Paradise Leased

Get full access to Outside Learn, our online education hub featuring in-depth fitness, nutrition, and adventure courses and more than 2,000 instructional videos when you sign up for Outside+.

Destinations, March 1997

Paradise Leased

Borrow a million-dollar boat. Cruise the Caribbean. Grin. A beginner’s guide to sailboat charters.
By Dan Dickison

The Eel Ate
My Homework

Sailing schools teach navigation, confidence, and a good fish story or two

Take this test: what is reefing? When do you use a barberhauler? And how much scope would it require to anchor in 15 feet? If you scored less than 100 percent, your first chartering experience should be with a sailing school. Like medical school but fun, a sailing course can impart practical, even lifesaving, information,
together with a nifty new vocabulary.

Offshore Sailing School (800-221-4326), based at the Prospect Reef Resort in Road Town, Tortola, will have you seaworthy in just a few days. For an intensive, hands-on approach, enroll in its weeklong course taught aboard a 26-foot sloop ($1,195 per person). You’ll sleep in a comfortable hotel bed every night, but you’ll also be
restricted to home base while the neighboring islands beckon. Offshore’s comprehensive Live-Aboard Cruising Course ($1,895 per person) places you aboard a 44-foot sloop for six days and five nights with a certified instructor to guide you through the sailing steps as well as the surrounding islands. For the final 24 hours you’ll be turned loose for a mini
cruise without the instructor.

Annapolis Sailing School (800-638-9192), based in Christiansted, St. Croix, also offers weeklong live-aboard cruising classes ($1,500 to $2,025 per person). Instructors talk you through techniques on the first day, but on the second you personally navigate a 35-mile passage to St. John. From there, you practice skills in the
British Virgins.

If you chafe at the thought of following a school’s itinerary, you can ask your charter broker to arrange for a qualified instructor to be assigned to your boat for part or all of your trip. He or she will give lessons, navigate, and probably pass along some good sea stories that you can later appropriate as your own.

The Other Islands

When sailing the Virgins’ palls, follow Gauguin

The Caribbean is the most convenient and easily navigable destination for U.S. charter sailors. But it isn’t necessarily the most paradisiacal. French Polynesia, halfway around the world, is arguably the loveliest spot on earth for sailing and lazing. Just ask Gauguin. And some of the most memorable moorings are along Rangiroa.
A 45-mile-long series of small islands surrounding a crystal-clear lagoon, Rangiroa is the second-largest atoll on earth, with a year-round population of 1,400. But once your catamaran pulls away from its biggest village, Avatoru, you’re unlikely to see another soul. Farther northeast, the lush, mountainous Marquesas remain virtually untouched by tourism.
If you don’t speak French, start practicing gestures–few islanders speak English, and the Marquesan dialect is mellifluous but incomprehensible to outsiders.

Bareboat charters are unavailable in Rangiroa or the Marquesas. Archipels Croisieres (011-689-56-3639) has a small fleet of 57-foot, crewed luxury catamarans ($1,790-$2,450 per cabin per week) that sail set itineraries in the Marquesas, Bora Bora, and Rangiroa.

To pick up your boat, fly first to Papeete, the largest city in French Polynesia. From there, Archipels Croisieres will arrange to have Air Tahiti fly you to the Marquesas, Bora Bora, or Rangiroa. Remember to bring lightweight raingear: December to March is the rainy season here, with frequent downpours. But then, with ocean
temperatures hovering at near 80 degrees, who cares if you’re a little damp before you slip over the side?

–Dan Dickison

Anchored off Green Cay in the British Virgin Islands, the sailboat sways easily, nudging you awake. In the predawn haze, you heat some coffee and watch the sun rise over Tortola. No one hectors you to hurry. No one thrusts an itinerary at you. You’re master of this floating world. But later in the afternoon, when the waves begin to swell, dry land seems distant, and the theme
from Gilligan’s Island starts to echo in your head, you remember the downside of being king of this dominion: You’re the only captain you can turn to.

Chartering a sailboat is one of the best ways to see the Caribbean, especially during the spring high season, when many resorts in the islands are booked solid. Where else can you and a handful of friends spend a carefree week aboard somebody else’s half-million-dollar yacht in 80-degree temperatures less than a day by air from any major U.S. city?

Both experienced sailors and those who’ve never before hoisted a sail or raised anchor can successfully charter. Boats can be leased either bareboat-style–meaning without a crew–or fully stocked with captain and expert sailors. Obviously, those who haven’t taken advanced sailing courses will do best to let an experienced crew do the actual work; they’ll even teach you to

As for finding a boat, dozens of charter companies operate from the 11th parallel up to the Bahamas. Finding the right one can be intimidating and time-consuming. For most first-timers, the easiest solution is to use a broker, much like a travel agent, who works with a variety of boat companies. A good broker can determine your needs over the phone and recommend a company, a
destination, and even the best style of boat for you, all at no charge. Among the more experienced Caribbean brokers are Ed Hamilton & Co. (800-621-7855), Lynn Jachney (800-223-2050), and Carole Borden at Aqua Safaris (800-524-3444).

Before finalizing your booking, be sure to ask your broker about expenses not included in the cost of the boat. Many charter companies don’t include customs duties, nightly mooring fees, or watersport gear, such as sailboards, in their prices. And never forget the one issue most likely to ensure a pleasant trip for all involved: “Just how spacious are the cabins, anyway?”

Sailboat chartering in its simplest form means just you, the boat, and whomever you take along. This is the waterborne version of camping: You’re independent and mobile, but you’ve also got to do your own dishes, navigate, and even manage light boat maintenance when necessary. Obviously you’ll need at least one experienced sailor on board. And don’t overestimate your abilities:
It’s a good idea to have passed at least one cruising course before considering a bareboat charter.

Of course, some people grow claustrophobic at the thought of spending a week on a single-hull sailboat, or they fear for their landlubber’s stomachs. For these folks, a catamaran is probably a better bet. You get twice as much deck space and considerably more stability, though you’ll pay about 15 to 20 percent more for a catamaran.

As for a destination, first-time Caribbean charterers will probably want to center their trip around the easy-to-navigate Virgin Islands, both U.S. and British. Consistent 15- to 20-knot breezes blow across this miniature archipelago, and the water is wonderfully clear, making navigation a matter of line of sight (stay in the dark blue water and avoid dark shapes, which
indicate rocks, and light turquoise water, which means shallows). The majority of these cruising grounds are also well protected from the Atlantic.

Finding a charter company in the Virgins, if you choose to do so without a broker, means navigating through an embarrassment of riches. Dozens operate here, most long-established. Prices and services vary, but count on paying at least $3,500 for a 40-foot boat, based on a week’s trip in high season (December-April). A boat that size will comfortably sleep four.

Tortola, the capital and nexus of the British Virgin Islands, boasts the lion’s share of the Virgins chartering companies, including Sun Yacht Charters (888-772-3502), The Moorings (800-535-7289), Catamaran Charters (800-262-0308), Tortola Marine Management (800-633-0155), and Freedom Yacht Charters (800-999-2909). For $19, you can take a ferry from St. Thomas up the Narrows to
Soper’s Hole on Tortola’s West End. One of the region’s largest bareboat firms, Sunsail (800-327-2276), sits across the anchorage from customs.

Of course, paradise has its price; everything save rum is more expensive here than in the United States. But you can save some money by doing your own provisioning. All boats come equipped with at least a two-burner gas stove and cooking utensils, and an extra fee will get you a full larder. You’ll usually spend less and get better food by buying your own, but the downside is
that you’ll waste a precious three hours in a cab and at the grocery store. Try Road Town Wholesale or Bobby’s grocery store in town; if you’re staying at West End, the pricey Ample Hamper is about the only option. Buy plenty of fresh food now, because you won’t find them in abundance once underway.

Chartering out of the USVI is often less expensive but logistically more complicated than on the British side. Most of the half-dozen companies there–including Caribbean Yacht Charters (800-225-2520), CYOA (800-944-2962), and Island Yachts (800-524-2019)–can get you out on the water the same day you climb off the plane, but it’s upwind sailing from there to the BVI. You’ll
also have to pay a cruising fee at British customs ($4 per person per day, plus a minimum of $15 per boat; 809-495-4221). As compensation, though, you can overnight along the way in scenic St. John’s Hawknest Bay or Leinster Bay.

Once in the BVI, make sure you take a day trip to The Baths at Virgin Gorda. This jumble of gargantuan granite boulders at the island’s southern end hides cathedral-like grottoes and pristine pools. It’s also on almost every charter boat’s hit list, so arrive early in the day (by 7:30 a.m.) or late (after 4 p.m.), when crowds have thinned. Then hook your boat to an open mooring
($15 per day) and head ashore for a few hours.

Northwest of Tortola lies Jost Van Dyke, legendary for its New Year’s Eve bashes at Foxy’s in Great Harbour. Overcrowded and touristy, it’s best avoided. Drop anchor instead in White Bay, just to the west (if your craft draws five feet or less). The Sand Castle bar, which created the rum-based Painkiller, a quintessential feature of Island cuisine, still affords a grand view of
the area’s mango-tinted sunsets.

For more experienced bareboaters, the Grenadines, a string of islets stretching from St. Vincent to Grenada, are also a popular destination. Getting here isn’t easy; the puddle-jumper airline Liat has three daily flights from Puerto Rico to St. Vincent for $220 to $307 round-trip (800-468-0482). But the trip is worth the hassle, since the Grenadines contain some of the
loveliest anchorages in the Caribbean, including Mustique and Bequia. The nearby island of St. Vincent, though, is larger and more convenient than its trendy neighbors. If you put in there, Charlie Tango (809-458-4720 or channel 68 on the VHF) can get you whatever you need–moorings, taxi service, dry-land sightseeing trips, ice, clean laundry, or provisions.

Before you leave the Grenadines area, head for the Tobago Keys. Protected by the government of St. Vincent and the Grenadines, these five remote, exquisite little islands (Petite Rameau, Petite Bateau, Baradal, Jamesby, and Petite Tobac) surround an azure anchorage. You won’t find airstrips, hotels, or shops here–just tropical vistas and, if you’re lucky, the elusive green
flash, a legendary emerald hue that momentarily suffuses the horizon just at sunset.

Depths on the surrounding reef don’t exceed ten feet, making it easy to view the kaleidoscopic corals, triggerfish, parrot fish, fry, and damsel fish. Sea turtles, nurse sharks, and maybe an oversize grouper will occasionally swim into view. One concern: Although the navigation in the Grenadines is generally no more difficult than in the Virgins, you will have to traverse open
ocean, complete with six-foot waves, to get there. Check weather conditions before heading out each day–advice that applies wherever you’re sailing.

Flotilla Charters
The concept of flotilla charters has been around since the days of Magellan and Columbus. Still a favorite of European travelers, flotilla charters put a decided emphasis on the social: parties, group excursions, joint dinners. Sunsail is the largest flotilla operator, offering customized outings that cover the complete BVI circuit, including distant Anegada–the most remote
location in the Virgins.

If you don’t mind voyaging in the company of five to 15 other vessels, you can book any of Sunsail’s 29- to 54-foot boats and spend up to two weeks sailing en masse, for around $2,000 to $5,000 per week during high season (December 15-April 15). Prices drop about 20 percent in the off season. But flotilla trips are popular year round; make bookings as far in advance as

After a day or two spent getting accustomed to the boat, you’ll play follow-the-leader across 15 miles of open water to Anegada, a low-lying island that sits adjacent to Horseshoe Reef. Getting through the reef is tricky, but a captain aboard the lead boat will talk you through the coral heads via VHF radio if necessary.

Once through, pull out your snorkeling gear: The reef is home to dozens of species of colorful fish, as well as barracuda and moray eels. Later, the tiny Anegada Reef Hotel will provide a traditional lobster bake ($30 per person). Don’t hurry back to your boat after dinner, though. Allow a few hours for a walk along the nine miles of deserted beaches on this
uncharacteristically wild Caribbean isle.

Crewed Charters
Flotillas, for all their collegial, floating party atmosphere, have one signal drawback: They require sailing experience. You won’t be able to keep up with even the most relaxed flotilla contingent without it. But there is an alternative: You can create a smaller party of your own, with a fully staffed boat, one that is captained and navigated by someone whose extensive sailing
experience can substitute for your own.

Crewed charters, the only option for novices, can sometimes be the best choice even for more experienced sailors. They allow for greater leisure. They remove all concerns about navigation and boat repairs. They impart essential sailing skills, if you choose to learn. And they can be economical. Rates start at about $125 per person per day, with the boats ranging from the simple
(a 40-footer with captain and mate doubling as chef, steward, and instructor) to the sublime (luxury vessels with private cabins, gourmet meals, and a full complement of aquatic toys).

The smaller crewed boats often are less expensive than their bareboating counterparts because bareboat companies typically charge extra for fuel, insurance, ice, cruising taxes, sailboards, and sea kayaks. Charter guests also are welcome to pitch in and steer, trim sails, or even drop and weigh the anchor if they desire. After a weeklong crewed charter, you may well be ready to
bareboat on your next trip.

There are a number of desirable crewed-charter destinations, but Belize is perhaps the epitome. With the world’s second-largest barrier reef, mangrove-laden shores, and slate-blue channels bordered by pastel-colored reefs, it’s the perfect place to sit back, luxuriate in the landscape, and let someone else maneuver you toward shore.

The Corpus Christi International School of Sailing (512-881-8503) offers an 84-foot catamaran, the Rendezvous, for charter in Belize. Fly first to Belize City ($435 round-trip from Houston on American Airlines; 800-433-7300). The crew will meet you and up to seven other guests and shuttle you out to the boat for a week’s sailing ($840 per person).
Sea kayaking and snorkeling equipment is available for use by guests. Then, at night, the on-board chef cooks locally caught seafood for dinner.

For those who prefer their aquatic adventures to include some time beneath the surface, the Blue Hole in Belize, a large, offshore sinkhole, is incomparable. Sailing is hazardous near this 412-foot-deep disc of azure ocean, though, so you’ll need to arrange an excursion with a local dive shop, such as the Blue Hole Dive Center ($175 per person; 011-501-26-2982).

The trip will last most of the day. But that’s another advantage of a crewed vessel: There’s always someone left to watch the boat.

Dan Dickison lived in the Caribbean for ten years, racing sailboats and captaining crewed charters.

promo logo