Why: Following the devastation caused by Hurricane Maria, travelers might be reluctant to visit the territory of Puerto Rico. But, on a recent visit to the island to help rebuild some of the most popular tourist attractions, I was thrilled to see that Puerto Rico is thriving and really is open for business. If you don’t have a passport — or if you have one that’s closed to expiring or being filled — one of the best parts about visiting Puerto Rico is that no passport is needed for U.S. citizens. With plenty to see both in San Juan — from the charm and bright colors of Old San Juan to checking out where one of the most famous rums in the world is made at the Bacardi Factory ($15 for a historical tour) — and outside, such as a trip to El Yunque National Forest, you'll be kept busy. Flights to San Juan generally will run you less than $250 from the East Coast, making it a perfectly close and affordable getaway. While there are several affordable chain hotels, boutique hotels flourish — especially in Old San Juan. Check out The Gallery Inn or Decanter Hotel.
Looking for something a little more luxurious? No problem. Check out our lists of the best hotels by island. If money is not so much the issue, we recommend Montage Kapalua Bay on Maui and Mauna Kea Resort on the Big Island. Both of these five star resorts are cozied up to beaches that have been voted #1 Beach in America by Dr. Beach. In addition, Montage Kapalua Bay is Hawaii’s newest Forbes Five Star property. Another bonus? They both usually offer specials along the lines of “get the 4th night free.”
Why: When it comes to cheap destinations, you can not beat Thailand. Phuket is a beautiful beach spot that is famously known for nice people, affordable hotels and amazing food. Low season is in the spring and winter. (Don't go during summer because it will rain everyday.) Once in Phuket, head to Patong beach at night: The nightlife is something to see, with loud music and constant entertainment. The next day you should head to Phuket Town. With its colorful buildings, Phuket Town looks like you stepped into Portugal. Stay at Andakira Hotel Patong for under $50 a night. Before you leave Phuket, make sure you take a ferry for around $30 roundtrip to the Phi Phi islands: It's a two-hour boat ride, but so worth it.
Why you should go: For all the greedy reasons: Its landscape varies from world-famous Pacific surf beaches to strikingly beautiful inland mountains, you’ll eat the best Mexican food you’ll ever have, the city is packed with pure magic. And for a selfless one: After a brutal past year of political rhetoric in the States, now is a great time to show our neighbors to the south some love. Whatever scant bucks you spend will boost their economy and help preserve the many indigenous cultures that call Oaxaca home. - Tess Rose Lampert, Thrillist contributor
Switch up the usual Caribbean getaway this winter and check out gorgeous Cartagena, Columbia. You'll find white sand beaches, plus a beautiful old city and vibrant culture. Your 4-star hotel is only steps from Bocagrande Beach and just five minutes away from historical downtown Cartagena. What's Included? Based on two people sharing, this vacation deal…