5 Sunny Award Travel Destinations for the Holiday Season

Oct 24, 2014

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I’m a sucker for warm climates pretty much any time of year, but I especially relish a nice beach getaway in the middle of winter. Today TPG Contributor Jason Steele points out some hot award travel vacation ideas that you can still book for this coming holiday season.

After last year’s Polar Vortex, many Americans would prefer a sunny Christmas over a white one. For award travel enthusiasts, many of the best seats for holiday travel disappeared earlier this year, but there are still some options left. Here are a few balmy destinations with award availability for the holiday season.

When was the last time you heard someone complain about a beach vacation for the holidays?
When was the last time you heard someone complain about a beach vacation for the holidays?

Cancun, Mexico

This destination has several advantages for award travelers. First, you can still book as many award tickets as you need with several discount carriers, and from several different cities. For example, Southwest now flies to Cancun non-stop from Austin, Atlanta, Chicago, Milwaukee, and Denver. Spirit also offers service from Dallas/Fort Worth, Detroit, and Fort Lauderdale. Frontier, a transfer partner of American Express Membership Rewards and Diners Club Rewards, offers service this winter from Denver, Washington-Dulles, Indianapolis, Milwaukee, and Salt Lake City.

Here is an example of award space to Cancun in Southwest's Wanna Get Away Far Class
Here’s an example of award space to Cancun in Southwest’s Wanna Get Away fare class.

In addition, Virgin America offers service to Cancun from Los Angeles and San Francisco, while JetBlue serves Cancun from Boston, Fort Lauderdale, New York-JFK, and Orlando. Lodging will be a little harder to secure at this point, but check out some options on our Destination of the Week post about Cancun & The Riviera Maya.

Puerto Rico

San Juan boasts an average high temperature of 84 degrees in December, and an average low of only 73. Since it’s a United States territory, American travelers only need to provide proof of citizenship or residency upon return such as a birth certificate or a drivers licence, not necessarily a passport. This can save families significant time and expenses if they haven’t yet purchased passports for their children. In addition, vacationers only need to pay the same TSA fees that apply when visiting other US destinations, not the large taxes and fees imposed on travel to other Caribbean destinations.

Like Mexico, Puerto Rico is served by Southwest and JetBlue, which are both discount carriers with revenue-based award programs. Southwest offers service from Atlanta (ends March 7, 2015), Baltimore, Fort Lauderdale, Orlando, Tampa, and seasonal service from Houston-Hobby. JetBlue serves San Juan from Boston, Chicago O’Hare, Fort Lauderdale, Hartford, New York-JFK, Newark, Orlando, Punta Cana, Tampa, Washington-National, and seasonally from Jacksonville. Spirit also offers service from Fort Lauderdale and Orlando.

Puerto Rico is home to many resorts that are part of popular loyalty programs. Starwood alone has five different properties in Puerto Rico, four of which appear to be available with points over Christmas.

Four of the five Starwood properties in Puerto Rico are still available December 22-27 of this year!
Four of the five Starwood properties in Puerto Rico are still available December 22-27 of this year!

For more information, see our Destination of the Week guide for San Juan.

Punta Cana, Dominican Republic

Just west of Puerto Rico is the Dominican Republic, with the resort city of Punta Cana near its easternmost point. In addition to its many beaches, activities include deep sea fishing and aquatic tours featuring whales and dolphins.

Punta Cana also happens to be home to one of the busiest airports in the Caribbean. Southwest offers service from Atlanta, Baltimore, and Chicago-Midway. JetBlue has service from Boston, Fort Lauderdale, New York-JFK, and San Juan, and even Frontier offers service from Denver and Spirit from Fr. Lauderdale.

There are fewer hotels available with points over the holiday season, but there are still some options, such as the Four Points by Sheraton Puntacana Village, which is a steal starting at just 2,000 points. The Westin Puntacana Resort & Club is more upscale, but still a good deal at 16,000 Starpoints for a room that goes for $669/night over the holidays.

Key West

This has to be the warmest and most attractive winter destination in the continental United States, and also the southernmost point. In fact, Key West is closer to Havana than it is to Miami!

Expect weather during the holidays to be warm, but not hot, with an average high temperature of 76 degrees in December. While Key West does have its own airport, it is now only served by American, Delta, US, and Silver Airways (a United Express carrier) from a handful of destinations. But don’t worry, you can take in a scenic drive (largely over the ocean) from Miami or Fort Lauderdale and get there in under four hours. This convenience makes it a great destination for travel with seniors, especially if (like me), you have a grandparent who already lives in South Florida.

Key West also has plenty of points hotels. Hyatt alone has four properties in Key West, each of them costing 25,000 points a night, and one at Marathon Key that costs only 12,000 points per night, all of which are showing availability for Christmas week.

All of these Hyatt properties in the Florida Keys can still be booked with points during Christmas week.
All of these Hyatt properties in the Florida Keys can still be booked with points during Christmas week.


While these first four destinations have been fairly popular tourists spots for some time, consider Colombia as an emerging destination this Christmas. I wanted to include it for several reasons. First, it’s near the Equator, so it’s warm year round and winter is the dry season. Second, US dollars go very far in Latin America, and Colombia is no exception. Third, Colombia appears to be a growing market for American discount carriers that are trying to reach across the Caribbean to find new destinations. For example, JetBlue offers service to Cartagena from New York and Ft. Lauderdale, to Bogota from Ft. Lauderdale and Orlando, and to Medellin from Ft. Lauderdale. Spirit also offers service from Ft. Lauderdale to Bogota, Cartagena, and Medellin.

Bogota is Colombia’s capital city and features several points hotels such as the Park Inn by Radisson, which is part of the Club Carlson group. Although Medellin has a bad reputation due to its association with drug cartels in the 80s and 90s, it’s now a safe, modern, well developed city. It boasts beautiful weather year round, and has a system called MetroCable that extends the public transit to the surrounding mountains using cable cars similar to ski gondolas. Finally, Cartagena is known for its beautiful beaches as well as the architecture in its old city.

The US State Department does still list a Colombia Travel Warning, but every source I read indicates that violence has been down dramatically for many years now, and that tourism is booming in its wake. Finally, I spoke to Shawn Coomer (who writes the blog Miles to Memories), who just visited Colombia this summer with his wife and teenage son. “We never felt unsafe at any time,” he explained, while noting the great food and abundance of family friendly activities there, such as beaches, amusement parks, museums and hiking trails.

What’s your favorite sun-soaked holiday destination? Please share your suggestions in the comments below.

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