Want to make your co-workers insanely jealous? Just casually drop "I’m holiday making in the Maldives this year" into conversation, preferably in the dead of winter. Or better yet, go there without mentioning it to anyone—then send them a "Wish you were here!" postcard.

One of the three principal islands of the Maltese archipelago, the island of Malta is the largest of the chain. Its capital Valletta, a lively, bustling city with many buildings dating back to the 16th century, teems with cathedrals, palaces and forts. The impressive Grand Harbour offers a dramatic arrival. The top archaeological attraction is the UNESCO-designated Hypogeum temple ruins, a macabre, 5400-square-foot underground necropolis and the world's only underground prehistoric temple.

Whether it’s day or night, the resort town of Sliema thrums with activity. Historic cathedrals, watchtowers, and forts spatter the area, while along the waterfront locals shop, dine, bar hop, or stroll along the promenade for views of the shimmering Mediterranean.

Classic whitewashed buildings line the labyrinthine streets of Mykonos, the largest town on the Greek island of the same name. Matoyianni Street is particularly charming. Iconic 16th-century windmills keep watch over the village from the hills above, and the fully functional Boni Mill is part of the Mykonos Agricultural Museum. The Aegean Maritime Museum and the Folklore Museum will give you a proper introduction to the area’s rich cultural and economic history.

It’s nicknamed the Eternal City for a reason. In Rome, you can drink from a street fountain fed by an ancient aqueduct. Or see the same profile on a statue in the Capitoline Museum and the guy making your cappuccino. (Which, of course, you know never to order after 11 am.) Rome is also a city of contrasts—what other place on earth could be home to both the Vatican and La Dolce Vita?