A boisterous port city on the surface, this urban capital of Crete hides millennia of history beneath its modern trappings. In Heraklion, scooters zip past Minoan and medieval relics such as the seaside Koules Fortress, while Turkish fountains bubble up in the shadow of apartment blocks.

Sandy, peaceful beaches and ancient ruins beckon travelers to Chersonisos, a one-time Roman port on the island of Crete. This is a family-friendly place, with plenty of activities for kids. The Lychnostatis Open Air Museum gives you the chance to explore the trades and lifestyles of early islanders. Exhibits include a herbarium, olive oil and wine presses and workshops on ceramics, shoe making and weaving. The aquarium showcases local sea creatures, as do the town's many traditional cafes, though in a completely different (and more delicious) manner.

Surrounded by water on three sides, Agios Nikolaos combines the sleepy feel of a seaside resort with all the amenities of a cosmopolitan port. Villas and tavernas spill over the town’s three hills to meet a harbor dotted with both mega-yachts and fishing boats.

Much of the old town district of Chania was developed around its harbor, which was built by the Venetians during the 14th century. Its lighthouse still proudly overlooks the Mediterranean. Here you’ll find several cinemas and historical attractions like the Archaeological Museum, a collection of Minoan and Roman artifacts that’s housed in the former Monastery of Saint Francis. Word nerds will especially enjoy the Museum of Typography.

Even if you’ve never been to this Cyclades island in the Aegean Sea, you’d still recognize it immediately – candy-colored houses carved into cliffs, sapphire waters, gleaming white buildings topped with half-spheres the color of a stormy sky. Here you’ll find peace as you roam the black sand beaches or the streets of a provincial village like Imerovigli. Beautiful Oia is world famous for its sunsets, which seem tinted with every shade of an artist’s palette.

Want to make your co-workers insanely jealous? Just casually drop "I’m vacationing 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.