Day Trips from Florence

Two worthwhile classical trips are:
- Pisa combined with Lucca. Easily done by train. Look for the connections on the Trenitalia website. (Have »Firenze S.M.Novella« as your departing station.)
- Siena. Best done by bus which delivers you at the Piazza Gramsci, close to Siena's city centre. Leaves from the bus station just across the road from Florence's main railway station. (This schedule might not be up to date, but shows it has frequent departures.)

For a day trip to wineries (a winery is called a cantina in Italian), a guided tour is best unless you speak Italian and want to call to make your own arrangements and have your own car. I can highly recommend Tours by Roberto for a tour of the Chianti area from Florence. Montepulciano is at least 90 minutes each way. You could rent a car for the day, but again you'd have to call wineries and make arrangements.

Some good info here on do-it-yourself touring in Chianti.

Check out these:
Siena
San Gimignano
Monteriggioni
Volterra
Panzano
Lucca
Pisa
Montecatini Alto and Montecatini
Certaldo
Orvieto
Panzano
Montelcino
Montepulciano
Vinci

And then you could just drive around and take in Tuscany, you don't have to just see towns and cities.

I second Ton's post. Lucca and Pisa are easy to do in one day. And Sienna makes a great day trip as well. Enjoy!!

If you do see Lucca and Pisa, do it in that order. That way, I got to Pisa later in the afternoon: the souvenir vendors were literally packing up, the tour bus crowds had mostly dissipated, and the marble in the Field of Miracles (where the Leaning Tower and Duomo are) was lovely in the afternoon light.

Other than vineyards, what do you want from your daytrips? That will help people give better recommendations.

Possibly the highlight of my 14 day trip to Italy was an escorted wine tasting trip through Chianti from Florence. It was the Chianti Wine and Food Safari by Walks About Florence (although we booked via Viator).

I don't normally go for escorted bus tours. However, this was an exception that I'm really glad we made. 3 wineries - one an agroturismo where we had lunch, and someone else handled the driving.

I was really concerned about the wine tastings and the lunch given some of the reviews I've read about some of these tours. However, the Walks About Italy tour was a real class act. The late morning wine tasting was at a very high end winery (Principe Corsini and it was accompanied by a very nice selection of cheeses, meats, fruits and jams. The lunch was serve d at an agroturismo named La Cantinette in Regnana outside Greve in Chiante. The food, was outstanding as was the wine. The final stop, after spending some wandering the square in Greve in Chianti, was Osteria 1126 in Cinciano - and again, the wine was superb.

This was a small group tour in a mini bus. Not too many people and very relaxed. I would highly recommend this trip.

As for Pisa and Lucca - I would visit in that order. Get to Pisa as early as you can (trains run VERY early) in order to beat the worst of the bus tour crowds. (Pisa was probably our least enjoyable part of the trip because the selfie-stick wielding horde was so obnoxious.) You can then head to Lucca, which is absolutely incredible, for a nice quiet afternoon. It's all very easily done via the train. The best train station to use in Pisa is Pisa S.Rossore but it no longer has attended ticket windows so make sure your credit cards work in Trenitalia ticket machines.

a place that is very easy to reach both by car or by train is Bologna that is famous to be the italy's capital of food and motors (being based in the area where are factories of ferrari, lamborghini, pagani, ducati, etc...).

also the city is a medieval one with arches across all the centre of the city and hosts the Europe's oldest university so full of students and places to eat.

also there are few good local companies offering local tours - we used this one and strongly recommend http://amazing-italy.com/tours/italy-day-tours/