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

Jan 7, 2020

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If the winter blues already have you feeling down, now might be just the perfect moment to plan a getaway to a sunny Caribbean island.

We’ve recently seen some incredible sales on both paid flights as well as on award tickets to the Caribbean from various U.S. cities on several airlines, but 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 Cayman Islands. (Photo by Westend61/Getty Images)
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.

Southwest flies to Grand Cayman, but you’ll have to connect in Fort Lauderdale (FLL). You can transfer Chase Ultimate Rewards to Southwest Rapid Rewards or consider opening a Southwest credit card such as the Southwest Rapid Rewards Premier Credit Card to stock up on points. Round-trip awards start at 7,020 points and $90 in taxes and fees.

Related: The best Southwest Airlines credit cards

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 $587 this winter, you can book awards for 85,000 points per night. That’s a little steep, but the Marriott Bonvoy Brilliant is currently offering 75,000 points after spending $3,000 in the first three months of account opening. The Marriott Bonvoy Boundless is offering 100,000 Bonus Points after you spend $5,000 on purchases in the first 3 months from account opening.

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 there are 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)
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 25,300 points plus $85. JetBlue is a transfer partner of Amex, Chase, Citi and Capital One.

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 are start at 60,000 points … or a whopping $1,067 this winter. Though that’s a great deal, you could instead spend just 50,000 points (or $616) per night at the Aruba Marriott Resort & Stellaris Casino, or 35,000 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), or the new Courtyard Aruba Resort. 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 currently offering rooms for around $490 or 25,000 points per night. With the current welcome offer on the World of Hyatt Credit Card, you could earn enough points for two nights after meeting tiered minimum spending requirements.

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.

Old San Juan City Walls in Puerto Rico. (Photo by Maremagnum/Getty Images)
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 Capital One miles or Chase Ultimate Rewards.

Related: To transfer or not to transfer: What to do with Capital One miles

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 of course 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 $793 per night.

The Resort at Coco Beach is newly affiliated with Hyatt, and a relative bargain at just $272 or 12,000 points per night.

Within Hilton’s Curio Collection of unique properties, the El San Juan Hotel has rooms for $379 or 70,000 points.

Related: How to choose the best Hilton credit card for you

Nearby, the stately InterContinental San Juan has rooms from $417 or 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

Although 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 The Platinum Card® from American Express ($550 annual fee, see rates and fees) or The Business Platinum Card® from American Express ($595 annual fee, see rates and fees) low-key St. Kitts is fast becoming a destination in its own right.

Saint Kitts Island. (Photo by Danita Delimont/Getty Images)
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 twice-weekly 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 despite those numbers, 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.

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

Curaçao. (Photo by Westend61/Getty Images)
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.

And, hey, since this is a former Dutch colony, you might even be able to find some Flying Blue Promo Awards on KLM’s nonstop from Amsterdam (AMS).

Where to stay

Within Marriott, 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.

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

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

If you have a card like the Capital One® Venture® Rewards Credit Card, you’d need 20,000 miles — still far lower than what a traditional frequent flyer program will likely charge you.

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.

Featured photo by Alan Copson/Getty Images.

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