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9 amazing places to use points for a trip to the Caribbean

Nov. 07, 2020
20 min read
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If the winter blues already have you feeling down, a getaway to a sunny Caribbean island might sound good about now. Many Caribbean islands are open to American tourists and some have even been declared COVID-free.

We’ve recently seen some incredible sales on both paid flights and award tickets to the Caribbean from various U.S. cities on several airlines. Still, there are also plenty of savvy strategies for using points and miles to fly there any time of year. Dozens of destinations have multiple points hotels to choose from, too, including fun-filled family resorts, budget-friendly all-inclusives and over-the-top luxury hideaways.

Here are nine of our favorite places for a carefree Caribbean vacation and tips for how you can use points and miles to travel there.

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Grand Cayman

Grand Cayman is one of our favorite picks for a Caribbean vacation, thanks to excellent hotels, phenomenal dive sites and friendly locals. While flights and hotel nights tend to be expensive, the good news is that Grand Cayman is actually a relative bargain if you have points and miles to redeem. The bad news? Only travelers who are dual citizens, own property in the Cayman Islands or relocating for a long-term work arrangement are allowed to visit.

The Cayman Islands. (Photo by Westend61/Getty Images.)

Flying there

Flights to Grand Cayman (GCM) tend to be expensive (with the exception of rare deals). The destination has one saving grace, though — it’s a relatively short flight from several major U.S. gateways. That means you might be able to find some mileage deals using British Airways Avios to fly American Airlines since British Airways' award chart is distance-based. Don’t have BA Avios? You can transfer points from American Express Membership Rewards, Chase Ultimate Rewards and Marriott Bonvoy.

Flying from Miami (MIA) to Grand Cayman, for example, requires just 7,500 Avios each way. And Dallas (DFW) to Grand Cayman is just 11,000 Avios.

American will charge you between 10,000 and 15,000 AAdvantage miles each way to fly its own flights.

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Related: How to earn British Airways Avios in time for the 50% award sale

Where to stay

Grand Cayman is small, so there aren’t too many points hotels, but there are still some fantastic properties to choose from.

Topping the list, The Points Guy himself once called the Ritz-Carlton in Grand Cayman “easily one of the best points hotels in the Caribbean.” Not only are the rooms luxurious, but there are two expansive pools, a beautiful beachfront, several restaurants and bars and a La Prairie Spa. While paid room rates start at $1,087 this winter, you can book awards for 100,000 points per night.

(Screenshot courtesy of

That’s very steep, but the Marriott Bonvoy Brilliant® American Express® Card is currently offering a bonus of up to 125,000 Marriott Bonvoy points: 100,000 bonus points after you spend $5,000 in purchases on your new card in your first three months. Plus, earn an additional 25,000 bonus points after your first anniversary of card membership. The Marriott Bonvoy Boundless Credit Card is offering 125,000 bonus points + 1 free night (valued up to 50,000 points) after you spend $5,000 in the first three months from account opening (total of up to 175,000 bonus points).

Alternatively, the Westin Grand Cayman Seven Mile Beach Resort and Spa costs just 60,000 Marriott Bonvoy points per night, or around $569 if you paid in cash.

For IHG Rewards Club loyalists, the Kimpton Seafire Resort and Spa is another top choice, thanks to its beautiful beach, spacious rooms and great service. Paid rates can cost well over $800 this winter, but there are plentiful award nights available for 70,000 points.


With long, sandy beaches, gentle currents and weather that is practically perfect all year round, Aruba is one of the Caribbean’s most family-friendly destinations with plenty of points hotels to choose from, including one with its own private island.

Palm Beach on the island of Aruba. (Photo by VW Pics/Getty Images.)

Flying there

The major U.S. airlines all fly to Aruba (AUA), so how you get there will really just depend on the type of miles you collect. Here are two options, though.

Delta flies to Aruba nonstop from Atlanta (ATL), Boston (BOS), Minneapolis (MSP) and New York-JFK. While flash sales — like one as low as 22,000 miles plus $85 round-trip — are rare, you can sometimes even beat that price if you’re willing to fly in basic economy. Remember, you can transfer Amex Membership Rewards points to your Delta SkyMiles account.

Related: The best credit cards for Delta flyers

We’ve also seen some amazing JetBlue Mint fares as low as $300 each way, or 20,400 JetBlue TrueBlue points from Boston (BOS) and New York-JFK, though these are also rare. Paid fares in economy round-trip from Boston seem to start at around $450 this winter, or 33,800 points plus $85. JetBlue is a transfer partner of Amex, Chase and Citi.

(Screenshot courtesy of

Where to stay

If you have Marriott Bonvoy points, you’re in luck. There are several wonderful hotels that are part of the program in Aruba. The top contender is probably the Ritz-Carlton, Aruba, where rooms start at 85,000 points or a whopping $803 this winter.

Though that’s a great redemption, you could instead spend just 40,000 points (or $531) per night at the Aruba Marriott Resort & Stellaris Casino, or 60,000 points per night at either the Renaissance Aruba Resort and Casino instead of $430 (where you can also hang out on a private island for the day). Remember, when you book four award nights at Marriott, you get the fifth night free, which is a handy 20% bonus.

Related: Maximizing redemptions with Marriott Bonvoy

The Hyatt Regency Aruba Resort Spa and Casino is offering rooms in January for around $670 or 25,000 points per night. With the current welcome offer on the World of Hyatt Credit Card, you could cover two nights after meeting tiered minimum spending requirements (30,000 Bonus Points after spending $3,000 on purchases within the first 3 months from account opening. Plus, up to 30,000 more Bonus Points by earning 2 Bonus Points total per $1 spend on purchases that normally earn 1 Bonus Point, on up to $15,000 in the first six months of account opening.)

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The Hilton Aruba Caribbean Resort & Casino has rooms available for 80,000 points or $572 per night.

Puerto Rico

After the devastation of Hurricane Maria in 2017, Puerto Rico has bounced back quickly and strongly, and there’s never been a better time to visit. All you need is a negative PCR test taken within 72 hours of arrival.

Old San Juan City Walls in Puerto Rico. (Photo by Maremagnum/Getty Images.)

Flying there

San Juan (SJU) is such a major hub for the Caribbean that how you fly there will really just depend on which airlines you tend to fly the most. We’ve seen some incredible deals, including East Coast flights for as little as $128 round-trip and from other parts of the country for around $200. With ticket prices as low as this, you might want to forgo traditional award searches and just book paid tickets using rewards like Chase Ultimate Rewards.

For instance, if you have the Chase Sapphire Reserve, your points are worth 1.5 cents apiece when redeemed for travel directly through the Ultimate Rewards portal. So, if you were to find a cheap fare on JetBlue like this one, you’d only need around 14,000 points round-trip.

Where to stay

Puerto Rico is about the size of the Big Island of Hawaii, so there are dozens of points hotels ranging from budget hideaways to over-the-top luxury resorts. Where you stay, then, will be based on your points accounts and what kind of experience you prefer.

To focus on the luxury offerings, the St. Regis Bahia Beach Resort is back and better than ever, with rooms for 85,000 points or $734 per night.

(Screenshot courtesy of

The Hyatt Regency Grand Reserve Puerto Rico is a relative bargain at just 12,000 points per night. Meanwhile, the stately InterContinental San Juan has rooms for just 50,000 points.

The Wyndham Grand Rio Mar Puerto Rico Golf & Beach Resort has rooms for $213 or 30,000 Wyndham Rewards points per night.

St. Kitts

Its tonier neighbor, Nevis, is home to luxury hotels like the Four Seasons, where you can maximize Amex’s Fine Hotels & Resorts benefits if you have either The Platinum Card® from American Express ($695 annual fee, see rates and fees) or The Business Platinum Card® from American Express; $595 annual fee ($695 if application is received on or after 01/13/2022) (see rates and fees). However, low-key St. Kitts is fast becoming a destination in its own right.

St. Kitts Island. (Photo by Danita Delimont/Getty Images.)

Flying there

Flights to this small Caribbean island tend to be expensive, starting around $500 round-trip in economy from most East Coast gateways, and closer to the $800 mark from other parts of the country.

This is another good place to redeem British Airways Avios for American Airlines flights, though, since flights in each direction from the airline’s hubs in Miami and New York-JFK are just 11,000 Avios.

Related: The best ways to earn British Airways Avios

United also has some availability on its nonstop from Newark (EWR) for 19,000 miles each way. The airline’s MileagePlus program is a Chase Ultimate Rewards transfer partner.

Where to stay

We’ll keep it simple. There are three properties where you might want to put your points to use for a St. Kitts vacation. Far and away, the nicest is the Park Hyatt St. Kitts Christophe Harbour. It has just 78 rooms and 48 suites total, but award nights are readily available. This winter, you can find rooms for $612 or 30,000 points per night.

Barring that, you can also book the mid-range St. Kitt’s Marriott Resort & The Royal Beach Casino for 30,000 to 40,000 points per night, or the Marriott St. Kitt’s Beach Club for $224, or 50,000 points per night.


With phenomenal surfing, interesting cultural activities and gorgeous beaches, Barbados is a sun seeker’s paradise. Travelers must produce a negative COVID-19 PCR test within 72 hours of departure.

Bottom Bay in Barbados. (Photo by TommL/Getty Images.)

Flying there

There are several excellent options for award flights, but the two best ones are probably American Airlines from either Charlotte (CLT) or Miami (MIA), or JetBlue from Boston (BOS), New York-JFK or Fort Lauderdale (FLL) since awards are plentiful on both carriers.

American AAdvantage will charge you 30,000 miles round-trip from either of its hubs, while British Airways requires just 26,000 Avios round-trip from Charlotte and 22,000 from Miami.

JetBlue is offering tickets from about 7,900 points one-way from New York-JFK to Barbados, plus taxes and fees throughout the winter.

Where to stay

There aren’t too many points resorts to choose from, but you can still consider the following ones. The Hilton Barbados Resort near Bridgetown has rooms starting at $485 or 70,000 points per night this winter.

The Radisson Aquatica Resort Barbados is more of a budget option with rooms for $170 or 50,000 points per night.


This interesting isle — equal parts windswept, balmy beaches and colorful, colonial charm — is so far south that it’s almost part of South America. Curacao is opening to select American tourists in November. The catch? Only residents of Connecticut, New York and New Jersey are allowed.

Curaçao. (Photo by Westend61/Getty Images.)

Flying there

The flight options to Curaçao (CUR) are more limited than to some other Caribbean destinations, but it’s still fairly simple to book award flights there. Your best options are to redeem Avios for one of American Airlines’ two daily nonstops from Miami or to suss out some inexpensive fares on JetBlue from New York-JFK and redeem TrueBlue points for those.

Where to stay

The Curaçao Marriott Beach Resort has rates starting at $216 or 35,000 points per night, while the Renaissance Curaçao Resort and Casino has rooms for $262 or 35,000 points per night.

Related: Which Marriott Bonvoy credit card is right for you?


Just under 200 miles off the Florida coast, the Bahamas are practically part of the U.S. — and OK, this collection of islands is technically not in the Caribbean — but a trip here feels like a world away thanks to tropical beaches and fabulous resorts. Travelers headed to the Bahamas must produce a negative PCR test within five days of arrival.

Paradise Island in Nassau in the Bahamas. (Photo by Pola Damonte/Getty Images.)

Flying there

Rather than getting into the nitty-gritty here, you can check out our comprehensive post on using points and miles to fly to the Bahamas. Generally, though, if you can fly a nonstop itinerary to the Bahamas, the best way to get to Nassau on miles and points is using British Airways Avios to book tickets on American, which has plenty of routings from the East Coast, including year-round nonstop flights from Philadelphia (PHL), Miami (MIA) and Charlotte (CLT).

JetBlue offers nonstop connections to Nassau from the East Coast, including Boston, Fort Lauderdale (FLL), New York-JFK, and Orlando (MCO). Delta also has year-round, nonstop service from Atlanta (ATL) and New York-JFK and Flying Blue — the loyalty program of SkyTeam members Air France and KLM — can be used to book Delta flights to the Bahamas.

Where to stay

With the plethora of points hotels available, the only hard part about booking a stay will be deciding which hotel is right for you.

One of our favorites is the Grand Hyatt Baha Mar, which has a jaw-dropping 1,800 rooms and suites (not to mention an enormous casino). Room rates this winter start at $240 or 20,000 points per night.

Related: Your guide to maximizing redemptions with Hyatt

The British Colonial Hilton has rooms for $247 or 50,000 points.

Marriott fields four hotels in Nassau at Atlantis, but the only one that currently has points reservations available is The Cove at Atlantis, where room rates start at $499 or 60,000 points per night.


Some travelers shy away from Jamaica, but the island has some of the Caribbean’s family-friendliest resorts and best all-inclusives. All travelers must produce a negative COVD-19 PCR test within 10 days of arrival and submit a pre-travel health authorization registration.

Ricks Cafe in Jamaica. (Photo by Doug Pearson/Getty Images.)

Flying there

Think a little more offbeat for this destination. Though you’ll find plenty of options on the legacy carriers from their hubs, Montego Bay (MBJ) is also served by Spirit out of Detroit (DTW) and Fort Lauderdale; and Southwest out of various airports, including Baltimore (BWI), Chicago Midway (MDW), Houston (HOU) and Fort Lauderdale.

Where to stay

Jamaica is the place to come if you’re interested in redeeming your points for a no-brainer, all-inclusive stay, especially if you have Hyatt points to burn. Next door to one another, the family-focused Hyatt Ziva Rose Hall and the adults-only Hyatt Zilara Rose Hall both have rooms starting at under $400, or 25,000 points.

Related: The best hotel credit cards

Nearby, the 489-room, all-inclusive Hilton Rose Hall Resort & Spa is a family favorite thanks to a long, white-sand beach, a fun-filled waterpark, and nine restaurants to enjoy. Rates there start at $271 or 66,000 points this winter.

U.S. Virgin Islands

Free from the crowds that throng some of the larger Caribbean islands in winter, the U.S. Virgin Islands are the perfect playground for a serene seaside sojourn this winter. Plus, this U.S. territory made our list of the top 20 places to travel in 2020. Best of all? No passport required.

Saint John's in the U.S. Virgin Islands. (Photo by Danita Delimont/Getty Images.)

Flying there

Although flights to the USVI are limited, American Airlines, Delta and JetBlue have gone head-to-head and toe-to-toe with fare sales several times per year in the past couple of years, so you can often find flights for under $200 round-trip to St. Thomas (STT). In such cases, you might want to redeem points directly at a fixed rate through programs like Chase Ultimate Rewards. In the case of $200 airfare, you’d only need 13,334 Chase points with the Chase Sapphire Reserve (16,000 if you have the Chase Sapphire Preferred Card or Ink Business Preferred Credit Card).

Where to stay

With Marriott, your two best bets are either the Westin St. John Resort Villas, where rooms start at 55,000 points or $569 per night, or the luxurious (and just reopened) Ritz-Carlton, St. Thomas, with rooms for $665 or 85,000 points per night.

Alternatively, the Wyndham Margaritaville St. Thomas has rooms starting at $205 or just 15,000 points per night.

Have any Caribbean dream destinations, or tips, of your own to share? Leave them in the comments below.

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Featured image by Getty Images
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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