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.
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.

It’s worth noting that if the original price isn’t always posted for these types of deals, so you may not know exactly how much you’re saving (or if you’re saving at all). And while Groupon does post the percent savings (and it’s often 50% off or even higher), some critics point out that the “original” prices for Groupon deals and other discount sites are occasionally inflated to make the deals look better.
Oahu, known as "The Gathering Place," is the most populated area in the island chain. It's also home to some of the most recognizable landmarks in the world like Diamond Head, the world-famous Waikiki Beach, and Pearl Harbor. Most people think of Honolulu, Oahu's largest city and state capitol, as a metropolitan with global flavor, but just a few miles outside of the city limits, quieter getaways can be found. Read more about Oahu
Why: Slovenia is in the heart of Europe and borders the alps and the Mediterranean Coast. It’s a country that has a little bit of everything — mountains, beaches, pristine lakes, 11,000 karst caves, castles, a Pannonian Salt Plain, healthy water springs and city life in Ljubljana, European’s Green Capital. No wonder it’s been called the New Zealand of Europe. One of my favorite towns to visit is Piran, located on Slovenian’s Istria on the Adriatic Sea. Explore this coastal town — a little Venice — and savor a fresh seafood meal for under $10. It’s the perfect place to visit on foot. Meander through the alleyways and visit the market. Climb up to the city walls and to the top of the bell tower for spectacular views. Or rent a bike and cycle through the countryside. It’s an easy day trip from Ljubljana, but if you plan to stay the night, check into a luxury four-star hotel like Hotel Piran for just $80 a night. How to get around? Visit GoOpti for airport transfers as low as $9. If you want to carpool from Slovenia to Italy or Croatia, check their site for great deals. For example, you can carpool from Ljubljana to Venice for as low as $18. Round About Slovenia offers deals for tours around the country and even Croatia (how about a $45 half-day tour to Lake Bled?).

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.


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

U.S.: Alabama: Birmingham; Alaska: Anchorage; Arizona: Sedona; Tucson; California: Burbank; Long Beach; Ontario; Palm Springs; Sacramento; San Jose; Santa Barbara; Colorado: Colorado Springs; Connecticut: Hartford; Florida: Clearwater; Daytona Beach; Ft. Walton Beach; Naples; Marco Island; Key Largo; Melbourne Area; Cocoa Beach; Vero Beach; Miami; Pensacola; St. Petersburg; Tampa; Georgia: Atlanta; Savannah; Idaho: Boise; Illinois: Chicago; Indiana: Indianapolis; Kentucky: Louisville; Maine: Portland; Maryland: Baltimore; Michigan: Detroit; Flint; Grand Rapids; Traverse City; Minnesota: Minneapolis/St. Paul and Mall of Americaopens in a new window; Rochester; Mississippi: Gulfport and Biloxi; Jackson; Missouri: Kansas City; St. Louis; Montana: Billings; Bozeman; Kalispell; Missoula; Nebraska: Omaha; Nevada: Reno and Lake Tahoe; New Hampshire: Manchester; New Mexico: Albuquerque; New York: Albany; Buffalo; Rochester; White Plains; North Carolina: Charlotte; Greensboro; Raleigh; North Dakota: Fargo; Ohio: Cincinnati; Cleveland; Columbus; Dayton; Oklahoma: Oklahoma City; Tulsa; Oregon: Portland; Pennsylvania: Pittsburgh; Rhode Island: Providence; South Carolina: Charleston; Greenville; Hilton Head; Myrtle Beach; South Dakota: Rapid City and The Black Hills; Tennessee: Chattanooga; Knoxville; Memphis; Texas: Dallas/Ft. Worth; El Paso; Virginia: Newport News/Williamsburg; Norfolk; Richmond; Washington: Spokane; West Virginia: Charleston; Wisconsin: Green Bay; Madison; Milwaukee; Wyoming: Casper; Cody
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.
Europe is a must vacation experience, offering something for everyone. Explore the vibrant theatre scene in London's West End and ride the London Eye for a spectacular bird's-eye view of the city's iconic skyline. One of the most romantic cities in the world, Paris delights at every turn, from the heights of the Eiffel Tower to the picturesque banks of the Seine. Italy is a feast for the senses, abounding in art, architecture, culture and cuisine, whether you visit Rome, Florence or Venice.
Prices based on searches conducted by fellow shoppers within the past 24 hours. There is no guarantee that these prices will be in effect at the time of your search. Vacation package savings are based on comparison to prices on Orbitz.com of the same components booked separately. Savings vary based on origin/destination, length of trip, stay dates and travel partners, and aren't available on all packages.
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.
While hotel prices might be cheaper in underrated locales, you do need to be aware that flight prices might be more expensive – and possibly at less convenient times with more stops – if it’s not a common route. For example, an August flight from Minneapolis to Rio de Janeiro, Brazil might cost around $857, but a flight at the same time from Minneapolis to La Paz, Bolivia costs $1,177. The distance is nearly identical, though most flights to La Paz require at least two (and, in many cases, three) stops, whereas there are flights available from Minneapolis to Rio de Janeiro with only one stop.
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.

Using a website like Hotels.com or TripAdvisor, set your minimum guest rating level high (start with four stars and above) and be open to hotels at any star rating. Once you’ve eliminated all but the highest-reviewed hotels, sort by price from low to high. As long as the hotels on the list have a reasonable number of reviews – around 100 or more – it’s a fair bet that the hotel makes the best of whatever amenities they have.
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.
Just how cheap is it? The food and accommodation aren’t fabulous bargains -- but, oh, the shopping is. In the tourist town of Victoria Falls, a hostel bed or a hired tent will cost you $15 to $20 per night, but I scored a carved stone necklace from a street vendor for the sandals I was wearing. Bartering is common at flea markets and on the streets, where second-hand clothes -- shoes, baseball caps, and sportswear (think basketball or soccer shirts) -- have real buying power. Fill your suitcase with gently used gear and exchange it for jewelry, handmade crafts, and souvenirs like devalued trillion dollar notes.
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.
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