When the squall hit our 43-footer, we were 100 yards shy of picking up a mooring in The Bight at Norman Island. A wall of 30-knot wind hit us and the air became dense with rain. On the bow, Sebastian shielded his eyes from the force of the hammering drops and watched for our target. Powering up to the mooring buoy I slowed too soon, the bow fell away to starboard, and took dead aim at the catamaran moored next door. I shifted hard into reverse and let Out of the Crisis, our 43-foot monohull, fall broadside to the wind, quickly making leeway and missing the cat by a few whiskers.

I powered forward again and aimed for another mooring in a slightly clearer area, but when we reached it my rain-soaked bowman found there was no pendant line attached. We fell away again, broadside to the squall. I throttled up and headed back toward the first mooring. This time I delivered the bow to the pick-up buoy, Sebastian speared it, and we were quickly secured.

First day in the BVIs

Not every day is perfect, even in paradise. On our crew's first full day in the BVIs, skipper John and able-seaman Sebastian watch for incoming squalls on a gray but warm run down Sir Francis Drake Channel. The stern-rail barbecue has been hog-tied to keep the lid on after a blustery night.


This was our first trip to the British Virgin Islands in nearly a decade, and some things were different. It was not only the windiest adventure my wife Rachel and I can recall having had in a BVI mooring field, it was also the first one she ever caught on video  — from an iPad shielded by dodger and Bimini. The other obvious difference was that Rachel would have normally been on mooring pick-up duty, but this time Sebastian, my daughter Isabel’s boyfriend, readily volunteered. No pressure.

British Virgin Islands map

The cruise started with a lap around Tortola in a MarineMax 433 sailboat and finished with a trip to Virgin Gorda and Anegada in a MarineMax 484 powercat. Unlike most charters, this one required a pit-stop to change boats at the MarineMax base in Hodges Creek.


Bareboat charter in the BVIs: our steed

When bareboating began back in the ‘60s, everyone rented monohull sailing yachts. And that was still the case on my first trip, with enough 20-something friends to fill two 40-footers. Subsequently on charters as a couple and later with a young family, Rachel and I have watched (and sampled) the rise of sailing catamarans to the point that they now outnumber the monohulls, thanks to their extra space and stability.

Power catamarans are now moving into the fleets in growing numbers, and a new company on the scene is MarineMax Vacations, which has a handful of sailboats plus a fast-growing fleet of power cats. We’d accepted MarineMax’s invitation to test a Dufour monohull customized as the MarineMax 433 against the flagship of their power fleet, the MarineMax 484. So after a nine-year absence from the islands, I had enrolled my family in the project, and we started out the week on the traditional vessel.

Formal attire only: Sophie and Olivia join in a birthday celebration for their sister Isabel (right) on a warm, wet, windy night.

Formal attire only: Sophie and Olivia join in a birthday celebration for their sister Isabel (right) on a warm, wet, windy night.

Today was Isabel’s 26th birthday. Not only was she long past being a teenager, her younger sisters Olivia and Sophie were adults as well—which meant that instead of avoiding The Bight’s infamous floating restaurant and bar known as Willie T’s, we were headed straight there for dinner. That evening, as wind and more rain blustered behind the weather curtains, we sat in rain slickers and bathing suit bottoms, consuming quantities of short ribs and dark ‘n’ stormies.

After dinner, Rachel and the girls lined up at the bar for the traditional “shot-ski”—four shot glasses mounted in line on a customized waterski. At some point after that the old folks were dinghied home, and I can’t say for sure how a couple of stylish William Thornton t-shirts made an appearance on our boat the next morning. Legend has it that they can only be earned by diving from Willie’s upper deck while adhering to a certain strict dress code.


Sandy Spit, north of Tortola, British Virgin Islands

For sun, sand, snorkeling, and scenic beauty, try Sandy Spit, north of Tortola (backround), just off the east end of Jost Van Dyke.


Why this is a sailor's paradise

In case you aren’t familiar with the British Virgin Islands and the remarkable holiday opportunity there for bareboat charterers, this is it in a nutshell. While the weather can be wet now and then, the constant climate is warm and a good wind usually keeps sails filled and cabins well-ventilated. A day’s voyage rarely takes more than a couple hours, and navigation is mostly line of sight, with few obstacles not readily apparent to the naked eye. Watersports, including scuba, snorkeling, and windsurfing, are easy to find. The food is good, and don’t forget the rum.

One thing that hasn’t changed on a BVI charter is that the safety, comfort, and pleasure of your crew comes first. Most of the time that means the captain’s job is the constant creation and recreation of an itinerary that delivers as many crew as possible to wherever they wish to go, preferably as comfortably and quickly as possible. If you macho sailing types don’t remember anything else from this article, remember that there’s a good chance you’re the only one aboard who cares more about the journey than the destination. You should relax and enjoy the destination, too.


Jost Van Dyke

I had planned to tour the islands counter-clockwise, but after the first night rolling on a mooring off Cooper Island in windy, wavy conditions, I abandoned the idea of going upwind to Virgin Gorda, and we headed downwind to the sheltered Bight on Norman Island instead. The next day, with the weather still unsettled, we snorkeled in the morning, sailed down to Soper’s Hole for a few provisions, and landed for a late lunch at Jost Van Dyke, where we found a reasonably protected mooring and a hike ashore. The weather finally broke favorably the next day for more snorkeling and beach time at Sandy Spit and an epic afternoon sail upwind to Scrub Island, where I booked a slip to spoil the crew in a pool, hot tub, and hot marina showers. But I’m getting ahead of my story.

Astern of every charter boat dutifully follows a small outboard-powered inflatable dinghy to take you ashore after anchoring. At Jost Van Dyke, we rode the dinghy in for dinner and specialty drinks at Foxy’s Taboo, and a smattering of rain blew through with a strengthening wind. The dinghy dock faces southeast, broadside to the prevailing wind, and we soon realized we were in for a wet ride back to the boat if we were lucky enough to avoid capsizing the dinghy at the dock. Over dessert, I also had visions of the difficult leap from the dinghy to the heaving stern of our boat, so along with a few other charter crews at Foxy’s, we realized the best plan was to simply wait a while. Fortunately, the breeze soon backed off, and my plan of shuttling the crew in two trips kept the payload light and all of us slightly drier. I do admit that once safely aboard Out of the Crisis for the night, I absorbed some medicinal rum to settle my nerves.

On holiday in the islands, many will turn on the engine when faced with an upwind leg. But not on my watch. After a long morning snorkel, we hoisted sails, sheeted them tight, and sailed from Jost Van Dyke to Guana Island Passage—most of the length of Tortola—in a bit under three hours. The monohull sliced through the waves with a comfortable motion in 15 to 25 knots of wind, and we took turns steering. (Watch our short video