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Chartering in the Virgin Islands

One of the charter world’s most iconic views: the Baths on Virgin Gorda

One of the charter world’s most iconic views: the Baths on Virgin Gorda

If you like the thought of easy sailing, affordable travel costs and a low hassle factor, you can’t beat the Virgin Islands for a wondrous winter charter. Whether you’re headed to the Spanish, British or U.S. Virgins, here are some tips on chartering in a tropical paradise that’s close to home, where the time change is minimal, English is prevalent and the remarkable scenery will make you forget the winter you’re fleeing from. Turn the page to explore your options….

How and Where to Charter

In the Virgin Islands, there are nearly three dozen charter companies to choose from. In the British and U.S. Virgins island groups, you’ll have your choice of large international companies such as The Moorings, Sunsail, Dream Yacht and Navigare, along with excellent regional companies such as Horizon Yacht Charters, Voyage, CYOABVI Yacht Charters and TMM, all offering late-model boats and excellent local customer service. For those charterers who want boats equipped with generators, watermakers, air-conditioning and Wi-Fi, expect the top-tier companies to charge premium prices. For those sailors who don’t feel the need a brand-new boats or all these mod cons, you can also enjoy the budget companies like Footloose and Conch Charters.

With so many companies to choose between, it can be difficult for new charterers to decide which one best suits their needs. It’s easy to spend a day or more looking into the offerings of the various companies in search of the best deals. The upside is that poor customer service and sub-par boats are increasingly rare in this age of social media, where news of bad experiences spreads quickly. However, to guarantee a stress-free resolution, first-time charterers might be better off going through a charter broker such as Ed Hamilton & Co, who can summarize your priorities and cut to the chase quickly and efficiently.

Deciding on a location is not as easy as it seems, either, as all three island groups have their own attractions. The British Virgins, for example, are home to most of the charter outfits, but can get crowded, while Dream Yacht and Sail Caribe operate in the Spanish Virgin Islands where the natural unspoiled beauty of Culebrita Island and the great diving off Vieques will make you forget civilization. In fact, the Spanish Virgins have been described as the BVI of two decades ago—all the beauty without the crowds and commerce.

In the U.S. Virgins, St. John offers unparalleled snorkeling and a selection of beautiful anchorages and mooring fields that rival anything in the region. St. Thomas too has its share of anchorages along with excellent shopping and restaurants. Of the companies based there, CYOA, Island Yacht Charters and Sail Caribe all offer bareboat charters.

Some charter companies offer extra days (like 10 days for the price of seven) so you can sail longer during low or shoulder seasons. Others like Sunsail and The Moorings offer shorter charters for quick getaways (perhaps only four nights) so you’re not locked into a full week or can start mid-week rather than the standard Saturday to Saturday run.

Since the 2017 hurricanes decimated the charter fleets, most of the cats and monos in the Virgins are less than two years old

Since the 2017 hurricanes decimated the charter fleets, most of the cats and monos in the Virgins are less than two years old

Choosing a boat

There are a number of things that go into choosing a boat, including your preferences, level of experience, size of crew and budget. For bareboat cruising, you’ll need experience in sailing, reefing, anchoring, catching a mooring, docking and dealing with changing weather. Bareboating is cheaper than crewed charters where you take on a professional (paid) captain, and it’s more flexible because you decide where to go and for how long. On a bareboat, you won’t need to share space with the captain and/or chef, and you’ll have more privacy. However, a captain can relieve you of the worry of something going wrong. He or she can also plan the itinerary, monitor the weather, teach skills and fix things that break. The choice is yours and there’s always a tradeoff.

Purists may want to charter a monohull for better sailing, especially upwind. However, the Virgins are well stocked with catamarans that offer more room, twin engines for easier maneuvering and stable movement to alleviate seasickness.

Cats are more expensive than monohulls. And again, newer boats, especially those with extra amenities such as flybridges, generators, electric winches, watermakers and air conditioning are more expensive than older ones.

For details on things like age, layouts and amenities, you can either go on online or call the charter company.

It doesn’t matter where you’re from, you’ll feel at home on Jost van Dyke

It doesn’t matter where you’re from, you’ll feel at home on Jost van Dyke

When to Go

Although most people’s thoughts swing to sun-kissed isles and turquoise waters when it’s hot cocoa weather at home, a shoulder or off-season Virgin Islands cruise also has many benefits. Hurricane season is technically June 1 to November 30, which logically enough, is also the area’s low season. Normally, a six-month season will produce 10 to 14 named storms, half of which may develop into hurricanes. Only 33 storms have reached Category 5 status, so timing is everything. Late August and early October can be sketchy, and the month of September is especially risky in the Caribbean. However, a Thanksgiving cruise can be spectacular.

Storms aside, there is much to be said for low-season chartering. Depending on when, where and with whom you charter, savings of 10 to 60 percent and upgrades to bigger and newer boats are possible. Often, the weather is no hotter than July/August can be in the States. Flights will likely to be cheaper as well.

Chartering during the shoulder seasons (May/June and November) also brings peace and quiet. In high season (mid-December to April) it can be difficult to find uncrowded anchorages, available moorings and bars with free tables. In the summer and fall, though, not so much.

Finally, Jay Pennington of CYOA Charters notes that, in addition to the smaller crowds in shoulder season, months like November also make some of the longer sails easier, which expands the available cruising grounds. “Southerly breezes and calmer seas make passages to Culebra, Vieques and western Puerto Rico as well as St. Croix easier and more enjoyable.” In contrast, during high season, the so-called “Christmas winds”—stronger than usual easterly trade winds—can blow up to 25 knots from early December to mid-January, often for days at a time.

In terms of precipitation, while you can be drenched by a short-lived tropical squall or shower at any time of the year, the least rainy months are February and March, and the rainy “season” per se is between August and the end of November.

Supermarkets are well stocked

Supermarkets are well stocked


Provisioning in the Virgins is a simple affair with most islands offering small grocers, local produce and fish markets, and even behemoth stores much like those in the States. Indeed, aside from Europe, the Caribbean is perhaps the easiest place to provision, even in the wake of Hurricane Maria that battered the BVI and Puerto Rico.

Beyond that, there are four ways to enjoy food on a bareboat charter: provisioning done by the charter company, provisioning done by you via grocery stores, ordering ahead for delivery from a grocery store and eating ashore.

If you have the charter company provision, you’ll complete a form ahead of time. Most bareboat charter companies offer two levels of provisioning: full or partial, with the latter being more flexible. Charter companies provide a list in English so you’ll know what you’re getting. Opt for a starter kit that includes easily overlooked items like matches, dishwashing detergent, sponges and trash bags. Alcohol is usually best left for your personal shopping adventures because you’ll probably find better choices and prices on your own.

Make a list. Don’t forget about happy hour, which can make your shore dinners much cheaper if you skip paying for appetizers and cocktails onshore. Be adventurous and try the local yogurt, tuna, jam and so forth, which will be cheaper than imported brands.

Less is more. Whatever you think you’ll need, cut it by a third. In the Virgins, it’s easy to shop small and often instead of loading up on a week’s worth of groceries at your point of departure. Your provisions will also fit better in small boat refrigerators and stay fresh. Plan for half of a gallon of bottled drinking water per person, per day in hot weather. Purchase water in large jugs and then use personal water bottles to save money and limit trash. Consider bringing spices in baggies from home. You’ll waste and spend less.

Although bareboats are most popular, many companies offer crewed charters

Although bareboats are most popular, many companies offer crewed charters

Paperwork & regulations

Nothing comes without some paperwork, and that will start with the booking of the boat. You’ll need to provide your sailing resume (some companies provide an online form to complete) and a crew list with names, ages and passport information. Next, you’ll need to either waive or complete the provisioning form. You’ll also need to complete insurance waivers and arrival information.

During the chart briefing, be sure to ask about mooring fields—where they are, how much they charge and if they’re necessary. For example, Maho Bay on the island of St. John in the U.S. Virgins is a marine park where you can’t anchor. Moorings run about $20 per night, but if you skip payment and get caught, you can be charged a hefty $5,000 fine.

If you plan to sail between the U.S. and British Virgin Islands, you’ll need to check-in and out of both countries. For example, you’ll have to check into St. John in Cruz Bay after checking out of the BVI in Soper’s Hole. Before you do so be sure to also get the charter company’s permission to take their boat “out of the country.” Repeat on the way back. In cases when you’ll visit for less than 24 hours, you can check-in and out simultaneously.

Some ports make easy work of the process, but at others, you may spend an hour watching three people (sitting within five feet of one another) make a dramatic show of officialdom. Be sure to budget time and money (sometimes $100 or more based on vessel size and number of crew). Refer to the cruising guide for smaller customs offices that aren’t crowded and are staffed by personnel who work with bareboats frequently.

Prepare paperwork ahead of time. You’ll need ship’s registration papers, crew passports and previous check-in and checkout documents. You may want to create a comprehensive crew list and ask the base to make you a dozen copies. Also, don’t forget to purchase any necessary cruising and/or national park permits. Finally, bring cash just in case. Some of the offices don’t have copy machines, much less the ability to run a credit card.

Its views like this one from St.John that  keep people coming back to the Virgins

Its views like this one from St.John that keep people coming back to the Virgins

Setting an itinerary

Charter companies typically offer outlines of seven- and 14-day itineraries online, and you’ll get more advice during your chart briefing on site. There may be no-go zones. Anegada in the BVI, for example, used to be off-limits to charter boats, at least in poor weather. Today, the passage is well marked, so most companies don’t ask charterers to check-in before sailing to that island.

If your crew has particular requests, like going diving or fishing, ask the local experts for the best spots. Make a general plan, but be prepared to deviate from it if the weather necessitates it, your crew becomes seasick or you want to spend extra time in a place.

Gauge the group. Nature lovers may want to visit Culebra National Wildlife Refuge in the Spanish Virgins while party-goers will love the Soggy Dollar Bar and Foxy’s in the BVI. Kids will love the caves of the Baths on Virgin Gorda. Shoppers may enjoy Skinny Legs shops on St. John.

And whatever you do, don’t over-plan your itinerary and plan to take each day as it comes. Sailboats are slow, winds don’t blow and rushing makes a lousy vacation. “Plan to be flexible,” says Dan Lockyer, general manager of Dream Yacht Charter. “Do not set yourself rigid itinerary plans. You may find a hidden gem you had not expected.”

Getting there

The British, U.S. and Spanish Virgins are all part of the Leeward Islands, the closest to the continental United States, so getting there is a matter of only one or two flights. Flying to San Juan airport in Puerto Rico for a Spanish Virgins charter is easy, and you don’t even need a passport. The U.S. Virgins are easily accessed via St. Thomas, where you don’t need a passport there either. For the British Virgins, you’ll need a passport, but you can fly directly to Tortola (the large island where most of the charter companies are based). However, flights from mainland U.S. tend to be expensive. If you have time, it’s usually considerably cheaper to fly to St. Thomas and take the ferry to Tortola for around $70-100 per person round trip.

Extraneous costs

There’s more to vacation spending than airfare, boat cost and provisioning. Little things add up, so make room in your budget, which will vary by location, company, size/type/age of boat, length of charter, number of people and time of year.

Chartering over popular holidays like Christmas, New Years, Easter and spring break can get pricey. For travel, scope out best fares on Google Flights or Kayak and check out Priceline for hotel deals.

You may be able to get travel insurance through most of the larger charter companies, which will be a lifesaver in case of an emergency or if the weather becomes an issue. Additional protection can be purchased via TravelGuard, Travelex, Access America and CSA Travel, to name a few. You’ll need to purchase the policy well in advance, but sometimes as late as 24 hours before a storm is named. Depending on the policy, you can recoup the cost of the charter, accommodations and/or travel.

Budget for taxis, rental cars, diving and shore side excursions. Expensive boat add-ons include toys like kayaks, SUPs and coolers that are charged by the day and therefore paid by the week. Some companies offer onboard Wi-Fi routers, but they’re not free either so compare the cost against a carrier plan on your phone.

If your experience is light, you may need to take a local captain at least for a day, which will add another couple of hundred dollars. Marinas will further increase your berthing as will moorings, and you may have to pay to take on more freshwater. Finally, don’t forget fuel, which is expensive in the islands. If you motor rather than sail and run the genset all night for A/C, get your VISA card ready.

Take the plunge

Challenges and costs aside, the various groups of the Virgin Islands are still great chartering destinations for newbies and old salts alike. The distances are short, the charter companies are many, and the navigation is predominantly line-of-sight. The lovely breezes are fairly steady so the sailing is mostly laid back, and the weather will surely beat the gray skies back home. 

October 2019



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