We spent 3 days in Kyoto recently and it was a fantastic trip, although complex to organize.
I present this itinerary for others, with a few suggestions that I hope help.
TripAdvisor City Guides. If you have not downloaded this application, you need to. I lived on it with my iPhone. It has all of the top restaurants, sites and hotels which you can easily search at any moment via a map. One of the best features is that I “saved” the sites we wanted to see and as we visited, I “checked-in” (turning the post to Facebook option off – no one needs to see we are not at home). At the end of the tour, it provides a complete list by day of what we visited, in chronological order as a journal and provides an area to write notes. Amazing app, available for many cities.
Our trip journal can be found at http://cityguides.tripadvisor.com/checkins/428596. The trip via Lightroom – quite a lot of ground covered.

We spent 3 days there and that was the perfect amount for us.
The first day was the Shinkansen from Tokyo, arriving at 11AM. Quick check into the Westin, an afternoon of exploring followed by private dinner with a Maiko (geiko/geisha in training) .. and yes, the experience was a once in a lifetime.
The second day went from 9AM to 6PM with a private tour guide hitting all of the highlights of Kyoto. A private guide is expensive but as we found out in Rome and in Egypt, worth every penny as it leads to a very different trip than going from site to site on your own and really not learning anything.
One of our frustrations with Japan is that it is very hard to learn the history and culture due to the language barrier. 3,000 years of isolationist history means that Japan is not really fussed about not sharing what happens at a location. We connected with Kyoto Limousine which was highly recommended by expat friends of ours and is well known among the concierges. Our guide Yoshida-san has hosted many celebrities, princes and even Jean Chretien the former Canadian Prime Minister (I apologized on behalf of Canada) and he was UNBELIEVABLE. At every site he shared the deep history of what had happened there, different religious insights and more history than we could ever retain. It was 9 fascinating hours learning about the real Japan, seeing the best sites in Kyoto (including many hidden gems that are off the beaten path) and truly enjoying his company. He was an amazing host and even followed up our day with an email listing every site we saw with internet links. Just look at the 2nd day of our itinerary and you will see just how much we covered, and more importantly – learned.
On the third day we hit the Monkey Park, explored a shopping area, had lunch and then trained home.
For us, 3 days was perfect.
On the seasons, this is also difficult to understand until you get hold of someone. Here is a rough guide; May brings the cherry blossoms and millions of people. June brings the sun and lots of Japanese children on school trips. It also gets hot, it was 32C and humid while we were there, and we were lucky to avoid rain. July and August are insanely hot but the slow season if you are brave. The fall brings the spring colors, with October and November being the best seasons for viewing the fall colors. We were there in green June and I visualized what it would be like in the fall – beyond stunning.
As an aside, 50M people visit this city of 1.3M every year … 50 million.
As many Japanese will tell you, Kyoto is the cultural center of Japan. A thousand temples, beautiful forests, castles, amazing cuisine, culture (geishas) and incredibly rich in history. It truly was an adventure of a lifetime and I have a few pictures and stories to share ahead.
Hopefully these few simple insights help others. If you can get there, you will not regret it.

(Golden Pavilion, Canon 5D Mark III, handheld HDR, Canon 28-70mm)
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