Walking tours of Chora usually take a couple of hours and cover the Old Port, the Paraportiani church, Little Venice, the Kato Mili windmills and the shopping lanes around Matogianni. Good guides add the history — the pirate-era layout, the Venetian and Ottoman periods, the 1950s and 60s arrival of the jet set — that turns pretty into interesting.
Island tours by minibus or private vehicle extend that to Ano Mera, the monastery of Panagia Tourliani, the north coast and a beach stop, and are the easiest overview for a first visit or a cruise stop.
Photography tours time the town for early light before the lanes fill, or for golden hour at the windmills. Early morning is also the only time Chora is genuinely quiet in summer.