Interested in chartering a yacht to explore the British Virgin Islands? Whether you want to hike, fish, scuba dive, surf, or just drink rum in the sun, you’ll have plenty of options. But in order to make the most of those vacation choices, there’s a certain degree of sailing industry lingo you should familiarize yourself with before embarking.

Boats in the BVI yachting industry can broadly be split into two categories: “bareboats” and “crewed yachts.” Bareboats, largely chartered in mega-fleets like The Moorings, are operated and provisioned entirely by the guests who rent them. Sometimes, companies will temporarily assign a captain to a rental to determine the client’s competence. Janet Oliver, the executive director of the BVI Charter Yacht Society, estimates that 95 per cent of the yachts currently sailing in the territory – roughly 650-700 vessels – are bareboats.

A much smaller chunk – Oliver estimates 45 boats – are crewed yachts. These boats are permanently staffed, usually by a captain and a chef, and maintained at a high level of luxury. Booking with a crewed yacht means every one of your needs – cooking, cleaning, provisioning, sailing, etc. – will be taken care of throughout the week of your vacation. They tend to offer more expensive, tailor-made tourism experiences. 

There are some hybrid forms: Tourists who don’t have sailing experience or a desire to handle a boat can book a bareboat captain or crew to guide them around the islands. This isn’t the same thing as a crewed yacht, however. The bareboat crew isn’t typically hired to facilitate every aspect of your tourism experience – their role will mostly be centred on transportation.

Oliver provides a useful metaphor to help clarify the distinction: Booking a bareboat, she explains, is like booking a rental car, booking a bareboat with a crew is like calling a taxi, and chartering a crewed yacht is like hiring a limousine.

Bareboats are often booked directly through a charter company. Tourists looking to hire a crewed yacht, however, often go through “charter yacht brokers” – specialized travel agents who know the crews personally and put customized sailing vacations together.

Kathleen Mullen, the director of Regency Yacht Vacations, a brokerage based in Road Town, says understanding the human element is one of the most important aspects of her job.

“A big thing is the crew,” she explains, “They’re human beings. It’s in a small space. Brokers have that first-hand knowledge.”

If a foodie is looking to charter a yacht, Mullen will set them up on a boat with a high-end chef. If she’s working with a big family, she can point them towards energetic, young crews ready to spend a week launching them from one activity to the next. If an elderly couple is looking for a relaxing, informative vacation, she’ll match them with a conversational crew with expansive knowledge of the islands and their history.

Brokers take deposits from clients and contact “clearing houses,” the administrative centres for individually owned and operated crewed yachts, to make bookings. After contracts are exchanged, the crew of the booked yacht will reach out to the clients to customize their vacation, and the client’s money will be held in an escrow account until 10 days prior to the start of the charter. Although crewed yachts do come with a higher initial price tag, Mullen notes that overall costs often come within only a 10 per cent difference of bareboat vacations, given bareboaters have to cover additional costs like provisions, insurance, etc.  

Mullen suggests booking crewed yachts at least a year in advance, particularly if you don’t have a ton of flexibility with dates. While the yachting busy season has traditionally run from mid-December through April, the broker notes bookings are now consistent through May, June and July as well. Few boats are available to charter during the peak of hurricane season in August, September and October.

Mullen also notes customers interested in docking at high-end resorts have slightly fewer options in the wake of the destructive 2017 hurricane season.

“People who might have stopped and checked out higher-end resorts, those are still not back online to the extent that we would like,” she says. “But I find that most clients are happy keeping it low-key. And they can still go to Oil Nut Bay. And Scrub Island is back open. So, it’s not like there are not any choices.”

Some repeat tourists have even preferred the less-developed experiences they’ve had post-2017, Mullen explains. Harbours are less crowded, and the BVI looks more like the old-style Caribbean landscape of decades past.

Besides offering administrative help, Mullen has one signature piece of advice she likes to offer clients about to embark on a charter.

“One thing I would tell prospective charter clients to do is to get on a boat, take a deep breath and relax,” she says. “Nothing is set in stone. Everything will be taken care of.”