Photo: Courtesy Sailrock Resort

The dream of ultra-luxury travel remains just that for many of us. It does not, however, need to remain an inaccessible fantasy. With a bit of luck, ingenuity and a few insightful tips, you, too, can indulge in a jet-set Caribbean travel experience well beyond your usual budget. Here’s how:

’Tis the Offseason

Cold weather up north makes winter months red hot for Caribbean travel. Demand skyrockets from mid-December through the end of April. The highest demand also yields the highest prices. Airfares, hotel and resort stays, excursions and rental cars are all more expensive during the winter months.

Luxury Travel in the Caribbean - Sailrock Resort
Curtain Bluff’s outdoor patio.
Photo: Courtesy Steve Bennett/Uncommon Caribbean

Summer is a whole different story.

Resorts and hotels across the Caribbean typically drop their rates by a good 30-, 35-, even 40-percent during the warmest part of the year. These big savings aren’t just reserved for big-brand resorts. Bespoke properties like Curtain Bluff in Antigua and Sailrock Resort in South Caicos all advertise special rates and value-packed incentive offers for off-peak summer travel.


Luxury Travel in the Caribbean - Sailrock Resort

Summer Sizzles in the Caribbean

When it’s plenty warm at home in the States, why travel to the Caribbean (aside from the incredible savings)?

Well, for one thing, while summer temperatures are similar, it almost always feels cooler in the Caribbean thanks to persistent offshore tradewinds.

And summer is also a major festival season. Crop Over in Barbados, Antigua Carnival, Spice Mas in Grenada, August Monday in Anguilla and Vincy Mas in St. Vincent are but a few of the large-scale cultural celebrations that sizzle with excitement.

Off The Shoulder Savings

While the savings are big during June, July and August, they’re even better during the fall and through early December, a period known as the shoulder season. There is one major caveat to the season’s savings: hurricanes.

The shoulder season coincides with the height of hurricane activity in the Caribbean. Many of the choicest hotels and resorts close up shop. Those that remain open, however, tend to offer hurricane guarantees. Miss out on a full day of pool and beach fun because you had to shelter from a major storm? No problem. If your resort or hotel offers a comprehensive hurricane guarantee, you can return in the future to make up for lost vacation time at no charge. Other guarantees allow vacationers to change travel plans impacted by hurricanes without penalty. 

And shoulder season travel investments will deliver a bigger bang for your buck than any other time of year.

At press time, nightly rates at the exclusive all-new Saba Rock Resort in the British Virgin Islands were priced $200 below winter rates. That’s a pretty nice discount for the Caribbean’s newest private-island escape.

Luxury Travel in the Caribbean - Saba Rock Resort
Enjoy a boat ride from Saba Rock’s private island resort.
Photo: Courtesy Saba Rock Resort

Even the ultra-posh Four Seasons Nevis isn’t immune to the discounting. A “fourth night free” offer, the type usually proffered by less esteemed resorts, is included in the property’s 2022 shoulder season offers.

Villa savings are even more pronounced. Take the incredible Nevaeh Anguilla. Prices at the seaside luxury compound can reach an astounding $24,500 per night during the height of the holiday season between December 16 and January 7. During the summer and shoulder seasons, the nightly rate can be as low as $5,500.

Spread the Wealth

That price tag for a luxurious private villa still might seem out of reach at first glance. But it pays to do the math and split the cost with travel companions.

Sharing a villa that sleeps eight among four couples often yields pricing comparable to staying at a much less swanky resort. But at a villa, you don’t have to share the pool, beach, fitness center, restaurant and other amenities with hundreds, sometimes thousands, of other people.

One option is definitely better than the other, especially for those who value privacy and the quality time spent with loved ones in paradise.

Spyglass Hill in Anguilla offers a great example. This luxury four-bedroom villa crests above lively Sandy Ground, a mecca of good times, nightlife and beach fun. Offseason nightly rates here are priced at $1,350. Split among four couples, that’s just $337.50 per pair for your own private slice of heaven.

Flying on Empty

Scoring a steal of a deal on an exclusive resort or tricked-out villa is one thing. Rocking a private jet is all kinds of next level. While it may seem hard to believe, deals can be had in this rare air as well.

They’re called empty legs, though in some circles they’re better known as “deadhead” flights. These come about when a plane needs to travel from one point to another with no passengers aboard, often when a private aircraft is chartered for a one-way trip and needs to return to its home port.

Empty leg flights can yield savings of up to 75-percent off private aviation travel. That’s the good news. The not-so-good news is that you have to remain very flexible to land one of these deals. The private aircraft have places to go. If you’re lucky, you might just be able to tag along for a song.

Aviation charter brokers and aggregator sites are among the best places to search for empty leg flights. Jet Partners, for instance, maintains a robust list of opportunities throughout the Caribbean.


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