Caj House

 SOUTH END

If any neighborhood stands as a measure of how cosmopolitan Boston has become, it's this worldly enclave embodying both the historic and trendy of the city. In the late 19th century, rich merchants and ship captains built large brownstones on the South End's waffle-iron layout of streets, and it became the place to see and be seen. Now, after decades of decay followed by gentrification and renovation, it's once again the hottest place to be. Sea captains may no longer roam its curbs, but in their place you'll find the chicest residents in town — a salad of artists and designers, young couples and a sizeable chunk of Boston's gay community. Most of the Victorian roughhouses have been converted to luxury condos, its parks and statues flank cutting-edge boutiques and galleries, and the eateries are a combination of intimate bistros and world-class dining.

It all starts on Tremont Street, where longstanding heavy hitters like Hamersley's Bistro sit next to instant classics like B & G Oysters, Ltd., a seafood bar for the new millennium. In fact, excellent bistros dot the street right and left — from the ultra-French Aquitaine and the always excellent Icarus on over to Washington Street's suave, nightclubby Pho Republique and the sleek likes of Union Bar & Grill. The crowds gather every evening for Italian dishes at snazzy Stella, and for cocktails and mini-burgers at 28 Degrees. And at all of the above, be warned: It pays to reserve ahead (especially on busy weekends) and to pay some heed to your outfit. These joints may welcome a rainbow coalition of patrons, but few of them arrive underdressed.

Before or after that culinary tour, don’t miss the chance to scour gifts stores like Posh on Tremont, find retro scented candles at Aunt Sadie's, and swing into the 23,000-square-foot rotunda that is the Cyclorama for avant-garde art exhibits, fashion shows and contemporary drama. Rather go highbrow? Buy tickets for a night at Symphony Hall, one of the top three concert halls in the world and home of both the Boston Symphony Orchestra and the Boston Pops. Evenings finish up nicely at The Butcher Shop, a clever, gourmet take on old-school butcher shops trumped up with a happening little wine bar.