WaRaiDo Guide Networks

STATS
Tour: Gion Night Tour (conducted in English)
Cost: ￥1,000/person, cash only.
Length: about 100 minutes
Times: Every Monday, Wednesday and Friday 18:00−19:40 (March-​November) and 17:00−18:40 (December-​February)
Pace: Relaxing
Meeting Place: Kitaza (the orange building). You can’t miss it, the orange sticks out from the more drab colors in other buildings AND the business you are meeting at is one of two companies that sell yatsuhashi, Kyoto’s «meibutsu» (food of a particular city/​region that one brings back as omiyage). Tour ends at the Kaburenjo Theatre in Gion Kobu.
I’m a HUGE proponent of walking tours as long as they’re in collaboration with a city’s official tourism association and/​or the type that will show you history and the real sights, not just take people to a bunch of shops and hope to make money off kickbacks. In collaboration with the Kyoto City Tourist Association, Waraido Guide Networks provides the guides for their 100 minute evening tour of Gion.
Note the start time, 6pm. 6pm is when the parties at the ochaya begin. Your group will be headed into Gion just when the geiko and maiko are scurrying to their first of several engagements for the night. Our group was lucky enough to run into several. As engagements usually last about two hours, you could also potentially see maiko from the Kaburenjo Theatre heading to their next engagement (which our group saw).
Our tour was a group of over 40, which had to be split into two groups. No1DP and I went into Meiko’s group. Meiko was such an excellent tour guide, her English skills were superb and with her informative and entertaining style she introduced our group to the «flower and willow world» that is the district of Gion and the geiko and maiko that inhabit it. With her cards she told us about geiko/​maiko and their traditions and showed us places around Gion that were central to the life of geiko/​maiko. With the minimal knowledge I had about Gion (*cough*memoirsofageisha*cough*) I would’ve been lost should the No1DP and I try to tackle the city by ourselves. Worse, we would have done it during the middle of the day — not the best time to spot geiko/​maiko. With the way she presented her information I was never bored and I would feel confident navigating around Gion by myself on the next visit.
Major props to her for helping us with picking the restaurant that the No1DP and I ate for kaiseki dinner — turns out that not only were they friendly to tourists with English menus, they were also recommended by several guidebooks as a reasonably-​priced (for kaiseki, which is still $ 50 *minimum* per person) introduction to kaiseki.
Should you want to see the maiko perform traditional Japanese arts the tour provides a discount for their shows every night — no reservation is necessary. It’s a bit touristy but the preferred option of getting someone to take you to an ochaya as their guest is notoriously difficult as ochaya don’t let anyone in without a proper introduction from a regular customer, much less take in tourists.
I would wholeheartedly recommend this walking tour to people interested in seeing Gion as well as people wanting to know more info about geiko and maiko and possibly spot one (or both).