3 Quick, Warm Getaways to Travel to This Winter

Rachel Morgan Cautero
By Rachel Morgan Cautero 
Edited by Mary M. Flory
warm vacation spots and quick warm getaways

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The holidays can be stressful for everyone. Whether it’s to de-stress after the celebrations or to avoid them altogether, you may be itching to find quick warm getaways this winter.

From flights to hotel stays and rental cars, here are cheap, warm places to travel, plus how to use your travel rewards points to save even more. Here are this winter's best quick warm getaways and vacation spots.

1. San Juan, Puerto Rico

Good news: Though the winter months are a popular time to travel to warm-weather locales, there are still some deals to be had this winter for a quick getaway. Just remember these offers were available when we found them, but prices and availability change often.

Fly Southwest from Chicago-Midway to San Juan, Puerto Rico for a week’s stay in February for just over 19,000 points and $11.20 round-trip. Puerto Rico is an easy getaway because it’s an American territory, which means you can use U.S. dollars and you won't need a passport. Plus, there’s plenty to do and the food is excellent.

cheap flights to san juan 2023

If you’ve opted for a wintertime jaunt to Puerto Rico, consider staying at the Sheraton Old San Juan Hotel. A four-night stay at this property in late January into early February will cost you just 129,000 Marriott Bonvoy points.

In San Juan, don’t miss landmarks like Castillo San Felipe del Morro, Catedral de San Juan Bautista and La Fortaleza, the latter of which is the governor’s mansion, though you won’t be able to enter. While you’re there, head over to the Capitol, which has an impressive rotunda.

Check out eateries like El Jibarito and don’t forget to use your favorite travel card, like the Chase Sapphire Preferred® Card, which offers 3x points on dining, 2x points on travel and 1x points on all other purchases. You can redeem these points through Chase Ultimate Rewards®.

» Learn more: AmEx vs. Chase points

2. Aruba

Or fly from Atlanta to Aruba this winter for just 41,000 miles plus $86 in fees on Delta. Bonus? These flights are nonstop, making your warm-weather getaway that much more efficient.

delta aruba costs

If you choose Aruba for your getaway, its beaches will likely occupy most of your time. For a break from sunning yourself, observe the local wildlife in Arikok National Park, or schedule a sailing and snorkeling cruise with Pelican Adventures, which offers various options for cruising, from private charters to sunset cruises.

3. Key West, Florida

If you want to stay domestic, consider Key West, one of our favorite cheap warm places to travel in U.S. It’s brimming with culture and good eats — and even features the former residence of prolific American author Ernest Hemingway and his famous six-toed cats (for the English nerds among us).

Flying to Key West from most other cities in Florida is a cinch, not to mention exponentially cheaper. But it may also be more cost-effective to pay for your flight with cash, as opposed to using points. Case in point: We found this fare on Silver Airways from Tampa to Key West for just $210 round-trip. Plus, you’ll earn TrueBlue points for your flight, since JetBlue and Silver Airways are partners.

silver airways winter getaways

If you’re staying stateside, book a room at the waterfront Hyatt Centric Key West Resort and Spa for just 30,000 points a night. The resort is close to Old Town, has a spa and is pet-friendly, which is nice if you plan to bring your furry friends along. Another perk: Book with points and you won't have to pay a daily resort fee of $50 plus tax.

In Key West, visit the southernmost spot in the contiguous United States and the aforementioned Hemingway estate. Or explore Mallory Square and shop along Duval Street. Since its more reachable than the aforementioned quick warm getaways, we file Key West as top contender for trip savvy warm weather weekend getaways.

You could use your Capital One Venture Rewards Credit Card to shop and fund your excursions. It offers 2x miles on all purchases.

Cheap warm places to travel, recapped

This winter, instead of succumbing to the cold weather blues, use your credit card and airline points to escape to someplace warmer. You’d be surprised at what a little sun and Vitamin D can do.


How to maximize your rewards

You want a travel credit card that prioritizes what’s important to you. Here are our picks for the best travel credit cards of 2023, including those best for:

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