Last updated on October 27, 2023 by Stefano Ferro, founder of MEL365, following extensive travelling in Tuscany

7 days in Tuscany, itineraries for 1 week

Culture, history and countryside make Tuscany one of the most fascinating Italian regions.

Seven days in Tuscany offers you the opportunity to visit most of the main attractions.

However, does one week really give you enough time to experience everything this region has to offer?

You will be surprised by how much you can see and do if you plan your itinerary in advance, 

That’s where this guide comes in, whether you are thinking of renting a car in Tuscany or using only public transportation.

Let’s start!

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7 days in Tuscany – in a nutshell

Just a quick few lines about the transportation to and around Tuscany

There are two major airports in Tuscany:

  1. Florence Airport, 20 minutes by bus from the city centre
  2. Pisa Airport (mostly low-cost airlines), 15 minutes to Pisa Centre and 1h15m to Florence Centre (Sky Bus or Autostradale Bus)

For public transportation in Tuscany, you can check:

Most Tuscan towns are well connected by train and bus, but if you wish to visit the countryside, you will need to rent a car. 

The best rental rates (read cheapest) can be found using DiscoverCars.com, a price comparison website.

The following map shows all of the major towns and attractions described in this guide.

Map with Tuscany itineraries and attractions
Map with Tuscany itineraries and attractions
  • 7 days in Tuscany without a car relaxed: in this itinerary, you get to experience the top towns, villages and attractions without a car. The itinerary is more of a relaxing adventure in which you stay at the same location for 3 or 4 nights and visit the local areas. Read more below on this itinerary
  • 7 days in Tuscany without a car on the go: this itinerary will suit you better if you are willing to travel more often and change accommodations more frequently. You will have to take more busses and trains, but you will experience a lot more as a result. Read more below on this itinerary
  • 1 weeks in Tuscany by car relaxed: hiring a vehicle in Tuscany will allow you to have a more flexible trip. There are, however, some drawbacks to it (read on). You will enjoy not just the final destinations, but also the trip itself through the lovely Tuscan roads. Find out more about this itinerary below.
  • one week in Tuscany by car on the go: There is a lot to see in this itinerary. The route is going to be not as relaxed due to more accommodation changes, but you will experience a lot more. Read more below for the 10 days plan
  • seven days in Tuscany by car only for the countryside: You will have trouble planning a trip to the best Tuscan countryside spots in only one week. Beautiful places are everywhere.  What’s my suggestion? Be flexible, because there are always beautiful corners to be found. You can check more information below including a map of some of my favorite attractions and viewpoints in the countryside, which you can use to plan your trip.

7 days in Tuscany without a car relaxed

In this itinerary, you will get to visit the most popular attractions of Tuscany, like the Uffizi Gallery in Florence or the Piazza del Campo in Siena.

However, you will have also some spare time for relaxing for a nice walk, by the pool at the hotel or just wandering around the countryside.

7 days in Tuscany without a car relaxed
7 days in Tuscany without a car relaxed
  • Florence stay – Day 1: Begin your day by visiting the Uffizi Gallery, one of the world’s most important museums. In this case, I recommend taking the Priority Entrance Tour, the best way to save time. Additionally, you will have a guide who will explain everything you need to know in a small group setting. Lunch is best enjoyed at Panini Toscani. A DIY tour of the Historical Centre will keep you busy all afternoon. Start with the surprising Piazza Antinori, then walk to the Basilica of Holy Trinity, ending at Piazza della Signoria. You can then reach Piazza di Santa Croce by following Borgo dei Greci Street. Lastly, proceed north towards Piazza del Duomo.
  • Florence stay – Day 2: To continue your tour of Florence, I recommend going to the Piazza Duomo and climbing the Dome via the Priority Entrance, skipping the crowds. It would be impossible to understand the history of the dome and cathedral without the included tour guide (you’ll visit the cathedral after the dome). After lunch, visit and cross Ponte Vecchio, an arched Roman/medieval river bridge that you must see if you are in Florence. Oltrarno is the neighbourhood directly across the Arno River. You can walk up Borgo S. Jacopo Street to get to St Trinity Bridge by turning right. Cross the bridge and visit the Gothic Basilica of Holy Trinity in the Historical Centre. After that, take Borgo Santi Apostoli Street to get lost in the maze of small streets.
  • Florence stay – Day 3: Time to visit the countryside with this well organised Tour in the Chianti Area, a lovely county with picturesque sceneries, rolling hills, and of course a few wineries to taste the world-famous wine
  • Florence stay – Day 4: Catch the train (1 hour) to see Pisa with a nice DIY walking tour. Begin with a visit to the famous Leaning Tower and the Cathedral. These are both very popular attractions, so I highly recommend purchasing a skip-the-line ticket to avoid long lines. For lunch, try I Porci Comodi in town, a small bar that offers local cured meats and amazing sandwiches. Then, either take a Self-Guided Bike Tour or explore the historical centre starting from the Museo della Grafica and Piazza della Pera.
  • Florence stay – Day 4 (alternative): enjoy a day of shopping at one of the best Designer Outlet in Italy, Barberino, take a Balloon Flight Over Tuscany or why not a romantic 6-Hour Vespa Tour (with traditional lunch).
  • Siena stay – Day 5: Time to move to Siena for the last 3 days. The train trip takes around 1h45m. Have a walk around the historic center after checking in to your hotel. For lunch, try Tigella Emilia‘s handcrafted pasta. Later, continue walking to Piazza del Campo, the Public Palace, and the Duomo Cathedral (skip-the-line tickets are highly recommended here as well). While you’re there, you may want to explore the nearby Baptistery of St John. Dinner at the Osteria Permalico, a charming restaurant in a wine cellar.
  • Siena stay – Day 6: Add a bit of relaxation with a visit to Radda in Chianti and the Castle of Brolio with this organised tour. You’ll also enjoy a visit to some wineries, as well as a delicious lunch made with local products from the Chianti Area.
  • Siena stay – Day 7: Last day dedicated to the Val D’Orcia, south of Siena. You would need to join a tour as public transportation is not really an option. I can’t stop recommending this Brunello di Montalcino Full-Day Wine Tour that drives through the rolling hills with a 360-degree spectacular view. Wine tasting is, of course, the highlight, however, you will experience it with a small group and a tour guide, the winemaker is always there to explain everything about the soil and the wine production process. 

Accommodations and experiences:

Read more options on where to stay in the Florence area.

7 days in Tuscany without a car on the go

In the previous itinerary, I missed two important towns: Arezzo and Cortona.

Both of them could be visited from Siena, or Florence, on a day trip, however, you would spend more time travelling than actually enjoying the destination.

In this plan, which I like to call the “perfect triangle”, you get to visit a lot, but you would have to change accommodation every 2/3 days.

7 days in Tuscany without a car on the go
7 days in Tuscany without a car on the go

The trip starts, as usual, in Florence.

  • Florence stay – Day 1: Similarly to the previous plan, start your day with the Uffizi Gallery (Priority Entrance Tour), lunch at Panini Toscani and explore the historical center to finish your walk in Piazza del Duomo.
  • Florence stay – Day 2: Another day fully dedicated to this beautiful city with Piazza Duomo (Dome via the Priority Entrance), Ponte Vecchio, a walk through Oltrarno and back to the historical centre. You may also want to check out the Forte di Belvedere (free entrance), a 15th-century fortress with a panoramic view of Florence and regular art exhibitions.
  • Florence stay – Day 3: Time to explore the famous Tuscan countryside. Join this Tour in the Chianti Area that will take you through stunning scenery, stopping at a few wineries for some wine tasting.
  • Arezzo stay – Day 4: Pack your bags, it’s time to move to the charming Arezzo (1h or less by train). Once you have checked in at your accommodation, have a walk in the historic centre. Start your exploration from the medieval Piazza Grande and the Santa Maria della Pieve Church. Then it’s time to visit the Arezzo Cathedral. For lunch, have a stop at CiĆ² che Piace, a family-run restaurant cooking local food at a great price. In the afternoon, keep going through the unassuming Arezzo visiting the Pretorio Palace for its unique facade (check out also the library inside), the Passeggio del Prato Park and of course the Fortezza Medicea. Walk down on the popular central Corso Italia till the end where you will find the Roman Amphitheatre and the interesting nearby Archaeological Museum.
  • Arezzo stay – Day 5: Day trip to the fabulous  Cortona. Take the train (20 minutes) from Arezzo Station to Camuccia Cortona Station. From there, grab the bus SU4 or SU5 to Cortona Piazza Mercato. Why is Cortona so special ….and popular? Well, surely because it was featured in the 2003 movie “Under the Tuscan Sun”. In saying that, it is really one of the most characteristic villages in Tuscany. From Piazza Mercato (the final bus stop), walk a few meters north to enter the town through Porta Bifora (the town has many “porta”, the ancient gates to the centre). From there take the Via Ghibellina lane to Piazza Repubblica and all that this town offers. 
  • Siena stay – Day 6: Time to move to the next destination, Siena. From Arezzo, you can either take the direct bus #138 leaving around 8:30 am or 1:30 pm (check the Tiemme Bus website for the latest time schedule) or the train (longer and less panoramic trip). Explore the historic centre after you have checked into your hotel. Lunch at Tigella Emilia for its handmade pasta. You can then walk to the Piazza del Campo, Public Palace, and Duomo Cathedral (skip-the-line tickets to save time). Explore nearby St. John’s Baptistery while you’re there. Dining at the Osteria Permalico, a restaurant housed in a wine cellar.
  • Siena stay – Day 7: Last day is dedicated to the Val D’Orcia, south of Siena. A tour is the only real option since public transportation isn’t really available, or doable. You can’t go wrong with this Brunello di Montalcino Full-Day Wine Tour that drives through the rolling hills and provides spectacular 360-degree views of the region. The highlights of the tour are the wineries (3 of them) and of course, the wine that you will taste together with the winemaker explaining everything about the vineyard and the wine-making process. 

Accommodations and experiences:

Ponte Vecchio, connecting Oltrarno to San Giovanni

1 weeks in Tuscany by car relaxed

Having a car in Tuscany will allow you to have more flexibility. The trip itself through the Tuscan countryside will be one of the highlights of the holiday.

Only 2 suggestions about a car trip:

  • driving through the countryside is easy and usually safe. However, driving into the old centres can be challenging due to the small and narrow streets. The major cities and towns like Florence and Siena have the so-called ZTL, a central area of the historical centre where you cannot drive inside. In this case, park the car outside the historical centre and walk or take a bus inside the town.
  • do not leave anything visible in the car, not even an empty bag, not even in the countryside. Thefts are uncommon in Tuscany, however, it may happen. Having a broken window for an empty bag is not really what you want to experience on your holiday, even less if the bag is full of expensive things like cameras, mobile etc.

I usually rent my cars through DiscoverCars.com, a great website that compares all the major rental companies providing the best available prices.

1 weeks in Tuscany by car relaxed
1 week in Tuscany by car relaxed

Start your trip with two days in Florence, where you will not need a car

  • Florence stay – Day 1: Similar to the previous plans, start your day with the Uffizi Gallery (Priority Entrance Tour), lunch at Panini Toscani and explore the historical center to finish your walk in Piazza del Duomo.
  • Florence stay – Day 2: Another day fully dedicated to this beautiful city with Piazza Duomo (Dome via the Priority Entrance), Ponte Vecchio, a walk through Oltrarno and back to the historical centre. You may also want to check out the Forte di Belvedere (free entrance), a 15th-century fortress with a panoramic view of Florence and regular art exhibitions.
  • Chianti Area stay – Day 3: Rent the car and start the adventure. Take the iconic SR222 Chianti Road to Greve in Chianti, the most iconic town in the Chianti Region. Visit Piazza Matteotti and the historical centre. Wander through the streets and go for some wine tasting in one of the wine shops. Lunch at Il Vinaio where you can try more wine. Explore the Azienda Agricola Manetti Leonardo winery, a few hundred meters from the centre, after lunch. You will have the opportunity to sample more wines as well as learn about the area. You can then visit the Wine Museum or the Castello di Uzzano where you can have a stroll among the wineries.
  • Chianti Area stay – Day 4: Pack your bags and drive through the Chianti Area, one of the prettiest places in the world. Start with a visit to the historical village of Montefioralle, a picturesque settlement surrounded by medieval walls. Absolutely stunning. Follow the SR222 south (direction Siena) to the Castello di Panzano in Chianti and the town of Panzano, where you can have lunch. Later, drive to another charming medieval village, Castellina in Chianti, along the SR222. Enjoy the interesting exhibition and some wine tasting at the Chianti Area Archaeological Museum. Keep going till Siena, where you will book your hotel for the last 3 nights (check with your hotel if and where you can park the car)
  • Siena stay – Day 5: Explore Siena in the morning. Take a walk around Piazza del Campo, the Public Palace, and the Duomo Cathedral (skip-the-line tickets are highly suggested). You can also visit the nearby Baptistery of St. John if you still have some time left. In the afternoon, take the car and have a drive to San Gimignano, a lovely medieval village famous for its white wine, unique in a land of reds. Dinner at the Osteria Permalico, a charming restaurant in a wine cellar
  • Siena stay – Day 6: Time to explore the Val D’Orcia. To truly appreciate how beautiful Tuscany is, drive to one of these panoramic viewpoints (SP18 Viewpoint, Cipressi di San Quirico and Cipressi di Monticchiello). All those spots are located close to a famous movie spot, Gladiator Point, where the Gladiator is famously seen between cypress trees in the movie. Really stunning countryside. Take a break from touring the Val D’Orcia at Podere Il Casale for lunch. The local food is outstanding and the views are breathtaking. Spend the afternoon in Montepulciano, one of the most beautiful medieval villages in Tuscany and home to one of the world’s most famous wines, the Nobile di Montepulciano. Take a stroll through the streets, where there are plenty of wine shops where you can taste the wine. While you’re still in Montepulciano, you should check out the Vecchia Cantina di Montepulciano, where you can taste more wine with the local winemaker and buy a few bottles at a great price. 
  • Siena stay – Day 7: More exploration of Siena in the morning. Lunch at Tigella Emilia for the great hand-made pasta. In the afternoon, drive to Montalcino, another incredible medieval village and the home of Brunello di Montalcino wine. Similarly to Montepulciano, you can sample some wine in one of the few shops in the historic centre. Have some free time? Visit the Azienda Tornesi (make an appointment in advance), just outside the town, where you can taste more wines.

Alternatively, if you prefer to stay in the countryside, why not book your accommodation in Val D’Orcia and visit Siena on a day or half-day trip by car?

Most of the hotels in Siena offer either a parking area or they will tell you where to park the car (public or private parking)

Accommodations and experiences:

One week in Tuscany by car on the go

Start your trip again with two days in Florence, a must, where you will not need a car

One week in Tuscany by car on the go
One week in Tuscany by car on the go
  • Florence stay – Day 1: Similar to the previous plans, start your day with the Uffizi Gallery (Priority Entrance Tour), lunch at Panini Toscani and explore the historical centre to finish your walk in Piazza del Duomo.
  • Florence stay – Day 2: Another day fully dedicated to this beautiful city with Piazza Duomo (Dome via the Priority Entrance), Ponte Vecchio, a walk through Oltrarno and back to the historical centre. You may also want to check out the Forte di Belvedere (free entrance), a 15th-century fortress with a panoramic view of Florence and regular art exhibitions.
  • Pisa stay – Day 3Rent the car and start your exploration of Tuscany. First stop is Pisa (1h by car) to see, of course, the Leaning Tower, the Cathedral and the Historical Centre. On a hot day, you can also think to drive in the late afternoon to Marina di Torre Beach for a swim and a drink for sunset.
  • Chianti Area stay – Day 4: time to leave, this is the itinerary on the go. In the morning drive to the lovely San Gimignano (~1h30m), a beautiful medieval village famous for its white wine Vernaccia di San Gimignano, one of Italy’s finest white wines, produced since the 12th century. Visit the historical centre and have a taste in one of the wine shops. You can also think to visit the boutique winery Tenuta Le Calcinaie (call for an appointment). For a quick lunch have a stop at RiccaPizza or, if you have more time, have a check at Le Vecchie Mura, great local food with an amazing view of the San Gimignano valley. Time to move east to Montefioralle, a lovely village perched on a hill, another great place to get lost. Time to check in at your accommodation in the Chianti Area and have some time to relax before dinner.
  • Siena stay – Day 5: pack your bags for your next destination. This is a day dedicated to the drive on the iconic SR222 Chianti Road from Greve in Chianti to Siena. There are a few stops along the way. The first one is Greve in Chianti, the gateway to the Chianti Region. Have here a walk in Piazza Matteotti and the historical centre. For some wine tasting, I suggest going to the Azienda Agricola Manetti Leonardo winery, a few hundred meters from the main square. Nest two stops are the Castello di Panzano in Chianti and the town of Panzano, where you can have lunch. Later, drive to another charming medieval village, Castellina in Chianti, along the SR222. Enjoy the interesting exhibition and some wine tasting at the Chianti Area Archaeological Museum. Keep going till Siena, where you will stay for the night (check with your hotel if and where you can park the car)
  • Val D’Orcia stay – Day 6: time to explore one of the most picturesque parts of Tuscany, the Val D’Orcia, where you will spend your night. Drive first to one of these panoramic viewpoints (SP18 Viewpoint, Cipressi di San Quirico and Cipressi di Monticchiello). All those spots are located close to a famous movie spot, Gladiator Point, where the Gladiator character is famously seen between cypress trees in the movie. Really stunning countryside. Take a break from touring the Val D’Orcia at Podere Il Casale for lunch. The local food is outstanding and the views are breathtaking. Spend the afternoon in Montepulciano, one of the most beautiful medieval villages in Tuscany and home to one of the world’s most famous wines, the Nobile di Montepulciano. Take a stroll through the streets, where there are plenty of wine shops where you can taste the wine. While you’re still in Montepulciano, you should check out the Vecchia Cantina di Montepulciano, where you can taste more wine with the winemaker and buy a few bottles at a great price. 
  • Arezzo stay – Day 7: pack your bags because the last night will be in Arezzo. Drive first, however, to Cortona (1 hour), one of the most picturesque medieval villages in Tuscany, a famous film set in the 2003 movie “Under the Tuscan Sun”. It’s a popular village, however, well worth your time there. In the afternoon drive to Arezzo where you will spend the last night. In Arezzo make sure to visit the Piazza Grande, the Santa Maria della Pieve Church and the Arezzo Cathedral.

Accommodations and experiences:

Beautiful rolling hills of Tuscany
Beautiful rolling hills of Tuscany

Seven days in Tuscany countryside by car

Honestly, there are so many amazing places to visit in the countryside that it is hard for me to suggest only a few.

I have already suggested quite a number in this guide, both in the Chianti Area and the Val D’Orcia.

Here are also a few public thermal baths, most with free entrance (they are rivers or small waterholes), that you may want to visit:

  • Acqua delle Terme di Sorano
  • Bagno Grande di San Casciano
  • Terme San Filippo
  • Chianciano Terme
  • Terme di Petrolio

I also share here the Google Map that I made public with all my saved places which I update regularly as I find new spots.

Map of the attractions in the Tuscan countryside
Map of the attractions in the Tuscan countryside – Check the Interactive Google Map

I leave it to you to draw the lines between these dots to build your own personal itinerary.

Tuscany rolling hills
Tuscany rolling hills
A corner of Tuscany
A corner of Tuscany
Ponte Vecchio at sunset
Florence Ponte Vecchio at sunset
Life in the lanes of Florence
Florence, the city of art
Florence, the city of art
The leaning Tower of Pisa
The Leaning Tower of Pisa
Lucca main square
Lucca main square
Arezzo dressed up square
Arezzo dressed up square
View of beautiful Siena
View of beautiful Siena
Siena - Palazzo Pubblico & Torre del Mangia
Siena – Palazzo Pubblico & Torre del Mangia
Stefano Ferro - MEL365.com Founder and Editor

About the Author

Stefano is a seasoned travel expert and the visionary founder of MEL365.com, a leading travel website with traffic across 6 continents. With a rich background in the travel industry, Stefano spent four pivotal years at Amadeus Travel Distribution System, gaining invaluable insights into travel technologies and distribution.

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