The Journey of a Lifetime
How to charter your own sailboat around the British Virgin Islands and beyond
LIFE IS SHORT...LIVE YOUR DREAM.
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SailNashville owner John Summers has over 40 years experience sailing. John is a USCG licensed captain.
He has sailed in the Bahamas, the British and U.S. Virgin Islands, the Windward Islands, the Chesapeake Bay, San Francisco Bay, the Florida Panhandle, the Florida Keys, San Diego Bay area, but mostly on Percy Priest Lake here in Nashville.
SailNashville is the only American Sailing Association affiliated sailing school in Tennessee. Since its inception in 2019, over 750 sailors have learned to sail and earned their certifications from SailNashville.
SailNashville has one of the most modern and comfortable classrooms in the US. The on-the-water portion of the class sails out of Hamilton Creek Marina on Percy Priest Lake.
SailNashville offer the best sailing instruction in Tennessee. Learn to sail in just 3 days.
Life Is Short...Live Your Dream.
SailNashville Flotillas
in the British Virgin Islands
2025-2026 BVI Flotilla Schedule
December 6 - 13th
One Catamaran - FULL
Let us know ASAP if you are interested in this December flotilla. We have one additional couple interested, but we need two more couples for a second boat.
Tortola/Virgin Gorda/Jost Van Dyke
Day 1 Nanny Cay to Norman Island
Day 2 Norman Island to Cooper Island
Day 3 Cooper Island to The Baths to Marina Cay
Day 4 Marina Cay to Leverick Bay
Day 5 Leverick Bay to Bitter End Yacht Club
Day 6 BEYC to Cane Garden Bay
Day 7 Cane Garden Bay to Jost Van Dyke
Day 8 Jost Van Dyke to Nanny Cay
January 31 - February 7th
January 31 - February 7th
2 double berths available- monohull
January 31 - February 7th
1 single berth available
January 31 - February 7th
4 berths available - catamarans
January 31 - February 7th
1 single berth available - catamarans
January 31 - February 7th
January 31 - February 7th
Tortola/US Virgin Islands/Spanish Virgin Islands
January 31 - February 7th
Day 1 Nanny Cay to Copper Island
Day 2 Copper Island to Marina Cay
Day 3 Marina Cay to Leverick Bay
Day 4 Leverick Bay to Anegada
Day 5 Anegada
Day 6 Anegada to Cane Garden Bay
Day 7 Cane Garden Bay to Jost Van Dyke
Day 8 Jost Van Dyke to Nanny Cay
March 7 - 14th
3 double berths available- monohull
1 single berth available
5 berths available - catamarans
0 single berth available - catamarans
Tortola/Virgin Gorda/Jost Van Dyke
Day 1 Nanny Cay to Norman Island
Day 2 Norman Island to Cooper Island
Day 3 Cooper Island to The Baths to Marina Cay
Day 4 Marina Cay to Leverick Bay
Day 5 Leverick Bay to Bitter End Yacht Club
Day 6 BEYC to Cane Garden Bay
Day 7 Cane Garden Bay to Jost Van Dyke
Day 8 Jost Van Dyke to Nanny Cay
April 4 - 11th
3 double berths available- monohull
1 single berth available
5 berths available - catamarans
2 single berth available - catamarans
Tortola/Virgin Gorda/Anegada/Jost Van Dyke
Day 1 Nanny Cay to Cooper Island
Day 2 Cooper Island to Marina Cay
Day 3 Marina Cay to Leverick Bay
Day 4 Leverick Bay to Anegada
Day 5 Anegada
Day 6 Anegada to Cane Garden Bay
Day 7 Cane Garden Bay to Jost Van Dyke
Day 8 Jost Van Dyke to Nanny Cay
May 2 - 9th
3 double berths available- monohull
1 single berth available
5 berths available - catamarans
2 single berth available - catamarans
Tortola/Virgin Gorda/Jost Van Dyke
Day 1 Nanny Cay to Norman Island
Day 2 Norman Island to Cooper Island
Day 3 Cooper Island to The Baths at Marina Cay
Day 4 Marina Cay to Leverick Bay
Day 5 Leverick Bay to BEYC
Day 6 BEYC to Cane Garden Bay
Day 7 Cane Garden Bay to Jost Van Dyke
Day 8 Jost Van Dyke to Nanny Cay
A Week of Sailing Fun
From Tortola to Virgin Gorda to Jost Van Dyke
Tentative Itinerary*
Our exact itinerary will vary month-to-month. But all three major islands, Tortola, Virgin Gorda and Jost Van Dyke will be visited during each flotilla.
*Please note that itineraries are subject to change due to weather conditions or other circumstances beyond our control.
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!
You can also earn your ASA 103, ASA 104 and ASA 114 on the trip.
The Basics
Monohulls
$2,495 per person/$4,990 per cabin*
Single berth monohull - $1895
Catamarans
$2,895 per person/$5,790 per cabin*
Single berth catamaran - $2175
*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.
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.
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.
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 weather in Nashville. 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.
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 for that special gift, the BVIs has it all.
Click Here to watch an informational video for the 2025 SailNashville Flotilla using passcode: bq#axsS0
Day 1 - Nanny Cay Marina, Tortola
We’ll meet Saturday morning at the Hotel on Nanny Cay to review our plans and preparations to get on our sailboats.
Our first sail will be a short 5.8 miles across the Sir Francis Drake Channel from Nanny Cay to the Bight on the western side of Norman Island.
Dinner at Pirate’s Bight. Then over to Willy T’s, a popular floating bar.
On the following Saturday, we'll sail back to Nanny Cay Marina, fuel and clean the sailboats, and disembark.
Anchorage Options
Days 2-8
Cooper Island
Trellis Bay
Scrub Island
Marina Cay
After breakfast in the morning, we’ll head northeast up the Sir Francia Drake Channel towards Virgin Gorda.
Here we have plenty of options as to where we want to go.
We can head east to Cooper Island or northeast to Trellis Bay on east side of Tortola or to the resort on Scrub Island.
The Baths
Virgin Gorda
The Baths are THE must-see destination in the BVIs.
The Baths have been designated a National Park.
They offer a maze of large granite boulders to explore. There are beaches in between several of the formations.
The Top of the Baths offers a beautiful panoramic vista to view the entire channel towards Tortola, plus lunch and/or drinks.
A quick taxi to Spanish Town offers additional lunch options.
Leverick Bay
Virgin Gorda
Leverick Bay on the north side of Virgin Gorda is one of our favorite destinations in the BVIs.
Leverick Bay Resort and Marina has everything you want or need, but not too much. It offers two restaurants, a pool, showers, laundry, grocery, a
Pusser's Company Store, an Arawak Shop, and much more.
We will definitely spend one night here.
Bitter End Yacht Club
Virgin Gorda
Across the North Sound is the Bitter End Yacht Club.
For over fifty years, the Bitter End Yacht Club has been a favorite destination for sailors. But in 2017, Hurricane Irma changed all of that making a direct hit on the islands.
The entire resort was destroyed.Four years later the new and expanded Bitter End Yacht Club reopened for business in 2021.
It's now a truly upscale destination, still geared to sailors.
Anegada
Anegada lies approximately 12 nautical miles north of Virgin Gorda.
Unlike the mountainous volcanic islands comprising the BVIs, Anegada is a low-lying island surrounded by large coral reefs.
Much less developed than the other major islands, Anegada offers great fishing and diving, plus beautiful white beaches.
Anegada is also known for its lobsters.
A trip to Anegada deserves a two-day stay.
Cane Garder Bay
Tortola
Cane Garden Bay is considered by many as the most beautiful anchorage in the BVIs.
Its picture-perfect white sand beaches lined with palm trees is a perfect backdrop for photographers.
There is a wide selection of bars and restaurants from which to choose.
Cane Garder Bay
Jost Van Dyke
A must see destination on any BVI trip is world famous Foxy’s.
Foxy has developed a series of bars, restaurants and gift shops that attracts visitors from around the world.
A side trip by taxi over to White Bay to visit the equally famous Soggy Dollar Bar is another must-do stop.
We'll spend the night at anchor at Great Harbor.
Day 8
Jost Van Dyke
Nanny Cay
A must see destination on any BVI trip is world famous Foxy’s.
Foxy has developed a series of bars, restaurants and gift shops that attracts visitors from around the world.
A side trip by taxi over to White Bay to visit the equally famous Soggy Dollar Bar is another must-do stop.
We'll spend the night at anchor at Great Harbor.
Click Here to watch an informational video for the 2025 SailNashville Flotilla using passcode: bq#axsS0
You can also earn your ASA 103, ASA 104 and ASA 114 Certifications on our flotillas.
We’re also offering the option for you to earn your ASA 103, ASA 104, and/or ASA 114 during the flotilla.
The classroom portion of the courses and the exam will be taught on Zoom prior to the flotilla. Exams can be given in Nashville or on Friday evening before we depart on Saturday.
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 over 40 years experience sailing 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, RPBA 1100, 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.
John's wife Catherine will hold a class on provisioning and cooking for the flotilla participants.
Click Here to watch an informational video for the 2025 SailNashville Flotilla using
passcode: bq#axsS0
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