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First Time to Japan..Itin Advice Needed

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I am headed to Japan on May 17th...so excited! I will be on a tour for 13 of my 19 days but have 2.5 days on front end and 3.5 days on back end to explore on my own and have a few logistical questions. I would love to get feedback, especially on my last three days.

I will land in Tokyo late afternoon the 18th and plan to take the JR airport express to my apartment rental. I will be staying in Shimokitazawa. I plan to see the usual tourist stuff and have breakfast at Tsujiki market. Is it a good idea to have book a tour for this visit? I have no desire to go the tuna auction. I just want to explore and eat my way around. The tour will begin in Osaka Saturday night and I will leave Tokyo Saturday morning and try to spend the afternoon exploring Osaka. Any specific recommendations for Osaka food, drinks or siteseeing?

On the hike, bike and kayak tour I will be visiting Osaka, Hiroshima, Kyoto, hiking the Kumano Kodo pilgrimage route, Katsura, Wakayama, Onomichi, Matsuyama and ending in Tokyo, I believe only Kyoto has 2 nights.

We end up in Tokyo on a Thursday morning and my tentative plan is to head out to the art islands for 2 days and then back to Tokyo the night before my flight home Sunday evening. Is this doable and a good use of my last few days in Japan? I love art and these islands look beautiful. I am about to book a hotel in Uno near the port but first wanted to check in here. Also many of the dinners we are on our own so would love any suggestions for can't miss meals in any of our stops. Some areas are easily researched and some not so much.

Also - I'm a public transport spaz and a little nervous about the trains but from all I've read they are easy to navigate with instructions in English on the machines etc. Any helpful tips?

Thanks for your time and thoughts Japan experts.

JenV

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