My husband and I will be traveling to Italy in October. Part of the trip will be spent in Florence, and from there we are planning on renting a car, and touring Siena on our way down to Montepulicano. (We will stow our luggage at the bus station in Siena.) Montepulicano will be our home base for 3 nights. After that we will travel to Orvietto for 2 nights, drop off the car, and then take a train to Rome.
I was planning on getting a private tour guide for the Chianti and Tuscany regions and wine tasting for two days. My question is this, should we hire a guide for 2 days and have the car, or can we visit the wineries on our own, and meet the winemakers? We make wine ourselves, so we really would like to speak with the small wine makers. And I don't know how plan this on our own.
The Tuscan roads are generally well paved but a little crooked. They well marked and easy to travel on. We found it very easy to navigate throughout the region without road maps even.
Go ahead with the rental car--picking it up in Florence at Hertz on Sansovino--2 miles from the train station.
We found Siena to be difficult with a car as parking is very difficult. The city is also very congested with apartments and housing outside of the center city.
We especially enjoyed Certaldo, San Gimignano and Volterra. Poggibonsi has 2 great supermarkets and that's where we picked up picnic and dinner supplies as we were cooking in our agriturismo apartment.
We went with tours by Roberto who went to 2 small wineries with a delicious lunch at one of the wineries. Going with a guide you wouldn't have to worry about drinking and driving. These are small group tours, I think up to six people but we ended up only having 1 other person. With the tour we were able to speak with both of the winemakers directly, you would have plenty of time talking with them.
You could do it all yourself. If you contact some wineries that you are interested in, tell them you are a produced, and ask if you could tour their facility and meet the crew I am sure many would love to host you. You really don't need a guide..
I have just returned from a trip to Piedmont, where we rented a car. I think it really depends on your comfort level with other people. I think I would have been better served for winery visits with a guide, but I think my tourism was better served without one. But I am an introvert, so didn't really book any winery tours (though we stayed on a winery, and got a full tour and tasting there). For me, a guide would have been better, if going to various wineries was on the itinerary.
If you are comfortable on the phone, doing the research to find wineries, by all means, just rent the car, do the extra work, save the guide money, spend it on wine and food.
Last, I used Waze on my recent trip, and it has most or all of the speed cameras marked, as well as an ability to find parking near your destination. I highly recommend it, though it doesn't consider ZTLs.