About a year and a half ago, RVing introduced us to a new friend who, like us, lives full-time on the road. He had previously lived on a sailboat, and after months of talking about it we finally arranged a sailing trip together to test whether sailing might become our next adventure.
In June 2017, we spent ten days on a sailing charter in the British Virgin Islands with our RV friend and two other couples.
This turned out to be one of the best trips I’ve ever taken. Even though we were sailing and vacationing for most of the month, I still earned well, which you can read more about in my income report from that month.
We’d visited the Virgin Islands before, but never the British Virgin Islands, and this was our first time on a sailboat—actually my first time on a sailboat at all.
Here are the highlights of our itinerary (photos are at the end of the article):
- Road Town, Tortola – The starting and finishing point of our charter.
- Virgin Gorda – We explored The Baths, which lived up to the hype, and anchored in Savannah Bay for two nights. We also visited the North Sound, moored at Bitter End Yacht Club, and stopped by Saba Rock.
- Anegada – A favorite stop for everyone on the charter. Anegada is famous for its secluded beaches like Loblolly Beach, incredible snorkeling (we saw a stingray), and even flamingos. We stayed two nights and enjoyed our longest sail with a dolphin escort.
- Sandy Spit – A tiny island surrounded by stunning blue water. We anchored overnight, visited Foxy’s for drinks, and hiked to the Bubbly Pool.
- Norman Island – We moored so we could visit Willy T’s, the famous floating party bar where you can jump from the top deck into the sea.
- The Indians – Some of the best snorkeling of the trip: abundant fish, a large barracuda, and a puffer fish.
- Beef Island – We tried to visit Cooper Island but couldn’t find moorings, so we anchored at Beef Island for the night.
- Cooper Island – We woke early to return to Cooper Island and spent our final charter day there. Even in the slow season the moorings filled quickly, so arrive early. We saw a sea turtle and dolphins while visiting.
Our boat was a Sunsail 51, a four-cabin monohull (a Jeanneau around 50 feet). Some might think that’s tight for seven adults, but the layout worked well—each person had a private cabin, and the boat handled our needs: sufficient water for the ten days, diesel to run the AC at night, and plenty of storage for food.
Getting to the charter
Most travelers fly into St. Thomas (STT) because it’s the largest and usually the most convenient airport, then take a ferry to Tortola where Sunsail and other charter companies operate.
We flew from Portland (where we’d left the RV) to Dallas, then to Miami, and finally to St. Thomas. From the airport it was a five-minute taxi to Charlotte Amalie ferry dock (about $10 for two), then the Road Town Fast Ferry to West End, Tortola—about a 45-minute ride and roughly $100 for the two of us. After clearing customs into the British Virgin Islands, our Airbnb host picked us up because the driveway was too narrow and steep for most taxis.
We stayed at an Airbnb with incredible views for a few nights while waiting for some friends, then checked in with Sunsail to begin our bareboat charter.
Who crewed the boat?
Our RV friend, who had lived on a sailboat, captained the trip, allowing us to bareboat charter and sail independently. Wes helped with sailing duties—he’d taken an eight-day sailing course and had prior experience sailing with family. The rest of us trusted them and enjoyed the ride.
If you want the bareboat experience but don’t know anyone qualified, charter companies like Sunsail can provide a professional captain for an extra fee.
Food and provisioning
On the day we picked up the boat we spent a few hours provisioning at local stores—Rite Way in Road Town and OneMart Superstore. Rite Way felt the most like a familiar U.S. grocery store.
For seven people over ten days we spent $3,808.40 on groceries, restaurants, drinks, and extras. We could have spent far less, but we indulged in experiences like dining at Saba Rock and two lobster dinners in Anegada. We also overprovisioned and ended up gifting much of the excess food and alcohol to another group.
Some of our best meals were cooked aboard—kudos to our onboard chefs. And yes, food seems to taste better at sea, just like I find that everything tastes better in an RV.
Seasickness
I tend to have a sensitive stomach and often get carsick when someone else drives, but to my surprise I didn’t experience seasickness during our ten days. Several people on the charter did get seasick, though. If you’re prone to motion sickness, common remedies include Dramamine or Bonine, wristbands, prescription patches, or a combination of measures.
What I loved about the trip
I loved nearly everything. I could have spent all ten days simply living on the boat, but the BVI islands are worth exploring:
- Freedom to set our own schedule—choose destinations and activities each day.
- The chance to explore multiple islands without feeling rushed.
- Moments of solitude—though the BVIs are popular for charters, we found peaceful nights with almost no one around.
- Breathtaking scenery—spectacular sunsets, excellent snorkeling, and rewarding hikes.
I highly recommend a British Virgin Islands sailing charter for anyone curious about island hopping by sailboat.
Practical sailing charter tips
Here are some practical tips for a successful BVI charter experience:
- Expect to pay customs fees entering and leaving the BVI. When arriving by ferry, we paid about $20 per person each way, though fees can vary.
- Bring a passport—it’s required for entry into the British Virgin Islands.
- Allow plenty of time when returning to St. Thomas to catch flights. Minimum check-in times can be strictly enforced; when we were there, the requirement was 180 minutes before departure and some services still needed 90 minutes.
- Use soft-sided luggage (duffel or soft backpack). Sailboat storage is limited and flexible luggage fits into cabins more easily.
- For internet, I used my phone as a hotspot with AT&T’s International Day Pass ($10 per 24-hour period), which allowed me to maintain work while only paying for days I used service.
- Bring clothespins for drying clothes on the lifelines.
- Taste bottled water before buying large quantities—we once purchased a big supply that tasted terrible and jokingly called it “pizza water.”
- Complete a thorough checkout before leaving the marina to ensure all safety items and comforts are present and in working order.
- Mark your dinghy with something distinctive—a bandana or handkerchief—since many dinghies look identical and it’s easy to hop into the wrong one.
- Skip heavy styling tools and makeup; bring practical clothing and plenty of underwear.
Above all, be courteous to other sailors and enjoy your time on the water.
Writing this recap brought back so many great memories—this was truly one of my favorite trips.
Are you considering a sailing charter in the British Virgin Islands or elsewhere? Why or why not?
Below are photos from our charter, some taken by friends who joined us on the trip.
