615-974-0100 | 5751 Old Hickory Blvd, Suite 207, Hermitage, TN 37076 | Directions

2025 SailNashville Flotilla in the British Virgin Islands

SailNashville is scheduling a flotilla for the British Virgin Islands for late February 2025 and we'd like you to come sail with us.

Our SailNashville students will be given the first option to sign up before we open it up to the entire sailing community.


Flotilla Informational Meeting

Wednesday, July 10, 7:00-8:00pm

SailNashville Teaching Center

5751 Old Hickory Blvd, Suite 207

Park in the rear of the building


Why Join a Flotilla?

Flotillas are a great way to introduce sailors and non-sailors to chartering. Even if you’ve earned your ASA certifications, you may still have some hesitations to head out on your own.  

A flotilla allows you to gain the experience and confidence you need, with the assistance of an experienced guide at a more affordable price. 

There will be a lead boat, plus an experienced guide on each boat to show you the best places to go.  If you have your ASA 101, we’ll even let you take the wheel!


The Details

  • Tentative Dates: February 22-March 2
  • Eight Days/Seven Nights
  • Departing Nanny Cay, Tortola, BVI
  • Three monohull sailboats, 41-49 feet
  • Three double berth cabins per boat

$2500 per person/$5000 per cabin*

*Pricing is based upon three full double cabins per boat. The cost and/or number of boats may be adjusted based upon response.

You are responsible for your airfare, transportation to the charter marina, provisioning, and any incidentals

Deposit**: 50% per person/$1,250 to reserve your place

Balance Due: Oct. 1, 2024

** Deposits are non-refundable once the boat is reserved.

We encourage you to purchase international travel insurance and can make it available to you through the charter company..


The British Virgin Islands

The British Virgin Islands offer some of the very best sailing in the world.

Our flotilla gives you an unforgettable sailing experience in crystal clear waters, with warm breezes, and plenty of exciting destinations. It will be a welcome change to the cold, dreary Nashville weather in February. And you will make new friends and memories to last a lifetime.

The four large islands of the BVIs are surrounded by over 50 smaller islands and cays. Beautiful anchorages are found everywhere. And whether you want to explore the history of the islands themselves, lie on a pristine white beach, snorkel, enjoy your favorite drink or a dinner at an open-air bar, or shop, the BVIs has it all.otillas are a great way to introduce sailors and non-sailors to chartering. Even if you’ve earned your ASA certifications, you may still have some hesitations to head out on your own.  


Tentative Itinerary
*Please note the itineraries are subject to change due to weather conditions or other
circumstances beyond our control

Our flotilla gives you an unforgettable sailing experience in crystal clear waters, with warm breezes, and plenty of exciting destinations. It will be a welcome change to the cold, dreary Nashville weather in February. And you will make new friends and memories to last a lifetime.

The four large islands of the BVIs are surrounded by over 50 smaller islands and cays. Beautiful anchorages are found everywhere. And whether you want to explore the history of the islands themselves, lie on a pristine white beach, snorkel, enjoy your favorite drink or a dinner at an open-air bar, or shop, the BVIs has it all.otillas are a great way to introduce sailors and non-sailors to chartering. Even if you’ve earned your ASA certifications, you may still have some hesitations to head out on your own.  


Day 1

After our checkout at Nanny Cay, we’ll sail across the Sir Francis Drake Channel to Norman Island, rumored to be the inspiration for Robert Louis Stevenson’s “Treasure Island.”

After dinner at Pirate’s Bight, we can continue the festivities at the infamous Willy T floating bar.

Day 2

After breakfast, those who want to snorkel can head for The Caves.

A short sail will take us up to Cooper Island where there are more snorkeling opportunities off Cistern Point.  

Later, we will head for the Cooper Island Beach Club for dinner and cocktails.

Day 3

We’ll sail to the Baths on Virgin Gorda for snorkeling and exploring one of the BVIs most spectacular and popular destinations.   Lunch is available at the Top of the Baths Restaurant and Bar.

We can then head to Spanish Town or over to Trellis Bay or Marina Cay for our overnight stay and dinner.

Day 4

In the morning we’ll head off to Leverick Bay. There we’ll find a marina, restaurants, and shops.

From here there are several options for sites to visit by taxi. We also have options to stay overnight in Leverick Bay or sail over to Saba Rock Resort or the Bitter End Yacht Club.

Day 5

Depending on our choices on Day 4, we’ll spend time around North Sound and spend the night in the area.  Lots of options.

Day 6

We’ll leave the North Sound and sail along the unspoiled North shore of Tortola heading for Jost Van Dyke. We’ll anchor in Great Harbor and plan on spending time at world famous Foxy’s, a must-see destination.  

Again, there are a lot of options for things to do here.

Day 7

After breakfast, we'll head back to Nanny Cay on Tortola to get ready for our check-in at the marina mid-day.


And you can earn your ASA 103 and ASA 104

We’re also offering the option for you to earn your ASA 103 and ASA 104 during the flotilla.

The classroom portion of the courses and the exam will be taught in Nashville at the SailNashville Teaching Center in early February. 

The practical skills portion of the course will be taught during the flotilla sail.


Capt. John Summers

Your instructor and lead flotilla captain

John is the owner of SailNashville, an ASA Sailing School in Nashville, sailing on Percy Priest Lake.

John has been sailing for over 40 years 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 1108, RPBA 1100, and AHA First Aid/CPR/AED.

A graduate of Vanderbilt University, John holds MS and JD degrees.

John will be assisted by his wife Catherine Hayden, who is a Family Nurse Practitioner with Ascension St. Thomas and his daughter Hayden, who is also an ASA certified instructor. Hayden is a senior at Rhodes College and has been sailing since she was five.

Catherin will hold a class on provisioning and cooking for the flotilla participants.