A Private Sailing Adventure in the BVI with Friends
Part of: Adventure Experiences • Caribbean • Sailing Adventures
The British Virgin Islands(BVI) have long been considered one of the world’s premier sailing destinations. Protected waters, steady trade winds, and short distances between islands make the BVI a paradise for sailors and charter guests alike.
For decades yachtsmen from around the world have flocked to these islands, and in recent years catamaran sailing yachts and motor yachts have become especially popular for charter vacations.
Several charter companies operate throughout the islands, including Voyage Charters, which rents fully equipped sailing catamarans to experienced sailors for bareboat charters.
Bareboating simply means chartering a yacht without a hired captain, allowing qualified sailors to captain the vessel themselves.
Our group would soon discover why the BVI is one of the most beloved cruising grounds anywhere.
📚 Planning the Trip
Anyone considering sailing in the BVI should pick up the excellent guide:
“The Cruising Guide to the Virgin Islands” by Simon Scott
This guide contains:
- detailed island charts
- anchorage information
- local regulations
- history of the islands
- snorkeling and dive locations
- restaurant and marina information
It’s essentially the sailor’s bible for the Virgin Islands and proved incredibly helpful for planning our adventure.
👫 A Wonderful Invitation
Fortune smiled on us when a friend invited Bob and me to join him, his partner, and two other couples for a week-long sailing trip through the BVI.
Our friend had been sailing the islands for nearly a decade and regularly chartered a 48-foot sailing catamaran from Voyage Charters. Since he was qualified to captain the vessel himself, we would be enjoying a true bareboat sailing experience.
The cost of the charter was shared among the four couples, making the trip surprisingly affordable for such a unique adventure.
Without hesitation, we enthusiastically accepted the invitation.
Most of our Caribbean travel had previously been on cruise ships, which only stop for a few hours at each island. Sailing between the islands at our own pace, guided by an experienced captain who knew all the best coves, sounded like the perfect way to truly experience the region.
And it absolutely was.
🧳 Preparations
Thanks to the experience of our captain, Capt. Robbie, preparations were straightforward.
He recommended we fly to Atlanta the night before departure to avoid travel delays and then fly together the next morning to Charlotte Amalie.
Two weeks before departure he also sent out a provisioning spreadsheet listing all the food and beverages normally stocked on the boat. We were invited to add anything we wanted.
The charter company handled everything.
For a small fee they fully provisioned the yacht with:
- meals and snacks
- beverages and mixers
- beer and wine
- spirits
- breakfast and lunch supplies
We were also provided a 30-page preparation guide explaining what to pack, what to expect, and how life aboard the boat would work.
Capt. Robbie and his partner Sandra even hosted a pre-trip gathering at their home so the couples could meet beforehand — a great idea considering we would soon be living together on a yacht for a week.
🛂 Arrival in the Islands
Finally it was time to head south.
After arriving in St. Thomas around mid-afternoon, we met a pre-arranged driver who took us to a private water taxi service.
The water taxi carried us across the channel to Soper’s Hole on the island of Tortola, where Voyage Charters is located.
Tip for travelers:
Public ferries run between St. Thomas and the BVI, but private water taxis are far more convenient. They guide you through customs and immigration and make the process quick and stress-free.
After clearing customs we boarded our home for the week.
⛵ Electrify — Our Floating Home
Our yacht for the week was a 48-foot sailing catamaran named Electrify.
This particular boat was unique because it had:
- onboard water desalination
- a self-propelled generator
- large battery storage
This meant we never had to worry about fresh water or electrical power during the trip.
The catamaran featured:
- two king cabins
- two queen cabins
- private bathrooms and showers
- a spacious salon and galley
- outdoor dining areas
- a shaded cockpit deck
- trampoline lounging nets at the bow
While the cabins were cozy, the shared living spaces were comfortable and perfect for socializing.
The shaded aft deck quickly became our favorite gathering place.
⛵ Setting Sail
We spent our first evening docked in Soper’s Hole enjoying dinner and drinks at the famous Pusser’s Restaurant before returning to the boat to relax.
The next morning the charter company staff conducted a safety briefing and systems check before guiding the boat out of the marina.
Then they waved goodbye.
From that moment on, we were sailing on our own.
Capt. Robbie took the helm and we set sail toward our first destination: Saba Rock.
🌴 Saba Rock and Beef Island
Our first stop was the beautiful anchorage near Saba Rock and Beef Island.
We planned to stay here for two nights.
The area offered:
- beautiful protected waters
- excellent snorkeling
- great restaurants
- quiet beaches
Lunch at Saba Rock Resort was outstanding, and the small island resort had been rebuilt after hurricane damage using massive beams designed to withstand future storms.
Back on the boat we relaxed, played cards, watched yachts arrive, and enjoyed spectacular sunsets.
🦞 Anegada — Lobster and Flamingos
Our next stop was the island of Anegada, located about eleven miles north of the main island chain.
Unlike the mountainous volcanic islands of the BVI, Anegada is a low coral island with a highest elevation of only about 28 feet.
It is famous for two things:
- huge populations of flamingos
- legendary Caribbean lobster dinners
A local taxi truck took us across the island to a beachside restaurant where we enjoyed lunch, walked along the sand, and relaxed by the ocean.
That evening we returned for the famous Anegada lobster dinner, cooked over an open fire.
It was delicious and easily one of the highlights of the trip. Later that night, we were treated to a marine ocean viewing as our boat lights attracted scores of many different types of fish to our stern.
🌊 Rough Seas to Jost Van Dyke
The next leg of the journey took us through rough weather.
With winds reaching 30 knots, Capt. Robbie ordered the sails reefed and used the engines to help stabilize the boat as we headed toward Jost Van Dyke.
Large catamarans handle rough water surprisingly well, and we safely reached the island despite the challenging conditions.
This experience reminded us that bareboating requires a skilled and experienced captain.
🍹 Jost Van Dyke and Foxy’s
Once anchored, we headed ashore for lunch and drinks at one of the island’s lively beach bars.
Life felt wonderfully simple:
sunshine, music, ocean views, and good friends.
The following day we visited the famous Foxy’s Bar, one of the Caribbean’s most iconic beach bars.
After lunch we met a taxi driver selling T-shirts from the back of her truck after her shop had been destroyed by a hurricane. Our group happily bought several shirts and hats while leaving her a generous tip.
🌅 Sailing Home
After several unforgettable days exploring the islands, it was time to sail back to Soper’s Hole.
The return sail was calm and relaxing, giving us time to reflect on an incredible week of sailing, island hopping, and shared adventures.
The next morning the water taxi returned us to St. Thomas and from there we began our journey home — carrying with us memories of one of the most unique vacations we’ve ever experienced.
✨ Final Thoughts
Bareboating through the British Virgin Islands offers a style of travel unlike anything else.
There are no rigid schedules, no crowded cruise ports, and no rush. Instead you explore beautiful islands at your own pace, dropping anchor in quiet coves and discovering beaches, restaurants, and local culture along the way.
For those comfortable on the water — especially with an experienced captain — it can be one of the most rewarding travel adventures imaginable.
Note: You’ll find a lot of information about cruising in the BVI available. The main source we relied on is called: “The Cruising Guide to the British Virgin Islands” by Simon Scott.
