One day tour from Florence into Tuscany

we did a day tour wine tasting in October 2024 with Fabrizio at Ciao Fabry Tours. He does all kinds of day tours for wine tasting, city sites, and even cooking classes in Montepulciano. I'm pretty sure he picks up across a ride range of locations including Florence. I would not hesitate to book him for one or more days. His English is great, he has fantastic local knowledge and connections, reasonable prices for what all we did, and he was incredibly fun. He's more than willing to customize itineraries to what you are looking for.
https://www.ciaofabrytours.com

No experience with any companies, but if you are interested in cities like Siena, that is something you can accomplish on your own by bus or train (bus is faster) for very little money. Siena is well served by frequent buses and trains.Lucca, Pisa, Pistoia, Arezzo, are equally easy to reach by train.

I would recommend a guided private tour only for small towns or countryside (like wineries) which are more time consuming to reach with public transit. For example look into the wine producing Chianti area and/or the small towns of Monteriggioni and San Gimignano.

ToursbyRoberto.com always gets good reviews
He books up early

Have you ever been to Florence or any of the surrounding towns? Day trips from Florence are abundant. Easy train rides to Lucca, Pisa, a pleasant bus journey to Siena, so many options.
Siena - Bus is the easiest method as that drops passengers in the centre of town rather than at the bottom of the hill where the rail station is located. Travel time on the Corse Rapide (express) buses is about an hour to 90 min depending on train. The bus station in Florence is very close to Firenze SMN rail station. A car is not needed or useful in Siena.

Lucca/Pisa - just gram the regional train and you are there in no time. We actually went to Pisa first, early morning, saw the leaning tower and the Field of Miracles, walked around a bit and jumped back on a train to Lucca for lunch, working our way back to Florence. Pisa Centrale is 25 minutes walk from the famous Leaning Tower, but some trains go beyond Pisa Centrale to Pisa San Rossore which is 12 minutes walk from the Leaning Tower Lucca was very enjoyable and a lovely town. Lucca has flat terrain and riding bikes on top of the wall is a fun way to spend the afternoon. Then hop on the train (literally across the street from the town) and get back to Florence later afternoon or in time for dinner. You don't need guides to do either of these. Pisa is about 60 min train ride, and stop off in Lucca on way back to Florence.

Pistoia is a 1/2 hour scenic train ride from Florence, very few tourists, good restaurants, and with nice 12 - 14th century buildings, many of them green and white striped. Everything is very walkable. Known for its chocolate

Florence to Cortona (we LOVE Cortona) - Train little over a1 hr. The Cortona station (called CORTONA-CAMUCIA) is at the bottom of the hill in the town of Camucia. You’ll need to take a shuttle bus to go up to Cortona. (10 min ride) and you can get tickets at the little market right next to the train station.

Fiesole is a 16 min bus ride or a 10 min. taxi.

All of the places are easy to tour on your own. It's fun to just meander around and explore on your own without being tied to a tour.

Tours by Roberto does pick ups from Siena and Florence in their late-model minivans driven by your guide. We greatly enjoyed a 7.5-hour day tour late May 2019 from Florence, post the RST Heart of Italy we had been on. It included a pick-up near the Duomo, picturesque, comfortable and narrated drive with photo stops in each direction, 2 winery visits/tastings; Azienda Tornesi with their wine tastings including complimentary light snacks served on their view terrace and a brief tour of the winery, and the much larger Santa Giulia winery where we paid extra euros for a more-than-worth-it fabulous lunch. The SG visit included an informative tour around their grounds including salume curing operation and lots of info on their entire growing and producing operation. Our third stop was a short self-guided 60 minute visit at oozing with Tuscan charm Montalcino. Only 3 members on the midweek tour, which has capacity of 8, our guide was fantastic, both wineries were distinctive and excellent (bought wine and grappa - still regret not buying the olive oil available) and it was really a quality excursion. Highly recommend.