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Why you should go: Sofia is one of Europe’s coolest overlooked capitals, with ancient ruins and salmagundi architecture in Ottoman mosques and Red Army monuments. In the past few years, its streets have proliferated with graffiti art, skateboarder girls, and shabby-chic bars where you can while away days and evenings. A city trip is easily paired with a few more days at the Black Sea on the Bulgarian Riviera. You’ll find a gorgeous seaside that rivals plenty of more-lauded Mediterranean stretches -- again but for a sweet fraction of the cost.
Why: For an affordable and sun-soaked vacation, southern Portugal’s Algarve region should be hot on your radar. The city of Albufeira boasts a beautiful climate, fabulous beaches, inexpensive apartment-style hotels and a central location within the Algarve. There are over 100 different restaurants, bars and nightclubs, and Albufeira even has a charming Old Town with traditional Portuguese streets and plazas within the city center. The prices for both food and wine are extremely reasonable; be sure to sample the wines of Portugal. While summer remains the busiest and most popular time to visit, I love visiting in late spring — the weather is pleasant and sunny, there are fewer tourists and hotel rates are very affordable. Albufeira also offers easy access to nearby towns such as Loulé, with its famous market and an authentic slice of Portuguese culture. Rent a car to see the church of São Lourenço in Almancil, famous for its exquisite blue tile. Head north of Lagos to see Ponta da Piedade, with its towering red rock formations against the sea. Play a round of golf in one of the many beautiful courses in the Algarve. The place to stay: the Epic Sana Algarve overlooking Praia da Falésia, where you can bask in the sun at one of its five outdoor pools and indulge at the beautiful spa.
Why you should go: Not only is it arguably the greatest swinging-around-a-stage-in-purple-sequined-zebra-print-pants anthem of David Lee Roth-era Van Halen, it’s a slinky, skinny swatch of land with the Caribbean Sea on one side and the Pacific on the other. Smaller than South Carolina, it boasts 1,800 miles of ocean coastline and 5 million acres of national parks on the inside. For those who enjoy stylishly restored ruins, Panama City’s old quarter, Casco Viejo, is a UNESCO World Heritage Site that dates back to the 1600s and is now filled with hipstery shit, because of course it is. This cobblestoned city center is surrounded by the ultra-sleek, modern, quasi-futuristic skyscrapers of Panama City, which kind of looks like Rio without the smog and soon-to-be decaying Olympic infrastructure. - Nicole Rupersburg, 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…