There are thousands of islands in the Caribbean, so why do so many travelers only visit one at a time? The typical Caribbean vacation means flying to a destination and staying put. Cruising is a little better, but even then you're only getting the briefest exposure to your ports of call. Island-hopping by regional airline is expensive, and ferry service between islands is often limited or nonexistent.
But as experienced boaters know, there is one great way to see multiple islands in the Caribbean while going at your own pace: chartering a private yacht, either crewed or "bareback" if you know how to sail. Bring along some friends, and this pricey-sounding adventure can even approach affordability -- or at least what you'd pay for a high-end hotel room. And unlike that room, this one can move from island to island!
Here's where and how to set sail on your Caribbean yacht adventure:
Where to Go for the Best Caribbean Yacht Experience
Yacht charters are available all across the Caribbean, and most islands have hidden beaches, beach bars, dive stops and sheltered anchorages you can plan an itinerary around. We've had a great time sailing from port to port in St. Lucia, for example, enjoying the magnificent views of the mighty Pitons all along the way.
That said, simple geography dictates that if you want to see more than one or two islands, you'll need to head to destinations that have multiple islands within an easy half-day (or less) sail from one another. In the Caribbean, that primarily means the Virgin Islands and the Grenadines as well as St. Maarten/St. Martin, which reasonably is close to Saba, St. Barths, St. Kitts and Nevis, and Anguilla. The Bahamas Out Islands are another potential destination, especially around the Abacos.
In the U.S. Virgin Islands, St. Thomas and St. John are a mere stone's throw from each other, and the British Virgin Islands are easily reached from either (although you'll need a passport to move between the two). Within the BVI there are an amazing array of islands you can work into a charter itinerary, including private island resorts, beach bars (including famed watering holes like Foxy's and the Soggy Dollar), and the Baths, one of the most dramatic dive spots in the Caribbean.
Who to Charter With
There are many yacht-chartering options in the Caribbean, ranging from individual owners who will happily serve as captain and crew and take you around the islands on their boat to big companies that have fleets of boats available for bareback, crewed, and learn-to-sail journeys. For example, during our stay at the Peter Island Resort in the British Virgin Islands we met Lindsay and Jason Geyser, crew of the Silmaril, a lovely Hans Christian sloop available for half-day, full-day, and overnight charters. There are many other crewed boats you can charter for a week or more.
Of the latter, The Moorings is one of the largest, and the company that we chartered with on our recent catamaran cruise around the British Virgin Islands. In fact, as we sailed around the BVI, a majority of the other boats we saw were charters from the Moorings or sister company Sunsail. The Moorings has operations in the BVI, St. Thomas, Grenada, St. Martin, and St. Lucia; Sunsail has bases in these destinations as well as Antigua, Belize, and the Bahamas.
Captain or No Captain?
Can you sail? Can you sail well enough to be entrusted with an unfamiliar boat in unfamiliar waters? Then you might consider a bareback charter in the Caribbean. For the rest of us landlubbers, the better option is to sign up for a crewed charter -- even if that "crew" means only a captain. In our case, "only" isn't the right word to describe our Moorings captain, Dunbar, who also acted as tour guide, historian, and occasional drinking companion. His advice was invaluable in helping us plan an itinerary that took in several private islands and beach bars over the course of three days, especially in terms of finding moorings where we could overnight in calm waters.
Note that your captain's job description does not include "chef" or "waiter": you'll need to bring your own food and prepare it yourself, as well as making your own bed and cleaning up your own messes, unless you want to pay for additional crew members to do those jobs. And at the end of your trip, a nice tip is certainly appreciated for a captain's job well done.
What Kind of Boat Should You Charter?
Your chartering options include sail yachts and power yachts, although that's a bit of a misnomer, since the sail yachts also are powered. For the sheer thrill of sailing, you can beat a monohull yacht -- the Moorings 54.5 can carry up to 11 passengers -- but for comfort and smooth sailing we'd go for a catamaran. Our Moorings 4800 (the Slow Motion) was ideal for navigating the calm waters of the BVI and was stable enough at rest that my motion-sickness prone wife slept like a baby every night. And we liked having the option to motor or sail, depending on the wind: not that we minded the sound of the engine, but the trip was remarkably more peaceful when we were under sail!
Our catamaran had four cabins and four bathrooms; as fate would have it, we had the boat to ourselves, but the 4800 seemed to be plenty spacious to share with three other couples, including a main cabin with a kitchen and big communal table, plus another table and ample lounging room on the aft deck.
By way of example, rates for this boat currently range from about $4,000 to $20,000 per week, depending on the season, plus another $228 daily for a captain and $180 per day for a cook. Divide that cost between four people and you can have a surprisingly affordable yachting trip in the BVI, especially in low season.
More Tips You Need to Know Before Your Charter
Here are some Things We Learned from our first yacht chartering experience:
- You need to provision your boat: that means stocking it up with enough food, drinks, and alcoholic beverages for the length of your trip. Start by bringing whatever you can from home. Depending on where you're sailing from, there may be local markets where you can pick up supplies. We got decent prices, for example, from the market at Trellis Bay on Tortola; the market at the Scrub Island Resort was well-stocked but more expensive. The Moorings base on Tortola has its own market as well as the nearby Rite Way Food Market. Generally, ports of call, marinas, and resorts catering to boaters will have at least some food shopping options. Moorings will also provision you boat in advance, for a fee.
- As mentioned, set aside some money to tip your captain: 15-20 percent of the cost of the charter is customary. Also, remember to buy adequate provisions for your captain, as well!
- Plan your itinerary in advance. Your captain can help you fine tune your trip, but it's helpful to have a general idea about where you want to go in advance. In addition to sailing distance, you'll need to factor in things like the availability of overnight moorings in your planning. Companies like Moorings may offer advice by phone or email in advance.
- Avoid overpacking. Charter yacht cabins are small, and you'll likely spend most of your days in a bathing suit and t-shirts. A single, soft-sided carryon should be more than big enough for a week on a yacht, even if you bring one nice outfit for a special dinner ashore. Overall, think light and casual -- flip-flops can be worn anywhere in the BVI, and bare feet are the rule onboard your yacht!
- Use nature's clothes dryer: simply pin your wet clothing up on the rail of your yacht and let the tropical breeze do the work.
- Don't forget your sunscreen and power cords for your mobile devices and speakers (yes, there are power outlets onboard, but they only work when the generator is on). It also doesn't hurt to make that perfect playlist in advance.
- Bring inflatable water toys (which can be packed in luggage) from home so you have something to play with, along with snorkel equipment.
- Remember to bring your passport and other necessary travel documents aboard if your itinerary involves crossing international borders.
- We'd recommend against it, but if you simply must stay connected on your vacation, Moorings lets you can rent a portable WiFi router for the duration of your trip. We got by perfectly fine just by logging into the WiFi during our port calls to briefly check emails and post photos of our adventure to social media.