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Chartering Off-season in the Caribbean

Contrary to perceived wisdom, the Caribbean can be a delightful place to charter in the summer. It’s true that yearnings for sun-kissed isles and turquoise waters tend to be strongest in the winter, but a mid-year Eastern Caribbean cruise has many benefits and may just become your best-ever charter.


Hurricane season is technically from June 1 to November 30, and the mere thought of a tropical storm has many crossing the Caribbean off their list during that time. But risk and reward come in inverse proportions, and those risks that can be mitigated are worth taking because the rewards are big and plentiful.

Five Reasons Why Summer can be Better Peace and quiet: The difference between high and low season, especially in the popular British Virgin Islands, is night and day. Open anchorages, available moorings and bars with free tables will be your reward in the summer. In fact, you may only encounter 20 percent of the usual traffic. Getting away from it all takes on a whole new meaning when the best snorkel spots are nearly private and the only footprints on a sandy beach are your own.

Besides other charter boats, you’ll also avoid most of the long-term cruisers, who ship out due to insurance policy rules. That makes an especially big difference, for example, when chartering in the Sea of Abaco. There, cruisers pay for moorings a month at a time in Hope Town, effectively calling “dibs,” whether they use them or not. (They’re often guarded with unbelievable ardor, as I noted on my last charter vacation.) Not one to duke it out over a mooring or even a bar stool, I find grabbing a Painkiller at the Soggy Dollar Bar on Jost Van Dyke or swimming with turtles in the Tobago Cays is always nicer without a crowd.

Good value: If it’s a bargain you seek, you’ll hardly do better than heading south for the summer. Not only are you more likely to get the boat model you prefer, you’ll also be able to shift vacation funds from charter boats and landside accommodations to souvenirs and nice dinners.

Depending on when, where and with whom you charter, savings of 10 percent to 60 percent are possible. Upgrades to newer and bigger boats are more likely and some charter companies, like Dream Yacht and CYOA will offer extra days (like 10 days for the price of seven) so you can sail longer during low or shoulder seasons at no extra cost. Others, like Sunsail and The Moorings, offer shorter charters for quick getaways (perhaps only five nights) that aren’t available during the busy season. Even some crewed charters offer savings up to $1,000.

More time: The kids are out of school, so quality family time is in order, taking advantage of the above bargains like extra sailing days. Also, smaller crowds will have you enjoying more time in each anchorage you visit. In the islands, you won’t be elbow-to-elbow with summer vacationers like those crowding the campgrounds and anchorages back home.


Weather: Summer in the Caribbean for better weather? Are you mad? Not really. Average temperatures in the BVI are 72° to 83° F in the winter and 77°to 88° F in the summer. To that small difference, add a nearly constant breeze and refreshing water, and the islands may be more comfortable than a scorching muggy July in the Midwest or along the Eastern Seaboard. If 88° F is too high and diving in to cool off isn’t an option, consider getting a boat with a genset and some good A/C.

Better sea state: Winter can be windy in the Bahamas and throughout the Caribbean, with breezes in excess of 20 knots daily. By comparison, winds in the summer are typically 10-15 knots, and that means smaller seas as well. When chartering with newbies or those prone to seasickness, this will be a blessing.

Also, winter storms in the North Atlantic set up a ground swell that sometimes makes anchorages open to the north untenable, which in turn can cut out some very scenic overnight spots. “These calmer conditions also make some of the longer sails easier, which expands the available cruising grounds,” says Jay Pennington of CYOA Charters. “Southerly breezes and calmer seas make passages to Culebra, Vieques and Western Puerto Rico as well as St Croix easier and more enjoyable.”

Finally, lighter winds are perfect for chartering power cats that are gaining ground with companies like Marine Max Vacations and The Moorings. Power cats are comfortable and especially fast, so you can cover lots of territory regardless of the direction or strength of the breeze. (Shhh, we won’t tell.)

The When, Where and How

Although Mother Nature can be unpredictable, trying something new may lead to your most memorable vacation. Here are some tips to help you navigate a summer charter. 

When: To some degree, the “when” of chartering has more to do with the mindset of the public than with the reality of the cruising grounds. That said, while hurricane season is technically from June to November, historically, June and November have been almost devoid of hurricanes and June and July combined typically see less than one named storm per year in the Eastern Caribbean. (Tropical depressions generally get a number first and a name if they develop sustained winds of approximately 34 knots or more.)

“The quietest seasons in the Caribbean would be August and September,” says Jennifer Richardson of The Moorings. “Of course, that’s also when there is the highest likelihood of a storm. In general, I wouldn’t hesitate to charter in the Caribbean with the exception of mid-August to mid-October. Of course, months out, you can’t predict a hurricane any more than you can a blizzard. Both consume a relatively short amount of time with glorious weather on either side.

“Delays or cancellations due to severe tropical disturbances are very rare,” she adds.

Ian Pedersen of The Moorings agrees, noting it is often possible to adjust plans to suit the weather. “Rescheduling and shifting dates by a few days here or there—pending boat availability, flight availability and the flexibility of our guests and their vacation time—is quite common during these months,” he says.

Another big plus is summer carnivals, craft and music festivals, fishing tournaments and regattas that most tourists never witness. Per Horizon Yacht Charters with bases in Grenada, Antigua and BVI, lots of businesses stay open during these times so there’s more to do ashore. Keep in mind that some shoreside facilities are closed during the riskiest two months.

“Most of the restaurants and bars start reopening around October 15,” says Cindy Chestnut of Conch Charters.


Plenty of space in St. Lucia’s historic Rodney Bay

Where: Historically, early-season hurricanes (June and July) have often reached farther west into the Gulf of Mexico, making Belize more susceptible to early storm troubles when the Eastern Caribbean fares better. But by late summer, the likelihood of a major storm in the Caribbean Sea increases. When and where go hand-in-hand during a low-season charter, but careful planning means there’s no reason to skip Antigua, St. Thomas, Guadeloupe or St. Martin over the Fourth of July. Many companies like Sail Caribe, Dream Yacht and The Moorings are also opening up new bases in Puerto Rico to cruise the Spanish Virgins, which are close to home and an easy last-minute escape without the need for a passport.

Additionally, some islands are considered “below the belt” and therefore a safer bet to avoid a hurricane. One school of thought is that anything below 12 degrees north latitude is unlikely to be hit by a tropical storm at any time—though apparently, no one told that to hurricane Ivan when it stomped across Grenada in 2004, doing major damage and surprising a few cruisers who made the island their hurricane home.

The ABC islands of Aruba, Bonaire and Curacao are also known as safe havens in the Caribbean, but while these islands are great for a land-based vacation, there are no large-scale bareboat charter companies there.

“The Windward Islands (St. Lucia to Grenada) are considered the least susceptible to inclement weather,” says Richardson. Numerous bareboat charter companies, as well as luxury crewed charters, operate out of Grenada, reaching up into St. Vincent and the Grenadines.

Virgin Gorda

In summer, you likely won’t have to compete for a mooring at the Baths on Virgin Gorda

How: travel insurance offers the ultimate protection, and most larger charter companies offer inclement-weather policies. Additional protection can be purchased via TravelGuard, Travelex, Access America or CSA Travel, to name just a few. “We strongly recommend that everyone coming down between mid-August and mid-October gets travel insurance for hurricanes,” says Chestnut.

Familiarize yourself with the policy so you know under what conditions coverage becomes available. You will need to purchase the policy in advance but can sometimes purchase a policy as late as 24 hours before a storm is named. Depending on the policy, you can recoup the cost of the charter, accommodations and travel.

Other tips include keeping more cash on hand during a summer charter. If a storm does hit and the power goes out, ATMs will be inoperable. Also, travel light so you don’t have to check your luggage and be separated from your toothbrush and fresh skivvies.

Finally, keep an eye on the weather before you go and once you cast off. Charter companies will be anxious about their assets, so most assuredly they will be keeping track of you and their boat as well. However,a good weather app still helps me sleep better at night.

Normally, a six-month season will produce eight to 14 named storms, half of which may develop into hurricanes. Only 31 storms have reached Category 5 status in recent history, but that will come as little solace to anyone in the path of a slow-moving, water-logged monster.

That said, consider these statistics on how often a given area is likely to see a hurricane of any strength: the Bahamas, once every 5.5 years, St. Maarten once every 6.5 years, the BVI once every 8 years, Puerto Rico once every 13 years. Islands farther south are typically hit only once every 20-30 years.

Yes, it’s a bit like Vegas, but unlike at a casino, the odds are stacked in your favor. So stop thinking like the other guys (or your aunt) and book what could become the summer charter that you and everyone else will remember as one of the best you’ve ever had.


In the summer, you may actually be lucky enough to get a mooring in Hope Town Harbour in the Bahamas

Caribbean Charter Companies

Barefoot Yacht Charters,

BVI Yacht Charters,

Conch Charters,

CYOA Yacht Charters,

Dream Yacht Charters,


Horizon Yacht Charters,


Sail Caribe,


The Moorings,

TMM Yacht Charters,


March 2017



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