Plush hotels are drawn to Bangkok's riverside because it's about the most attractive setting in the city. But the tree-lined lanes leading away from the river are also a treasure chest of classic colonial-style buildings, shophouses, and godowns (warehouses) converted into restaurants and antique stores.
An easy starting point is Saphan Taksin BTS station or nearby Tha Sathorn (Central Pier) river pier—many hotel ferries stop here. Walk away from the river and take the first left into the (1) Shangri-La Hotel (89 Soi Wat Suan Plu, New Road; www.bangkok.com/shangrila/) for a chance to actually walk along the river. Keep going until you can go no further, exit the hotel and head right. Past the tuk tuks (three-wheel, motorized taxi cycles) and hawkers you'll come to busy Th Charoen Krung; turn right for street food and the (2) Bangrak Market, or left to continue the walk. After about 200 yards turn left, through the schoolyard-cum-parking lot, and walk through to red brick (3) Assumption Cathedral, built in 1809.
The cathedral sits at the heart of Bangkok's old European trading quarter. As you exit through the front door, walk through the small park and turn right, beneath an overhead walkway linking two of these old buildings, then turn left. You'll find yourself at the (4) Oriental Pier, and standing in front of the fading classical Venetian-style facade of the (5) East Asiatic Company, built in 1884. The company was central to developing trade between Thailand and the rest of the world and this building was its headquarters. The surrounding area is filled with godowns, Chinese-style warehouses, in varying states of repair.
Walk back down Soi 38 and turn left into the (6) Oriental Hotel (48 Charoen Krung Soi 38), Bangkok's most storied abode that was founded in 1876 and where Somerset Maugham, among others, stayed way back when. Check out the original building, now called the Authors Wing.
Exit the way you entered, walk away from the river and turn left, then left again. You'll pass the (7) Oriental Plaza on the right, a department store built in 1905 and now home to expensive antique stores, and the French Embassy on the left. Turn left after the embassy, and pass the small restaurants towards the river. The big but decrepit building you'll see is (8) Old Customs House, built in 1880. It's currently used as a fire station, but under the grime it's one of Bangkok's most impressive buildings of its era (Chinese cinema fans might recognize it from Wong Kar Wai's In the Mood for Love).
Head out and turn left down a narrow lane behind Old Customs House into tranquil (9) Haroon village, a Muslim enclave in the middle of the city full of playing kids, wooden houses, and small stores selling food. Meander through here until you reach a larger street running away from the river. Follow this and just before the main road you'll come to (10) Harmonique (22 Charoenkrung 34), an atmospheric but not-too-spicy Thai restaurant.
Turn left onto Th Charoen Krung, past the art deco-style (11) General Post Office and take the second left towards the (12) Portuguese Embassy (26 Captain Bush Lane), Bangkok's oldest embassy building; though this is best viewed from the river. Continue past the Sheraton hotel to (13) River City (23 Yota Road), a busy indoor mall selling a mix of antiquities, reproductions, cheap souvenirs, and food. If you do shop here, be aware that many antiquities are not, in fact, very old, while some genuine antiquities will have been removed from their country of origin without government permission. River City is also the departure point for Chao Phraya dinner cruises, and most riverside hotels have regular shuttles from here.
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