Package vacations are a great choice for effortless traveling, as they are quick and easy to book and ensure that everything will be taken care of for you. For example, if your flight is canceled, it’s the travel provider’s job to find a new flight for you. You can rest easy knowing that your vacation will be stress-free and you are protected in case of changes to your itinerary.
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
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."
Maui, nicknamed "The Valley Isle," is consistently rated by travel experts to be among the top island destinations in the world. Maui has some of the finest luxury beach resort accommodations and activities in the islands, especially along Kaanapali Beach. All of these high-end resorts amid the romantic beach backdrops make Maui a popular honeymooning spot. Read more about Maui

If you’re tempted to make a vacation-related purchase but are a little put off by the price tag, add the item to your electronic cart – but don’t go all the way through with the purchase. Before doing this, be very careful to make sure that it’s not a one-click purchase or a website where your payment details are stored, or anything else that will rope you into a purchase that you’re not ready to make.
Priceline’s “Name Your Own Price” Option. When using Priceline, you can enter the day you’d like to fly (or the day you’d like to stay at a hotel) and the price you’d like to spend. Priceline comes back with an offer of a flight or hotel, if there’s something available that meets your criteria. You find out the times of the flight and the star rating and general location of the hotel, but you won’t get to know the airline or specific hotel name until you book. Priceline claims that you can save 40% off published prices by using this method. Priceline also offers traditional booking services if you’d rather know exactly what you’re getting.
If you’re looking for a deep-dish pizza, world-class hockey, or a walk through Millennium Park, we can help you see—and eat—it all with a Chicago vacation package. There’s always something to do here in the crown jewel of Illinois, from a walk on Navy Pier to the gorgeous boutiques on the Magnificent Mile. Pardon our pun, but we’re sure “The Windy City” will “blow” you away!
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
Chosen By: Amie O’Shaughnessy, founder and CEO of Ciao Bambino. After having her son, Amie searched extensively for credible resources to provide family-focused advice, direction and useful accommodation information. She quickly realized that there were no relevant resources available, particularly for a discerning traveler, so she decided to help solve this problem and started Ciao Bambino.
Travel Auctions. There are two kinds of travel auction sites. One allows you to enter your preferred travel dates, destination, and class of service (such as economy or business class), and travel companies compete to offer the lowest-priced trip that meets your criteria. Flightfox is one site that operates this way: It charges a per-trip fee, and while the exact price depends on the trip itself, you can expect to shell out around $30. The other type of travel auction operates the opposite way: Companies offer flights, hotels, or packages, and users can bid on the trips. When the auction closes, the top bid wins. SkyAuction.com operates using this model. It’s free to bid – though you should be aware that additional taxes and fees are unlikely to be included in your bid price, so you will end up paying more than your bid if you win.

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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