Five myths about high season in the Caribbean

For many travelers, a winter vacation in the Caribbean is the very definition of paradise. But given the cost of airfares and lodging, it seems like an impossible dream for many of us. Or is it? Here are five myths about high-season Caribbean vacations.

1. You can never find decent airfares to the Caribbean in winter.

Lower fares do exist to the Caribbean in winter, but finding them depends on when — and where — you fly.

“As long as you don’t travel during school break peak travel days, fares to the Caribbean are much lower than they were 10 or 15 years ago,” says George Hobica, president of Airfarewatchdog. Hobica says that’s because many more airlines now fly to the islands from the United States and more airlines are on the way. He notes that “JetBlue has added routes, and Spirit Airlines, despite its high fee structure, is keeping the competition on its toes.”

Hobica says that prime days to avoid flying to the Caribbean this winter are Jan. 13 ,14, 17 and 24; Feb. 8,9, 15, 16, 21 through 23 and the Easter holiday period. The other sage bit of advice he offers is to choose your island hub with care.

“Some islands are more expensive than others,” Hobica says, “but if you fly into San Juan, Nassau or St. Thomas it’s often cheaper to examine separate fares on airlines like Winair or Bahamasair to go onward. Just leave plenty of time for connections.”

This two-airline strategy can pay off. For example, Hobica says that the lowest fare he found using a search on Kayak.com for flights from JFK to St. Barts in January was a $1,300 round-trip fare. But he also turned up non-stops from JFK to St. Martin for under $400 on American and then a non-stop flight from St Martin to St. Barts on Winair for $171 round-trip, a big savings indeed.

2. Hotels are just too expensive in the Caribbean in winter.

Look past the allure of five star properties and you’ll find hotels for all budgets in the Caribbean. Places like Jakes Treasure Beach Hotel on Jamaica, owned by Jason Henzell, son of filmmaker Perry Henzell, who made the legendary reggae movie, The Harder They Come. “My father was in the film business and my mother was an artist and they always wanted Jakes to remain affordable to travelers and creative types from all walks of life,” Henzell says. With a style that’s more beach bum than boutique, Jakes is rustic, off the beaten path and has rooms that start at just $95 a night.

For those who want a more conventional property, Lisa Leavitt of ActiveTravels.com, a Newton, Mass.-based boutique travel agency, says that “We have the best luck at more familiar outposts like Turks and Caicos, which offer a variety of lodging for all budgets. Our clients love the reasonably priced Sibonne Beach Hotel on the pearly white sands of Grace Bay Beach.”

Then there are package deals. Hobica says that “If you’re planning a last-minute trip, you can save a lot of money with a package deal since packages use fares that don’t carry a last-minute booking penalty.”

As an example, he found an all-inclusive, four-night package on JetBlue from New York to Puerto Plata, in the Dominican Republic, at the Gran Ventana Resort with just a few days’ advance purchase. The price was $862 per person including flights, at a time when last-minute flights alone were going for $702 round-trip.

“It doesn’t take a math genius to figure out that it’s a steal.” Hobica says.

3. Even all-inclusives are too pricey in high season.

Bob Beukema, president of Le Grande Tour, a Tripology Agency in Richmond, Va., states that “I certainly believe that if clients are traveling in high season to the Caribbean, and plan on eating and drinking well, that they’ll do much better financially with an all-inclusive resort where there are multiple restaurants, drinks and wine, as well as non-motorized water activities included.”

Beukema compared two top resorts in Ocho Rios, Jamaica, during the week of March 7 to 14. The Jamaica Inn is a five-star hotel and one week in a superior category room starts at $4,000 per room. They offer free airport transfers but since it’s on the European plan, there are no meals included. By comparison, he points to Sandals Grande Riviera, a five star all-inclusive. The starting rate of $3,500 per week includes all meals, unlimited premium liquors, unlimited Beringer wines, transfers and non-motorized water sports.

“The all-inclusive resort is less expensive than the European plan resort even before meals and drinks are included,” he notes.

4. We want to travel with friends and family and it’s just too expensive to rent a bunch of hotel rooms.

Forget a hotel and consider renting a villa. Companies like WIMCO and VRBO offer hundreds of private homes for rent throughout the islands. While the upfront price can seem high, once it’s costed out per person it’s often a far better deal than any hotel could ever offer. That’s especially true for high-end villa properties like Villa Aquamare, a private waterfront compound with three villas on the shores of Virgin Gorda in the British Virgin Islands. Each villa is 8,000 square feet and has five master suites and its own infinity pool, making it a prime and private getaway for celebrities. The $23,500 price tag for nine nights might seem steep. But that costs out to $2,611 a night. Divided among 10 people, it comes to $261 per person, per night. It’s five-star luxury but at a more manageable price.

5. I’d love to go on a Caribbean cruise but high season means high prices.

Not according to Linda Boyce, a Tripology agent with CandL Travels in Brooklyn, who says that “winter cruises are a great way to escape the cold wintry season and there are some deep values to be found on them.”

Boyce suggests looking at Carnival’s four-day cruises from Miami during the month of January with a starting rate of just $149, pointing out that “the same cruise in April is listed from $369.”

Another example she offers is from Royal Caribbean, which has a five-night cruise from Fort Lauderdale with a starting rate of $199, which jumps up to $314 in April. At these prices, it might be cheaper to travel to the sun this winter than to stay home.