Why: While the devastating hurricanes of 2017 impacted just a portion of the Caribbean region, it damaged some of its more cruise-popular spots, like Tortola in the British Virgin Islands, St. Martin, Puerto Rico, St. Bart's, and the U.S.V.I.’s St. Thomas, St. Croix and St. John. While all are under significant rehab and rebuilding — and most are actually now open to cruise ships and tourists, this could be a perfect year to explore more exotic islands. That’s because lines like Windstar, which had, pre-hurricanes, planned to offer BVI-centric trips, relocated ships to other parts of the Caribbean. The winning trip? We love Wind Surf, one of the line’s sailing vessels, with its trip out of Barbados; ports include Martinique, Guadeloupe, and Montserrat — all islands that heretofore have often been bypassed by established cruise lines. And get this: There’s plenty of cruise capacity in this region, particularly when it comes to small ship sailings. In part, excess cabins are available because many skittish travelers canceled their bookings. As well, they can typically be more expensive (look for $300 per person, per day) than big ship vessels. But do the math: Windstar, and other small ship lines like Crystal, Regent Seven Seas, Seabourn, Azamara, Oceania and Viking Oceans, can actually be quite a good value when compared to land-based properties because they’re more price inclusive. Look for deals that include cocktails, gratuities and shore excursions not to mention pre- and post-cruise hotel stays and, in some cases, airfare to the ships’ port of embarkation.
Discover why the Islands of Aloha are home to treasures unlike any other on Earth. Hawaii is more than just the birth place of modern surfing and hula, it's a land of relaxation, adventure, natural beauty, and of welcoming locals. You'll find the itineraries in Hawaii are endless. From adventure tours to family fun; from soaking in the cultural sights to a hike on a volcano; you can do it all or you can simply lie on the beach all day.
In 2014, CheapAir.com also analyzed nearly 2 million international trips covering 3,184 markets. International flights usually open for booking slightly less than a year in advance. CheapAir.com found that prices “stay fairly flat for a few months” after flights open for booking – but, of course, not all of us are ready to lock down travel plans nine months in advance. After the initial flat period, prices “start to creep up slowly, until about 90 days before departure when the pace of increase starts to accelerate.”
Couchsurfing hosts sometimes take great pride in serving as tour guides and cultural ambassadors for their visitors. The website features quotes from visitors, such as Sam, who said, “Nong showed me the sights and helped me search out the best street eats (insects included!) during my week in Bangkok. She also helped me with more practical matters, like getting my Myanmar visa and planning the next leg of my Thailand trip.”
Why you should go: Don’t let the name fool you; Isla Grande is an intimate, gorgeous Caribbean island just a 45-minute boat ride from Cartagena, full of exceedingly friendly locals and all the hallmarks of a tiny paradise. You’ve got your idyllic beaches, your lagoons of bioluminescent plankton that turn the water bright blue, your fresh seafood and multiple options for diving and canoeing. The chance to visit such a place is probably why you bother to earn money in the first place. - Daniel Cole, Thrillist contributor
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!

Up in Tennessee, “Music City” is calling your name, and you can’t help but listen! This country music city feels like a small town—and its siren call resonates with those looking for simpler times and Johnny Cash cover bands. You can spend your Nashville vacation taking in performance after performance at the Grand Ole Opry, but leave time for the art collection at the Parthenon at Centennial Park.
Not only will you save money booking your flight and hotel together, but Las Vegas vacation packages are typically packed with fun extras that you won’t get if you book all your travel details separately. Wha t kind of stuff? Think dining discounts, free nights, room upgrades, nightclub promotions, show tickets, dining deals, attraction add-ons, and more.
Why: Zanzibar may sound like an expensive, bougie honeymoon island, but take it from this solo affordable adventure traveler; it's more budget friendly than you think. Not to mention, absolutely beautiful. You can take the ferry from mainland Tanzania to Zanzibar for only $35 ($50 if you want a VIP seat), but flights to and from there are usually less than $100. Yes, there are many luxury resorts like Tulia Zanzibar and Melia Zanzibar that you should definitely splurge on if you can. (Tulia has a jungle waterslide and pool floaties. Enough said.) But there are also budget options. In fact, I found an Airbnb called the Surf Escape that was only about $40 per night, right on the beach, and had on-site surf, paddleboard and wind-surfing lessons.

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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