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The best credit cards to get for an almost-free Caribbean vacation

Jan. 19, 2020
28 min read
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It's the dead of winter and you need a beach vacation with lots of sun — as soon as possible. We get it. We also get that you might be trying to keep your budget in check, so you're looking for a Caribbean vacation without a big credit card bill waiting at the end of the journey.

This is exactly the scenario where points, miles and credit card welcome bonuses can come into play in a major way. And since we are talking about the relatively nearby Caribbean and not the other side of the world like Bora Bora or the Maldives, this is a vacation you can absolutely put together even if you are fairly new to points and miles and don't have tons of rewards to work with yet.

As a lifelong East Coast resident, I can attest to the wonders of vacationing in the Caribbean using points and miles. It's a destination that really checks lots of boxes -- you don't waste a ton of time in transit, there are no jet lag issues and you'll have minimal time zone adjustments to make. Plus there is plenty of variety among the islands, excellent lodging options and some absolutely gorgeous beaches and views.

Related reading: Points and miles guide to the Caribbean

Add to that mix the plethora of points-friendly hotels in destinations including Puerto Rico, Aruba, Grand Cayman, St. Kitts, Jamaica and other islands, and you can easily put together an incredible beach vacation using your miles and points. Whether you are on the East Coast, live the heartland or beyond, if you'd love to steal away to the Caribbean without having it steal away a chunk of your bank account, here are the credit cards that can make your Caribbean dream a reality.

Kimtpon Seafire Resort on Grand Cayman (Photo by Scott Mayerowitz/The Points Guy)
Kimpton Seafire Resort on Grand Cayman. (Photo by Scott Mayerowitz/The Points Guy)

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The best credit cards for a Caribbean vacation:

  • Chase Sapphire Preferred Card: Points transfer to United, Hyatt, Southwest and more
  • The World of Hyatt Credit Card: Hyatt has high-end resorts across the Caribbean you can book with points
  • The Platinum Card® from American Express: Unlock Fine Hotels and Resorts perks; points transfer to partners such as Hilton and Delta
  • Southwest Rapid Rewards Priority Credit Card: Southwest Airlines has an extensive Caribbean route network and the Companion Pass makes all of the flights essentially buy one, get one deals
  • Hilton Honors Aspire Card from American Express: Unlock a nice welcome bonus and Hilton Diamond elite status
  • Marriott Bonvoy Boundless Credit Card: Current limited time offer and earn annual award nights to use across the Caribbean

The information for the Hilton Aspire Amex card has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

Who flies to which islands?

Before we dive into specifics on which credit cards can help you get to the Caribbean islands for less than you think, let's talk about flights. If you're not sure what airlines fly to the island you've got your heart set on, we've got some tips. Go to and type in the airport code for the island you're interested in. Then, click "Country" and check the "USA" box. Click the orange "Apply" button. The website will then return the results that include the U.S. gateway cities, flight times and which airlines fly from those cities to your island destination.

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Armed with that data, you can more easily decide where you'd like to go and what type of miles/points you might need to book an award flight.

Related reading: Best credit cards for airport lounge access

Chase Sapphire Preferred Card

The Chase Sapphire Preferred Card is one of the most powerful credit cards out there, regardless of where you want to travel. With this card, you earn Chase Ultimate Rewards points at a rate of 2x points on all travel and dining purchases and 1x on everything else. These points are worth 1.25x on travel expenditures made directly through Chase's travel portal or are transferrable to a variety of airline and hotel programs that can take you to the Caribbean.

Here's a review of the Chase Sapphire Preferred Card. The current welcome offer looks like this: Earn 60,000 bonus points after you spend $4,000 in the first three months. The annual fee is $95.

Related reading: Best ways to use Chase Ultimate Rewards points

If you've been on an application spree recently, remember that Chase has its 5/24 rule. You won't be approved for a new Chase credit card if you've open five or more credit cards over the last 24 months. There are some nuances to that rule (including some small business cards that don't count toward that total). If that situation may describe you, here's everything you need to know about Chase's 5/24 rule.

Here are a few scenarios in which you can use Chase Ultimate Rewards points from the Sapphire Preferred to plan a fantastic beach getaway.

Transfer points to United to fly to Aruba, the Cayman Islands, St. Kitts and more

United Airlines is one of 10 Chase Ultimate Rewards airline transfer partners, and that's good news since the airline flies to many Caribbean destinations, including Aruba, the Cayman Islands, Dominica Republic, Jamaica, Puerto Rico, St. Kitts, the U.S. Virgin Islands and Turks and Caicos.

United, like many airlines these days, uses dynamic award pricing, so the award price can and does vary from day to day. For example, if you planned to fly from Newark (EWR) to St. Kitts (SKB) in March, you could lock in flights for 17,500, 34,000 or 40,000 miles each way.

Here's a round-trip flight on peak dates in March for 35,000 miles and $69.45 per person. Your 60k-point sign-up bonus from the Chase Sapphire Preferred Card could cover one round-trip and gets you close to two.

Never transfer points from Chase to United or any other program until you see the award you want is available. For flights on United partners, it's never a bad idea to call United to confirm award availability. Phantom award space that shows on United's website but isn't actually available is a problem with a few partner airlines (though more so with airlines flying to Europe than the Caribbean).

Related reading: The 9 best credit cards for flying United

Transfer points to fly JetBlue to the Cayman Islands, Barbados, Jamaica and more

JetBlue is another Ultimate Rewards airline transfer partner, and its network includes plenty of Caribbean destinations. It also prices awards dynamically, which, in this case, means the points price varies depending on the cash price of the ticket. When you see a good fare, you can transfer Ultimate Rewards points to the airline. Here's a sample points fare from New York-JFK to Grand Cayman (GCM). If you want to go in style, look for JetBlue flights with Mint Suites that will allow you to fly to the Caribbean in a lie-flat seat.

Related reading: JetBlue Plus Card vs. JetBlue Business Card

Use your points to stay at the Park Hyatt St. Kitts

The Park Hyatt St. Kitts Christophe Harbour continues to get great reviews from travelers, and award availability using World of Hyatt points is very good -- even during peak times like winter break. Since Hyatt is a transfer partner of Chase Ultimate Rewards, your Sapphire Preferred can get you some nights at this beachfront hotel.

(Photo by Zach Griff/The Points Guy)
Park Hyatt St. Kitts (Photo by Zach Griff/The Points Guy)

You can book a 527-square-foot Park King or Park Queen room for 30,000 Hyatt points, meaning that the Sapphire Preferred card's 60k bonus could cover two nights of a stay.

Or, get $750 in flights

If you don't want to mess with transferring Ultimate Rewards points to an airline or hotel, you can instead use your points to pay for a purchase in Chase's Travel portal. A 60k-point bonus is worth $750 in flights booked directly in Chase's portal. Here are details on how to do that.

The World of Hyatt Credit Card

Hyatt may have a smaller footprint of hotels around the globe than say, Marriott or Hilton, but the hotels in Hyatt's portfolio are compelling -- especially in the Caribbean. From the above-mentioned Park Hyatt St. Kitts to the Hyatt Ziva and Zialara all-inclusive resorts, to a variety of Small Luxury Hotels in the region, you may find the perfect Caribbean island getaway as you search Hyatt's website.

Related reading: Best ways to use Hyatt points at new luxury hotels

Hyatt Can Cana in Punta Cana (Photo by Summer Hull/The Points Guy)

If you're already a Hyatt fan, or have plans to visit a resort under the Hyatt umbrella, consider signing up for The World of Hyatt Credit Card. You'll earn up to 50,000 bonus points: 25,000 points after you spend $3,000 in three months and an additional 25,000 points after you spend a total of $6,000 in the first six months of account opening. You'll also receive a free night certificate (Category 1–4 hotels) on the card anniversary, as well as Hyatt Discoverist elite status.

Use Hyatt points in the Turks and Caicos

For a long while, travelers didn't have many options if they wanted to book a hotel using points in the Turks and Caicos. But Hyatt's partnership with Small Luxury Hotels has opened up two exciting possibilities: Point Grace Resort (on Providenciales) and Sailrock Resort (on South Caicos island).

Sailrock Resort on South Caicos (Photo courtesy of
Sailrock Resort on South Caicos. (Photo courtesy of

When award nights are available at both properties, they cost 40,000 World of Hyatt points per night. Chase's welcome bonus would get you one night and change at these gorgeous beachfront resorts.

Stay at one of Hyatt’s all-inclusive resorts

Hyatt has two all-inclusive resort brands: Hyatt Ziva for families and the adults-only Hyatt Zilara. You'll find both options in Rose Hall, Montego Bay, Jamaica, and the Dominican Republic's Cap Cana (though that resort is newly opened and still may be working out some kinks).

Both of these all-inclusive resorts cost 25,000 World of Hyatt points per night for double occupancy. Any additional adult or child costs 12,500 points per night, though children under three can stay at no additional charge.

Hyatt Cap Cana (Photo by Summer Hull/The Points Guy)

A couple could each get a World of Hyatt Credit Card, meet the requirements to earn the complete 50,000-point welcome bonus and use those points to stay at any of the Hyatt all-inclusive resorts for four nights for free.

Use your free anniversary night at the Hyatt Regency Trinidad

You get a free night certificate for any Category 1–4 Hyatt hotel each year on the anniversary of your World of Hyatt Credit Card, as well as the opportunity to earn a second one with spending $15,000 on the card per cardmember year. There's currently only one Caribbean hotel that fits that Category 1 - 4 bill: the Hyatt Regency Trinidad. This Category 3 property can be booked on points (a 390-square-foot room with a king or two double beds) for 12,000 points per night.

Hyatt Regency Trinidad. (Photo courtesy of

The Platinum Card from American Express

The Platinum Card® from American Express is one of the most powerful premium credit cards available and it's packed with tons of benefits that will help you both get to the Caribbean and have an upgraded stay while you're there.

With the current welcome offer on the card, you can earn 60,000 welcome Membership Rewards points after spending $5,000 in the first three months. Earn 5x points per dollar on flights booked directly with airlines or with American Express Travel, and 5x points on prepaid hotels booked on The annual fee is $550. Check out the card's full review (see rates and fees).

Related reading: Battle of the premium travel rewards credit cards

Book Caribbean accommodations with Amex Fine Hotels & Resorts

The Fine Hotels & Resorts program from Amex allows Platinum cardholders to book rooms at hotels and resorts around the world. The booking includes some value-added perks like a room upgrade (when available), included daily breakfast for two, guaranteed 4 p.m. late checkout, noon check-in (when available), free Wi-Fi and an amenity like a spa or food and beverage credit. There are a variety of Caribbean destinations where you may not find a Hyatt or Marriott type of property, but you will find smaller properties where you can leverage Amex FHR perks.

With Amex FHR bookings, you can earn 5x points per dollar with your Platinum Card or even use American Express Membership Rewards points.

To give an example of what is available,The Ritz-Carlton, Aruba priced out at $469, which includes a $100 resort credit, daily breakfast for two and more.

Related reading: The ultimate guide to the American Express Fine Hotels & Resorts program

Transfer your Membership Rewards for Delta flights

American Express Membership Rewards can be transferred to Delta SkyMiles instantly at a 1:1 ratio. The instant transfer is a boon because Delta often runs flash sales for well-priced Caribbean flight awards. In recent months we've seen round-trip SkyMiles awards to the Caribbean price at 10,500 miles, 12,000 miles, 16,000 miles and 20,000 miles.

Delta also uses dynamic pricing for its awards, so you'll need to spend some time searching for awards to find the best options when you're ready to book. Here's a recent deal for a round-trip flight from Boston to the Turks and Caicos for 18,000 SkyMiles and $98.05 per person.

Related reading: Why the Amex Platinum might be the best card for Delta flyers

Fly American Airlines from 7,500 points

American Airlines is not a Membership Rewards transfer partner. But, British Airways is -- and you can use British Airways Avios points to book flights on its partner, American Airlines.

As an example, you could transfer Membership Rewards to your British Airways Avios account and use 9,000 Avios points per person to book American Airlines flights from Miami to Aruba (18k for a round-trip). Since British Airways uses a distance-based award chart, and the Caribbean isn't very far (at least from the eastern half of the U.S.), this can be a great option.

In this case, a 60,000-point welcome bonus could get you three Miami (MIA) - Aruba (AUA) round-trip flights (other than taxes) -- and you'd still have 6,000 points leftover from the bonus.

Related reading: Choosing the best credit card for American Airlines flyers

A natural pool in Arikok National park on the North coast of Aruba. (Photo by Marc Guitard / Getty Images)
A natural pool in Arikok National park on the North coast of Aruba (Photo by Marc Guitard/Getty Images)

Southwest Airlines Credit Cards

Southwest may not immediately come to mind when planning a trip outside of the United States, but it actually has a very robust international network. Some of its Caribbean gateways include Aruba, the Cayman Islands, Dominican Republic, Jamaica, and Puerto Rico as well as the Turks and Caicos. This means that Southwest credit cards such as the Southwest Rapid Rewards Priority Credit Card.

Related reading: The best Southwest Airlines credit card for family travelers

Leverage Southwest's Companion Pass

Southwest's Rapid Rewards loyalty program has one of the most incredible perks in the industry: a Companion Pass. Once you earn the Companion Pass, you can take a friend or family member on each flight with you for just the cost of taxes, as long as a seat is available on the plane. That's pretty incredible.

Earning the Companion Pass requires earning 125,000 qualifying points in a calendar year. However, bonus points earned from getting and using the Southwest credit cards count as qualifying points.

You can currently earn up to 75,000 bonus points on the Southwest Rapid Rewards Plus Credit Card, Southwest Rapid Rewards Premier Credit Card and Southwest Rapid Rewards Priority Credit Card — 40,000 points after you spend $1,000 in the first three months, and another 35,000 points after you spend $5,000 within the first six months of card membership. If you earn all 75,000 points, you're more than halfway to earning the Companion Pass.

Once you have the pass, you could book this ticket from Atlanta (ATL) to Punta Cana (PUJ) and then add on a companion for just the price of the ticket's taxes.

Related reading: How to use the Southwest Companion Pass

Or, book your flights with Rapid Rewards points

If you don't have a Southwest Companion Pass, or don't think you'll be able to earn one, getting a Southwest credit card can still make a lot of sense so you can build your stash of Rapid Rewards points.

Southwest Airlines doesn't use a fixed award chart, but instead ties the points price to the cash price. That isn't great for travelers when cash prices are high, but it means sometimes there are great deals to be found. Here's a round-trip from Ft. Lauderdale (FLL) to Grand Cayman (GCM) that priced at 7,020 Southwest Rapid Rewards points (plus taxes) per person.

So, a family of four would spend 28,080 points on round-trip tickets. If you earned the full 75,000-point welcome bonus from any of the above-mentioned Southwest cobranded credit cards, you'd still have nearly 47,000 Rapid Rewards points to use on a future trip.

Enjoying the beautiful water in Grand Cayman (Summer Hull/The Points Guy)

You could also head from Fort Lauderdale to Aruba on Southwest. We found round-trip flights in April for as low as $277 per person, or 11,700 points plus $84.95.

Hilton Honors American Express Aspire Card

Hilton has several cobranded credit cards with very nice welcome bonuses, but let's talk specifically about the Hilton Honors American Express Aspire Card when it comes to the best credit cards for a Caribbean vacation.

With this card, can earn 150,000 welcome points after you spend $4,000 in purchases in the first three months. You'll also receive one weekend night reward with your new card and one every year on renewal, plus valuable top-tier Hilton Diamond status. Terms apply.

You're probably already seeing the possibilities. Get the card, earn the welcome bonus and then wait until your card anniversary, when you'll have two free weekend night rewards to use for a Caribbean getaway. Pair those two award nights with using points for the other nights. In fact, since the card gives you elite status, you can even use points for four nights and then get the fifth night free.

In essence, you could then book a seven-night stay for just the points price for four nights. And, don't forget that your Hilton Diamond status may very well result in free breakfast for the duration of your stay.

Related reading: Hotel credit cards that come with a free annual night

Zemi Beach House - Anguilla
Zemi Beach House in Anguilla, new to LXR Hotels & Resorts, one of Hilton's luxury brands. (Photo courtesy of the hotel)

Visit Aruba with your Hilton Honors points

With your Hilton Honors points, you can stay at the Hilton Aruba Caribbean Resort & Casino. Hilton doesn't have an award chart and instead prices its awards dynamically. But, you can get an idea of the points range by searching for your desired hotel at Hilton's Points Explorer tool.

The Hilton Aruba costs 78k - 80k points per night based on the Hilton Points Explorer tool:

Hilton Aruba (Photo courtesy of Hilton)
Hilton Aruba. (Photo courtesy of Hilton)

Use your points at a Dominican all-inclusive

If you like the idea of an all-inclusive resort, and you have Hilton Honors points, look to the Hilton La Romana. There are two sections of the resort: one is adults-only and the other is family-friendly.

Hilton La Romana (Photo courtesy of Playa Hotels)
Hilton La Romana. (Photo courtesy of Playa Hotels)

Interestingly, on the dates we searched, the family resort was 10,000 points per night cheaper than the adults-only option. However, only children 2 and under stay for free beyond double occupancy. The resort will charge an additional $95 per child per night for kids 3–12. Children 13 and older are considered adults and cost $99 extra per night. But still, 150k bonus points go a long way when award rates are around 50k - 60k points per night.

Head to St. Lucia

The Harbor Club St. Lucia, Curio Collection by Hilton is bookable via Hilton Honors points. When we checked, rates were around 56,000 points per night. If you earned the entire Hilton Aspire welcome bonus, that's about three nights at this resort.

Harbor Club St. Lucia (Photo courtesy of Curio Collection)
Harbor Club St. Lucia. (Photo courtesy of Curio Collection by Hilton)

Marriott credit cards

Marriott has one of the largest hotel portfolios in the world, so Bonvoy points are valuable almost no matter where you want to go -- including the Caribbean.

Ritz-Carlton St. Thomas (photo courtesy of

There are several Marriott cobranded credit cards available right now with nice welcome offers.

  • Marriott Bonvoy Boundless™ Credit Card: Earn 100,000 points after you spend $5,000 on purchases in the first three months. You'll also get a 35,000-point free night certificate on your card anniversary and Silver Elite status.
  • Marriott Bonvoy Bold™ Credit Card: Earn 50,000 points after you spend $1,000 on purchases in the first three months of account opening.
  • Marriott Bonvoy Brilliant™ American Express® Card: Earn up to 125,000 Marriott Bonvoy points. Earn 100,000 bonus points after you spend $5,000 in purchases on your new Card in your first 3 months. Plus, earn an additional 25,000 bonus points after your first anniversary of Card Membership. Enjoy complimentary Platinum Elite status with your Card for the 2021 status year. Offer Expires 1/13/2021. Terms Apply
  • Marriott Bonvoy Business® American Express® Card: Earn 100,000 Marriott Bonvoy bonus points after you use your new Card to make $5,000 in eligible purchases within the first 3 months of Card Membership. Plus, earn up to $150 back in statement credits on eligible purchases made on your new Card within the first 3 months of Card Membership. Offer ends 5/12/21. Terms apply.

Use a free night certificate in the Caribbean

In addition to the points, there are also two types of Marriott free night certificates that are gifted on the anniversary of having specific Marriott-branded credit cards. One certificate is good at any hotel that charges 35,000 points or less per night. You can get that type of certificate with both the Marriott Bonvoy Boundless Credit Card and Marriott Bonvoy Business American Express Card.

Marriott St. Kitts Beach Club
St. Kitts Marriott available for 35k points per night. (Photo courtesy of hotel)

You could use that certificate at any of these Caribbean-based Category 5 properties on standard or off-peak dates:

  • Renaissance Aruba Resort & Casino
  • Four Points Sheraton Havana
  • The Westin Puntacana Resort & Club
  • The Ocean Club a Luxury Collection Resort, Costa Norte
  • St. Kitts Marriott Resort & The Royal Beach Casino
  • Curacao Marriott Beach Resort
  • Renaissance Curacao Resort & Casino
  • Sheraton Puerto Rico Hotel & Casino
  • Renaissance St. Croix Carambola Beach Resort & Spa

Related reading: Great uses of Marriott Bonvoy 35,000-point free night certificates

If you have the Marriott Bonvoy Brilliant Amex card, you'll receive a free night worth up to 50,000 points per night on your card's anniversary. You can use that certificate at any Category 6 hotel on standard or off-peak dates or even a Category 7 on off-peak dates.

The Ritz-Carlton, Aruba (Photo by Trey Ratcliff)
The Ritz-Carlton, Aruba (Photo by Trey Ratcliff)

A Marriott 50k certificate could potentially be used at these Caribbean resorts:

  • Aruba Marriott Resort & Stellaris Casino
  • Marriott's Aruba Ocean Club
  • Marriott's Aruba Surf Club
  • Grand Cayman Marriott Beach Resort
  • Marriott's St. Kitts Beach Club
  • San Juan Marriott Resort & Stellaris Casino
  • La Concha Renaissance San Juan Resort
  • The Ritz-Carlon, Aruba (only on off-peak dates)
  • The Westin Grand Cayman Seven Mile Beach Resort & Spa (only on off-peak dates)
  • The Ritz-Carlton, San Juan (only on off-peak dates)
  • Laluna, Grenada, a Member of Design Hotels (only on off-peak dates)
  • The Westin St. John Resort Villas (only on off-peak dates)
  • Marriott's Frenchman's Cove (only on off-peak dates)

Related reading: 13 ways to redeem the Marriott Bonvoy Brilliant 50k free night award

Punta Cana perfection

Let's consider a stay at The Westin Puntacana Resort & Club during off-peak dates.

The Westin Puntcana Resort & Club (Photo courtesy of the hotel)
The Westin Puntcana Resort & Club (Photo courtesy of the hotel)

When we searched dates in October, we found a Premium king-bed room with an ocean view for 32,500 points per night. That's 130,000 points for five nights (since Bonvoy members get the fifth night free on award stays).

If you earned the entire 100,000-point welcome bonus from the Marriott Bonvoy Boundless Credit Card, you've almost got enough points to cover that entire stay just from the bonus. If you have Chase Ultimate Rewards points, you can transfer them to your Marriott account at a 1:1 ratio. Finally, you could also use a 35k free night certificate to extend your vacation for a sixth night.

A trifecta in Grand Cayman

Marriott has three properties on Grand Cayman: the Grand Cayman Marriott Beach Resort (Category 6), The Westin Grand Cayman Seven Mile Beach Resort & Spa (Category 7) and The Ritz-Carlton, Grand Cayman (Category 8).

Photo courtesy of the Westin Grand Cayman

With the 100k current sign-up bonus from the Marriott Bonvoy Boundless Card, you could book a two night stay for as little as 80k total points (plus resort fees).

Bottom line

Vacationing in the Caribbean doesn't have to be expensive. You can use miles and points to significantly defray the cost of your flights and hotel rooms. This is true even if you are starting with almost no points right now and want to select the best credit cards to make your Caribbean dreams come true.

Use this guide to the best credit cards for a Caribbean vacation to help you identify the best ways to leverage airline miles, hotel points, elite status and more to go where you want for less than you think.

The Caribbean is definitely within reach. Have you planned a Caribbean vacation on points? Where did you go and how did you pull it off? Tell us in the comments below.

For rates and fees of the Platinum Card, please click here.

Featured image by Courtesy of Ritz Carlton Grand Cayman
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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