Getaway Day: 7 Strategies For Getting Upgrades At Caribbean Resorts

Photo credit: Artem Pochepetsky via Unsplash.

By Sharyn Alden 

Years ago I began to systematically visit as many Caribbean countries as I could. I stayed at resorts, and always tried to investigate how my room looked and smelled and where it was situated before even considering asking for an upgrade.

Not anymore. Now, when I book a stay at a Caribbean resort at a standard or lower rate, I’m already thinking about how I might get an upgrade.

Please understand that by “getting an upgrade,” I don’t mean, “lying to get an upgrade.” If you do that, and want to revisit a resort, your dishonesty may come back to haunt you.

So don’t tell the resort manager that it’s your birthday or anniversary if it isn’t. Don’t tell the front desk that your room is fraught with imaginary problems. And forget about talking about bugs, unless there are lots of them, or even a lizard or two. This is the Caribbean, after all.

I have asked for upgrades when an iguana shared my room in the Dominican Republic, and when I found a spider nest in a closet in Belize. Neither upgrade happened. Why? The resort was packed; there was no place to move me. But both resorts gave me an upgraded voucher for future stays. Benefits like these count unless returning to the property is absolutely out of the question, upgrade or not.

However, the outcome was different when local wildlife moved into my casita on the island of Dominica. Charming, though noisy, orange frogs appeared in the bathroom and squeaky bats found their way in through cracks in the stucco. It was too chummy for me. I got a very nice room upgrade the same day I brought up the intrusions.

There are no magic formulas for getting a room upgrade in the Caribbean, especially during the Christmas-through-April peak season.

But there are some upgrade strategies you can try no matter when you’re heading to a Caribbean resort. Often it’s all about inventory. If a property has several empty extra rooms and doesn’t want to lose your business, they may give you an upgrade.

If you’re looking to upgrade, try these strategies:

  • Be a favored traveler. Join a frequent flyer, hotel or resort program. If you’re looking for a Caribbean resort upgrade, it usually helps if you’re a member of the club.
  • Ask for a legitimate upgrade. It sounds simple and it is. When booking, tell the front desk or hotel manager you’ve chosen their property because you’re celebrating a special occasion and you’d appreciate an upgrade. This may or may not work, depending on how filled the resort is. For instance, when checking into a Virgin Islands resort I mentioned that my parents had stayed at the same resort many times over a period of 15 years, and I described several things we enjoyed about the property. I got an upgrade – despite the fact that the current staff didn’t know my family.
  • Use miles for an upgrade. Sometimes travelers forget about using airline miles for hotel upgrades. That may be an option if you buy a fly-and-stay package.
  • Book at times when most kids are in schoolResorts may be more flexible to upgrades when they aren’t expecting waves of families or students on high-school or college breaks. (Tip: If you want a quiet getaway, don’t go to a Caribbean resort that’s expecting a large number of school-break guests. If you’re concerned about this, call and ask before you book. I wish I’d asked that question before choosing a resort in San Juan. It was a nightmare experience with college kids partying around the clock, and no extra rooms (upgrade or not) were available to move me away from the noise.)
  • Look for package deals. Some all-inclusive resorts and websites that bundle airfare with hotels and resorts may automatically give you a better deal than if you were booking each piece of your travel individually. Study the itinerary, connections and details before booking to make sure the deal works for you.
  • Arrive late at the resort. This is a gamble, and I wouldn’t try it throughout the Caribbean or at small resorts with limited rooms. At larger resorts, if you arrive near their cut-off time to charge your credit card for the night, they might upgrade you if you ask. Late in the day they usually know how many open rooms they have that night, and they may be able to upgrade you.
  • Dress nicely, be polite and patient. When you inspect your room and find it’s not what you expect—it’s facing a pool or a garden and not the ocean you expected, if you appear nicely (that doesn’t mean expensively) dressed, cool-headed and in control of your temper, you may have a better shot at an upgrade. If it’s a “no,” don’t threaten to give the resort a bad name on social media.

In a survey last year, Consumer Reports found that only 28 percent of survey respondents tried bargaining for a better hotel rate – but 78 percent of the hagglers gained an upgrade or a lower rate. Interestingly, people who called the hotel direct were more successful than those who asked for an upgrade or lower rate in person.

One last tip: Regardless of your upgrade strategies, protect your trip with travel insurance from BHTP. It’ll cover you for everything from bad bug bites to weather-related interruptions.

Sharyn Alden is a long-time travel writer with a media-relations business, Sharyn Alden Communications, Inc., based in Madison, Wis. Contact her at