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
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.
There is another way that the practice of almost purchasing can pay off. You’ve probably already noticed that, after conducting a web search for a specific item, the advertisements on the Internet pages you visit are chock full of that very item. Those ads might annoy you, but they also might contain tailor-made discounts on the exact hotel, cruise, or vacation package you were looking for. It’s worth a second glance.
Why you should go: With some 6,000 islands, Greece is the Mediterranean’s powerhouse beach destination. While only 200-some are inhabited, an island-trotting adventure for everyone here, whether you’re looking for wildlife adventures, historic discoveries, or quite frankly, drinking ouzo and boogying. Athens makes an energetic springboard into the Aegean, with its own archaeological ruins, hipster cafés, and hangouts ranging from dynamic industrial to retro chic.
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.
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.
The East Coast has it all: beautiful beaches, stunning vistas, historical importance, and some of the most famous cities in the world. First stop on your Eastern Seaboard getaway: the “Big Apple.” A trip to New York City means you get to see the sights that are talked about all over the world, like Lady Liberty, Broadway, and Central Park. If you want to delve into U.S. history, a Washington D.C. vacation filled with monuments, museums, and galleries is for you. Speaking of history, the American Revolution got its start in a city a few hours to the north. Your Boston vacation will bring you to one of the most popular spots on the East Coast. Indulge in some of the best clam chowder in the world, then walk back in time on the Freedom Trail, which hosts 16 sites that played a huge role in the founding of the nation.
Puerto Vallarta travel experiences are made complete by a visit to these twin gems. The Plaza de Armas is the heart of the town, a square full of life and color, music and dancing around the clock. Check out the Presidencia Municipal and Los Arcos amphitheater en route to the Malecon, a mile-long seafront walkway filled with sculptures and home to the much-photographed La Parroquia de Nuestra Senora de Guadalupe church.
Why: Following the devastation caused by Hurricane Maria, travelers might be reluctant to visit the territory of Puerto Rico. But, on a recent visit to the island to help rebuild some of the most popular tourist attractions, I was thrilled to see that Puerto Rico is thriving and really is open for business. If you don’t have a passport — or if you have one that’s closed to expiring or being filled — one of the best parts about visiting Puerto Rico is that no passport is needed for U.S. citizens. With plenty to see both in San Juan — from the charm and bright colors of Old San Juan to checking out where one of the most famous rums in the world is made at the Bacardi Factory ($15 for a historical tour) — and outside, such as a trip to El Yunque National Forest, you'll be kept busy. Flights to San Juan generally will run you less than $250 from the East Coast, making it a perfectly close and affordable getaway. While there are several affordable chain hotels, boutique hotels flourish — especially in Old San Juan. Check out The Gallery Inn or Decanter Hotel.
JetBlue TrueBlue. U.S. News & World Report ranked JetBlue TrueBlue as number one on its list of Best Airline Rewards Programs. JetBlue primarily flies out of the East Coast and Florida, but if you live in either region and tend to travel domestically, this is one program to consider. Points can also be earned by traveling on its partner airlines, Emirates and Hawaiian Airlines. You can also earn points with hotel stays, car rentals, and “purchases with retail partners” – so you can rack up a whole bunch of points on a single trip.
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