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City and Hotel recommendations for 3 night stay in Tuscany

I am seeking out recommendations on the following: (I am staying in Florence and then traveling to Tuscany for 3 nights at the end of September, 2024.

  1. What city is highly recommended for overnight accommodations as a first time visitor to Tuscany.

  2. What are the top 2 recommended wineries to visit.

Thank you
Chris

Posted by
3299 posts

Well Florence is in Tuscany itself, so you are asking for another Tuscan town to stay in and visit wineries. Will you rent a car, or do you plan to take a winery tour or take a bus to the winery from town?

Posted by
7 posts

*I wanted to mention, that we plan to use tour services, high speed train, local transportation. We do not plan to rent a car. Thanks for asking.
*

Posted by
8600 posts

I'd choose Siena which is itself just wonderful. Get a hotel like the Athena on the edge of the center with views out over the Tuscan countryside. Lots of tours run from Siena and you can also get a bus to St. Gimignano and other interesting places from there.

Also consider staying longer in Florence and booking tours from there to Tuscan sites. We won't have a car this trip and will be booking a tour to an Abbey, Volterra and St. Gimignano -- we have never seen the particular Abbey and not been to the other two in 20 years and want to see them one last time.