If you are staying in Florence and want to experience Chianti, it is possible to do your own tour in one day. It is possible to reach many of the Chianti towns by public transport, but if you want to make the most out of a day trip the best way to do it is to rent a car and cruise the Chiantigiana SR 222 highway.
Here is what a one day itinerary of a road trip in Chianti might look like:
Florence to Strada
First you can stop at Strada which will give you fantastic views of the surrounding area and inspire your love for the Tuscan countryside. This town is just 20 km outside Florence and many visitors also chose to stay here for the convenience of getting around.
...on to Greve
...Panzano and Castellina
If you get back on the main road you can follow it to the town of Panzano for its medieval castle and stunning panoramic views. Then make your way to Castellina which is famous for its summertime car races and for an Etruscan necropolis.
At the end of the day you could decide to double back to Florence for the night or spend the night in Siena, at the end of the Chiantigiana.
If you want to visit somewhere off the beaten track, consider going to the charming town of Barberino Val D'Elsa with its tall walls and medieval town centre. If you are nearing the end of your day, you could stop in the picturesque town San Casciano Val di Pesa to wander around the shops and find somewhere to eat in one of their many restaurants.
I suppose you have a car. Chianti is extended between Florence and Siena and it’s very easy to go through it, given that only one road crosses the whole area: the via Chiantigiana. It starts at Florence and ends in Siena, or vice versa.
Starting from Florence you can have your first stop in Panzano in Chianti. Recently Panzano got famous because of the Antica Macelleria Cecchini, where you can have your florentine steak cut while hearing poetry from the Divine Comedy by Dante.
Then you can rest – and also eat if you like – in Castellina in Chianti, to me the most beautiful little town in Chianti. The most valuable Tuscan charcuterie is made here and it would be a shame not to try local cuisine.
If you have time, I suggest you go to visit Siena and have dinner there. Otherwise, you can go back to Florence from the very same road you took to come until here.