The coastal village of Kamari features the beaches and ruins that are typical of Greek islands, but also boasts unusual attractions like an open-air cinema. Stray from the black pebble shores and head up to the site of Ancient Thira, where the stone remains of houses, markets, baths and temples will impress you with their size and structure. Sip local vintages at the Gaia Winery, then relax at an outdoor café as you watch the sun sleepily drop below the horizon, washing the sky with warm Aegean light.

A spot of white in the turquoise waters of the Aegean Sea, the island of Naxos is a unique blend of ancient ruins and beach culture. The largest of the Cycladic Islands, Naxos is the childhood home of none other than Zeus, king of the gods. Upon arrival in Naxos, hike over a causeway to Palatia, where the Portara, a stone gateway to an ancient temple that no longer exists, stands alone, the symbol of the island. At sunset, the views of the island, and the sea beyond, are breathtaking.

Known as the "Island of Colours" thanks to its jewel-coloured waters and building painted in vivid primary tones, the horseshoe-shaped island of Milos floats serenely in the Aegean Sea. It was here that the world-famous Venus de Milo statue was discovered. Though she now holds court at the Louvre, Milos has other beauties to admire. There are dozens of beaches, all different colours and all different combinations of sand, stone and shell. Explore the ancient theatre, catacombs and windmills in Tripiti village, then cap off your day with a cinematic sunset.

The Cyclades are a group of Greek islands with beautiful, white sandy beaches, rugged mountains and lush valleys. Glamorous Santorini and Mykonos attract the jetset, while lesser-known islands such as Milos and Naxos, are perfect for beach lovers. Ruins, including the 11th-century Dorian settlement and volcanic ash-preserved ancient Akrotiri in Santorini, amaze those with a bent for ancient history. Sifnos' cuisine wins it admirers. Hydrofoils, ferries and catamarans connect the islands.

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.

A world away from Crete's bustling capital, laid-back Elounda features fishing villages, uninhabited islands, and tranquil bays. There's plenty to explore in this sprawling town settlement—from luxury resorts and nature preserves to a fortress and former leprosy colony.

Serving as the main port town for the island of the same name, the town of Ischia has been inhabited for centuries, famous for its beaches and the healing waters of its spas. The town is divided in two: Ischia Porto is the harbor district and commercial center of the island, filled with brightly lit taverns and bars, and Ischia Ponte, the historic quarter, with its ancient castle and its stone streets seemingly frozen in time.

Sunbathing, al fresco dining and late-night discos are a way of life in Hammamet, the Tunisian St-Tropez. Located on the fertile Cap Bon Peninsula, about 40 miles south of Tunis, the bayfront resort is surrounded by verdant hills and citrus groves. When not basking on Hammamet Beach, browse the markets for local pottery or wander through the medina (old city) with walls that date to 1500. Summer brings festival fever to the city with plenty of music and theatrical offerings.

Olbia (Greek for “happiness”) is a popular jumping-off point for those visiting the white-sand beaches of the Costa Smeralda, but those who linger in the coastal city uncover a historic centre filled with archaeological landmarks, piazzas ringed by wine bars, and authentic eateries.

Far from Ibiza's party towns, Santa Eulalia del Rio attracts a calmer clientele with its white-sand beaches and laid-back nightlife. Traditional Mediterranean buildings and a 16th-century church overlook a yacht-filled marina, while Ibiza's only river borders the town's southern reaches.

The kings of the Wodeyar dynasty set the bar high for the southern cultural capital of Mysore. Ornate palaces and the Gothic St. Philomena's Church with its 175-foot spires pack a visual punch; local institutions keep Carnatic classical music and dance in the public eye. A prominent 11th-century temple sits atop 1,000 steps on the city's outskirts. Dress to the nines and party like a rock star in celebration of Mysore heritage during the lively Dussehra festival, held for 10 days in October/November.

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.