Tuscany itinerary for 7 days: Florence, Chianti, Siena and Val d'Orcia

A week in Tuscany works best with two bases and a rental car for part of it. Start with Florence by train, collect the car when you leave, then drive through Chianti to Siena and on to the Val d'Orcia. This plan sits inside the Tuscany travel guide, and the Italy guide shows how it fits a longer route.

The rule is one main stop per day and one long lunch. Tuscan towns are small, and the road between them is half the pleasure, so a schedule with four stops a day turns the trip into a drive. Our guide to where to stay in Tuscany compares five bases for the countryside nights.

Check opening days before you plan around a church, museum or winery, and book timed tickets for the big Florence museums in advance. If you are traveling in July or August, start early; the hill towns are hot and busy by midday.

Day 1: the center on foot

Start at the cathedral and its dome, then walk to Piazza della Signoria and the Ponte Vecchio. The core is flat and compact, so a morning on foot is enough to see the main squares. Leave the afternoon for a museum, and book the slot ahead through the official ticket page. The Uffizi is closed on Mondays and adds a booking fee to tickets bought in advance, so plan the museum for a Tuesday to Sunday and keep a Monday for walking and churches.

Dinner in the Oltrarno, across the river, is calmer than the center. The Florence travel guide covers the sights, ticket rules and where to base.

Day 2: a second museum and a viewpoint

Spend the morning at a second major museum or a smaller one such as a palace or a church with frescoes. Walk up to a viewpoint at sunset, such as the hill above the river, and eat late, as locals do.

If you want a day trip instead, ride a train to Pisa or Lucca, which takes about an hour each way. See the Pisa guide and the Lucca guide for how to fit either into a Florence stay.

Day 3: the Chianti road

Collect your car on the edge of Florence and drive south on the Chianti wine road. Stop at Greve in Chianti for its triangular square, then at a village such as Radda or Castellina. Book a winery visit or a tasting in advance, and choose a driver or a tour if you plan to taste more than a sip.

The direct road from Florence to Siena takes about an hour, and the slower wine road through Chianti takes noticeably longer, so a lunch and a village stop fill the day. Sleep in a farm property if you want quiet, or continue to Siena for the evening.

Day 4: Siena

Walk from the cathedral to the shell-shaped Piazza del Campo and decide how to see Siena from above. The Opa Si Pass covers the cathedral complex, including the panorama from the unfinished facade, for €14 (€16 while the floor is uncovered, which in 2026 runs until 31 October). The Torre del Mangia cannot be booked: tickets are sold only at the Museo Civico office on the Campo on the day, in groups of 25 every 45 minutes. The center is closed to most cars, so park outside the walls.

Siena is also a base for San Gimignano, a tower-studded hill town about an hour away. Go early or late to avoid the day-trip crowds, and see the Siena travel guide for the rest.

Day 5: Montalcino and the wine road

Drive south from Siena to Montalcino, about an hour away, for the brunello wine town and its fortress. Tastings are by appointment at many cellars, and some close for lunch. See the Montalcino guide for the rest.

In the afternoon, take the back roads to the Val d'Orcia, where cypress lines and wheat fields make the postcard view. Stop at a thermal pool in Bagno Vignoni if you want a short soak.

Day 6: Pienza and Montepulciano

Spend the morning in Pienza, a small Renaissance town, and the afternoon in Montepulciano, a hill town with wine cellars under its streets. The Montepulciano guide covers the town and its cellars.

Keep this day flexible. Weather, tastings and slow roads can change the plan, and a long lunch is part of the day.

Use the last day to drive north to a hill town. San Gimignano has the famous towers, and Volterra is quieter, with an Etruscan museum and alabaster workshops. Choose one, not both, and leave time to return the car near Pisa.

If your flight is early, check your rental terms for after-hours drop-off. A final night near Pisa airport, in Lucca or Pisa itself, takes the pressure off the morning.

Rent the car after Florence, not before. The center of Florence is a restricted traffic zone (ZTL), and parking is scarce, so collect the car from an office on the edge of town or at the airport on the morning you leave. Hill towns work the same way: park in the lots outside the walls and walk in. Ask your hotel which gate its guests may use, since cameras issue fines to cars that enter without permission, and fines can reach you months after you return home.

Roads between towns are narrow and winding, and signs are not always clear, so allow more time than a map suggests. A drive that looks like 40 minutes can take an hour with a tractor or a stop for a view. Fill the tank before you leave a big town, since stations in the countryside can close at midday and on Sundays.

Plan around closures. Many churches, small museums and wineries close for a long lunch, and some shut for a day in the week. Restaurants in villages often serve lunch from noon to two and dinner from about seven, and some close in August. A phone call or a message to book a table solves most problems.

April to June and September to October are the best months for this route. Days are mild, the countryside is green in spring and golden in the harvest, and the hill towns are less crowded than in midsummer. July and August are hot, and some restaurants close for the August holidays, so confirm your dinner plans before you rely on a village.

Book in this order: the Florence museum slots first, then the countryside nights, then the car. Rural stays and small hotels in Siena are the first to sell out, and the car is easiest to find a few weeks ahead outside peak dates. Winery visits take appointments, so send a request a few days before. Our best time to visit Italy page explains how the seasons affect prices and closures.

Allow slack. A seven-day plan has six driving or moving days, and a delay on one day pushes the rest. If a day goes wrong, drop the afternoon stop rather than rushing, and keep the long lunch.

Skip a second big museum in Florence if you only have two days. One well-chosen museum and a long walk across the river gives more than two rushed visits. Skip trying to see both San Gimignano and Volterra on the same day as Siena, since the drive eats the afternoon.

Skip the coast on a first week unless beaches are the goal. The Tuscan coast is a separate trip, and the drive from the Val d'Orcia is long. If you want a sea day, add a night near Pisa at the end and read the Pisa travel guide.

Skip midday in the hill towns in summer. Day-trippers arrive between 10 and 4, and the heat peaks in the same hours. Go early or stay late, or choose a farm with a pool for the middle of the day.

The week above compresses easily. For five days, drop the Val d'Orcia: spend two nights in Florence, two in Siena or Chianti and finish with San Gimignano or Volterra on the way to Pisa. That keeps the car rental to three days and removes the longest drive. For ten days, add the two things a week cannot fit: a night in Lucca or on the coast at the start or end, and a third night in the Val d'Orcia so a slow morning does not push the plan back.

The order matters more than the length. Start with the city that has the strictest ticket rules, which is Florence, and end with the place where a delay costs the least, which is a hill town near the airport. If your flight lands in Pisa, reverse the route: Lucca and Pisa first, then the hills, then Florence last, so that you return the car before you enter a limited-traffic zone. A one-way rental can add a fee, so compare it against returning to the pick-up point.

Tuscany in rain is a different trip. Vineyard roads turn muddy, cypress views disappear into cloud and open-air viewpoints lose their point. Use the bad day for the indoor items you already planned: a Florence museum, the Siena cathedral complex or a winery tasting with lunch. Keep the museum for the day with the worst forecast and book it a week ahead, since the only flexible items in this plan are the winery and the walk.

Wind and heat have a pattern too. In July and August, start by 8am, finish sightseeing by 1pm and rest through the middle of the day. In spring, mornings are cool and the afternoon is the best light for the Val d'Orcia. Autumn mornings can bring fog on valley roads, so allow extra time for the first drive of the day.

The common mistakes are all about time. Travelers pick up the car on arrival and then pay for parking for three days in Florence. They plan four hill towns in a day and spend the day on the road. They book a winery for noon, arrive at 2pm and find it closed for lunch. And they forget that the Uffizi is closed on Mondays, which turns a free day into a wasted one.

Two money mistakes are worth a line. If your driver's license was issued outside the European Union, ask the rental company and your own motoring organization whether you need an international driving permit before you travel, since the rules differ by country and the rental terms may ask for one. And do not rely on a rental company's "free" ZTL help: a rental agreement often passes a camera fine on to you, sometimes with an administration fee.

You can do a Tuscany week by train and bus. Base in Florence for three nights, Siena for two and Lucca or Pisa for two. Buses run from Florence to Siena and Chianti villages, from Siena to San Gimignano and Volterra, and trains link Florence with Pisa and Lucca.

The cost is the countryside. The Val d'Orcia is hard to reach without a car, so skip it or join a guided tour from Siena. Check timetables before you plan, since regional buses run less often on Sundays and holidays.

Whichever version you choose, consider Italy by train off-peak for tips on rail tickets between cities. Landing from outside the Schengen area? Read about the EES border checks so you allow time at passport control.

For a base-by-base comparison, read where to stay in Tuscany, and for a different region compare it with Umbria in Tuscany or Umbria. If your route also includes the coast to the north, Cinque Terre is about 1.5 to 2 hours by train from Pisa, so it can be a side trip on the way out, though it deserves a night of its own.