8-night Tuscany Itinerary

I think your itinerary looks good with just a couple of notes:

Tue 7 Oct - arrive in FLR, walk a few, dinner, rest, sleep in FLR
Wed 8 Oct- full day in FLR; sleep in FLR
Thu 9 Oct - bus to Siena; enjoy afternoon/evening and sleep Siena - I would try to get an early bus to Siena so you have more time. Siena really deserves at least a whole day.
Fri 10 Oct - rent a car in AM and drive around; sleep in Siena - If time allows, try to get to the Abbey of San Galgano - it's about 45 minutes from Siena but worth it and the countryside is breathtaking. The abbey is very special, one of my favorite places in Italy.
Sat 11 Oct - drive to Volterra via San Gimignano; sleep in Volterra
Sun 12 Oct - drive around and enjoy Volterra; sleep in Volterra
Mon 13 Oct - leave Volterra for Pisa, drop off car; sleep in Pisa
Tue 14 Oct - take early train to FLR and spend the day there; sleep in FLR
Wed 15 Oct - depart FLR

Siena, Volterra, San Gimignano are all within 50-60 minutes drive from one another, they are very close.

Do you really need to change hotels (Siena and Volterra)? Changing hotels is time consuming (unpack, repack, check out, check in, re-unpack). I would choose one location (any of the 3 or even Monteriggioni or Colle Val D’Elsa area, which is central to all) and do day trips from there.

I also see no reason to sleep in Pisa, which is a one pony trick town. I would spend an extra night in Florence (at the beginning or the end of your journey) and visit Pisa by train from Florence. By train from Florence it’s really convenient and fast (50-70 minutes), and you don’t have to worry about cars or returning tha car at the airport. It takes just a couple of hours or so to see Pisa, and actually you could even pair it with Lucca (half hour from Pisa), which is nearby and even more interesting than Pisa.

You can also rent your car in Florence and go to Siena area by car.

Thank you for your suggestions.

Agreed on all counts - too many stops for an area that is approx. 150km x 150 km square. I had not checked this information when I put the itinerary together.

With that said, if we made only one base/hub, and all our trips are day trips, which town would be best to anchor ourselves? What is the best way to travel between places? Prefer not to drive, but open to a day or two of driving, if required.

What if we made two bases, instead of one, which ones would give us the maximum flexibility?

We are now thinking FLR and maybe Volterra, from where we can cover the country side?

The choice depends on whether you want a car or not, and whether you prefer a small village or even a country villa/farmhouse (car required), or if you prefer a bigger town.

If you don’t intend to rent a car, the choice is really one only: stay in Siena. Siena is the transportation hub for the area so you can take buses to all towns in the province. Volterra is in the province of Pisa and to get there by bus from Siena you will probably need to change buses in Colle Val D’Elsa.

If you rent a car, you can still stay in Siena, if you prefer to be in a bigger place with more night activity. Just choose your accommodations carefully because the city center of Siena is off limits to cars, so you need a hotel outside of the forbidden zone.

If you prefer a smaller town or country villa or farmhouse, then the choice is endless. The area of Colle Val D’Elsa/Monteriggioni is probably the most central to the places you mentioned and has easy access to the Siena-Florence freeway, but pretty much any place halfway between Florence and Siena would work.

Pisa (and Lucca) is a day trip to take from Florence (by train). So if you want to visit it, add an extra night to your Florence stay.

Thank you again for two excellent alternatives for a base outside of Florence.

If we did stay at Colle Val D'Elsa or Monteriggioni, would you recommend staying in a farm house and rent a car? How does one move around in the region, if you want to explore different towns/wineries, etc? This is our primary consideration - flexibility to move around, without having to be stuck to a schedule of a bus or a train or a tour operator. We may do that for the winery tour, but the rest, we want more flexibility.

Look forward to your thoughts.

agree with smay, need more time in Siena.

We loved Volterra and San Gimignano. We took a tour and it was very clear that parking could be a parking for driving a rental car.
Consider taking tours.
https://www.tripadvisor.com/Attraction_Products-g187895-t16389-zfg17447-Florence_Tuscany.html

https://www.viator.com/Florence-tourism/d519-r18115554971-s110212331?m=33953&supag=1241349698219647&supca=676713227&supsc=kwd-77584695600670&supai=77584489401737&supdv=c&supnt=o&suplp=74961&supli=1892&supti=kwd-77584695600670&tsem=true&supci=kwd-77584695600670&&msclkid=abfbfd2792f61ebb19bc95f1514b3cbf&gclid=abfbfd2792f61ebb19bc95f1514b3cbf&gclsrc=3p.ds&gad_source=7&gad_campaignid=22478136886

https://tour.siena.it/siena/tickets-and-tours/details/from-siena-san-gimignano-chianti-and-montalcino-day-trip

hey hey RolwalingRunner
you've received much info here about your itinerary. my opinion is too many places to sleep in, cut back on places and do day trips. takes at at least half day to move place to place as roberto mentions. check out is 10-11am and check in 3-4pm.
october is a very busy month with fairs and festivals with harvest season. (discovertuscany.com/ october in tuscany: food festivals and fall celebrations) the cities you have chosen are always mentioned so expect crowds, private & bus tours mornings to afternoons.
all drivers will also need to get an IDP (aaa.com.com/IDP) which is mandatory in italy. some rental car business may or may not ask but if you are stopped or pulled over for whatever reason, they will ask. if no IDP you will be fined $$$
another issue is parking, can be a PITA. does hotel have free parking, if not how far away is garage/parking spot, ZTL zones, luggage in car safety. so much to think about. you'll have a great time and enjoy
take a tour if wine tasting, italy is very strict with drinking and driving, read up about the laws and rules about it.
aloha

Feedback and suggestions are all much appreciated. We've decided to limit our stay in two places only - FLR and one more (which one we do not know yet). No renting car. We will do the organized tours instead, leaving the driving to someone else.

hey hey RolwalingRunner
happy to hear about your decision. here's a few sites to check about activities if interested. been a few times to florence few years ago, things have changed so look at tickets/time slots for main attractions at their own websites.
paintandwineflorence.it
as it says, fun time (couple hours) to let your mind run wild even as a beginner.
visitflorence.com/ top gelato shops in florence
we were on "missions" roaming around tasting gelatos and which we liked best. took picture of shop to remember
educated-traveler.com/ wine windows of florence
read up about the history of this area. have a glass of wine, appetizers, enjoy. follow map at bottom of page
florencetown.com
florence boat tour on the arno river with wine
mercatocentrale.com
read up about this big market with everything in it. click artisans, scroll down to their faces, run mouse over face gives info what their store/shop is. we spent lots of time just roaming, having glass of wine and a small chacuterie tray.
eatingarounditaly.com
favorite pastry shops, my big downfall :) yummy yummy bought something for next month or late night snack
airbnb/experiences/florence
no need stay at an airbnb to look and reserve something. check out activities
eatwith.com/ florence
click experiences, top of page gives you what they do, some even are lunches or dinners in a local residence home
guruwalk.com/ florence
click anything they offer (free & guided tours, top activities, day trips)
gpsmycity.com/ florence
self guided walking tours, download app, check what interests you. enjoy have fun
aloha

If you decided not to rent a car, then stick to Florence and Siena only. There will be plenty of tour companies/private drivers that you can hire in both cities, and also convenient buses to San Gimignano, Monteriggioni, Colle Val D'Elsa (the San Gimignano bus #131 stops in Monteriggioni and Colle Val D'Elsa along the way). For Volterra you can also take a bus (bus change in Colle V.E.).

For winery visits then a private driver, or organized small tour is recommended.

If you change your mind and prefer to stay in a smaller village/town or, especially, a country villa or farmhouse (agriturismo), then a rental car is an absolute must.

For renting cars I use: www.autoeurope.com
An International Driving Permit is mandatory in Italy, unless you have a European driver's license. You can get it at any AAA office (you can also apply online). It takes minutes.
Road signs in Italy follow the International Road Signage system used throughout Europe. Become familiar with the symbols as some are different from what used in North America. You can find them here.
Also become familiar with the Restricted Traffic Zones (or Z.T.L.) in Italy's historical city centers.

Closing this discussion out. Thanks to everyone for their wonderful suggestions, which resulted in the following itinerary: 2 nights in FLR + 3 nights in Siena + 3 nights in FLR. Not renting a car. Will do one day tours from each base.

Any recommendation on lunch + wine tour. Must be a good restaurant with vegetarian options. Let me know.

Well done.
If you can, and if your flight arrival time permits, I’d suggest to go to Siena upon arrival. There are frequent trains and buses (buses are 15 min faster), to Siena. And the bus trip is only 75 minutes. Then you would concentrate your Florence stay to the last nights of your journey. By doing so, you would minimize the number of hotel changes. Basically you could have one hotel in Siena for the first 3 or 4 nights, then another hotel in Florence for the last nights before flying home.

For restaurants in both cities you can use the search box above. There have been many posts about suggested restaurants anywhere over the years. I also use TripAdvisor or The Fork when I go to places I don’t know in Italy. Both are greatly used by Italians. Yelp is not used much by Italians, so most of those reviews in Yelp are from non Italian tourists.

All restaurants in Italy will have vegetarian choices. Mediterranean cuisine is not meat heavy, so half of the choices in the menu will be vegetarian by default. When I lived in Florence my girlfriend was vegetarian so we used to go often to the restaurant called Il Vegetariano. It’s an institution in Florence, probably the very first fully vegetarian restaurant in Florence (opened over 40 years ago). Their menu changes every day. They used to open for dinner only on weekends, not sure nowadays.

Roberto, thank you for your suggestions. Given the volume of tourist arrivals, hotels, tours and restaurants are seeing high demand, so reservations are challenging. I agree with you though, that going straight to Siena, and then to FLR would have reduced the number of hotel check-ins/outs, but at this stage we are keeping our schedule and rounding out the rest of the trip. As I mentioned, I am still looking for a one day private tour for two people in Siena, either on 10 or 11 October.

Check toursbyRoberto.com