*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

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Vacation rental prices vary as much as hotel prices. Case in point: A search of one-bedroom vacation rentals in Manhattan during September results in options ranging from $60 per night to $2,800 per night. Vacation rentals are ideal for longer stays (seven nights or more). Many vacation rentals require minimum stays, so if you’re hoping for a weekend getaway, you may have to look elsewhere.
Why: As the gateway city to celebrated tourist destinations like the Amalfi Coast, Capri and Pompeii, Naples is finally getting its well-deserved time in the spotlight and intrepid travelers are flocking to the stunning southern city in droves. Naples is one of the oldest cities on the European continent and filled to the brim with intriguing cultural sights and monuments, from seaside castles and underground catacombs to show-stopping Baroque architecture and a plethora of contemporary art. It also boasts one of Italy's most cherished cuisines and is well-known as the birthplace of pizza, which you can enjoy for as little as €4 ($5), accompanied by views of the Bay of Naples and Mount Vesuvius (free). Neapolitan pizza making has just been recognized by UNESCO as part of its Intangible World Heritage list, so now is a great time to visit and enjoy its effervescent energy and fabulous cuisine.
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
Since no one has time to check flight prices constantly throughout the day, it’s a good thing that you can ask someone else to do the searching for you. Sign up for a fare alert, which is a subscription notification (usually via email) that provides a selection of flights and prices to a chosen destination. For example, I receive a daily email that tells me the cheapest flights over the next six months to London, Paris, and Bora Bora.

Why: With so much to see in Namibia, Windhoek, the country’s capital, is just the jumping point. Best of all, the U.S. dollar is strong enough to make travel, accommodations and activities all relatively inexpensive in the country — even for some luxury experiences. Windhoek is cheap in itself and has plenty of see, between exploring the local scenes like at the Namibia Craft Centre and checking out the city's German influence like at the Christuskirche church. Five-star properties, such as the Hilton Windhoek and The Olive Exclusive All-Suite Hotel can be booked for less than $150 per night, thanks in large part to the preferable exchange rate to Namibian dollars. But some of the best sights to see are located outside the city limits. Consider day or multi-day trips to get your outdoor fix and to see the stunning scenery and dunes that makes up the majority of the country. Tours, which often include meals, camping, activities and more, can be found for reasonable prices. If you’re more interested in seeing the beautiful country on your own, consider renting a car and driving to all of the sights. Entrance fees to national parks, such as the Etosha National Park, go for as little as $6 per day. Throughout the country, don’t anticipate spending a lot on food — you can find good, local dining for less than $10 per meal.
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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