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How To Plan the Ideal Tuscany Itinerary (7 Days)

Trying to plan the best Tuscany itinerary? Try no more, because here you’ve found the perfect guide by an Italian to exploring the region and tasting its wines and delicacies in one week.

There’s a fat chance you’ve heard of Tuscany before today. If you’re planning a trip to Italy, Tuscany is indeed the region you should add to your travel list. It’s so beautiful!

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.

Here you’ll find the best Tuscany itinerary for 7 days, so you get to explore the most wonderful areas of the region.

👉 I recommend starting and ending your Tuscany road trip in Florence, the capital of the region. It’s not only the easiest starting point but also a beautiful city to explore.

Image of Tuscany countryside from above, showing a road flanked by cypress trees, a villa, and rolling green fields around it, with mountains in the background, inserted in a post about a road trip Tuscany itinerary

In this Tuscany itinerary are included many wineries (of course, isn’t this one of the main reasons for your visit?!), magnificent landscapes (I mean, it’s Tuscany’s best treat), and incredibly delicious food, as well as Medieval towns scattered all over. Let your Italian adventure begin!

Renting a Car in Tuscany

Since you’ll be driving in Tuscany, make sure to book your rental car in advance.

Can you do this trip without a car? Honestly, it would be really hard to complete this itinerary by public transport. It’s doable, but you’d have to be based in one or two bigger cities and go on tours from there.

Renting a car in Florence is fairly easy, although you don’t want to drive in Florence! Most areas in the historical center are a limited traffic zone (ZTL) and you could get fined for driving or even parking there. But you’ll need a car to head out of the city, and this can be easily arranged.

There are quite a few rental companies in Florence, and two main areas where to pick up your car: in the airport (which is not ideal, since you’ll be two days in Florence before starting the road trip) and in the city center.

Driving in Italy is a breeze if you’re an experienced driver. While some roads will be windy or narrow when you head into the countryside, it’s still very safe to drive there. In Italy they drive on the right side, so that shouldn’t be an issue either.

If you follow this itinerary, you won’t need a car for the first 2 days, so you can rent it from day 3 onwards.

👉 I usually use RentalCars to compare prices and find the best deal for car rentals. You can get a quote for your trip in the search box below.

Tuscany Itinerary

This Tuscany itinerary will allow you to plan a perfect week to discover the stunning Italian region. From cities to vineyards and jaw-dropping sights, it’s all covered in this comprehensive travel guide. Read on and go from dreaming to preparing your trip!

Day 1-2: Florence

Florence is the capital city of the Tuscan region of Italy and its history is really long, even if Florentine most known historical period is the Renaissance. Between 1300 and 1550 was really a prime time for the amazing richness of the arts.

Despite all the years that have passed, Florence is still an amazing city today where to see great art.

👉 I’ve written a detailed post about the ideal itinerary for 2 days in Florence. You can read that, or get the main info here below.

Day 1: Florence Highlights

On the first day of your Tuscany itinerary, Florence will be the highlight, so avoid the car and just make sure you have comfy sneakers for a day out and about.

The Florence in a Day Walking Tour is a great option for first-time travelers, as you’ll get to visit some of the top attractions, including the Florence Duomo and the David, with an expert local guide. You’ll also learn about the history, art and architecture of the city, and wander its charming streets. ➥ BOOK IT HERE

Otherwise, you can do the tour on your own! First, book a visit and enjoy the Uffizi Gallery, where artworks by Michelangelo, Caravaggio, and Raphael are housed.

➤ Your Uffizi Gallery Ticket can be customized to include different benefits. You can choose priority entry and an audio guide; skip-the-line tickets; or join a guided tour to learn everything about the art and history of the gallery from your host. ➥ BOOK IT HERE

Image of a river with a colorful closed bridge above it, and vibrant buildings to the side, reflected on the water. It's the Arno river in Florence, a must on any Tuscany itinerary

After your visit to the Uffizi Gallery, walk on the nearby Ponte Vecchio and glance at the Arno river on one side of the Gallery, then wander in Piazza Della Signoria on the other side.

If you decide not to cross the river, just a few blocks north you can see St John’s Baptistery, Giotto Bell Tower, and Florence’s Duomo Santa Maria del Fiore. This square with its black and white coloring is in fact one of my favorites in all of Tuscany!

➤ You can visit Florence’s Cathedral with a guided tour to get priority entrance (no queuing!) and learn all about this magnificent piece of architecture and its story. ➥ BOOK IT HERE

➤ The Brunelleschi’s Dome reserved entrance allows you to skip the line upon arrival and enjoy your guide’s insights about the unique dome. After exploring the cathedral and marveling at its mind-blowing frescoes, you’ll get to climb to the top and appreciate the views of Florence from above. ➥ BOOK IT HERE

➤ You can otherwise join a Guided Tour of the Dome to learn about its architecture, art, and construction. You’ll enjoy skip-the-line access and marvel at the frescoes, stained-glass windows, and astounding views of the city. ➥ BOOK IT HERE

You may conclude your first day of artful explorations with a visit to Santa Maria Novella Basilica, one of the most important Gothic churches in all of Tuscany, built between 1279 and 1357.

The facade alone is worth your visit (fun fact: it’s the only church in Florence that retains its original facade) but on the inside you’ll find masterpieces that include Giotto’s Crucifix or Masaccio’s Holy Trinity.

➤ The Santa Maria Novella tickets include a skip-the-line entrance and a video guide that showcases its history. You’ll also get to see the frescoes, 13th-century tombstones, and fascinating architecture. ➥ BOOK IT HERE

Day 2: Pitti Palace, Boboli Gardens, Piazzale Michelangelo

Day 2 in this gorgeous city in Tuscany should also be car-free; don’t worry, you’ll start driving soon enough! Start your day enjoying the south shore of the river Arno by visiting the Pitti Palace.

The palace is an impressive estate built in the mid-15th century by a Florentine banker named Luca Pitti. After his death, the palace served as home to three different dynasties, including the Medici, for around 4 centuries. Nowadays Pitti Palace can be visited, so you can feast your eyes on the 500 pieces of art and its incredible frescoes.

➤ Purchasing your Palazzo Pitti ticket in advance grants you access to the Palatine Gallery (where you’ll find the art pieces), the Royal Apartments, the Treasury of the Grand Dukes, and a few of its galleries. Of course, you’ll also get to explore the Palace itself, and skip the line at the entrance. ➥ BOOK IT HERE

👉 As an alternative, if you’ve had enough of history and want to savor another side of Florence, you can join one of these food tours in Florence or maybe join one of the best Florence cooking classes!

Nearby are the Boboli Gardens, a historical park that offers fantastic views over Florence and features 111 acres (45 ha) of magnificently landscaped gardens.

➤ The Ticket to Boboli Gardens also includes access to the Bardini Gardens and the Porcelain Museum. ➥ BOOK IT HERE

Since you’re already in the area, make sure to stop by the Forte di Belvedere, a hilltop fortress on the northeast side of the gardens that’s also worth the visit.

Afterward, if you walk toward the east along the river, you can easily reach Piazzale Michelangelo, one of the best viewpoints in Florence from where you can get fantastic views of the entire city.

If you are into weapons and armors and are looking for something unusual to do in Florence, spend your second afternoon at the Stibbert Museum, located on top of the Baden Powell Gardens. The museum features more than 30,000 artifacts including large collections of weapons, armor, and clothing.

Its rooms are heavily decorated with antiques from all over the world, so it’s very easy to lose yourself in the contemplation of it all. The Stibbert Museum is a bit far from the city center, but it will certainly make for a unique trip! ➥ GET YOUR TICKETS HERE

End your day with dinner and some rest, because you’ll be embarking on your Tuscany driving itinerary in the morning!

▶ For a more comprehensive itinerary of the city, check out my post about spending 2 days in Florence! You’ll find restaurant recommendations, fabulous viewpoint suggestions, and a detailed guide for your two days.


LUXURY: Ville Sull’Arno
MID-RANGE: La Farina Apartments
ON A BUDGET: Hostel Archi Rossi

Day 3: Chianti and Arezzo

On day 3 your drive around Tuscany begins (told you it would be soon enough!) Depart from Florence and go south, toward the rightly famous Chianti territory. This is where the delicious Chianti wine is produced!

In addition, the whole area is sprinkled with medieval towns and fortresses which you can easily tour in a day. You need to include this region in your itinerary; some of the most amazing wineries in Tuscany, Italy are here!

Morning: Chianti and Wine Tasting

From Florence, the first stop is Greve in Chianti, known as the door to the Chianti region and one of the best places to visit in Tuscany. It’s located around 22 miles (35 km) from Florence, and here you can enjoy the several artisan and wine shops under the porticos surrounding the main square.

Otherwise, just out of town you can get your wine tasting down at Viticcio, a family-owned vineyard that offers tours and wine for purchase.

When you’re done here, about 20 km south you’ll find Castellina in Chianti, a small town that boasts a fortress and scenic walk in Via Delle Volte. As an alternative, you can head to Radda for two fun activities (related to wine, that goes without saying!)

➤ The first one is a Private Tuscan Cooking Class and Wine Tasting. You’ll learn to make a couple traditional Italian dishes in a local farmhouse, and when the food is ready, you’ll enjoy it with a glass of wine. Wine and olive oil tastings are included, and there are vegetarian or vegan options. ➥ BOOK IT HERE

➤ The second option is a Tour and Tasting at an Organic Winery in the heart of the Chianti area. You’ll sample 5 different wines paired with some snacks, and learn about the local wine-making methods as you tour the beautiful winery. ➥ BOOK IT HERE

Finally, if you add a 40-km ride to the east, you’ll arrive at Castelnuovo Berardenga, which sits on the other end of the Chianti and offers a great view of the whole region. 

Afternoon: Arezzo

In the second half of the day, cover the 50 kms that separate Castelnuovo Berardenga from the city of Arezzo, the next destination on your Tuscany trip itinerary.

Arezzo, a town of Etruscan origins where the oldest university in Tuscany was built, is nowadays a sparkling jewel for travelers from all over the world.

Make sure not to miss a visit to the simple-looking San Francesco Basilica, where I assure you the frescoes by Piero Della Francesca will make you remain in awe.

Also visit the nearby Casa Vasari Museum (via XX Settembre 55), where famed artist and art critic Giorgio Vasari lived in the early years of 1500 and where you can now see the wonderfully decorated walls and the roof garden.

On your way to the museum, you should also stroll (and buy an espresso!) in Piazza Grande and admire its iconic trapezoid shape.

➤ A great activity to do in Arezzo, especially if you skipped it at Radda, is the Traditional Home Made Coloured Pasta Cooking Experience. You’ll discover the secrets of Italian pasta with a professional chef and make your own dinner, sauces included, to later enjoy it with a glass of red wine. ➥ BOOK IT HERE

👉 If on day 3 of your Tuscany driving tour you prefer to explore the Chianti territory with a group and a guide rather than on your own (or no one’s volunteering to be the sober driver), these are some opf the best wine tours from Florence.

➤ The Chianti Colors & Flavors day trip departs from Florence and takes you wine tasting in two different wineries. You’ll then get to visit the beautiful little town of Greve in Chianti. It’s one of the best Tuscany wine tours in the area! ➥ BOOK IT HERE

➤ Otherwise, you could join the Tuscany Wine Tasting Tour designed for independent travelers between ages 18-35. Besides tasting 7 different wines, you’ll enjoy balsamic vinegar and olive oil tastings and a professional wine-tasting lesson. After all the drinking, you’ll get to go shopping and ice cream licking in the town of San Gimignano. ➥ BOOK IT HERE


LUXURY: Graziella Patio Hotel
MID-RANGE: de’ Montetini
ON A BUDGET: Santo Spirito

Day 4: Siena

Siena, one of the most renowned cities in Tuscany, Italy, is about 46 miles (75 km) from Arezzo and 45 miles (72 km) from Florence, so wherever you spend your third night you can enjoy day 4 in this beautiful city.

Morning: Explore Siena

Start with the shell-shaped Piazza del Campo and climb up to the 88-meter-high Tower of Mangia, the only place that really offers you a view of the square.

You can then visit the Siena Cathedral, a magnificent medieval church built in 1196. The Piccolomini Altarpiece is the reason most people visit the Duomo: 4 original Michelangelo statues are located there.

➤ The Fast Pass Entrance Ticket to the Siena Duomo Complex allows you to skip the line at the Cathedral to marvel at its art treasures, frescoes, and impressive architecture. You’ll have access to the Baptistery of San Giovanni, the Piccolomini library, and the Crypt, as well as the Museo dell’Opera. ➥ BOOK IT HERE

➤ Go on a City Walking Tour to visit the most important landmarks and discover Siena’s traditions and culture from your local guide. You’ll stop for pictures in front of the most popular attractions, and you can also add an optional Siena Cathedral Tour to visit the Duomo with a guide. ➥ BOOK IT HERE

I recommend also spending some time losing yourself in the medieval streets and among local vendors, just to end up with a last cultural visit at the Pinacoteca Nazionale (via S. Pietro 29). 

If you’re visiting in early July or mid-August, you won’t be able to miss overwhelming references all around town to the Palio di Siena, the centuries-old horse race that occurs in Piazza del Campo twice a year.

If horse races aren’t your cup of tea or you’re simply visiting at another time of year, practice your adventurous tongue by tasting some wild boar (or cinta senese) and hare.

Afternoon: Cooking Class in Siena

Wondering what to do with the rest of your afternoon? Prepare for dinner, of course!

➤ The Tuscan Cooking Class in Central Siena is the perfect opportunity to learn the most traditional Italian recipes, including homemade pasta, from starter to dessert. At the end of the 4-hour class you’ll sit down to indulge in your homemade dinner and some wine! ➥ BOOK IT HERE

As you can see from the number of cooking classes in Tuscany, food is as important as wine in the region (and Italy as a whole, why deceive ourselves?) so don’t forget to enjoy the traditional cuisine during this one week road trip through Tuscany.


LUXURY: Il Giardino di Pantaneto
MID-RANGE: B&B Tetti di Siena
ON A BUDGET: Domus Il Palio

Day 5: Val d’Orcia

Very much like on day 3, dedicate day 5 to exploring the countryside and going on a scenic road trip. Leave Siena and drive southwest toward Val d’Orcia. This valley hosts some of the most stunning landscapes of central Italy and you won’t get enough of them, I assure you!

👉 If you’d rather visit Val d’Orcia with a guided tour from Siena, to avoid the preoccupations about orienting yourself or having a little wine with lunch, you can easily do so.

➤ The Pienza and Montepulciano Wine Tour takes you to the Tuscan towns of Pienza, Montalcino, and Montepulciano from Siena, and allows you to explore their Medieval castles and historic towers, as well as taste the amazing food and wines of the region at local wineries. ➥ BOOK IT HERE

After about 55 km from Siena, you’ll find Pienza, a UNESCO World Heritage site where you can very easily imagine what it must have been to live in the Middle Ages as you taste the amazingly good pecorino cheese.

Cover another 18 km and arrive in Rocca d’Orcia, a fortress-like medieval village in which you shouldn’t miss a visit to the fortress, the Rocca di Tentennano. The view from there is really something.

The village is tiny, and believed to have been founded in the Etruscan age (BC!!) You can expect it to look like it’s thousands of years old, and it won’t disappoint. Rocca d’Orcia is built around a main square, Piazza della Cisterna, and along with the 12th-century fortress and the church, it’s the major landmark in town.

You won’t spend more than a couple of hours in Rocca d’Orcia – it really is small, but incredibly charming!

After savoring a local lunch, it will only take you 15 minutes to arrive at your next destination, the hamlet of Bagno Vignoni. This is where you’ll be stunned by centuries-old hot springs that popes and princes have enjoyed.

A few minutes away is San Quirico d’Orcia and my favorite thing to see here is definitely the city garden Horti Leonini, just next to the main square. It will be impossible for you to not feel like a Renaissance city dweller.

➤ You can visit both towns with the San Quirico & Bagno Vignoni Private Tour. You’ll get to wander around this ancients hamlets with a guide, learning about their history and significance while enjoying the landscape and picturesque streets. ➥ BOOK IT HERE

Last but not least, end your fifth day in Montalcino (7 miles/14 km from San Quirico d’Orcia). Montalcino is known for its wine (Brunello di Montalcino lovers, where are you?) but it has a lot to offer in addition to wine-tasting opportunities.

Among other things, don’t miss the 1361 fortress and the central square Piazza del Popolo, built in 1000 and almost unchanged since.

➤ To further experience this destination, enjoy a Brunello Wine Tasting & Lunch in a Tuscan Castle. You’ll visit a Medieval castle in the heart of Montalcino, admire the fantastic landscape as you taste different local wines with snacks, and finish with a traditional Tuscan lunch. ➥ BOOK IT HERE


LUXURY: Drogheria e Locanda Franci
MID-RANGE: Si Montalcino Hotel
ON A BUDGET: Scalette di Piazza B&B

Day 6: San Gimignano and Volterra

On Day 6 is time to drive back north from Val d’Orcia, pass by Siena, and arrive at yet another jewel dressed as a town: San Gimignano. About 80 km separate Montalcino from San Gimignano but don’t despair, you’ll start seeing this walled town from far away (and it’s already quite a view!)

Morning: San Gimignano

In 1282 the then-medieval city council passed a law that prevented the construction of new buildings unless the new ones were more beautiful than the old ones…thus the city stopped growing, fell into decadence, and ironically preserved itself for us today.

In other words, when you get to San Gimignano, park your car and walk everywhere, as this is a real Medieval town (as well as a UNESCO World Heritage site!)

Make sure to visit the Cathedral, the facing square, and the Piazza della Cisterna, a great place to rest with a gelato. If you’re quite into your medieval history and don’t get squeamish easily, take a peek into the Museum of Torture and Death Penalty (Porta San Giovanni 125).

If that’s not for you, grab a delicious lunch at Perucà restaurant (Via Capassi 16) and continue your Tuscan trip. 

San Gimignano has yet more to offer, besides its gruesome history and Medieval ambiance. Below are some of the best activities to enjoy while you’re here.

➤ Set off on a Truffle Hunt in an oak forest with a professional guide and trained dogs. You’ll first learn how to recognize them and then scan the forest for the precious truffles; once you’re done, you’ll enjoy a delicious Tuscan lunch and sample different wines. ➥ BOOK IT HERE

➤ Go horseback riding through the Tuscan countryside to appreciate the wonderful vineyards, olive groves, rolling hills and native woods from a different perspective. Being an expert horserider is not a request, as you’ll have an orientation lesson at an old riding school before your horse ride begins. ➥ BOOK IT HERE

➤ The Wine and Food Tasting Experience takes place on an organic farm surrounded by countryside. You’ll visit the family-run olive grove, vineyard, and cellar, and taste three organic wines paired with cheeses, olives, and cold cuts. ➥ BOOK IT HERE

After lunch, it’s time to leave the province of Siena and travel toward the sea to the west.

Afternoon: Volterra

On the way, stop in Volterra (about 18 miles/30 km from San Gimignano). This town is much less touristy than your previous destination, and you’ll fall in love with its narrow streets and high walls (parts of them, like the Arco Gate, dating back to the 5th century!)

In town, don’t miss the Santa Maria Assunta Cathedral and explore Volterra’s Etruscan past, by visiting the Enrico Fiumi park, where the old Etruscan city plan is still visible, and the Guarnacci Etruscan Museum.

Last but not least, enter the unique Alabaster Ecomuseum (via dei Sarti), where you can explore this centuries-old artistry of soft rock shaping and bring home some very unique souvenirs. 


LUXURY: Hotel San Lino
MID-RANGE: Albergo Etruria
ON A BUDGET: Casa Mosaico

Day 7: Pisa and Lucca 

We’ve arrived you your last day of this Tuscan itinerary! Day 7 of your road trip in Tuscany has in store for you two very famous (and very cool) towns, Pisa and Lucca.

Morning: Pisa

We’ll start with Pisa, located about 40 miles (65 km) away from Volterra, and housing the world-famous leaning bell tower, the Pisa Tower.

Are you still wondering why on earth this 13th-century tower is leaning? Well, the ground underneath first gave away during construction and the problem was never fixed.

I actually recommend spending quite a bit of time around the tower, in Piazza dei Miracoli, as you’ll have the opportunity to see the Cathedral, the Baptistery, and the Monumental Cemetery. The whole area is a really stunning architectural feat.

➤ The tickets for the Leaning Tower of Pisa grant you fast-track entrance to the tower, so you can climb up and admire the views from above, and also access the beautiful Cathedral of St. Mary of the Assumption. ➥ GET YOUR TICKET HERE

➤ If seeing the Pisa Tower from below is enough, you could instead visit the Cathedral, Baptistry, and Graveyard, all of them symbolic buildings of Miracle Square. You’ll get to see the largest baptistry in Italy, the frescoes that were damaged by fire in WWII, and learn about the fresco-making process at the Sinopie Museum. ➥ GET YOUR TICKET HERE

➤ If roaming around the attractions on your own is not very appealing, you could join an All-Inclusive Guided Tour to discover the jewels of Miracle Square with a professional guide. You’ll have access to the Cathedral and Baptistry, and can also opt to include the Pisa Tower in your tour. ➥ BOOK IT HERE

Miracle Square is Pisa’s main attraction, but by far the only one. The city also boasts several museums, more than 20 (!) churches, and lovely views over the River Arno to stroll along. The architecture in Pisa is also stunning beyond the leaning tower and baptistery, so I’d recommend walking around its center and checking it out!

Santa Maria della Spina, Palazzo dei Cavalieri, the Botanical Gardens, and Ponte di Mezzo should be on your list! In the afternoon, drive across the approximately 12 miles (20 km) that separate Pisa from Lucca.

Afternoon: Lucca

On the Serchio river, Lucca is known for the Renaissance walls that encircle it, which are still standing in their entirety since they were first built.

Lucca boasts terracotta-colored rooftops and vibrantly painted houses, and incredible history. First established in 180 BC, the town showcases historical architecture, including archaeological remains and a Roman amphitheater, a stunning main square, narrow alleys, and a bell tower from where to catch the views.

I recommend visiting the stunning San Martino Cathedral (one of my favorites in the region) and the Volto Santo temple, encased in one of the side walls. Don’t forget to visit the Guinigi Tower and its tower-top garden before you leave. I promise it’s quite a unique experience!

Lucca can be explored on foot or by bike – make sure to take your time and soak in all the history and charm it exudes. It’s not a town to rush in!

➤ To really get a sense of the town and its history, join the 2-Hour City Center Walking Tour that will take you around Lucca’s old town, into the Church of San Michele, which is over 1200 years old, and stroll among the ancient streets and on the 16th-century walls that surround the town. ➥ BOOK IT HERE

➤ A good alternative is taking a Cooking Class in Lucca’s Historic Center. Starting at the market, you’ll pick your own fresh ingredients to prepare a 4-course lunch inside an 18th-century palace. After your cooking lesson, you’ll enjoy your Tuscan meal paired with regional wines, and go home with a recipe book to be able to show off your skills. ➥ BOOK IT HERE


LUXURY: Hotel Ilaria
MID-RANGE: La Bohème
ON A BUDGET: B&B Cento Passi Dalle Mura

And this is it! A 50 mile-drive (80 km) will take you back to Florence, where you can return your rented car, take a plane back home (or continue exploring Italy!) and keep dreaming about the new Tuscan memories you just created during the last week.

Tuscany Itinerary FAQ

What is the best time to visit Tuscany, Italy?

The best time to visit Tuscany is during the spring, between the months of April and May, or in the early fall, between September and October, as the weather will be more enjoyable and the landscape at its best.

What is the prettiest town in Tuscany?

Tuscany is sprinkled with Medieval, gorgeous little towns all over. One of the prettiest is San Gimignano, a hill town located in the province of Siena.

How many days in Tuscany is enough?

You can explore the best of Tuscany in 7 days, with enough time to enjoy the art and culture of its cities and the great wineries and food of the region.

What’s the closest airport for Tuscany, Italy?

There are two international airports in Tuscany, Amerigo Vespucci Airport in Florence and Galileo Galilei Airport in Pisa.

  • Stefania Guglielmi

    Stefania Guglielmi is the founder of Every Steph. Originally from Bologna, Italy, she's been traveling full-time since 2016 and has visited over 50 countries across 6 continents. She believes sustainable travel and luxury travel can go hand in hand and has been advocating for responsible tourism since 2014. Stefania's advice and travel experiences have been featured in important publications such as Business Insider, Refinery29, and Yahoo Money.

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