All of those excursions departed around 9:45-10:00 am and returned/ended around 5:00-6:00 pm. We had about 2 hrs each with guides in Pisa and in Lucca—totally at our speed and doing what we wanted.

As I lead group tours for a living, I always want to have a private guide whenever possible. My husband, in particular, enjoys the details a guide often provides. I move at a much faster pace but we usually find a nice compromise...or else I also can wander off and reconnect whenever the tour or my husband get too glacial for my tastes. (My husband says my favorite way to see a museum is to fly over it in a 747.)

The last time we were here in Florence and Tuscany, we did drive ourselves. This time, I wanted to do it with a car and driver and guide when appropriate. Especially since we had my mother, who also appreciates the details like my husband (and who moves much more slowly).

Having the car and driver made things very easy in Chianti. Having the tour company owner with us as a guide provided a lot of intimate and very interesting information and details we wouldn’t have gained otherwise. His presence also allowed him to see exactly what we liked and adjust accordingly. He changed our winery visits the second day based on my responses from the first day.

The final Chianti-Siena-Pienza excursion actually saved me from having to do a separate transfer between the StR Florence and La Bandita Townhouse in Pienza. I also didn’t want to rent a car with my mother and deal with GPS and parking issues in the many small hill towns in rural Tuscany. That allowed us to do whatever we wanted and have the car ready to meet us wherever and whenever we wanted. For me, that’s the luxury for which I’m paying.

I save a lot of money by using points for our luxury hotel stays, including both our rooms at the StR Florence, one of our rooms at the La Bandita Townhouse, and both our rooms again at Atlantis by Giardino in Zurich. Makes it much easier to spend money on luxury for our tours and our fine dining.

I obviously appreciate that not everyone will pay for private guides or for cars and drivers, but this is the Luxury Forum.

I guess I should mention that I also arranged in advance (for an extra 500 euros charged by the winery) for one of the Chianti wineries (Badia Di Coltibuono) to open older vintages for us. We had tastings of their 2011, 2006, 2000, 1988, 1980, 1977, 1974, and 1966 Chianti Classico Riserva bottles. It was incredible. The 1977 and 1966 bottles actually were corked, and I noticed and said so...but it took the winery rep a good 10 min and a check with superiors before she agreed! So they opened a second bottle of each bottle with their original corks...causing the 1966 cork to basically disintegrate on opening, requiring a decant. So we tasted and then got the entire decanted bottle to enjoy with our lunch there at the winery. That’s what I call a priceless experience. A 52 year old Chianti. It was sublime. And worth every euro.