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Tuscany- September trip, itinerary ideas

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We're 4 middle aged American women, 3 of whom have never been to Italy. We're planning a September trip. We want to visit Florence and Siena. (Some family will be in Siena @ the same time we're going.) We want to see SLOW things down. We all like a slower pace, and the opportunity to get back to the hotel in later afternoon for a lie down, shower or nap, and "re-group" before going back out for dinner, etc.

We looked into tours, but they were way TOO AMBITIOUS for our body clocks. We want to stop and "smell the roses' (or taste the proverbial wine or gelatto, if you will). We're afraid to drive ourselves, but have gotten wonderful information on these boards about hiring a PRIVATE DRIVER for a day trip outside Florence and a day trip outside Siena.

I'm considering flying into Pisa (since it's non-stop from NYC). Then TRAIN into Florence.
Day 1-arrive Florence, stroll shop eat relax and absorb our first day upon arrival
Day 2- Florence - YEAH!
Day 3- Day trip outside city, either a small group tour OR private driver. Greve? Radda? San Gimi? (Or should they all be our day trip from Siena?)
Day 4- private driver, to countryside, vineyard visit, lunch somewhere beautiful, with driver bringing us to our destination in Siena
Day 5- arrive Siena later in afternoon, and stroll shop eat relax and absorb the area
Day 6- Siena
Day 7- day trip outside Siena (small tour or private driver), or cooking class
Day 8 - Siena
Day 9, return to Pisa to fly home

I APPRECIATE EVERYONE'S INPUT. I've planned other trips to Amsterdam/Brugges and Stockholm/Copenhagen and got TERRIFIC ADVICE on these boards. Thank you all.

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