Where to Stay

Recently opened and incongruously-located inside the city's half-glitzy, half-tacky Phoenix MarketCity shopping mall, Design Hotel by jüSTa is a quirky option from the creative team at Urban Studio in Mumbai. For five-star accommodations, you can't go wrong at the business-styled Park Hyatt Chennai or the sea-facing Leela Palace Chennai.

Where to Shop

For splendid take-home Kanchipuram-style silk weaving and hand-painted kalamkari textiles, stop at the Kalakshetra Craft Centre on Kalakshetra Road.

Where to Eat

As predictable as it may sound, a vegetarian meal at Saravana Bhavan (a chain with branches in nearly 20 countries around the world) is both delicious and dependable, although we also like any of the Junior Kuppanna outlets for a lively lunchtime thali. The garden cafe (plus boutique and florist) at Amethyst on Whites Road is where you'll find society folk and expats throughout the day.

Get out of town...

An hour and a half south, the beachside, 7th-century, monumental rock carvings of Mahabalipuram are truly spectacular, illustrating dramatic events from the Mahabharata. A new option for an overnight nearby is the swanky InterContinental Chennai Mahabalipuram Resort, a good pit stop before continuing another 70 miles to charming Puducherry (also known as Pondicherry, or Pondy).

Pondicherry (Puducherry)

Once the heart of French India and capital of the Compagnie des Indes Orientales from 1675 onwards, it became a Union Territory only in 1954. The aptly-named and atmospheric French Quarter is easily explored on foot or by bike.

The Must-Sees

Stop to visit the Notre Dame Des Anges, modeled on the Basilica at Lourdes, Our Lady of the Immaculate Conception Cathedral, and Gothic Basilica of the Sacred Heart of Jesus.

The strikingly white Aayi Mandapam (Park Monument) was built during the time of Napoleon III as a miniature Arc de Triomphe.

Streets lined with yellow and white houses and colorful bougainvillea might look familiar—the entire first act of Ang Lee's Life of Piwas filmed here (the town's Botanical Gardens from 1826 stood in for a zoo, CGI tiger aside).

Where to Stay

Favorite historic hotels are Le Dupleix, housed in the 1700 mansion of a French mayor, and the Hotel de L'Orient from the folks at Neemrana Hotels. More playful and modern, La Villa Shanti has bright rooms and a wonderful on-site restaurant for upscale dinners. A suite at The Promenade hotel comes with fantastic views of the town's lighthouse.

Where to Eat

Two blocks in from the seaside promenade, Café des Arts is a perfect spot for a late breakfast or light lunch, and wouldn't look out of place in the south of France. Kasha Ki Aasha has a lovely roof terrace cafe open daily from 10 a.m. to 7 p.m. as well as a boutique for local crafts and books.

Get out of town...