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.

One of the most popular resort towns on the Italian Riviera, little Portofino has just over 500 permanent residents. But that all changes on summer days when the sun is shining and the yachting set drops anchor in the harbor to wander about. Boutiques, art galleries, cafes and restaurants line the tiny streets. Diving, hiking and beach-going are popular local pastimes, and there are even some historic sights like the Church of St. Martin (Divo Martino) and the Castello Brown hilltop fortress.

Situated amidst lush green, forested hills on the highest peak in the Aravali range, Mount Abu is the summer capital for the Indian state of Rajasthan. Its cool and soothing climate makes it an ideal retreat. Explore a number of Jain temples, including the Dilwara Temples, a complex carved of while marble, or visit the nearby Achalgarh fort, which houses many beautiful temples of its own.

Matheran is all about the views. Easily accessible via scenic rail from Mumbai, this refuge in the Sahyadri Hills is blissfully free of motor vehicles and affords nearly three dozen lookouts over the Western Ghats and the region's village-dotted plains. Porcupine Point is anything but prickly—rather, it’s an ideal spot for gorgeous sunsets, especially at the aptly named Panorama Point. Avid hikers hit the densely forested and wildlife-rich route to the ruins of Prabalgad Fort.

The city of Mahabaleshwar is a pinnacle of greenery, boasting one of the only evergreen forests in the world. The landscape abounds with lush hills, valleys and lookout points such as Lodwick Point, Arthur's Seat and Babington Point, all of which offer spectacular views. Trot along on horseback for a delightful four-legged tour of the gorgeous Venna Lake area, and savour juicy native strawberries, mulberries and corn.

Blossoming bougainvilleas, crumbling cathedrals on leafy boulevards and 18th-century colonial buildings colour the former French colony of Pondy, which sits on the Bay of Bengal. But it's also unmistakably Indian, with colourful festivals throughout the year, several mosques and the Sri Aurobindo Ashram. Quiet beaches stretch north and south from town, good for swimming and sunrise strolls. Pondy is a popular weekend getaway destination from Chennai and is easy to navigate on foot or by bicycle.