Osaka

Highly photogenic Dōtombori is the city's liveliest night spot and the centre of the southern part of town. Its name comes from the 400-year-old canal, Dōtombori-gawa, now lined with pedestrian walkways and with a riot of illuminated billboards glittering off its waters. Don't miss the famous Glico running man sign. South of the canal is a pedestrianised street that has dozens of restaurants vying for attention with the flashiest of signage.

This famous tako-yaki (octopus dumplings) stand, just north of Dōguya-suji arcade, uses custom copper hotplates (instead of cast iron) to make dumplings that are crisper than usual (but still runny inside). There's a picture menu and tables and chairs in the back. One popular dish to try is tako-sen – two dumplings sandwiched between sembei (rice crackers).

West of Midō-suji, Amerika-Mura is a compact enclave of hip, youth-focused and offbeat shops, plus cafes, bars, tattoo and piercing parlours, nightclubs, hair salons and a few discreet love hotels. In the middle is Triangle Park, an all-concrete 'park' with benches for sitting and watching the fashion parade. Come nighttime, it's a popular gathering spot.

After unifying Japan in the late 16th century, General Toyotomi Hideyoshi built this castle (1583) as a display of power, using, it's said, the labour of 100,000 workers. Although the present structure is a 1931 concrete reconstruction (refurbished in 1997), it's nonetheless quite a sight, looming dramatically over the surrounding park and moat. Inside is an excellent collection of art, armour, and day-to-day implements related to the castle, Hideyoshi and Osaka. An 8th-floor observation deck has 360-degree views.

This César Pelli–designed tower, which opened in March 2014, is Japan's tallest building (300m, 60 storeys). The observatory on the 16th floor is free, but admission is required for the highly recommended top-level Harukas 300 observation deck, which has incredible 360-degree views of the whole Kansai region through windows that run several storeys high. There's also an open-air atrium. It houses Japan's largest department store (Kintetsu, floors B2–14), the Abeno Harukas Art Museum, a hotel, offices and restaurants.

A century ago, Shin-Sekai ('new world') was home to an amusement park that defined cutting edge. Now this entertainment district mixes down-at-heel with retro cool. It's centred on the crusty, trusty, 103m-high steel-frame tower Tsūten-kaku – built 1912, rebuilt 1956 – and surrounded by ancient pachinko and mahjong parlours that draw some truly down-and-out characters. At the same time, Shin-Sekai draws plenty of visitors for nostalgia and cheap eateries behind over-the-top signage, especially for kushikatsu (deep-fried meat and vegetables on skewers).

The classical performing art most associated with Osaka is bunraku, which makes dramatic use of highly sophisticated puppets. Visiting the theatre is a half-day event: shows, which include scenes from different plays, top four hours. Too long? Unreserved, same-day single-act tickets are sold, when available, at the venue from 10am. Rent the English-language audio guide (full performance/single act ¥650/300).