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.

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 harbour dotted with both mega-yachts and fishing boats.

Glamourous Santorini is deliciously different. Geographical newness is in part to thank. The island’s popular black volcanic Perissa and Kamari beaches are big draws, as is its arguably most famous Red Beach near Akrotiri (which is the place to go for archaeology buffs). Santorini curves round a giant lagoon in the Cyclades islands, offering stunning views from sky-high towns, eclectic cuisine, lovely galleries, thriving nightlife and excellent wines.

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.