If You Do One Trip in 2026, Make It This Spring Drive Through Tuscany

If you only have room for one unforgettable trip in 2026, make it this: a slow, sun-soaked drive through Tuscany in spring.

This is when the region feels at its absolute best—vineyards turning green again, wildflowers stretching across the hills, and golden light spilling over medieval towns without the peak-season crowds. It’s the season where everything feels alive, but nothing feels rushed.

This isn’t just another itinerary. It’s a route designed to help you experience Tuscany the way it’s meant to be—unhurried, scenic, and full of those “pull over right now” moments. Think winding roads through Chianti, long lunches with local wine, and quiet evenings in the countryside.

If you’re going to do Tuscany once, this is how to do it right.

The perfect Tuscany road trip, a must-take in 2026

Let me start with a short introduction to this awe-inspiring Italian region (in case you have stumbled upon this article and you are not familiar with Tuscany yet).

1. What is Tuscany?

Tuscany is a world-celebrated region in Italy famous for its masterpiece towns of Florence, Siena, and Pisa, charming hilltop towns, striking landscapes, rich history, artistic and architectural heritage, and world-class wine.
Stunning Tuscany is one of the top vacation destinations in the World.

2. Where is Tuscany?

This famous Italian region is located in central Italy.
The capital of Tuscany is Florence (or, Firenze in Italian). The neighboring Italian regions of Tuscany are Liguria in the northwest, Emilia Romagna in the northeast, Marche in the east, Umbria in the southeast, and Lazio in the south of Tuscany.

3. What is the best time to visit Tuscany?

The best time to visit Tuscany is from May to October. 
The peak of the tourist season is July and August, with daily temperatures going above 30°C.
May or September are the best months for visiting Tuscany if you wish to escape tourist crowds and enjoy the Tuscan nature and countryside with pleasant temperatures.
April is a good month for visiting Tuscany. In April days get warmer, nature awakes, and the countryside gets colorful, while hotels, B&Bs, and farm stays reopen. April marks the start of tourist season in Tuscany.

4. How to plan the best Tuscany road trip

Here is how I planned my Tuscany road trip.

I was interested in visiting the best places in Tuscany by car.
I wanted to see the ‘crème de la crème’ of Tuscany. So, when tailoring my perfect road trip to Tuscany, I was researching the best places to visit in Tuscany by car.

I researched, and several must-see towns in Tuscany showed up on my Tuscany bucket list. Those towns in Tuscany have regularly appeared on numerous lists of the most beautiful in Italy and the most romantic in Italy.
The cities of Florence, Pisa, and Siena were at the top of my Tuscany road trip itinerary.

But, most of all, I was looking forward to the best scenic drives in Tuscany, visiting charming medieval hilltop walled towns in Tuscany, picturesque Tuscan villages, hills, fields, vineyards, farmhouses, old fortresses, castles, villas … and of course, tasting flavorsome authentic food in Tuscany and sipping some popular Italian drinks.

I wanted to stay in the serene Tuscan countryside. I wanted to be away from the hustle and bustle of the main tourist spots, but still easily reachable. I was looking for a base in the heart of ethereally beautiful Tuscany.

So, I opted for a Tuscany road trip from one base. I didn’t want to see Tuscany in a rush and to take one of those ‘drive until you die road trips, as I call them.
I wanted to visit Tuscany slowly. I wished to enjoy Tuscany!

I looked at the Tuscany map, and I found Montaione.

Montaione is a small Tuscan town, located in the middle of the Florence-Pisa-Siena triangle, in the Chianti region in central Tuscany. 
Montaione is about 22 mi (35 km) southwest of Florence, 47 mi (75 km) northeast of Siena, and 40 mi (64 km) south of Pisa.
Roughly, Montaione is only one hour’s drive from Florence, an hour’s drive from Pisa, and an hour’s drive from Siena.
The small town of Montaione was my perfect base in Tuscany.
Montaione was my Tuscany road trip base. If you are looking for the best places to stay in Tuscany by car, I highly recommend Montaione in the Chianti region.

Montaione distances:
FLORENCE: 22 mi (35 km); 1 hour
SIENA: 47 mi (75 km); 1 hour
PISA: 40 mi (64 km: 1 hour
SAN GIMIGNANO: 13 mi (20 km); 30 min
COLLE DI VAL D’ELSA: 25 mi (40 km); 40 min
MONTEREGGIONI: 28 mi (45 km); 45 min
VOLTERRA: 19 mi (30 km); 40 min
LUCCA: 38 mi (62 km); 1 hour
VIAREGGIO: 56 mi (90 km); 1 hour 15 min
LIVORNO: 43 mi (70 km); 1 hour

In addition, if you are looking for where to stay in the Tuscany countryside, or the best region to stay in Tuscany, the world-famous Chianti region is the best area to stay in Tuscany. In that sense, I would recommend Montaione again. Montaione in the Chianti region is a top place to stay in Tuscany.

The 4-star Boccioleto Resort in Montaione in the middle of Tuscany is absolutely beautiful and peaceful, with stunning views of the Tuscan hills. It offers spacious apartments, a seasonal outdoor swimming pool, excellent breakfast on the terrace, and free parking. This outstanding resort offers good value for money.

5. Best places to visit on a Tuscany road trip

My research on the best places to visit in Tuscany before my Tuscany road trip resulted in a list of places in Tuscany, which I included in my Tuscany road trip itinerary.

• FLORENCE – Florence is the capital of Tuscany and the cradle of the Renaissance. The historic center of Florence is a UNESCO World Heritage site. Florence is one of the most beautiful cities in the world. Like anyone else, I wanted to see one of the most beautiful Italian cities! After all, no trip to Tuscany is complete without visiting Florence!
• SIENA – Siena is one of the most beautiful medieval towns in Italy. It is famous for the Piazza del Campo and Il Palio horse race, museums, art, Siennese cuisine, and Siena Cathedral. The historic center of Siena is a UNESCO World Heritage Site. It is not a secret that Siena is one of the most beautiful Italian towns!
• PISA – Pisa is best known for the Leaning Tower. The Square of the Miracles with the Leaning Tower in Pisa is a UNESCO World Heritage Site. Since I am a lover of World Heritage sites, the Leaning Tower of Pisa was a must-see site in Tuscany!
• SAN GIMIGNANO – San Gimignano is one of the most picturesque hilltop towns in Tuscany. It is nicknamed ‘Manhattan of the Middle Ages‘. It is famous for its 14 medieval towers, great wines, and the best gelateria in Italy (the World’s champion in gelato making is in San Gimignano).
• LUCCA – Lucca is one of the most charming towns in Tuscany and Italy overall. It’s a walled medieval town. The historic center of Lucca is on the tentative list of UNESCO World Heritage Sites. Regardless of the UNESCO listing, Lucca is a must-see medieval town in Tuscany.
• VIAREGGIO – Viareggio is a famous seaside resort town in Tuscany with beautiful Art Nouveau architecture. Viareggio is one of the main cities of the Tuscan Riviera. Of course, I wanted to see the Tuscan beaches on my road trip to Tuscany!
• LIVORNO – Livorno is a seaport town with great seafood-based local cuisine and great beaches. Some more beach time in Tuscany, always!
• VOLTERRA – Volterra is a scenic medieval hilltop town known for its Etruscan origins and fictional Volturi vampires from the Twilight series. Volterra is a must-see hilltop town in Tuscany and a must-stop on a Tuscany road trip!
• MONTERIGGIONI – Monteriggioni is an impressive medieval hilltop village. It’s one of the oldest villages in all of Italy. Of course, I wanted to see one of the oldest villages in Italy on my road trip to Tuscany!
• COLE VAL D’ELSA – Cole Val d’Elsa is a cliff-standing medieval town between San Gimignano and Monteriggioni. Do you find a cliff-standing town awe-inspiring? I do! Cole Val D’Elsa was added to my Tuscany road trip itinerary!
• MONTAIONE – Montaione is a village in Chianti near Florence, Pisa, and Siena. It is in the middle of the Florence-Pisa-Siena triangle in Tuscany. Montaione is an excellent base for exploring Tuscany by car. Naturally, I chose Montaine for the base of my Tuscany road trip!

6. Where to start a road trip to Tuscany

I started my Tuscany road trip driving from Florence. But you can start your road trip through Tuscany also in Pisa, or even in Rome.
If you fly to Florence, Pisa, or Rome, you can rent a car at the airports in Florence, Pisa, and Rome and start your Tuscany road trip there.
DiscoverCarRentals is my favorite site for renting cars. It is an aggregator website that provides rental cars from multiple companies. 
The offer of rental cars and their prices are easily checked online from the comfort of home in a few minutes. Once you have chosen a car, it will wait for you at the airport. It will be ready to be picked up upon your arrival.  The process of renting a car via DiscoverCarRentals and picking it up at the airport is quick and smooth.

• Start your road trip to Tuscany in Florence: Check out car rentals ad Florence Airport
• Start your road trip through Tuscany in Pisa: Check out car rentals at Pisa Airport 
• Start your Tuscany road trip in Rome: Check out car rentals at Rome Airport 

7. Tuscany driving itinerary

Driving Itinerary Tuscany – 11 perfect stops on the ultimate road trip to Tuscany:

7.1. The 1st stop on a Tuscany road trip: FLORENCE

Florence was my first destination in Tuscany.

How to find proper words to describe the center of the Italian Renaissance and one of the most beautiful cities in the World?! How many pages should be written to decently describe the charm and beauty of this UNESCO World Heritage Site?!
In short, has the art, architecture, and history of Florence left any visitor indifferent?!
It is hard to believe so. I fell in love with Florence at first sight.

My absolute favorite things to do in Florence were admiring Botticelli’s The Birth of Venus in the Uffizi Gallery and Michelangelo’s David in the Accademia Gallery, climbing the Cupola del Brunelleschi and enjoying breathtaking panoramic views of Florence, visiting the glorious Palazzo Medici with stunning Boboli Gardens, and strolling the Arno riversides.

Unquestionably, the best sites to see in Florence are the famous Uffizi Gallery, the unique Florence Cathedral with its marvelous cupola, the grand Pitti Palace and Palatine Gallery, the celebrated Palazzo Vecchio, and the famed Medici Palace.

Read more:
The Best Things to Do in Florence
The Perfect One Day in Florence Itinerary
The Ultimate 2-Day Florence Itinerary
Must-Try Food in Florence, Italy

RECOMMENDED THINGS TO DO IN FLORENCE, TUSCANY
Must-visit places in Florence:

• Uffizi Gallery
• Galleria dell’Accademia with Michelangelo’s David
• Florence Duomo
• Cupola del Brunelleschi
• Giotto’s Bell Tower
• Palazzo Vecchio
• Pitti Palace and Palatine Gallery
• Santa Maria Novella church
• Medici Chapels

Book: Uffizi Gallery Priority Entrance Tour – The queues in front of the Uffizi Gallery, the Academia Gallery, and the Cathedral are often extremely long. Book your tickets to skip the lines and save your precious time in Florence.

Where to eat in Florence?

• All’Antico Ristoro di Cambi is a famous family-run restaurant in Florence. Prosciutti hang from its brick ceiling while the bottles of ruby red Chianti wine line the bar. The restaurant serves typical Tuscan cuisine. To try a perfect Florentine stake in Florence, go to Antico Ristoro di Cambi. It is in Via Sant’Onofrio 1/R in the San Frediano area.
• Osteria Santo Spirito is a cozy restaurant with a terrace in the Santo Spirito neighborhood. It is a casual restaurant. Nothing fancy. The restaurant is known for its generous portions and delicious, inexpensive food. It is a casual restaurant with a great atmosphere. It is not surprising that it is one of the most popular restaurants in Florence. This is also my favorite restaurant in Florence! Osteria Santo Spirito is in Piazza Santo Spirito, 16/R in the Santo Spirto neighborhood.

Plan your Tuscany road trip

Rent a car at Florence Airport: Rent a Car at Florence Airport  
Buy tickets:
Uffizi Gallery Skip-The Line Ticket
Galleria dell’Accademia with Michelangelo’s David Entry Ticket
Pitti Palace and Palatine Gallery
Book tour:
Cupola del Brunelleschi

7.2 The 2nd stop: MONTAIONE

I headed to Montaione after visiting Florence.

People often ask: ” How far is Tuscany from Florence?
Well, first of all, Florence is in Tuscany, and Florence is the capital of Tuscany. But when someone mentions Tuscany, the gorgeous Tuscany countryside is most likely on everyone’s mind.
In my case, an hour’s drive took me from Florence to Montaione. In other words, I drove an hour from Florence to central Tuscany.

I booked my stay in the 4-star Boccioleto Resort in Montaione before starting my trip to Tuscany. This exceptional resort was a perfect choice! Its superb location, paired with beautiful decoration and outstanding hospitality, made all my dreams of a relaxing Tuscan countryside stay come true.

For the next several days, the peaceful countryside setting of Boccioleto Resort in Montaione was my home base for exploring Tuscany.

However, if you prefer a more upscale stay for your Tuscany road trip, check out a 5-star boutique hotel Il Castelfalfi in the nearby medieval village of Castelfalfi.
Il Castelfafi Hotel is a dream-like luxury retreat featuring a nature preserve, olive grove, vineyards, 27-hole golf course, swimming pools, and villas spread out over 2,500 acres of countryside.

7.3 The 3rd stop: LUCCA

After a relaxing time, enjoying delicious Italian food and Tuscan wine in the Tuscan countryside in the Castellare di Tonda area, I headed to explore Lucca.
The distance between Montaione and Lucca is 38 mi (62 km), or about a one-hour drive.

Lucca is a small walled town that can easily be walked on foot. It is the hometown of the composer Giacomo Puccini. Lucca hosts several music events such as the Lucca Summer Festival, Lucca Blues Festival, and Lucca Jazz Donna every year.

RECOMMENDED THINGS TO DO IN LUCCA, TUSCANY

Must-Visit Places in Lucca in Tuscany, Italy

• Climb Guinigi Tower to enjoy the most beautiful view of Lucca
• Admire Lucca Cathedral
• Have a cup of genuine Italian cappuccino at Piazza dell’Anfiteatro
• Observe the intricate architecture of San Michele in Foro church
• Visit Puccini’s Birth Home
• Stroll the Walls of Lucca
• Visit Clock Tower in Lucca (Torre Delle Ore)

Insider and off-the-beaten-track Lucca:

• Enjoy in Hot Air Balloon Ride over Tuscany from Lucca 

Where to eat in Lucca?

• Buca di Sant’Antonio is an iconic restaurant in Lucca. It is one of the oldest restaurants in Lucca in the heart of Lucca. It is also one of the most beautifully decorated restaurants in Lucca. The old copper pots and pans hang from the ceiling. Buca di Sant’Antonio is in via della Cervia 3, near  Piazza San Michele. This Michelin-star restaurant serves classic Italian and Tuscan dishes.

Plan your visit to Lucca
Book Lucca: 2-Hour City Center Walking Tour
Buy Lucca: Puccini Festival Opera Recitals and Concerts Ticket

7.4 The 4th stop: VIAREGGIO

Viareggio was the next stop on my road trip in Tuscany.

The distance between Lucca and Viareggio is about 19 mi (26 km), or a 30 min drive.

Viareggio is a popular and glamorous seaside resort in northern Tuscany on the Ligurian Sea, facing the Tyrrhenian Sea. I strongly believe that strolling the Passegiata Margarita, the seafront promenade with beautiful Art Nouveau architecture, and tasting some Italian seafood at the restaurants or just drinking a cappuccino in one of the cafes on the promenade should be on any Tuscany itinerary.

7.5 The 5th stop: PISA

The city of Pisa was the next stop on my Tuscany road trip.

Pisa is easily reachable from Viareggio. The distance between Viareggio and Pisa is 14 mi (23 km), or only a 30 min drive. The driving distance between Pisa and Florence is an hour and 40 minutes.

The Pisa Cathedral with the iconic Leaning Tower of Pisa and the Baptistery of St. John on the Piazza Dei Miracoli (the Square of the Miracles) are world-famous, exquisite examples of Pisan-Romanesque architecture.

If you are doubting about visiting Pisa on the same day as Lucca and Viareggio or not, you need to know that the distance between Montaione and Pisa is about 37 mi (60 km), or a one-hour drive.

RECOMMENDED THINGS TO DO IN PISA, TUSCANY

Must Visit Places in Pisa:

•  Visit Pisa Cathedral, Pisa Baptistery and climb the Leaning Tower of Pisa for marvelous views of the Miracle Square (Piazza Dei Miracoli)

Insider and off-the-beaten-track Pisa: Take a Food Tour in  Pisa

Where to eat in Pisa?
V Beny is a fine-dining restaurant that serves Tuscan, Italian, and Mediterranean cuisines. The restaurant is in Piazza Chiara Gambacorti 22, 56125, Pisa, Italy.

Plan your visit to Pisa
Buy an Entry Ticket to the Leaning Tower of Pisa & Cathedral
Rent a car at Pisa Airport:  Rent a Car Pisa Airport 

7.6 The 6th stop: LIVORNO

Don’t miss out on visiting the city of Livorno on your Tuscany road trip!
A 40-minute drive from Pisa will take you to Livorno, called Leghorn by the Brits.

This port town on the Ligurian Sea with a medieval fort is also well-known as the birthplace of the famous painter Amadeo Modigliani. In the 15th century, Livorno became a part of Florence when the Medici family bought Livorno and Pisa from Genoa.

Walking along the town’s waterfront promenade or taking a boat tour in the New Venice district deserves to be on a Tuscany bucket list.

RECOMMENDED THINGS TO DO IN LIVORNO, TUSCANY

Must-Visit Places in Livorno:

• Visit the central market in Livorno with more than 200 stalls selling local vegetables, fruits, cheese, and salami
• Go to the Porto Mediceo to watch the ships going to the islands of Elba, Sardinia, and Corsica
• Head to New Venice (Nuova Venezia), Livorno’s district with channels and bridges from the 17th century
• Visit Santuario di Montenero
• Stroll Terrazza Mascagni, the waterfront promenade of Livorno

Experience Livorno differently: Explore Livorno by Hop-On Hop-Off Bus

7.7 The 7th stop: VOLTERRA

After visiting Pisa, Lucca, and Viareggio in western Tuscany in a day, I suggest returning to Montaione.

Plan to visit charming places like Volterra, San Gimignano, Colle di Val d’Elsa, and Monteriggioni in central Tuscany in the next few days.

Volterra is one of the most beautiful hilltop towns in Tuscany and one of the oldest towns in Italy. It dates back to the 7th century BC and the Etruscan era.
Recently, the town of Volterra has become known as the fictional hometown of the Volturi, ancient vampires from the TV series Twilight.
Talking about distances, Volterra is a 40-minute drive from Montaione (19 mi, 30 km).

THINGS TO DO IN VOLTERRA TUSCANY

Must-Visit Places in Volterra:

• The Fortress of Volterra
• Palazzo di Priori, the city hall in Volterra
• Teatro Romano, the Roman amphitheater in Volterra
• Palazzo Viti, one of the most beautiful historic private residences and art museums in Italy
• Volterra Museum of Torture
• Pinacoteca, the art gallery with works of Tuscan artists from the 14th to the 17th century
• Etruscan Museum

7.8 The 8th stop: SAN GIMIGNANO

San Gimignano, or the Town of Fine Towers, is one of the most visited medieval Tuscan hilltop towns.

UNESCO protected the historic center of San Gimignano as a World Heritage Site.
14 remaining towers, out of 72 towers, built by noble and wealthy families in the 12th century, dot the town’s landscape. The towers were symbols of power and wealth. The higher the tower, the more power and money the family had.
Sampling the best gelato in the World is a must-do in San Gimignano. Gelateria Dondoli in San Gimignano was awarded the World’s gelato-making champion for many years. San Gimignano is also home to one of the finest Italian wines, the fabulous Vernaccia di San Gimignano.
READ MORE: 15 Top Things to Do in San Gimignano

San Gimignano is a 40 min drive from Volterra. The distance between Volterra and San Gimignano is 20 mi (33 km).

RECOMMENDED THINGS TO DO IN SAN GIMIGNANO, TUSCANY
Must-Visit Places in San Gimignano:

• Palazzo del Popolo
• Piazza del Duomo
• Torre Grossa
• Collegiate Church of San Gimignano
• Santo Agostino Church

Experience San Gimignano in a different way: San Gimignano by Horseback Riding

Insider and off-the-beaten-track San Gimignano:

• Vineyard Walk & Lunch with Wine Tasting
• Truffle Hunting with Wine & Lunch

Best trips from San Gimignano: Explore Chianti by Vespa from San Gimignano 

Where to eat in San Gimignano?

San Martino 26 is a fine-dining Michelin-star restaurant set in the wine cellars of an old palace in the historic center of San Gimignano. It serves Italian, Mediterranean, and European dishes. The restaurant is in via San Martino 26, San Gimignano.
Also, check out Osteria del Carcere in Via del Castello, 13, if you like old taverns. Or, check out Locanda Di Sant’Agostino in Piazza Sant’Agostino 15, San Gimignano, for a bohemian atmosphere and great food. The Locanda Di Sant’Agostino was an unexpected find on my recent visit to San Gimignano.

Plan your visit to San Gimignano

Book
San Gimignano by Horseback Riding
Vineyard Walk & Lunch with Wine Tasting
Truffle Hunting with Wine & Lunch

7.9 The 9th stop: COLLE DI VAL D’ELSA

Colle di Val d’Elsa is a 20 min drive (9 mi, 15 km) from San Gimignano.

It is a true hidden gem in Tuscany, located just a 10-minute drive from the Chianti Classico area. The Chianti region, with towns such as Castellina di Chianti, Panzano in Chianti, and Greve di Chianti, is just around the corner. In short, the best Tuscan wines are just in front of your nose.
The ‘Hill of Elsa Valley’ on the river Elsa is another medieval hilltop town in Tuscany.
Colle di Val d’Elsa is a well-preserved and genuine Tuscan small town with narrow paved lanes, beautiful old palaces, and homes of noble families from the 16th and 17th centuries.

To give you a better perspective of where Colle di Val d’Elsa is, let me add that Colle di Val d’Elsa is a 45-minute drive from Florence and a 35-minute drive from Siena.

Luckily, Colle di Val d’Elsa is not a touristy place. So, if you want to escape the crowds, noise, and prices of Florence and Siena, head to this hidden gem of Tuscany.
This small town holds 15% of the world’s crystal glassware and art. To shop world-class glass and crystals, put Colle di Val d’Elsa on your Tuscany road trip itinerary to shop world-class glass and crystals.

7.10 The 10th stop: MONTERIGGIONI

Monteriggioni is another walled historic town on the way from Colle di Val d’Elsa to Siena. It is a gorgeous, walled small town!

Monteriggioni Castle was built in the 13th century as one of the most important strategic castles in Siena province. Today, you can take a short walk along the town’s walls overlooking roads to Siena and contemplate the battles once fought between warriors of medieval Florence and Siena.

A 15-minute drive from Colle di Val d’Elsa will take you to Monteriggioni, as the distance between Colle di Val d’Elsa and Monteriggioni is only 7 mi (12 km).

7.11 The 11th stop: SIENA

A 20-ish min drive (12 mi, 20 km) from Monteriggioni took me to the last destination on my Tuscan road trip – Siena!

Does the UNESCO World Heritage Site of Siena need some special introduction?!

Who hasn’t heard of this Gothic masterpiece city yet?! Who hasn’t dreamed of drinking a glass of Aperol spritz, or a glass of famous wine from the nearby Chianti region, and people-watching on one of the most beautiful squares in the World?!

Stunning Siena is one of the most beautiful towns in Tuscany, Italy, and its Piazza del Campo is one of the most beautiful squares in Italy.

A legend says that Siena Senius, the son of Romulus, founded Siena. Hence, you will find the statues of the mythical Capitoline Wolf all over the city.
Globally known for its beauty, Siena sits on the three hills connected by three main streets forming a Y shape that ends with the Piazza del Campo, the heart of the city. From its rich history, let me just point out that in the 14th century, Siena was a rival to Florence, Genoa, and Venice. But not only for its power but also for its beauty!
READ MORE: The Best Things to do in Siena, Italy

RECOMMENDED THINGS TO DO IN SIENA, TUSCANY

Must-Visit Places in Siena:

• Piazza del Campo, the public square and historic center of Siena, hosts the famous Palio, a horse race twice a year (in July and August)
• Siena Cathedral (Siena Duomo)
• Palazzo Publico, the 13th-century palace in Siena
• Basilica of San Domenico, a Gothic cathedral in Siena
• Torre del Mangia, the 14th-century tower, is the most famous landmark of Siena
• Piccolomini Library, the library with Pinturicchio frescoes within the Cathedral of Siena
• Palazzo Chigi-Saracini
• Baptistery of San Giovanni with a bronze relief by Donatello and 15th-century frescoes

Where to eat in Siena?
Antica Osteria da Divo in Via Franciosa 25-29 is a culinary institution in Siena. This famous restaurant is set in a historic building made of a series of caves below Siena that date back to Etruscian times. Dining in Antica Osteria da Divo is a bucket list experience in Siena.

Best trips from Siena:
Vespa and Chinati Tour in the Tuscan Hills
Horseback Riding from Siena
Tour Chianti countryside  by Vintage Fiat 500 
Please keep in mind that queues for the main attractions in Pisa are often long.

Plan your visit to Siena
Book Siena 2-Hour Walking Tour & Skip-the-Line Duomo Tickets

Return to Montaione to relax in the tranquil Tuscany countryside after sightseeing in Siena.

8. Tuscany road trip map

Tuscany Italy Map: Tuscany road trip map with driving directions through Tuscany

Please press button ‘+’ on the map to enlarge the map

9. Road trip to Tuscany route

Tuscany road trip route: stops + driving distances + driving times

10. How many days to spend on a Tuscany road trip?

My trip through Tuscany lasted 10 days, but you can squeeze your Tuscany road trip into one week. If you wish to see all these places in Tuscany, please don’t make your tour Della Toscana less than 7 days. Otherwise, you will be running from one Tuscan town to another without enjoying it! Don’t make this mistake!
This ultimate road trip to Tuscany deserves at least 7 days in Tuscany!
You want to experience Italian la dolce vita and eat Italian gelato, drink Aperol spritz, or visit a fabulous Tuscan winery on your Tuscany vacation, right? Then, follow my road trip to Tuscany and plan 10 days in Tuscany!

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Milijana Gabrić

Author at World Travel Connector

Milijana is an independent female solo traveler from Croatia. She enjoys nature, history, art, culture, and spiritual pursuits. Milijana is a foodie who enjoys sampling cultural food around the world, and a hiking enthusiast who did numerous trail around the globe. She greeted sunrise from the top of Mount Sinai in Egypt after a night hike and said hello to the Atlantic Ocean from Finisterre in Spain on one-month-long hike. However, she is not reluctant to rent a car and embark on a spectacular road trip. She believes that some scenic destinations like Tuscany in Italy and Andalucia in Spain are best enjoyed by car.

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