7-Day Tuscany Road Trip Itinerary: Hidden Villages & Scenic Routes

Discovering Tuscany is like visiting an immense open-air museum. Every curve is a new story, every village a page of history, every landscape a painting that leaves you speechless.

Away from the places of mass tourism, it becomes easier to connect with the authentic atmosphere of the region. From the green hills to the beaches of the Tyrrhenian coast, and up to the mountains in the north of the region, you will discover a cultural and natural wealth unique in the world.

And with a 7-Day Tuscany road trip itinerary, you’ll fully savor the taste of adventure and spontaneity, exploring hidden gems with the freedom to stop wherever you want whenever you desire, experiencing an unforgettable journey in the heart of a land that will welcome you with the warmth of its history, the beauty of its landscapes and the authenticity of its traditions.

Discovering Tuscany on the road means embracing a different pace, uncovering magical landscapes that change with every turn. Our 7-day itinerary is perfect for those who love to travel slowly—ideal for couples, families, and anyone seeking authentic experiences among rolling hills, historic cities, and timeless villages.

By following the scenic drives in Tuscany, you'll uncover hidden treasures at your own pace, stopping whenever inspiration strikes and tailoring the journey to your personal interests and curiosities—for a truly unique and memorable experience.

That’s why this route, although it starts and ends in Florence for greater convenience related to transportation and car rental, winds through less known areas, among towns and villages that retain an untouched and wild aura, rich in wonderful attractions waiting to be discovered.

From Arezzo to the Val di Chiana, from the Tyrrhenian coast to Volterra, reaching San Miniato, the Apuan Alps, and Castelnuovo di Garfagnana, and finally heading back towards Florence after a last stop in the picturesque town of Vinci. Discover the most enchanting and hidden places that will reveal the true and unforgettable soul of Tuscany.

Tuscany road trip itinerary highlights:

- Day 1: Arezzo, visit to the historic center.


- Day 2: Civitella in Val di Chiana, Monte San Savino and Trequanda.


- Day 3: From the stunning Val d’Orcia to Castiglione della Pescaia.


- Day 4: From the sea of Cala Violina to Volterra.


- Day 5: Through the villages of Lajatico and San Miniato.


- Day 6: Apuan Alps Regional Natural Park and Castelnuovo di Garfagnana.


- Day 7: Vinci, Leonardo’s Birthplace and Museum, and return to Florence.

Tuscany’s hilltop towns are small gems nestled in the landscape, each one telling centuries of history. From San Gimignano, with its medieval towers shaping the skyline, to Montepulciano, surrounded by vineyards and Renaissance palaces, every place preserves a strong identity made of traditions, well-preserved architecture, and breathtaking views.

Travel through the best towns to visit in Tuscany and let yourself be enchanted by timeless atmospheres. Over these 7 days, you’ll come across villages like Volterra, with its Etruscan walls and perfectly preserved historic center, and San Quirico d’Orcia, lying peacefully among the region’s most iconic hills.

There are also hidden gems that are just as unmissable: quiet, secluded places like Castelnuovo di Garfagnana, framed by the Apuan Alps, or San Miniato, where art and architecture meet the unmistakable scent of white truffle.

These stops are ideal for travelers in search of an authentic bond with this land, far from the beaten path. Here, you enter the true soul of Tuscany — a place where every step invites you to slow down, observe, and let yourself be inspired.

Florence, as a key destination especially for international travelers, serves as the starting point for our Tuscany road trip itinerary. However, the true journey to the most fascinating and unconventional places in the region begins in the splendid and elegant Arezzo, which can be reached in about an hour by following the A1 highway south.

Located in the Val di Chiana, Arezzo is a perfect blend of art and culture. Among the things to do in Arezzo, some must-see stops stand out for art lovers: Piero della Francesca’s frescoes in the Basilica of San Francesco, Crucifix of Cimabue in the Church of San Domenico, and the Casa Vasari Museum. The entire historic center retains a wonderful medieval atmosphere, starting with Piazza Grande, one of the city’s most charming spaces.

If you visit Piazza Grande on the penultimate Saturday of June or the first Sunday of September, you will discover the Giostra del Saracino, a type of equestrian tournament held twice a year that represents an authentic medieval historical reenactment. Meanwhile, the first weekend of each month hosts the Fiera Antiquaria, the oldest and largest antiques fair in all of Italy.

Speaking of events, Arezzo is home to the Arezzo Intour Foundation, dedicated to tourism and cultural promotion, as well as organizing itineraries and activities to discover the beauties of the city and its surroundings.

The entire Aretine territory is a hidden treasure: the Foundation's goal is to highlight the rich historical, artistic and natural heritage of Arezzo, allowing visitors to appreciate its authenticity, with a special focus on preserving sustainable tourism.

Only by traveling at a leisurely pace and enjoying a more intimate and relaxing experience can you fully appreciate the history, traditions, cultural sites, and natural landscapes that surround the city. This is why, if you have the opportunity, don't limit yourself to a quick excursion in the historic center, but dedicate at least a couple of days to visiting these very special places.

Day 1 highlights:

- Journey from Florence to Arezzo (59 km).


- Historic center of Arezzo: Piazza Grande.


- Basilica of San Francesco.


- Church of San Domenico.


- Casa Vasari Museum.

The second stop of our itinerary takes us through the Val di Chiana. After leaving Arezzo, take the Strada Provinciale 21 towards Civitella in Val di Chiana, a small village about 20 kilometers away.

Civitella, an ancient Lombard stronghold, retains much of its medieval structure, including the remains of the 11th-century castle and the Church of Santa Maria Assunta, rebuilt after being set on fire in 1944 during the massacre perpetrated by the Nazis against over 100 defenseless citizens.

After paying due tribute to this tragic episode, head to the panoramic terrace on Via Martiri di Civitella and connect with the territory by admiring the surrounding landscape.

Once you leave Civitella, return to the junction between SP21 and SP22, and turn right following the signs for Monte San Savino, about 9 kilometers away. In its perfectly preserved historic center, this village offers a unique Tuscan experience.

You can admire the Loggia dei Mercanti, an elegant Renaissance structure, or visit the Palazzo di Monte, an architectural gem with spectacular views over the Val di Chiana. Monte San Savino is also known for its tradition of ceramic craftsmanship, which you can experience up close by visiting local artisan workshops.

The last stop of our Val di Chana itinerary is Trequanda, 25 kilometers further south. Spend the evening strolling through the streets of the small center, and discover the excellent local cuisine. From pici all’aglione to Florentine steak and olive oil: every dish or product tells the culinary story of the region, allowing you to fully connect with the authentic soul of Tuscany.

Day 2 highlights:

- Journey through the Val di Chiana (59 km).


- Civitella in Val di Chiana.


- Monte San Savino.


- Trequanda.


- Traditional dinner.

Leave Trequanda and the Val di Chiana behind and head towards the Tyrrhenian coast, which is less than a two-hour drive from here. Instead of taking the most direct route, consider a detour near the village of Montisi to reach the Val d’Orcia. Travel along the road between Pienza and San Quirico d’Orcia, rejoining the main route just before Montalcino.

This way, you can admire some of the most beautiful landscapes in the region, with spectacular views of the Tuscan hills, cypress trees, white roads, charming villages, and a wonderful atmosphere of peace and serenity.

The itinerary extends nearly to Grosseto. Before reaching the city, leave the SS223 and follow the signs for Castiglione della Pescaia, a charming coastal village in the heart of the Maremma, renowned for its crystal-clear waters, sandy beaches considered among the best in the area, and its picturesque historic citadel perched on the hill.

The panoramic view from the terrace of the Castle (built between the 10th century and the Renaissance, but now private and not open to visitors) is truly breathtaking, spanning from the sea to the islands of the Tuscan Archipelago and the surrounding hills.

While maintaining a tranquil atmosphere, summer evenings in Castiglione are quite lively. You can start with an aperitif and a walk along the seafront, continue with a typical dinner featuring Maremma specialties, and enjoy live music in the squares, bars, or nightclubs.

Day 3 highlights:

- Val d’Orcia.


- Arrival in Castiglione della Pescaia (115 km).


- Visit to the Castle.


- Aperitif on the seafront.

The fourth stop of our road trip in Tuscany will take you from Castiglione della Pescaia to Volterra, for a journey of about an hour and a half.

Along the way, make a stop to immerse yourself in the fascinating scenery of the Tuscan sea. Shortly after Castiglione you can explore the beautiful area of Cala Violina, walking through a green pine forest to reach the beach and venture to the small and hidden Caletta Icardi, with its crystal-clear waters accessible only by sea or by climbing the rocks from Cala Violina.

Once you arrive in Volterra, spend the rest of the day (or even the next day, if you have more time) exploring the charming historic center.

If you're wondering what to see in Volterra, start from Piazza dei Priori, home to the oldest town hall in Tuscany (13th century); the Cathedral of Santa Maria Assunta (12th century), with its picturesque bell tower and the Baptistery of San Giovanni; the Roman Theater from the 1st century BC (best appreciated from the panoramic viewpoint on via Lungo le Mura del Mandorlo) and the nearby 3rd-century AD Roman Baths.

And you’ll find also the Etruscan Museum Guarnacci, the Medici Fortress and its park, historic residences, and more. End your day strolling among the artisan shops in the center, famous for their alabaster work. You can watch the craftsmen at work and purchase unique items as souvenirs.

Day 4 highlights:

- Journey towards Volterra (112 km).


- Cala Violina.


- Volterra: Piazza dei Priori, Cathedral, Roman Theatre and Baths, Etruscan Museum, and Medici Fortress.

From Volterra, head north into the lush countryside of the Pisa province. The next stop is Lajatico, a small town known as the birthplace of a great Italian artist: tenor Andrea Bocelli.

In this hidden corner of Tuscany, besides the pastoral landscapes, trails and white roads offering enchanting views of the valleys, you can admire a truly unique and special place like the Teatro del Silenzio. This open-air amphitheater, designed by Bocelli himself, hosts a concert every summer with the stunning backdrop of the Tuscan hills.

After Lajatico, continue on SP11 to Pontedera, then take the Firenze-Pisa-Livorno highway towards Florence. From here, in less than 20 minutes, you’ll reach the picturesque village of San Miniato.

In the shadow of the Torre di Federico II, a historic 13th-century building commissioned by the eponymous King of Swabia, you can breathe in an aura of tranquility and charm. The streets of the historic center, shaded squares and medieval buildings create a relaxing and ancient atmosphere.

Local traditions, such as the white truffle festival, bring San Miniato to life with unique colors, flavors, and aromas, making the town a perfect place for those seeking a genuine experience away from the beaten path.

Day 5 highlights:

- From Volterra to Lajatico (21 km).


- Lajatico: Teatro del Silenzio.


- From Lajatico to San Miniato (44 km).


- San Miniato: Torre di Federico II and historic center.

For the penultimate stop on our Tuscany road trip itinerary, leave San Miniato and drive towards Pisa. After passing around the city, take the E80 road (direction Genoa) to Versilia, and follow the signs to Castelnuovo di Garfagnana, for a total journey of about 2 hours.

Along the way, you won’t have a chance to get bored, as after Versilia you'll traverse the Regional Natural Park of the Apuan Alps. This area is characterized by spectacular mountains, rich biodiversity, and the prestigious Carrara marble that has shaped art and architecture for centuries. The park is ideal for outdoor activities, like hiking Apuan Alps, and offers a truly unique cultural heritage.

For example, not far from the small village of Pontestazzemese, you can find the ancient Calcaferro mines, a fascinating site that immerses you in the region's mining history, with Roman or medieval galleries and breathtaking views.

Further along, you'll also find the Antro del Corchia, one of Italy's largest cave and underground gallery systems, extending over 60 kilometers. Stopping here will provide a unique experience among stalactites, stalagmites, and spectacular geological formations.

Finally, upon reaching Castelnuovo di Garfagnana, spend the afternoon exploring the imposing medieval castle (the Monte Alfonso Fortress) and the Rocca Ariostesca, located in the historic center.

Above all, breathe in the atmosphere of the town, which fully reflects its natural context in the heart of Garfagnana. The fresh, clean air creates an enchanting and authentic environment, typical of Tuscany's mountain tradition.

Day 6 highlights:

- From San Miniato to Castelnuovo di Garfagnana (128 km).


- Apuan Alps Regional Natural Park: Calcaferro mines and Corchia Cave.


- Castelnuovo di Garfagnana.

The “unconventional” journey through the most beautiful and lesser-known places in Tuscany concludes where it began: in the magnificent Florence. However, between Castelnuovo di Garfagnana and the capital, you must make a stop in Vinci, a charming village and the birthplace of the great Leonardo da Vinci.

Here, you can visit the Leonardo da Vinci Museum, located in the center of town, to admire copies of his drawings and reconstructions of the machines that made him famous.

Moreover, if you want to enrich your visit, also stop by the Leonardo’s Birthplace (located just a few kilometers from the center of Vinci) for a deeper experience into the life and works of one of history’s most brilliant artists and scientists.

Despite the presence of such important artistic sites, the village remains peaceful and authentic, surrounded by the Tuscan countryside landscape, rich in olive groves and vineyards.

From Vinci, it's only 50 kilometers to Florence. Thus, our Tuscany road trip itinerary comes to an end, but the route you traveled, the places you visited, and the magical atmospheres of Tuscany you discovered along the way will forever remain etched in your memory.

Day 7 highlights:

- From Castelnuovo di Garfagnana to Vinci (85 km).


- Vinci: Leonardo da Vinci Museum and Leonardo’s Birthplace.


- Return to Florence (44 km).

Four or five days can be enough for a captivating taste of the region, but a true Tuscany road trip requires at least 7 days: you need enough time to calmly explore the most charming villages, art cities, and stunning natural landscapes.

Yes, absolutely. Renting a car allows you to discover hidden corners, small villages, and rural landscapes that are hard to reach by public transport. It’s the best way to explore the most beautiful scenery in Tuscany.

The cost varies depending on the season, the length of the trip, and the type of accommodation chosen. On average, you can expect a budget between 100 and 150 euros per day per person, including car rental, fuel, meals, and lodging.

Spring (April-May) and autumn (September-October) are the ideal periods: mild weather, fewer tourists, and spectacularly colorful landscapes!

No, driving in Tuscany is fairly easy. The main roads are well signposted and in good condition. Just be careful with ZTL (Limited Traffic Zones) in historic city centers.

Besides Lajatico and San Miniato, our itinerary includes small gems like Volterra and Vinci, perfect for those seeking authenticity away from the crowds of Florence. Then there are other charming villages nearby, such as San Gimignano, Pienza, and Colle di Val d’Elsa, each with a unique atmosphere and spectacular views that enrich the experience of a Tuscany road trip.

The roads between Volterra, Lajatico, and the Apuan Alps offer breathtaking rural and mountain landscapes, perfect for those who enjoy a mix of nature and historic villages. Also not to be missed are the famous “strade bianche” (white gravel roads) winding through the hills of Val d'Orcia, providing spectacular views of wheat fields, vineyards, and cypress trees.