, primarily the BVIs. He holds a USCG Captain’s license and is certified to teach ASA 101, ASA 103, ASA 104, ASA 110, ASA 118, Ab 101, and American Heart Association First Aid/CPR/AED.
A graduate of Vanderbilt University, John holds MS and JD degrees.
John will be assisted by his daughter Hayden, who is also an ASA certified Instructor. Hayden is a 2025 graduate of Rhodes College, Hayden has been sailing since she was five.
Please Note. This itinerary is meant to serve as an example of what a week-long sailing journey on a flotilla might cover. However, it is important to note that the captains may adjust the schedule to ensure optimal sailing conditions and the best possible experience for guests.
*Pricing is based upon three full double cabins per monohull boat.
**Pricing is based upon three full double cabins per catamaran.
***There are a limited number of single berths available on each boat. These are very “spartan” crew cabins, most of which require you to enter from the deck. These will be offered at approximately 75% the per-person rate. Email us for more details.
The cost and/or number of boats may be adjusted based upon response and availability of sailboats.
You are responsible for your airfare, transportation to the charter marina, provisioning, and any incidentals.
Deposit Due: Now*
Balance Due: 90 days before flotilla date
* Deposits are refundable minus $100 processing fee until boats are reserved. Deposits are non-refundable once the boat is reserved. We will reserve boats as they fill.
We encourage you to purchase international travel insurance and can make it available to you through the charter company.