Planning Your Lux Caribbean Retreat on a Budget


It helps you keep track of what you’re spending and identify places to make easy savings. It also leaves you with a lot left over for the finer things in life.

Follow these basic tips to keep your costs down while planning your luxury Caribbean vacation.

Pick a Less Famous Destination

Everyone is familiar with the Caribbean titans of Montego Bay, Havana, Turks and Caicos, and Grand Cayman. If you’re willing to branch out to newer and less traveled destinations you can see significant savings.

You can find some gorgeous 5-star resorts, luxury villas, and overwater bungalows all over the Caribbean and Latin America. By staying away from the most famous destinations you avoid crowds and can score a real bargain.

Some great islands to check out include:

  • Tobago
  • Water Island in the U.S. Virgin Islands
  • Guadeloupe Island
  • Curacao

These all offer beautiful white sand beaches and luxury accommodations. In many cases, you can see significant savings over more well-known islands.

Travel Off-Season

Probably the best way to save money on any travel is to avoid the high season. For the Caribbean, that’s going to be from mid-December to mid-April.

If you’re willing to go during the summer especially you can see serious savings. A good thing to keep in mind though is that it will be hot. Like really, really hot.

Summer in the tropics can be a major change if you’re used to a temperate climate. It will be very humid. Another thing to remember is the dates of hurricane season. You don’t want a storm to ruin your week.

Make sure to purchase travel insurance that covers trip delays and interruptions related to weather. This will protect your expenditures in case of a hurricane.

Find the Cheapest Flights

A major expense when traveling internationally is airfare. This is especially true if you’re planning to fly business or first class.

Check out deal sites like Secret Flying or The Points Guy to get a lead on airline sales. Many major carriers will offer flash sales, miles redemption bonuses, and other discounts for great flights.

If you’re a frequent flyer, you’re no doubt familiar with the various airline and credit card loyalty programs. They offer one of the best ways to use your business expenses and corporate travel to pay for your luxury retreats.

Depending on your tolerance for flying economy you can see significant savings by bidding on an upgrade. Most full fare American carriers have a system in place for this. As long as you buy a standard ticket you can bid for business or first class seats. In some cases you can score an awesome seat for 50% or less of MSRP.

Plan Your Accommodations Carefully

If you’ve always booked your room or villa straight through the hotel, you’ve probably been overpaying. Sites like Luxury Retreats or Airbnb can offer substantial savings off hotel prices.

Airbnb is the undisputed king of the room share economy. They have a massive selection of rooms and homes to rent all over the world. They’ll have availability pretty much anywhere you want to travel, but they generally cater more towards budget travelers.

Luxury Retreats is for when you want to travel in style. They offer some of the finest and most exclusive waterfront villas, over water bungalows, and 5-star suites in the world. You can limit your search to specific islands, regions, or the entirety of an area. It’s a great way to book luxury accommodations for large groups too.

Many of the finest villas will sleep 10-20 guests. This is great for a partner’s retreat, buyout celebration, or to bring the whole family down just to show off a little.

Because you aren’t dealing directly with hotel management you can often see serious savings. This frees up the rest of your budget for sword fishing charters, massages, dive trips, and any other kind of adventure you can think of.

Remember to Relax

A luxury trip to the Caribbean should be a time for rest and relaxation. Bask in the sun outside your villa, or enjoy a waterfront massage by the infinity pool. Make sure you always budget in some money to blow on whatever. There’s nothing quite as fun as splurging on yourself in paradise.


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