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Book activities now or later for AC (boat), Tuscany (bike), cooking class?

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Traveling to Rome, Positano, and Tuscany in late Sept/early October and there are several activities that I think we want to do, some of which may depend on the whether. So I am wondering if I should book activities now or wait until I am in Italy to have a better sense of the weather. Also if you have recommendations on particular tour companies, that would be great. In the AC, we would like to take a semi-private boat trip to Capri and the surrounding area. In Tuscany, we would like to do a day bike tour. Also planning on a cooking class (half day or so) in both places. As always, your feedback is much appreciated. Thank you.

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