7-Day Tuscany Itinerary: A Road Trip by an Italian

This 7-day Tuscany itinerary takes you from Florence through Chianti, Siena, the Val d’Orcia, San Gimignano, and Volterra, with a final stop in Pisa. It’s a road trip with time for the places between the famous sights, too.

I grew up in Bologna, just an hour away from Florence, but the landscapes of Tuscany keep blowing my mind every time I visit. In my opinion, there are few places in Italy that are better for a road trip.

The plan below includes arrival in Florence on Day 1 and seven nights in Tuscany. You’ll leave on the morning of Day 8. Spend the first two days without a car, then pick one up for the countryside. Think of this as a starting point for your trip. You can shorten it or swap a stop to suit your interests.

Your 7-Day Tuscany Itinerary at a Glance

Start and finish in Florence. Your overnight bases are Florence for two nights, Siena for three, Volterra for one, and Florence for the final night. Staying in Siena for three nights gives you a full city day and a countryside day without packing again.

Day 8 is your departure day. This version assumes you arrive and depart via Florence, by train or plane. Leave the car return on Day 7 so it doesn’t compete with a flight or train the following morning.

Before You Start: Cars, Parking, and Bookings

When to pick up and return your rental car

Rent the car from the morning of Day 3 until the late afternoon of Day 7. You won’t need it for the first two Florence days, and keeping it out of the city saves parking costs and stress.

For this route, I’d use the Florence airport rental area for pickup and return. The airport’s rental companies are at Palagio degli Spini, reached by a shuttle from the terminal. Allow time to get there from your hotel, take the shuttle if needed, and complete the paperwork.

A city depot can work, too, but ask the rental company for its recommended route out of the restricted area. Check the exact office address, opening hours, return deadline, and fuel policy before booking. An airport location doesn’t automatically mean every desk stays open late.

I usually use Discover Cars to compare prices and rental companies. Check the deposit, insurance excess, mileage, and cancellation terms as well as the headline price. ➥ COMPARE FLORENCE CAR RENTAL PRICES

Book an automatic early if you need one. Choose a car that fits your bags in the trunk, but avoid going bigger than necessary for village streets and parking spaces. Check your rental company’s license requirements, including whether you need an International Driving Permit for your country of issue.

How to handle ZTLs and parking

A ZTL is a restricted traffic zone, usually in a historic center. Cameras monitor access, and a navigation app can still send you through a restricted street. Park outside the center and walk in unless your hotel has given you specific access instructions.

A hotel reservation is not permission to drive into a ZTL. Ask whether your license plate needs registering, which entrance to use, and where you may unload. Florence also has seasonal evening restrictions. The official Florence ZTL guide explains how access works.

I’ve included practical parking starting points for each driving day below. Follow the current signs and your hotel’s directions. Parking availability, market days, and local restrictions can change the approach.

The driving times are planning estimates, not door-to-door promises. Add time for parking, walking uphill, lunch, and check-in. On Days 6 and 7, put luggage out of sight before arriving at a stop and carry valuables with you.

What to book before the trip

Book your hotels, rental car, main Florence museum, and any timed climbs first. Uffizi tickets and the Florence dome climb control Day 2. Pisa’s tower controls Day 7 if you want to go up.

The Uffizi closes on Mondays. If Day 2 falls on a Monday, move it to Day 1 only if your arrival leaves a reliable buffer. Otherwise, use the outdoor Florence route and choose another open attraction. Don’t plan a timed museum visit immediately after an uncertain flight arrival.

For winery visits, decide on transport before booking a tasting. The driver should skip the wine. The Siena-based tours on Day 5 let everyone take part, while Florence departures belong in the separate car-free plan.

Day 1: Arrive in Florence

Keep today flexible. Drop your bags at the hotel, have something to eat, and get your bearings. If you arrive late, dinner and a short walk are enough. You have a full Florence day tomorrow.

For more detail on the city sights and museum options for these two days, see my 2 or 3 days in Florence itinerary.

Piazza della Signoria and Ponte Vecchio

If you arrive with an afternoon to spare, walk to Piazza della Signoria. Palazzo Vecchio and the open-air sculptures of the Loggia dei Lanzi make this a great introduction to Florence without needing a reservation.

Continue toward the Arno and cross Ponte Vecchio, the bridge lined with jewelry shops. It’s a short walk, but leave time to stop along the river rather than rushing straight across.

Have an easy dinner near your hotel or across the river in Oltrarno. A late arrival is a good reason to keep the evening local.

Where to stay in Florence

For the first two nights, choose somewhere walkable to the center. The Santa Maria Novella area is practical for train arrivals and the trip out to the airport rental area. For the final night, you can return to the same hotel or stay nearer your departure point.

Day 2: Art, the Duomo, and the Arno

Today’s default route is the Uffizi in the morning, lunch, Duomo square, and a relaxed afternoon across the river. Pick one major museum so there’s still time to enjoy Florence between reservations.

Start at the Uffizi

Book an early entry and allow two to three hours for the Uffizi. Botticelli’s Birth of Venus and Primavera are among the highlights, but the gallery is huge. A focused visit is more enjoyable than trying to see every room.

➤ If seeing Michelangelo’s David matters more to you, swap the Uffizi for the Accademia and book your Accademia tickets in advance. Don’t squeeze both into this independent route.

Lunch and Piazza del Duomo

After the museum, take a proper lunch break before walking north toward the Duomo. A sandwich is the quick option; a sit-down lunch gives your feet a break before the afternoon.

Piazza del Duomo is one of my favorite places in Florence. The cathedral’s pink, green, and white marble, Giotto’s Bell Tower, and the Baptistery make the square worth visiting even if you don’t climb anything.

The cathedral itself has free entry, with security checks and a separate queue. It is closed to tourist visits on Sundays, so keep the square as your default stop if you’re here that day. Cathedral admission and the dome climb are different things.

➤ Want to climb Brunelleschi’s dome? Reserve an afternoon slot and replace the longer Oltrarno wander or Piazzale Michelangelo. There are 463 steps and no elevator, with narrow passages along the way. This isn’t a gentle add-on after a tiring museum morning.

See the official Brunelleschi Pass information for the timed-climb rules and access conditions. Keep the rest of the afternoon flexible around your confirmed slot.

Oltrarno or an optional sunset view

Cross the river for Oltrarno, where you can spend the rest of the afternoon around Santo Spirito, with little shops, cafes, and time for a gelato. This is the easy version of the afternoon.

➤ If gardens or palace interiors interest you more than the Uffizi, replace the morning museum with Pitti Palace or the Boboli Gardens. Choose one main visit and check its opening details for your date. They don’t belong on top of the museum, a dome climb, and a sunset walk.

Pitti Palace also closes on Mondays. The Boboli Gardens close on the first and last Monday of each month, and closing times change with the season. Neither is an automatic Monday backup.

Piazzale Michelangelo is optional. Walk or take a taxi up if the weather is good and you still have the energy. Sunset changes a lot through the year, so don’t tie dinner to a fixed sunset time.

For other viewpoints, see my guide to the best views of Florence. If food is your priority, one of these Florence food tours or Florence cooking classes can replace the afternoon wander and your usual dinner plans. Check the start time and whether a full meal is included.

Overnight: Florence, second night. Pack tonight so you can leave for the rental pickup without a rushed morning.

Day 3: Chianti on the Way to Siena

Today is about Chianti’s villages and countryside. Pick up the car, stop in Greve and Castellina, and continue to Siena. Two towns are enough once you include the rental paperwork, lunch, and hotel check-in.

As a rough plan, leave your Florence hotel around 8:30 AM for a morning pickup. Allow at least an hour at the rental area, then aim to reach Greve in the late morning. The exact timing depends on your depot and traffic.

Greve in Chianti

Start with a walk around Piazza Matteotti, Greve’s main square, lined with arcades and food shops. Browse the local cheeses, olive oil, and wine, then have lunch before continuing south.

A visitor parking option is Piazza della Resistenza, outside the core. Don’t navigate directly into Piazza Matteotti, where access is restricted and the Saturday market can make the center busier. Allow about two hours for a walk and lunch.

Castellina in Chianti

Continue to Castellina in Chianti for an afternoon stroll. Walk along Via Ferruccio and the covered passage of Via delle Volte, then take in the countryside views. You don’t need a long museum visit to enjoy this stop.

Follow signs for public parking outside the center, such as Il Cantinone. Allow around an hour to an hour and a half before driving to Siena. Aim for a late-afternoon arrival so you have time to check in and settle the parking before dinner.

If you book a winery visit, use it instead of Castellina and allow for its exact location and duration. Book ahead rather than assuming you can walk in. The driver should skip the tasting; Day 5 has transport-inclusive alternatives if everyone wants to enjoy the wine.

Where to stay in Siena

You’ll spend three nights in Siena, so parking matters as much as the room. A central stay works beautifully for evenings on foot, but ask how luggage drop-off and overnight parking work before you arrive.

If your hotel doesn’t provide parking, Santa Caterina car park on Via Esterna di Fontebranda is a useful option, with escalators toward the center. Check the tariff for your actual stays and exits: a continuous multi-day stay is not necessarily an in-and-out pass.

Day 4: A Full Day in Siena

Leave the car parked today. Siena deserves more than a hurried stop between villages. Spend the morning around Piazza del Campo and the cathedral, then choose a relaxed afternoon or a cooking class.

Piazza del Campo and Siena Cathedral

Begin in Piazza del Campo, the shell-shaped square at the heart of the city. Take in Palazzo Pubblico and Torre del Mangia, then wander through the surrounding lanes before the day gets busy.

Walk uphill to Siena Cathedral. The striped marble, richly decorated interior, and Piccolomini Library make this the main paid visit I’d prioritize today. Allow about an hour to an hour and a half for the cathedral and library, plus time for entry.

Check the cathedral complex’s official visiting information for service-related changes. If you visit on a Sunday, you may need to move the cathedral to the afternoon. The uncovered marble floor also has specific viewing periods.

You don’t need to visit every part of the complex just because it’s included. For a view, choose Facciatone rather than adding another tower climb. Leave Torre del Mangia and extra museums for a longer stay.

Lunch, a slow afternoon, or a cooking class

Take a lunch break after the cathedral. Look for pici, the thick local pasta, or a Tuscan soup if you want something lighter. Then leave the afternoon for the lanes around the center, little shops, and a coffee stop.

For a hands-on alternative, the Tuscan cooking class in Siena runs for about four hours, normally starting at 4 PM, with dinner included. It takes place in central Siena with a maximum of 15 participants. Use it instead of late-afternoon sightseeing and a separate dinner, and follow your booking’s meeting instructions.

Overnight: Siena, second night. There’s no hotel move tomorrow, either.

Day 5: Pienza and the Val d’Orcia

Today’s independent route is a loop from Siena through Pienza and San Quirico d’Orcia. Give the landscape some time, stop for lunch, and resist the temptation to turn every nearby village into another stop.

If wine is the main event, choose the small-group Brunello di Montalcino wine-tasting trip instead. It spends about nine hours visiting three wineries, with lunch and stops in Montalcino and at Sant’Antimo Abbey. Groups are capped at eight, with a morning meeting point by San Domenico in Siena, not hotel pickup. This also replaces the full Day 5 drive.

My guide to wine tours from Siena compares the different regions and formats if you want a more wine-focused day.

Pienza in the morning

Leave Siena around 9 AM and allow roughly one hour and 15 minutes to one hour and a half to reach Pienza. This little Renaissance town is a good place to slow down: walk through Piazza Pio II, explore the lanes, and follow the panoramic walk along the edge of town.

Use the paid visitor parking around Via Mario Mencattelli, outside the walls. The local visitor information page lists parking and services. Don’t drive into the historic center looking for a closer space.

Leave time for lunch and some pecorino di Pienza. You can try the sheep’s-milk cheese in a simple sandwich or as part of a sit-down meal. About three hours for the town and lunch is a comfortable starting point.

Palazzo Piccolomini is an optional indoor visit. Add it by shortening the shopping and wandering, not by pushing a third town into the afternoon. Check its current opening calendar before making it part of the plan, especially on a Tuesday.

San Quirico d’Orcia in the afternoon

Drive about 15–20 minutes to San Quirico d’Orcia. Walk along Via Dante Alighieri, see the Collegiata from outside, and visit the formal Horti Leonini gardens if they’re open. This is a small-town afternoon, not another long sightseeing checklist.

Look for public parking around Via dei Fossi outside the historic center and follow the current ZTL signs. Allow about an hour and a half for a stroll and a drink, then roughly an hour to return to Siena.

Optional swap: Bagno Vignoni

For a smaller, quieter stop, visit Bagno Vignoni instead of San Quirico. Its central square is an enormous historic thermal pool, surrounded by stone buildings. You can look at the pool, but bathing in it is not allowed.

Park in the signed visitor area near Parco dei Mulini and spend about an hour walking around. A spa session needs a separate booking and more time, so it would replace most of the afternoon rather than fit between the two villages.

Day 6: San Gimignano and Volterra

Check out of your Siena hotel after breakfast. Visit San Gimignano in the morning, have lunch there, then drive to Volterra for the night. This gives you a proper evening in a hill town instead of another return drive to Siena.

San Gimignano’s towers and squares

Try to reach San Gimignano around 9:30 AM. The medieval towers make a memorable first impression, but the town is just as enjoyable at street level. Walk through Piazza della Cisterna and Piazza del Duomo, then explore a few of the side streets.

P1 Giubileo usually means a longer walk uphill, while P2 Montemaggio is closer to the southern entrance. Check the official parking information for current access and availability. Keep your luggage out of sight before you park.

Choose one paid stop: Torre Grossa for the climb and views, or the Duomo for its frescoes. Torre Grossa and the civic museums generally open 10 AM–7:30 PM from April to October, with last admission at 7 PM; winter hours are shorter. Check the municipal museum timetable for your date.

Allow around three hours for the town, including your chosen attraction, then have lunch. A gelato fits nicely before the drive, but don’t let the stop turn into an extra half-day of museums. Aim to leave around 2 PM.

An afternoon and evening in Volterra

Reach Volterra in the midafternoon and check in or leave your bags at the hotel. Start with Piazza dei Priori, then wander toward the cathedral area and Porta all’Arco, a surviving reminder of the town’s Etruscan past.

Volterra is also known for alabaster. Leave time to browse the workshops and shops, then enjoy the town after the busiest part of the day. Dinner here is part of the reason for staying overnight.

If Etruscan history is a priority, the Guarnacci Museum can replace the longer town walk. In the main season it normally stays open until 6:30 PM, but winter days can be shorter and Tuesdays can be closed. Check the museum’s current hours before relying on a late visit.

For more ideas to use on a longer trip, see these charming villages in Tuscany. I’d keep this day to San Gimignano and Volterra rather than adding another stop.

Where to stay in Volterra

Stay close enough to walk to dinner, and confirm the parking approach before arriving. La Dogana, the underground car park at Piazza Martiri della Libertà, is a useful central option if your accommodation doesn’t offer parking.

Day 7: Pisa and Back to Florence

Have breakfast, check out, and drive to Pisa. Spend the late morning around Piazza dei Miracoli, have lunch, then return the car in Florence. You’ll sleep in Florence tonight and depart tomorrow.

Choose a morning tower slot if you want to climb. Allow for the drive, parking, walk, ticket instructions, and bag storage before the entry time. Don’t book the earliest possible slot unless you’re happy to leave Volterra early.

Piazza dei Miracoli and the Leaning Tower

The Leaning Tower gets most of the attention, but the cathedral and Baptistery are part of what makes this square so beautiful. Give yourself time to walk around the complex before deciding how many interiors you want to see.

The tower visit lasts about 30 minutes and involves 251 steps. Children must turn eight during the year of the visit to enter, and visitors under 18 need an adult. Bags go into the designated cloakroom, which is for the visit and is not suitcase storage.

Read the official visitor rules before booking. Late arrival can mean losing your entry. Cathedral access is included with a monument ticket, but the tower’s timed slot is separate from visiting the cathedral.

Lunch and the drive back

After the monuments, walk toward Piazza dei Cavalieri for a little more of Pisa, then stop for lunch. If the tower visit runs late, shorten the city walk rather than squeezing the rental return.

Use the Via Pietrasantina visitor parking information to plan your arrival. The historic center has restricted traffic areas, so don’t follow the navigation app into a ZTL to save a few minutes of walking.

If you are visiting Pisa by train from Florence instead, my Florence to Pisa day trip guide covers the journey and a walking route through the city.

For example, if your rental return is booked for 6 PM, aim to leave Pisa around 3 PM. That leaves room for traffic, refueling, and the return process. Use your actual supplier’s deadline, then transfer to your Florence hotel for a final dinner.

Optional swap: Lucca instead of Pisa

If you’d rather walk along city walls and explore a compact historic center than climb the Leaning Tower, replace Pisa with Lucca. Don’t try to visit both before returning the car.

Allow roughly one hour and 20–40 minutes from Volterra to Lucca, and around an hour from Lucca to the Florence airport area, before traffic and rental-return time. Park in a signed visitor lot outside the walls using the official Lucca parking map.

Walk a section of the walls, continue to Piazza dell’Anfiteatro, and make time for the cathedral, one of my favorites in the city. Finish with lunch before setting off for Florence. This version can be gentler if you skip tower climbs.

The two-hour Lucca city-center walking tour is an option if its departure fits your return deadline. Commentary can be in both English and Italian; cathedral admission costs extra if you choose to enter. Use it instead of your independent walk.

Overnight: Florence. The hotel suggestions under Day 1 also work for tonight. If you have an early flight, choose the location around that departure rather than planning a late evening across town.

How to Adapt This Tuscany Itinerary Without a Car

You can enjoy a week in Tuscany without driving, but I’d change the bases and day trips rather than try to recreate every stop by bus. Florence and Siena are useful bases; the countryside is where organized transport helps most.

One workable version is four nights in Florence and three in Siena, with the final departure arranged from Siena or with enough transfer time back to Florence. From Florence, visit Pisa by train and choose a countryside excursion. In Siena, keep one full city day and use a Siena-departing tour for the Val d’Orcia.

If your flight leaves Florence early, move the final night back to Florence. This version leaves out the Volterra overnight and the independent village-to-village drives. Each countryside tour takes a full or half day, so choose the experiences you care about rather than booking them all.

➤ If you would rather stay in Florence and let someone else handle the driving, compare these Tuscany day tours from Florence.

Both tours depart from Florence, so book them while you’re staying there. For a closer comparison of the tasting options, see my wine tours from Florence guide.

➤ If Siena is your priority, compare these Siena tours from Florence for options that let you visit without changing hotels.

Tuscany Road Trip FAQs

Is seven days enough for Tuscany?

Seven days gives you a good first trip with Florence, Siena, and several countryside stops. This itinerary uses seven nights and departure on Day 8, so the arrival day can stay relaxed. It won’t cover all of Tuscany, and that’s fine.

How can I shorten this itinerary?

If you have six nights, drop the separate Val d’Orcia day and spend two nights in Siena instead of three. Keep the final Florence night if you have an early departure.

For a much shorter trip, base yourself in Florence and choose one or two day trips rather than trying to fit the entire driving loop into four days.

When is the best time for this road trip?

Late spring and early fall are good starting points for a balance of sightseeing and countryside time.

Summer can be hot and busy, especially in Florence, Siena, and San Gimignano. Winter offers a different pace, but shorter daylight and reduced attraction hours mean you should plan fewer stops.

Can I stay in an agriturismo instead of Siena?

Yes. A countryside stay near Siena can work for the three-night base if you prefer space and quiet. Check the drive to Siena, dinner options, and tour meeting points before booking. You’ll lose the convenience of walking out for dinner, and you’ll need a plan if everyone wants wine with the meal.

Should I choose Pisa or Lucca?

Choose Pisa if the Leaning Tower and cathedral complex are priorities. Choose Lucca for a slower day of squares, lanes, and the city walls. Pick one for Day 7 so you still have time for lunch and a comfortable rental-car return.