This Tuscan hill town will transport you back to the Middle Ages. Siena's grand cathedral, built in the 1200s, has treasured artworks and marvellous marble floors. The Piazza del Campo, the main town square, is a UNESCO World Heritage Site. It's also home to the Palio, perhaps the most infamous horserace in the world. No goofy hats and mint juleps here—this is a mediaeval tradition involving bareback riders racing on cobblestones (so as you might imagine, it's quite dangerous). Siena is an easy daytrip by train from Florence, just 43 miles away.

Everyone who visits Paris for the first time probably has the same punchlist of major attractions to hit: The Louvre, Notre Dame, The Eiffel Tower, etc. Just make sure you leave some time to wander the city’s grand boulevards and eat in as many cafes, bistros and brasseries as possible. And don’t forget the shopping—whether your tastes run to Louis Vuitton or Les Puces (the flea market), you can find it here.

If you’re looking for a Robinson Crusoe experience, you can still find that thatched-hut-on-the-beach vibe in the North Malé Atoll. But this chain of 50 or so palm-shaded islands in the Maldives has been stepping up its game lately with sleek, stylish accommodations. These days, even the islands themselves are designer. The newly opened Patina Maldives and Ritz Carlton Maldives sit on an archipelago that construction crews built in the Indian Ocean. Divers love North Malé Atoll for spots like Manta Point, where manta rays congregate so they can be “cleaned” by small fish. You can even snorkel with curious hawksbill turtles. North of the capital city of Malé are some prime surf spots.