Chosen By: Michaela Guzy, an American media executive, entrepreneur and on-air show host. She is the executive producer for two online television shows, Michaela’s Map and OhThePeopleYouMeet. Based in New York City, she is also an adjunct professor at New York University School of Professional Studies, where she teaches a course called "Travel Storytelling: Creating Video Content."
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.
The Big Island of Hawaii, or simply "the Big Island," is the largest island in the island chain. Due to its size, the Big Island's regions vary considerably. There are twelve distinct climate zones here, ranging from East Hawaii's tropical rain forests and the frozen slopes of Mauna Kea to Kau's arid desert in the south. The dramatic size of the largest Hawaiian Island creates a microcosm of environments and activities. Read more about the Big Island
Just how cheap is it? Bulgaria’s capital Sofia is the girls’ getaway paradise you never knew existed, where full-body waxes run about $20 and the full-meal deal of manis, pedis, and haircuts are much cheaper (because Bulgarian women like looking on fleek). A three-course dinner plus vino also shouldn’t cost more than $20 (and the local cuisine here is known to be hearty). Despite its post-Communist exterior, Sofia is also incredibly modern, and you’ll be able to find international bites from tapas to sushi.

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.”


Cruise around charming cobblestone streets and hidden alleyways to come across some of the best bargains in Mexico. Buy handmade pottery, silver jewelry and leather goods for insanely low prices, and peruse the sidewalk artwork by local artists. The food is a steal, too, so be sure to check out the carts selling mouthwatering fresh fruit and margaritas.
Just how cheap is it? The aftershock of the debt crisis can still be felt at plenty of Greece’s tavernas, restaurants, and supermarkets (though not so much in touristy areas). On a popular island such as Mykonos, you’re likely to spend at least €25 or more on a lush evening meal -- but you can also get a bottle of godly nectar and cook at your Airbnb or hotel kitchenette for a sliver of that. On smaller, less touristy islands and in some parts of Athens you’ll feel less of a wallet pinch, especially when it comes to accommodation.
Prices quoted are examples, valid for travel during dates listed above. Rates may be higher for other days of the week. Surcharges apply to weekends, holidays, special events, and convention periods. Restrictions apply. Rates are subject to change until purchased. Seats are limited and may not be available on some flights that operate during peak travel times and holiday periods. See our Terms and Conditions for more information about our policies. Free Night offers must be reserved for consecutive nights to receive the free night. Offer valid for room and tax only. Additional fees may apply. Limited number of rooms available. Promotion Code not combinable with any other offer. Promotional code intended for redemption by individual consumer only. Valid on published scheduled SWA-operated service only. Packages must be booked on southwestvacations.com and at least one day before departure date before 6 pm Central Time.
*Unless otherwise noted, fares include ROUNDTRIP AIRFARE via U.S. certified air carrier, hotel transfers (in Mexico and the Caribbean), hotel tax, resort baggage handling, fuel surcharges and all pre-collected U.S. and foreign taxes and fees including September 11th Security Fee. Packages in Turks and Caicos or San Juan, Puerto Rico do not include airport transfers. Packages flying into Cancun but staying in Cozumel require supplemental ferry transfers at an additional cost. More details
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…
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