Tuscany itinerary: 7 days and what to skip

On paper Tuscany costs you no driving time: the famous places are rarely more than an hour apart. The real cost is something else. Try to fit Florence, Pisa, Lucca, Chianti, Siena, San Gimignano and the Val d'Orcia into a week and you pack your case every night and see the hills mostly from car parks. Seven days are enough if you make choices, and this route does: Pisa and Lucca stay out, Chianti becomes an option, and you sleep in three places instead of six.

The route at a glance

Driving times: route calculation based on OpenStreetMap, without breaks. On the hill roads around Volterra and in the Val d'Orcia, add about a third. If you fly home from Rome instead, Pienza to Fiumicino airport is 221 km, about 3:05 hours.

1. Florence
2. San Gimignano
3. Volterra
4. Siena
5. Bagno Vignoni
6. Montalcino
7. Pienza
8. Montepulciano

Base map: Natural Earth

Which airport?

From the UK, check Pisa as well as Florence: a direct flight from London takes about 2.5 hours. If you land there, stop at Lucca on the way: from Pisa airport it is 39 km, about 0:45 hours, then another 77 km, about an hour, on to Florence. That turns the week into eight days. Florence airport is the more convenient for the route itself: tram T2 reaches the centre in about 20 minutes, and the car hire desks are outside the restricted zone.

Days 1–2: Florence, without a car

Don't drive into town. The city itself says the historic centre is not suitable for cars. According to its official tourism site, the restricted ZTL zone applies Monday to Friday 7:30 to 20:00 and Saturday 7:30 to 16:00. Cameras record every number plate, and an extra night-time rule applies in summer. Since July 2025 there has also been the larger Scudo Verde zone for especially old vehicles. The fix is simple. Take tram T2 or a taxi from the airport (see Florence airport to the city centre) or book a transfer from Florence airport^*, and pick up the car from the airport on the morning of day three.

Two days cover the cathedral, the Uffizi and the Oltrarno if you buy tickets ahead. See how many days in Florence for what fits.

Florence trip planDay by day, with map and tips

Day 3: San Gimignano and Volterra

The mistake today would be reaching San Gimignano at eleven. San Gimignano is only about an hour from the airport, so set off early. UNESCO says its 14 surviving towers preserve the look of a feudal town run by rival factions. A morning is enough for the main street and the view from the Rocca.

Then comes the counterpoint: Volterra, 37 minutes further on a hill between the Era and Cecina valleys. It was one of the main Etruscan city-states, has a double ring of walls and is known for alabaster, and many day-trippers never get this far. You reach Siena in the early evening. Park outside the old town and ask your hotel in advance how to arrive, as its lanes are closed to general traffic too.

The Chianti alternative: if wine matters more to you than towers, drive from Florence via Greve in Chianti to Siena: 72 km, about 1:30 hours. You can't sensibly do both in a day.

Day 4: Siena

UNESCO describes Siena as a whole city built around the Piazza del Campo and devised as a work of art. The shell-shaped square becomes a racetrack for the Palio twice a year. Stay on foot today: the cathedral, the Campo, the districts with their flags. In Piazza Jacopo della Quercia you can still see from the columns how large the cathedral was meant to become, until the Black Death of 1348 ended the plans. You can compare tickets for Siena^* here.

This is also the one sensible option without a car. A train links Florence and Siena in about 1:30 hours, as our day trips from Florence explain. It won't get you comfortably into the Val d'Orcia, though. If you only want cities, stay in Siena and skip the car.

Day 5: Bagno Vignoni, Montalcino, Pienza

Now comes the picture that brings most people to Tuscany in the first place. The Val d'Orcia is a UNESCO cultural landscape: flat chalk plains with almost conical hills topped by fortified settlements, deliberately shaped by Siena in the 14th and 15th centuries.

Head first to Bagno Vignoni. The village square is one big pool of water, fed by springs at about 49 °C that the Tuscan tourist board says have been valued since Roman times. Montalcino on its hill is the home of Brunello. In the evening you reach Pienza.

Day 6: Pienza and Montepulciano

According to UNESCO, Pope Pius II had his birthplace Pienza remodelled from 1459 by Bernardo Rossellino, which made it the first place where Renaissance town planning was put into practice. The square is small, and the view from the wall behind it is huge. Go in the morning and again in the evening, because the light is the real attraction here.

In the afternoon it is 18 minutes to Montepulciano, on a limestone ridge between the Val d'Orcia and the Valdichiana, known for Vino Nobile. The cypress rows along the country roads around San Quirico d'Orcia are easy to take in on the way. Only stop where there is a proper place to pull in, because the roads are narrow.

Day 7: back to the airport

Pienza to Florence airport is 136 km, about 1:50 hours, mostly on fast roads. Don't book a flight before midday, so that you have room to return the car. Fill up first, and follow the signs for the airport rather than the centre.

With more or less time

5 days: Drop Volterra and sleep in Siena and Pienza, with just one full day in Florence.

9 to 10 days: Start in Pisa with a day in Lucca, whose old town is ringed by massive walls, and finish with a day in Chianti. Florence to Pisa airport is 86 km, about 1:30 hours.

Where to stay

Three bases are enough:

• Florence (2 nights): central, on foot, no car.
• Siena (2 nights): at the edge of the old town with parking, and ask about access first.
• Pienza or a farm stay in the Val d'Orcia (2 nights): here the evening view matters more than being close to restaurants.

When to go

May, June and September are the best choice: daily highs in Siena are then 22 to 28 °C, and in May the hills are still green. July and August average about 32 °C, and the heat in the hill towns will slow you down. October gets rainy, though the vineyards turn colour. See the best time to visit Italy for more.

Climate in Siena: 2015–2024 averages from the ERA5 reanalysis (Open-Meteo), rounded.

Good to know before you go

• Hire car: picking up and returning at the same place avoids a one-way fee. Compare offers at the airport with car hire from Florence^*.
• Restricted zones: ZTL signs appear in the hill towns too. As a rule, park outside the town gate and walk the last bit.
• Entry and mobile data: Italy is in the EU and the Schengen Area. If your plan doesn't cover Italy, see our eSIM comparison for Italy.
• Other Italian trips: if you would rather have the sea, look at Sicily in 10 days.

How YesTrip helps with this trip

Add Florence, Siena and Pienza as stops in YesTrip. The map shows you right away what is close together, the AI turns your wishes into a day plan, and you see the weather for your travel days. The packing list follows the forecast, which helps in spring when nights drop to around 7 °C. Florence has a ready-made city plan, and the offline map helps in the Val d'Orcia if your signal comes and goes. You book with the linked partners, and YesTrip itself books nothing.

* Ad – Partner link: if you book there, we earn a commission. Your price stays the same.