Room
Refreshingly unlike a bland chain hotel, the Holiday Inn Charleston–Historic District has big rooms and savvy concierges, and is close to the City Market (843-805-7900; holidayinn.com; doubles, $170–200). King George IV Inn is in a 1790s Federal House in the Historic District (843-723-9339; kinggeorgeiv.com; doubles, $89–$189).

Lunch & Dinner
Brent's serves Southern lunch-counter fare (meatloaf, green bean casserole) to business types beneath soaring nineteenth-century ceilings or in the courtyard (40 Broad St.; 843-853-8081; entrées, $7–$8). Locals love FIG, where chef Mike Lata prepares dishes like fish stew en cocotte (232 Meeting St.; 843-805-5900; entrées, $22–$28).

Tip
Watch the sun set over the church spires and centuries-old homes as you sip a Pavilion Punch at the chic rooftop Pavilion Bar, in the Market Pavilion Hotel (843-266-4222). Explore the local Gullah culture and history with a guided tour of landmarks through Gullah Tours (843-763-7551; gullahtours.com).

Where
Singapore

Why
The city-state's historic buildings have found new life as cultural centers, cafés, and boutiques. The glass-and-steel galleries of the neo-Palladian National Museum of Singapore host cutting-edge exhibits (65-6332-3659; nationalmuseum.sg; admission, $7). Built in the 1860s as government offices, the Asian Civilisations Museum has an interactive gallery tracing the island's origins (65-6332-7798; acm.org.sg). The St. James Power Station is known for its buzzy bars (3 Sentosa Gateway; 65-6270-7676).

Room
The art-filled 30-room New Majestic Hotel was created from four 1928 Chinese shophouses (65-6222-3377; newmajestichotel.com; doubles, $200–$382). On a grander scale, the neoclassical river-front Fullerton Hotel was built in 1928 as the General Post Office (65-6733-8388; fullertonhotel.com; doubles, $337–$464).

Lunch & Dinner
Ya Kun Kaya Toast's grilled bread with coconut-and-egg spread ($3) has been popular since 1944 (18 China St.; 65-6438-3638). Crowds gather nightly at Boat Quay. a strand of bars and eateries and one of the city's first heritage redevelopment projects. Try the spicy Indonesian fare at House of Sundanese Food (55 Boat Quay; 65-6534-3775; prix fixe, $8–$11).

Tip
No one knows more about the ghosts that lurk in the Lion City than the entertaining docents of Singapore Walks. The "Time of Empire" route (Mondays only) pays particular attention to the architecture of the British era (24A Sago St.; 65-6325-1631; singaporewalks.com, $17–$31).