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

Dec 6, 2020

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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. 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 favourite places for a carefree Caribbean holiday and tips for how you can use points and miles to travel there.

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In This Post

Grand Cayman

Grand Cayman is one of our favourite picks for a Caribbean holiday, 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 travellers 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)
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.

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.

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 (about £815) this winter, you can book awards for 100,000 points per night.

Ritz Carlton Grand Cayman rates Feb 2021
(Screenshot courtesy of Marriott.com)

Alternatively, the Westin Grand Cayman Seven Mile Beach Resort and Spa costs just 60,000 Marriott Bonvoy points per night, or around $569 (about £426) 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 £600 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.

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 BOS-Aruba fares Feb 2020
(Screenshot courtesy of JetBlue.com)

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 (about £602) this winter.

Though that’s a great redemption, you could instead spend just 40,000 points (or £398) 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 £322 (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.

The Hyatt Regency Aruba Resort Spa and Casino is offering rooms in January for around £502 or 25,000 points per night.

Hyatt Regency Aruba
(Screenshot courtesy of Hyatt.com)

The Hilton Aruba Caribbean Resort & Casino has rooms available for 80,000 points or $572 (about £429) 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)
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.

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 (about £550) per night.

St. Regis Bahia Beach Jan 2020 rates
(Screenshot courtesy of Marriott.com)

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 (about £160) or 30,000 Wyndham Rewards points per night.

St. Kitts

Its tonier neighbour, Nevis, is home to luxury hotels like the Four Seasons, where you can maximize Amex’s Fine Hotels & Resorts benefits if you have The Platinum Card from American Express. However, 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 around £460 from London, including a stop along the way — usually in Miami (MIA).

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 holiday. 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 (£459) 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 (£168), or 50,000 points per night.


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

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 or cash flights. From London, you can fly with either British Airways or Virgin Atlantic. Flights this winter can generally be had for around £345 return.

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 (£363) or 70,000 points per night this winter.

The Radisson Aquatica Resort Barbados is more of a budget option with rooms for $170 (about £127) or 50,000 points per night.


This interesting isle — equal parts windswept, balmy beaches and colourful, colonial charm — is so far south that it’s almost part of South America. Curacao opened to select tourists in November.

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.

You can also opt for a cash ticket. Flights from London hover around the £530 mark, including a couple of stops along the way.

Where to stay

The Curaçao Marriott Beach Resort has rates starting at $216 (£162) or 35,000 points per night, while the Renaissance Curaçao Resort and Casino has rooms for $262 (£196) or 35,000 points per night.


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

Flying there

The best way to get to Nassau on miles and points is using British Airways Avios.

You could also fly nonstop from London to Nassau as of February 2021 with British Airways. Flights are quite expensive, however, as BA runs the seasonal route. Expect to pay around £730 return.

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 favourites 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 (£180) or 20,000 points per night.

The British Colonial Hilton has rooms for $247 (£185) 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 (£374) or 60,000 points per night.


Some travellers shy away from Jamaica, but the island has some of the Caribbean’s family-friendliest resorts and best all-inclusives. All travellers 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)
Ricks Cafe in Jamaica. (Photo by Doug Pearson/Getty Images.)

Flying there

You’ll find nonstop options with Virgin Atlantic to Montego Bay (MBJ). Expect to pay around £440 for a return ticket in economy. Alternatively, you can fly nonstop with BA to Kingston (KIN) for around £685 return.

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 £300, or 25,000 points.

Nearby, the 489-room, all-inclusive Hilton Rose Hall Resort & Spa is a family favourite thanks to a long, white-sand beach, a fun-filled waterpark, and nine restaurants to enjoy. Rates there start at $271 (£203) 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.

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

Flying there

Flights to the USVI are limited. While there are no nonstop options from London, you could fly via the U.S. with an airline like United, American or Delta. Expect to pay around £500 for a return flight to St Thomas (STT).

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 (£426) per night, or the luxurious (and just reopened) Ritz-Carlton, St. Thomas, with rooms for $665 (£498) or 85,000 points per night.

Alternatively, the Wyndham Margaritaville St. Thomas has rooms starting at $205 (£154) or just 15,000 points per night.

Featured photo by Pola Damonte via Getty Images/Getty Images

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