Florence/Tuscany Excursion

Many choices, all equally desirable. Below are some of the most popular (not in any particular order)

Easy by public transport:
Siena (by bus)
Lucca+Pisa (both by train, with more time devoted to Lucca).
Arezzo+Cortona (by train, with Cortona, the farther, done first, then Arezzo on the way back).

Easier by private car, although possible also by bus:
San Gimignano
Volterra
Chianti Hills

I looked to see if there were any special events in mid-October, but I didn't see any.

As usual, Roberto came through with some great suggestions.

I'd recommend a drive down through Greve and Castellina to San Gimignano and Volterra. It would be a long day, you'd get back late in the evening.

If you have to use public transportation, there's buses and trains to Siena. Trains leave every hour and it takes a little more than an hour to get there. You don't have to make train reservations and the tickets are ~$11 each way.

We visited all the places I mentioned. Siena is a lovely town, but the experience is similar to Florence. If you want a taste of the Tuscan countryside, going south from Florence along SR222 is magical but requires a car.

Thanks for the information, will research and make our decision.

We just went on slow day tours to Tuscany. We loved it. Simon was a wonderful your guide. We went to two wineries and ate lunch in a small town. Definitely recommend! http://www.slow-days.com/booking.html

Although I only used them for a ride to from the airport in Pisa to hotel in Florence with a stop off at Pisa Tower for site seeing I highly recommend Professional Tour Tuscany, Elisabetta and her husband Fabio run this small company and offer guided tours and rides for very reasonable cost, they were absolutely genuine and delightful people.
[email protected]
Email Elisabetta for a quote or more information, she writes and speaks perfect English and knows the area inside and out.

With only one day you really need to figure out what interests you most.
There are many options from Florence for a day trip.

We self toured driving a car from Florence to Siena, parking there and spending a day in Siena which is lovely and different than Florence. This gave no countryside views though, for that we took a few nights and drove to Pienza staying there and seeing the countryside by car from there, staying overnight 2 nights in Pienza.

You could choose a different hill town in the countryside, or more popular places like Lucca, San Gimingano.
On your own with one day I would not try to do more than one main town or region.
With a tour guide you could probably do a couple in one day and if I only had one free day to see more than Florence is why I recommended the tour group above.

We used tour company "Walkabout Florence" and did "The best of Tuscany Tour" taking off from the Florence Train Station in an air conditioned bus with the first stop in Siena, then we had Lunch at a vineyard (Organic wine served with the meal), onto San Gimignano and then finally to Pisa. It was a long 12 hour day with lots of walking and just enough time in each place to shop, walk around, grab a coffee. I would recommend this company to anyone, the guides were really knowledgeable but they do move at a brisk pace. The company has great reviews on trip advisor and was one of the highlights of our stay in Florence.

I did the same excursion with Walkabout Florence and had a lovely time. Of course the time spent in the towns is limited, but you get a good idea of what they are like and perhaps would want to visit again.

Another vote for the Walkabout "Best of Tuscany" tour - was one of our favorite days of our whole trip to Italy. We didn't have enough time in our trip to explore Tuscany thoroughly, but were really glad that this tour provided a way to get a taste of the Tuscan countryside. The only downside was that we felt the time in Pisa was too long (we were kind of twiddling our thumbs after taking the standard "holding up the tower" photos), so the tour kind of ended on a low note in our opinion, but we still enthusiastically recommend it to our friends.

FYI, in Pisa they will tell you that you need a ticket to get into the church. We didn't get one because at that point we didn't want to pay for yet another site in our long trip around Italy. Only at the very end did we find out that the ticket would have been free...so maybe that would help to make Pisa a more meaningful last site.

Another vote for the Walkabout "Best of Tuscany" tour - was one of our favorite days of our whole trip to Italy. We didn't have enough time in our trip to explore Tuscany thoroughly, but were really glad that this tour provided a way to get a taste of the Tuscan countryside. The only downside was that we felt the time in Pisa was too long (we were kind of twiddling our thumbs after taking the standard "holding up the tower" photos), so the tour kind of ended on a low note in our opinion, but we still enthusiastically recommend it to our friends.

FYI, in Pisa they will tell you that you need a ticket to get into the church. We didn't get one because at that point we didn't want to pay for yet another site in our long trip around Italy. Only at the very end did we find out that the ticket would have been free...so maybe that would help to make Pisa a more meaningful last site.

Another vote for the Walkabout "Best of Tuscany" tour - was one of our favorite days of our whole trip to Italy. We didn't have enough time in our trip to explore Tuscany thoroughly, but were really glad that this tour provided a way to get a taste of the Tuscan countryside. The only downside was that we felt the time in Pisa was too long (we were kind of twiddling our thumbs after taking the standard "holding up the tower" photos), so the tour kind of ended on a low note in our opinion, but we still enthusiastically recommend it to our friends.

FYI, in Pisa they will tell you that you need a ticket to get into the church. We didn't get one because at that point we didn't want to pay for yet another site in our long trip around Italy. Only at the very end did we find out that the ticket would have been free...so maybe that would help to make Pisa a more meaningful last site.

Just a side note regarding the free ticket for the church in Pisa. When we were there in 2015 the ticket was free, but it was timed. We would have booked ahead if we had realized this. We ended up spending an extra 2 hours in Pisa to fill time before we could enter the church (which is beautiful).

Thank you for all your comments and suggestions. Based on the information received, we were able to hook up with a very small group through Tours by Roberto. Pick up is in Siena, touring the Chianti Region, stopping at Montacino and Val Da'Orcia returning to Siena. This gives us the opportunity to explore Siena ourselves yet have the luxury of a Chianti Region guide. Of course, we will need to take an express bus from Florence to Siena at 8:10AM, the driver will meet us at the depot. Pricing is extremely reasonable based on other tours. All in all, very pleased!

Thanks, I am in Florence now and will try him.

Those of you who mentioned WalkAbout, there were some complaints that it was way too many people, over 50 I think. Was that the case? That sounds terrible. Thanks!