How to Experience 5 Popular Caribbean Islands Using Points

With winter storms howling, you may be dreaming of flying south for a sunny escape. For some travelers, chasing summer during the winter months is the only reason to stockpile points and miles during the rest of the year. If that sounds like you, now is the time to figure out where you’d like to go and where to spend your points and miles.

If you’re longing for a tropical getaway, why not head to the Caribbean? Here are a few of our favorite Caribbean destinations to consider for your next escape.

Dominican Republic

It may seem like everyone is headed to the Dominican Republic for vacation, but it’s a favorite destination for a reason. Beyond the white sand and turquoise waters, Punta Cana is full of surprises from the time you touch down at the airport. As a nice treat for Priority Pass Select members (complimentary with cards like the Chase Sapphire Reserve® and the Hilton Honors Aspire Card from American Express), the Punta Cana airport VIP Lounge has an outdoor pool. Terms apply.

Aside from using your branded credit cards for comfort during your transit, you may have a stash of World of Hyatt points lying around; one of the best places to spend them is in Punta Cana. You have two choices: Bring the whole family to the Hyatt Ziva Cap Cana, or enjoy an adults-only getaway at Hyatt Zilara. These properties are both all-inclusive resorts that start at just 25,000 World of Hyatt points per night. Whether you pick Ziva or Zilara, expect to soak up some rays while stretched out on the warm sand.


Sand and sun are a near-guarantee in the Caribbean, but if you’re anything like us, you really travel for the food. In that case, Jamaica is a must-visit for jerk chicken and spicy island flavors (don’t forget to try some conch, too). Nothing tops a post-swim barbecue on the balcony, sunshine keeping you warm and sea breeze cooling you down.

If that’s the vibe you’d like to ride, grab your stash of Hilton Honors points and book the Hilton Rose Hall Resort & Spa. This all-inclusive starts at just 68,000 Honors points per night. Enjoy exclusive access to prime Montego Bay beachfront by day, then feast on incredible Jamaican barbecue by night at the on-site restaurant, Annie’s Smokehouse BBQ.

Puerto Rico

If you’re a U.S. citizen who doesn’t hold a passport, Puerto Rico is a great Caribbean destination for you. As of Oct. 1, 2020, the U.S. will officially require identification that is Real ID compliant in order to travel domestically. This identification will also get you into Puerto Rico if you do not hold a passport. In fact, it’s a great idea to travel to Puerto Rico and visit a corner of the United States that is sometimes overlooked.

Visiting Puerto Rico in the winter could be just the ticket; if you’ve been collecting IHG points, the InterContinental San Juan is a great option. Currently, rooms at the InterContinental San Juan start at 50,000 points per night. If you’ve never been to Puerto Rico, it’s definitely worth checking out!


If you’re interested in flying even farther south, stop just north of South America to visit the ABC Islands: Aruba, Bonaire and Curacao. Colorful Curacao has a Spanish and (more recently) Dutch colonial past — a true conglomerate of cultures.

The largest hotel empire in the globe hosts a lovely property on Curacao, where you can put your Marriott Bonvoy points toward a stay at Renaissance Curacao Resort & Casino. This is a Category 5 property, but with Marriott’s dynamic pricing model, the points price will change depending on when you book. Standard pricing is 35,000 points per night, while off-peak nights will cost 30,000 points. During peak times, it’ll cost 40,000 points for a night at this gorgeous property.

Trinidad & Tobago

While there are many branded points properties in Trinidad, Chase Sapphire Reserve® and Chase Sapphire Preferred® Card holders can leverage their Ultimate Rewards® into award nights at many more properties that are bookable through Expedia. This makes amazing properties like Eagle’s Base Villa & Cottage accessible to Chase cardholders who wish to either book with their card or use Chase Ultimate Rewards® points.

All information about the Hilton Honors Aspire Card from American Express has been collected independently by NerdWallet. The Hilton Honors Aspire Card from American Express is no longer available through NerdWallet.

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