8 Amazing Caribbean Vacations You Can Take With Points and Miles This Winter

Jan 26, 2019

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Caribbean tourism took a hit from several devastating hurricane seasons in a row and the spread of Zika. However, the region is on the rebound thanks to the opening (and reopening) of several major resorts, successful recovery efforts in some of the hardest hurricane-hit islands and an increase in airline service to and from the US.

Now that winter has truly set in across much of the US, with torrential rainstorms on the West Coast and brutal cold snaps out east, it’s the perfect time to plan a winter escape to the sun-soaked beaches of the Caribbean.

Luckily, there are myriad ways to use your airline miles to fly to various islands, and points hotels galore to choose from once you arrive. You might even luck out with a mileage flash sale this winter.

So whether you’re looking for a fun-filled family getaway, a leisurely all-inclusive idyll, a bucket-list diving expedition, or simply to relive your spring break glory days, here are eight Caribbean vacations you can take this winter using points and miles.

Playa Blanca, Punta Cana, Dominican Republic, Caribbean Sea.
Now is the time to put your points to use on a Caribbean vacation. Playa Blanca, Punta Cana, Dominican Republic, Caribbean Sea. Photo via Getty Images.

Grand Cayman

Grand Cayman is a great choice for families who want a safe, easy getaway and scuba enthusiasts who want to dive in some of the best spots in the Caribbean. Though paying to fly and stay can be an expensive proposition, the wide availability of award flights and nights makes this a true tropical bargain.

The Ritz-Carlton Grand Cayman.

Getting There

Although flights to Grand Cayman (GCM) can be costly, part of the reason it’s such a great choice is that you can easily find awards on American Airlines flights from its hubs in Miami (MIA) and Dallas (DFW) using British Airways Avios. Don’t have any? Remember that you can transfer points from American Express Membership Rewards, Chase Ultimate Rewards, Citi ThankYou Rewards and Marriott Rewards into your BA Executive Club account.

From Miami to Grand Cayman, you’ll need just 7,500 Avios each way.

And Dallas to Grand Cayman is just 10,000 Avios.

Compare that to the 15,000 AAdvantage miles American would charge you to fly its own flights.


Southwest flies nonstop from Ft. Lauderdale (FLL) to Grand Cayman, but flights this winter aren’t cheap. You can transfer Chase Ultimate Rewards to Southwest Rapid Rewards to book them as awards, and if you’ve taken advantage of the recent limited-time credit-card Companion Pass offer, you can cut your expense in half.

Where to Stay

There aren’t a ton of points hotels on the island, but there are still a few great choices.

The Westin Grand Cayman Seven Mile Beach Resort and Spa is now part of Marriott. It was recently renovated and has the largest freshwater swimming pool on the island as well as an award-winning seafood restaurant called Beach House. Award nights cost 50,000 points each, versus $721 if you paid cash.

The Kimpton Seafire Resort + Spa was the chain’s first hotel outside the US. The resort has 266 cheerful guest rooms and suites, an oceanfront pool and several restaurants, including Avecita for tapas and Coccoloba for poolside snacks. Though paid nights are over $700 this winter, award nights cost 70,000 points each.

Finally, the Ritz-Carlton, Grand Cayman is a TPG favorite thanks to its gorgeous beachfront setting, six restaurants, two huge outdoor pools and its La Prairie Spa. Award nights there are just 60,000 points each (compared to room rates well over $1,200!).

Just be sure to book sooner rather than later, as this property will shift to Category 8 in March, boosting standard award rates to 85,000 points per night.


This windswept speck of land in the southern Caribbean remains a popular getaway thanks to beautiful beaches and even more beautiful hotels.

(Photo by Martin Passchier via Unsplash)
The beach on Aruba. Photo by Martin Passchier via Unsplash.

Getting There

There are plenty of airlines to choose from, but let’s focus on two. Delta flies nonstop from Atlanta (ATL), Boston (BOS), Minneapolis (MSP) and New York-JFK, and is offering flights as low as $380 round-trip in economy from many destinations in the northeast. Award flights are readily available for as low as 22,000 miles plus about $84 round-trip from several cities, including Boston. Remember, the Delta SkyMiles program is a transfer partner of American Express Membership Rewards.

Another great choice is JetBlue, especially if you want to fly business, since the airline offers its flagship Mint lie-flat seating and service from both Boston and New York at certain times — though it flies planes without Mint most days. Here’s a sample round-trip economy itinerary from New York to Aruba for 15,200 points and $84 in economy. Mint costs around 200,000 points each way when it is available, unfortunately. JetBlue’s TrueBlue program is a transfer partner of American Express Membership Rewards, Citi ThankYou Rewards and Chase Ultimate Rewards, though since the program is revenue-based, you may be better off simply purchasing the flights and saving your transferable points for more of a sweet spot redemption.

Where to Stay

There are several options on this island as well. If you’ve stocked up on Marriott Rewards points, you can spend 35,000 points per night at the Renaissance Aruba Resort and Casino instead of $428; 50,000 points at the Aruba Marriott Resort & Stellaris Casino instead of $636; or 60,000 points per night at the Ritz-Carlton, Aruba instead of $1,140 per night. Remember, if you have the points and award availability is there, you can also get a fifth award night free when you book four consecutive nights, cutting your cost by 20%.

You can also use the program’s Points Advance feature if you don’t have enough points to cover the entire stay at time of booking.

Hyatt loyalists can spend 25,000 points per night on a standard room at the Hyatt Regency Aruba Resort Spa and Casino, or 33,000 points on a Club Room, instead of $407 and $457, respectively.

Meanwhile, the Hilton Aruba Caribbean Resort & Casino has rooms available for $587 or 80,000 points per night.

Puerto Rico

This US territory was hit hard by Hurricane Maria in 2017 and is still rebuilding, but tourism is a great way to help it recover.

Castillo San Felipe del Morro
Castillo San Felipe del Morro also known as Fort San Felipe del Morro or El Morro Castle, is a 16th-century citadel in San Juan, Puerto Rico. Photo by felixairphoto / Getty Images.

Getting There

Really, this just depends on what kind of miles you want to use since American, Delta, JetBlue, Southwest, Spirit and United all fly here from their various hubs. Why not fly Delta, since you know the airline will get there no matter what, based on their previous hurricane-dodging record? The airline flies nonstop from both Atlanta (ATL) and New York-JFK with awards as low as 13,000 miles round-trip, though most awards will be in the 26,000 to 45,000-mile range.

Where to Stay

Though there are dozens of points properties around the island, focus your search on the higher-end hotels. The St. Regis Bahia Beach Resort is a gorgeous getaway right on the beach and has easy access to popular nearby sites like El Yunque National Forest. It has rooms available for 60,000 points per night, compared to paid room rates of $830 per night (though it too will shift to Category 8 in March).

El San Juan Hotel is part of Hilton’s Curio Collection and is a swanky seaside retreat in leisurely Isla Verde, just to the east of central San Juan. Rooms there are available for $381 or 70,000 points.

Also in Isla Verde, the imposing InterContinental San Juan has rooms from $264, or 50,000 points.

Easily one of the most gorgeous resorts on the island, the Dorado Beach, a Ritz-Carlton Reserve, does not offer points redemptions, but it’s a part of American Express Fine Hotels & Resorts. So if you have The Platinum Card® from American Express, you can book through there and receive benefits such as room upgrades, daily breakfast for two and a $100 spa credit.

St. Kitts

Long lost in the shadow of its flashy neighbor, Nevis, St. Kitts is finally enjoying its day in the sun.

The Marriott on St. Kitts sits beachfront and has its own casino.

Getting There

Airfares to this small Caribbean island aren’t cheap, at around $400 round-trip in economy. However, you can catch an American flight from Miami (MIA) to St. Kitts (SKB) for just 20,000 British Airways Avios round-trip plus about $140 in taxes and fees.

United flies nonstop from Newark (EWR) and awards are plentiful for 35,000 miles round-trip, plus about $70 in taxes and fees that will depend on whether you have elite status.

Where to Stay

On St. Kitts itself, you’ll find two major points hotels. The first is the mid-market St. Kitts Marriott Resort & The Royal Beach Casino, where rooms go for $342 per night, or 35,000 points.

The second, more upscale choice, is another TPG favorite: the Park Hyatt St. Kitts Christophe Harbour. It has just 78 rooms and 48 suites, plus two swimming pools, three restaurants and a spa. Paid rates start at $620 per night, but awards are available for 30,000 points per night.

If you have one of the cards in Amex’s Platinum family, you can use Fine Hotels & Resorts to book the luxurious Four Seasons on Nevis where you’ll enjoy daily breakfast for two and a $100 property credit, among other perks (think: 5x points).


Located at the far eastern edge of the Caribbean, Barbados is a dream destination for sun-seekers and surfers alike.

View of Harry Smith Beach, Bottom Bay, Barbados.
View of Harry Smith Beach, Bottom Bay, Barbados. Photo via Getty Images.

Getting There

There are a few good possibilities for award flights, but your two best bets are likely American Airlines from Charlotte (CLT) or Miami (MIA), and JetBlue from New York-JFK or Ft. Lauderdale (FLL).

American will charge you 30,000 miles round-trip from either, while British Airways requires just 25,000 Avios round-trip from Charlotte and 20,000 from Miami.

As for JetBlue, the airline is offering tickets for as low as 18,300 points this winter, like this round-trip from New York to Barbados:

Where to Stay

There are just a handful of points properties on Barbados, but there are still good ones to choose from.

The Hilton Barbados Resort is near Bridgetown and has two white-sand beaches, a pool complex, four bars and restaurants and an Eforea spa. Room rates there this winter start at around $470, or 70,000 points.

The Radisson Aquatica Resort Barbados is located on Needham’s Point near several beaches, and has 124 rooms and suites and a beachfront pool. Room rates there this winter start at $245, or 44,000 points.

One of the island’s landmark luxury resorts is Sandy Lane, and happily it’s a member of Amex Fine Hotels & Resorts, which confers a complimentary round of golf for two if you book through that channel. However, it’s also a member of Leading Hotels of the World, so you can take advantage of the new Leaders Club earning and redeeming rates plus stay-related benefits.


This former Dutch colony is practically off the coast of South America, and is known for its historic pastel buildings and excellent diving off its “blue edge.”

Waterfront Of Otrabanda In Willemstad, Capital Town Of Curacao, Netherlands Antilles. (Photo By: MyLoupe/UIG Via Getty Images)
Waterfront of Otrabanda In Willemstad, Curaçao, Netherlands Antilles. Photo by MyLoupe/UIG Via Getty Images.

Getting There

The flight options to Curaçao (CUR) are a bit more limited, but American Airlines flies nonstop from Miami (MIA) and JetBlue offers nonstop flights a few times a week from New York-JFK. Using the same Avios method, you’ll need just 10,000 each way for American’s flights. As for JetBlue, the cheapest awards this winter seem to be 38,000 TrueBlue points round-trip.

Where to Stay

Among the points properties on the island is the Hilton Curaçao, which is located on 23 acres of beachfront tropical gardens on the site of a former 16th-century fort and has its own on-property PADI diving center, among other amenities. Room rates there this winter start at $238 per night, or 40,000 points.

The Renaissance Curaçao Resort and Casino is another good option in historic Willemstad and close to sights like the Curaçao Sea Aquarium, the Curaçao Museum and Christoffel National Park. The colorful resort has 237 rooms, three restaurants including a beach bar and a large outdoor infinity pool. Rates there this winter start at $249 per night, or 35,000 points.

The Bahamas

Thanks to its proximity to the East Coast, Nassau (NAS) has a plethora of possibilities for travelers hoping to use airline miles for a winter break to the Caribbean.

A colorful image of the waterfront area in downtown Nassau showing a water taxi and several huts.
The waterfront of downtown Nassau. Photo via Getty Images.

Getting There

American Airlines flies from Charlotte (CLT) and Miami (MIA); Delta flies from New York-JFK and Atlanta (ATL); JetBlue flies from Ft. Lauderdale (FLL) and New York-JFK; United flies from Chicago (ORD), Houston (IAH) and Newark (EWR); and Southwest flies from Baltimore (BWI) and Ft. Lauderdale (FLL).

United’s award availability on all three of its nonstop routes looks pretty good at this point, with round-trip tickets going for 35,000 miles plus about $112 in taxes and fees.

Where to Stay

Though points hotels abound, let’s keep the focus on a few for this winter. The Grand Hyatt Baha Mar might be enormous, with a whopping 1,800 rooms including 230 suites and residences, but that doesn’t mean it skimps on service or amenities. It has six pools and a 100,000-square-foot casino, plus guests can take advantage of more than 30 restaurants and bars spread across the Baha Mar property. Room rates there this winter start at $282 per night, or 20,000 points.

Several of the resorts at Atlantis are part of Marriott’s Autograph Collection, including the Beach, the Coral, the Reef, the Cove and the Royal. At the moment, the only ones with award availability for the rest of the winter season are the Coral, the Cove and the Royal at the following rates:

The British Colonial Hilton is another interesting option in the heart of Nassau, with a picturesque beach, four restaurants and a cute waterfront pool. Room rates there this winter start at $248 per night, or 50,000 points.

Montego Bay, Jamaica

There’s no doubt that this island has some of the Caribbean’s best family-friendly resorts, best coffee and most laidback vibes.

Montego Bay, Jamaica.

Getting There

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 Ft. Lauderdale (FLL); and Southwest out of various airports including Baltimore (BWI), Chicago Midway (MDW), Ft. Lauderdale (FLL) and St. Louis (STL). Yes, we said Spirit, but sometimes you just can’t beat the cash rate.

Where to Stay

Montego Bay is home to two of Hyatt’s all-inclusive properties: the Hyatt Ziva Rose Hall for families and the adults-only Hyatt Zilara Rose Hall next door. The 277-room Ziva Rose Hall has two swimming pools, a Zen Spa and 16 dining outlets. Guests at the 344-room Zilara can use the Ziva facilities, but also have their own adults-only pool and a handful of additional restaurants to choose from. Rates this winter start around $420 at both, or 25,000 points.

Nearby, the 489-room, all-inclusive Hilton Rose Hall Resort & Spa is a favorite with families thanks to the fact that it has the longest white-sand beach on the island as well as its largest water park. The resort also has nine restaurants to choose from and a Radiant Spa with ocean-view cabanas. Rates there this winter start at $449 per night, or 70,000 points.

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

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