Tour 2 - From San Gimignano to Siena, Florence and through the Chianti area
Content
Siena, Florence, and the Chianti region in between can easily be combined into a week – with a fixed base and day trips instead of constantly packing and unpacking. This suggested itinerary uses San Gimignano as a base and follows the Chiantigiana (SR 222), the classic wine route between Florence and Siena, through the Chianti region.
The tour at a glance
- Duration: 1 week with rest days (also doable in 3-4 days)
- Location: San Gimignano or surrounding area – approx. 40 km to Siena, approx. 55 km to Florence
- Chianti Route: SR 222 Chiantigiana via Castellina, Panzano and Greve, Siena–Florence approx. 70 km
- transport: By car; to Florence it's better to use Park & Ride or bus
- Important: The old towns of Siena, Florence, and San Gimignano are ZTL zones – entry without a permit will result in a fine.
Route overview
| Tags | Stage | Distance (approx.) |
|---|---|---|
| 1–2 | Arrival and rest day in San Gimignano | – |
| 3 | Excursion to Siena | 40 km each way |
| 4 | A day of rest by the pool or an excursion into the surrounding area | – |
| 5 | Excursion to Florence | 55 km each way |
| 6 | Chianti Day on the Chiantigiana (SR 222) | Round trip approx. 100–130 km |
| 7 | Departure | – |
San Gimignano location
Located between Siena and Florence, San Gimignano is an ideal base. An agriturismo or winery in the surrounding area is usually quieter and more affordable than a hotel within the city walls. You can find accommodations around the town, for example, on Booking.com (San Gimignano).
Arrive and breathe deeply
Those arriving on Saturday should treat themselves to Sunday: pool, terrace, and views over the vineyards. In the evening, a stroll into the old town is worthwhile. After about 18 p.m., once the day-trippers have departed, the Piazza della Cisterna becomes significantly quieter, and you'll experience San Gimignano as the locals know it.
Excursion to Siena
Siena's old town is compact and a UNESCO World Heritage Site. Its heart is the shell-shaped Piazza del Campo, home to the Palazzo Pubblico and the Torre del Mangia. Take some time for a coffee in the Piazza before continuing on to the cathedral with its famous marble floor (the floor is only fully uncovered at certain times of the year). For more tips, see our article on the most beautiful sights in Siena and our city tour of Siena.
Parking in Siena
The old town is a ZTL (Limited Traffic Zone) – do not drive into it. Parking garages on the outskirts, such as Il Campo, Il Duomo, Santa Caterina, or San Francesco, are signposted; escalators (risalite) lead from Santa Caterina and San Francesco up to the center. Tickets for the Torre del Mangia and guided tours are available, for example, from GetYourGuide (Siena).
Excursion to Florence
Florence can't be seen in a single day – decide beforehand what's important to you. A classic walking tour leads from Santa Maria Novella train station to the Duomo, across the Piazza della Signoria past the Uffizi Gallery to the Arno River, and over the Ponte Vecchio to the Pitti Palace. There are 463 steps to the top of the Duomo dome; a reservation with a specific time slot is required for the climb. Our Florence city tour offers detailed tips.
Getting there and parking in Florence
The city center is a large ZTL (Limited Traffic Zone) with camera surveillance; fines are also sent abroad, often weeks later. A more relaxed option is Park & Ride: The Villa Costanza parking lot is located directly on the A1 motorway, from where the T1 tram takes you to the city center in about 20 minutes. Alternatively, buses run from San Gimignano or Poggibonsi to Florence – ask at the tourist information office for the current timetable.
Tickets for the Uffizi Gallery
For the Uffizi and the Galleria dell'Accademia (David), you should book tickets with a time slot in advance during the season, otherwise you risk long queues – for example via GetYourGuide (Uffizi without queuing).
Through the Chianti region on the Chiantigiana (SR 222)
The SR 222 Chiantigiana connects Florence (Badia a Ripoli) with Siena, passing through Grassina, Strada in Chianti, Greve, Panzano, and Castellina, right through the vineyards of Chianti Classico. From San Gimignano, you drive via Poggibonsi to Castellina in Chianti and follow the Chiantigiana northwards to Greve – those who wish can stop along the way in the walled town of Monteriggioni.
Places of interest along the route
- Castellina in Chianti: medieval town with fortress and covered walkway (Via delle Volte)
- Panzano in Chianti: small village on a hill with a wide view over the Conca d'Oro
- Greve in Chianti: with the funnel-shaped Piazza Matteotti, on Saturdays Market
- Detour: Radda and Gaiole in Chianti lie east of the SR 222.
We present more places under beautiful places in Chianti , background information about the region can be found under Chianti – in the heart of Tuscany.
Wineries and wine tasting
Numerous wineries along the route invite you to tastings; many sell directly from the estate. Our article on DOC and DOCG in Chianti explains what lies behind Chianti and Chianti Classico with their distinctive black horse . Before you go, make sure you know who will be driving: In Italy, the blood alcohol limit is 0,5 per mille, and for novice drivers, it's 0,0 per mille, and enforcement is strict. For a more relaxed tasting experience, book a guided wine tour in Chianti with transfers through GetYourGuide.
Find accommodation in San Gimignano
Frequently asked questions about the Siena – Florence – Chianti tour
How far is it from Siena to Florence through Chianti?
The SR 222 Chiantigiana is about 70 km long. Due to the winding road and the towns along the way, you should allow at least 1,5 hours of driving time; with stops, it could take a whole day.
Which places are located along the Chiantigiana?
Coming from Florence, the road passes through Grassina, Strada in Chianti, Greve in Chianti, Panzano and Castellina in Chianti, among others, before reaching Siena.
Where is the best place to stay for day trips to Siena and Florence?
San Gimignano, Poggibonsi, or Chianti villages like Castellina are conveniently located between the two cities. An agriturismo in the surrounding area is often quieter than accommodation in the city itself.
Is it possible to drive into the old town of Florence or Siena?
No, both old towns are ZTL zones. Anyone entering without a permit will be photographed and will receive the fine even abroad. Park on the side of the road or use Park & Ride facilities.
How many days do you need for Siena, Florence and Chianti?
At least three days: one each for Siena, Florence, and the Chianti route. With rest days in between, a week is a relaxed one.
