The First-Timer's Guide To Sailing On A Crewed Yacht Charter In The British Virgin Islands

Here are nine things to know before you embark on your inaugural voyage with The Moorings.

Spread across 56 square miles of cerulean Caribbean seas, the British Virgin Islands comprises more than 60 islands and cays. And if you want to discover their secret coves and stunning natural beauty, there's no better way than on a leisurely cruise from one anchorage to another on a crewed charter. With a professional captain, chef, and steward on board, all you have to do is relax and let the islands come to you. 

I've been fortunate enough to explore the BVI this way four times, most recently with The Moorings, an outfitter founded in Tortola 54 years ago, which operates a fleet of more than 300 vessels there. If you're new to private chartered yachting, here are my best tips for making the most of your cruise.

Bring Soft Luggage 

You know that new piece of checked luggage you bought during the pandemic for when you finally started to travel again? The one that can hold enough stuff for two weeks away? Leave it at home. In comparison to a hotel room, your cabin will be decidedly compact, and it's unlikely there'll be space to store something so bulky. 

Instead, bring a soft-side duffel bag or wheelie that can be folded flat once you've unpacked, then tucked out of sight in a cupboard or under your bed.

Pack Light 

For a 7-night cruise on a regular cruise ship, you'll need resort wear and swim wear for daytime, and dressier pieces for dinner. But on a Caribbean yacht charter, you'll be living in swimwear, supplemented by a pair shorts, a coverup, and maybe—just maybe—a maxi dress or other smart casual outfit if you choose to have dinner onshore. 

On my recent Moorings sailing I wore five swimsuits (I like to have choices!) and not much else. My best advice: Pack more swimwear (so you always have a dry suit) and fewer "real" clothes than you think you'll need.

Get a Pedicure 

If you've never been on a yacht or catamaran before you probably don't know that shoes usually aren't allowed onboard (they can damage the finish on the deck). But this is one of the first things the crew will tell you. Fling your flip-flops into the boat's shoe basket, and don't give them another thought until it's time to go ashore. 

But please, consider your fellow sailors and make sure your bare feet are presentable. Cracked heels and callouses are not a good look!

Take Cruise Control

One of the best things about a crewed charter is that, within reason, you set the itinerary. On previous Moorings sailings, breakfast was followed by a briefing with the captain, who'd spread his map on the table to show you where you are, suggest places you could go that day, and what you could do when you get there. 

Whether you want to snorkel (the waters around The Indians, off Norman Island, are stellar); to shop at an island boutique (there are good ones on Cooper Island and at Saba Rock); or simply to sip rum punch all day as you watch sandy islets float by, your captain will make it happen. 

There Will Be Painkillers 

The Caribbean is the birthplace of several cocktails, including Puerto Rico's piña colada and the Cayman Islands' mudslide. In the BVI, the local libation is the Painkiller, a potent combination of rum, coconut cream, and pineapple and orange juices, topped with a dusting of freshly grated nutmeg. 

It was invented at The Soggy Dollar, a beach bar on Jost Van Dyke, so you'll have to try the original there. But Painkillers and variations thereof are served at every bar in the BVI. And since you're not doing the driving, it'd be rude to refuse them, no?

Go with the Flow 

Whenever you sail, particularly on a small vessel, you're at the mercy of the weather. Choppy seas can make anchoring off some islands difficult. Or you may arrive at a popular spot late in the day and find there are no mooring balls available. The beach bar you had your heart set on visiting might be unexpectedly closed. 

My point: Things don't always go according to plan, so you'll need to be flexible. 

It Could Get Rough 

Of course, The Moorings and other boat charter companies pull their boats out of service if there's a hurricane on the horizon. But sudden "pop-up" storms can lead to less-than-ideal sailing conditions. So, if you're prone to motion sickness, arrive prepared with the appropriate meds or a pair of anti-sea sickness wristbands. 

Ninety percent of the time it'll be smooth sailing; don't leave the remaining 10 percent to chance.

Re-Entry Can Be Rough, Too 

Obviously, returning to reality after several languorous days at sea will be a shock to your system. But the actual process of leaving the boat and getting back to the airport can be a more complex and longer process than you'd imagine. 

On my cruise, getting to the airport in St. Thomas required a 20-minute boat ride to BVI Customs at West End (where we waited 40 minutes to be cleared); then a 15-minute boat ride to Cruz Bay, St. John to clear U.S. Customs; followed by a 10-minute sail to Red Hook in St. Thomas, from where we drove 30 minutes to STT. Phew! 

Allow yourself ample time to get back to your departure airport. The good news: American Airlines has announced non-stop flights from Miami into Tortola, BVI, beginning in June.

You’ll Want to Do it Again

Perhaps next time you'll bring different friends or family members with you (The Moorings' boats sleep between 6 and 10 people). Maybe next time you'll summon the courage to jump off the top deck of the infamous floating bar, the Willy T. On a return trip, you could even sail all the way out to Anegada, the furthest flung island in the archipelago, to sample its famously tasty lobster. 

There are so many reasons to want to repeat an idyllic week in Paradise—and any one of them will do!