Get ready for the ultimate Tuscany road trip! I’m about to share an awesome itinerary that will take you through stunning landscapes, charming towns, and unforgettable experiences. Picture yourself cruising down winding roads, surrounded by rolling hills and vineyards as far as the eye can see. My Tuscany road trip itinerary covers the best spots to visit, from famous cities like Florence and Siena to hidden gems like Volterra and Montepulciano.
I’ve driven all over Tuscany, and let me tell you, it’s the perfect place for a road trip. You’ll have the freedom to explore at your own pace, stop for impromptu wine tastings, and discover secret viewpoints that will take your breath away. Plus, driving in Tuscany is easier than you might think – the roads are well-maintained, and the scenery makes every journey a joy.
Whether you have a week or two weeks to spare, I’ve got you covered. My itinerary is flexible, so you can adjust it to fit your schedule. We’ll visit iconic sights, sip world-class wines, and dive into the rich history and culture of this amazing region. Get ready for the adventure of a lifetime in beautiful Tuscany!

Planning Your Journey
Getting ready for a Tuscany road trip is exciting. I’ll share some key tips to make your planning easier and ensure you have an amazing time.
Determining the Best Time to Visit
I love visiting Tuscany in spring or fall. The weather is mild and there are fewer tourists. April to May and September to October are ideal.
Summer can be hot and crowded. Winter is cooler and quieter, but some attractions may have limited hours.
Shoulder season (late spring/early fall) offers a nice balance. You’ll enjoy pleasant temperatures and smaller crowds at popular spots.
Local festivals happen year-round. I try to time my visits with events like the Palio horse race in Siena (July and August) or grape harvests in September.

Must-Knows Before Driving in Italy
Driving in Italy can be an adventure. I always make sure to have an International Driving Permit along with my regular license.
Be aware of ZTL zones (limited traffic areas) in city centers. I once got a ticket for accidentally entering one – not fun!
Italians drive on the right side of the road. Highways are easy, but rural roads can be narrow and winding.
Parking can be tricky in towns. I look for lots on the outskirts and walk in.
Gas stations may close for lunch or on Sundays. I try to keep my tank at least half full.
Choosing the Right Accommodation
Tuscany offers many lodging options. I love staying in agriturismos – working farms with guest rooms. They’re often in beautiful rural settings.
For a luxurious experience, you can’t beat staying in a renovated castle or villa.
In cities, I pick hotels near the center for easy exploring. But I make sure they have parking if I’m driving.
Airbnbs are great for longer stays. I’ve rented apartments in charming hill towns for a more local experience.
No matter where I stay, I always book ahead. The best places fill up fast, especially in peak season.
Iconic Cities and Hidden Gems
Tuscany’s iconic cities and hidden gems offer a perfect blend of history, art, and charm. I’ve explored bustling urban centers and quiet hilltop towns, each with its own unique character. From world-famous landmarks to lesser-known treasures, there’s so much to discover on a Tuscan road trip.
The Renaissance Splendor of Florence
Florence took my breath away with its stunning Renaissance architecture and art. The Duomo, or Cattedrale di Santa Maria del Fiore, dominates the skyline with its massive dome. I spent hours wandering through the historic center, a UNESCO World Heritage Site.
The Ponte Vecchio, Florence’s oldest bridge, is lined with jewelry shops and offers beautiful views of the Arno River. For the best panorama of the city, I climbed to Piazzale Michelangelo. The sight of Florence bathed in golden light at sunset is unforgettable.
Don’t miss the Uffizi Gallery and the Accademia, home to Michelangelo’s David. I loved getting lost in the narrow streets, stumbling upon charming piazzas and local cafes.

Medieval Majesty in Siena and San Gimignano
Siena captivated me with its medieval atmosphere and stunning architecture. The heart of the city is Piazza del Campo, a shell-shaped square where the famous Palio horse race takes place twice each summer. I climbed the Torre del Mangia for amazing views of the city and surrounding countryside.
San Gimignano, known as the “Town of Fine Towers,” transported me back in time. Its skyline of medieval towers is truly unique. I enjoyed wandering the narrow streets, sampling the local Vernaccia wine, and taking in the views from the town walls.
Both cities have beautifully preserved historic centers that are UNESCO World Heritage Sites. Their winding streets, Gothic churches, and centuries-old palaces make for unforgettable exploring.

Pisa’s Architectural Wonders
Pisa is famous for its Leaning Tower, and it’s even more impressive in person. I was amazed by how much it actually leans! The tower is part of the Piazza dei Miracoli, or Square of Miracles, which also includes the stunning Pisa Cathedral and Baptistery.
While the Leaning Tower is the star attraction, I found the whole square to be a marvel of Romanesque architecture. The pristine lawns and white marble buildings create a striking contrast.
Don’t rush through Pisa – there’s more to see beyond the famous tower. I enjoyed strolling along the Arno River and exploring the lively university district.
Lucca and Cortona: A Step Back in Time
Lucca charmed me with its well-preserved Renaissance walls, which now serve as a peaceful promenade. I rented a bike to cycle around the top of the walls, taking in views of the city’s red-tiled roofs and church spires.
The oval-shaped Piazza dell’Anfiteatro, built on the ruins of a Roman amphitheater, is a unique sight. I climbed the Torre Guinigi, topped with oak trees, for panoramic views of Lucca and the surrounding hills.
Cortona, perched on a hillside, offers stunning views of the Val di Chiana valley. This Etruscan town gained fame from the book “Under the Tuscan Sun.” I loved wandering its steep, narrow streets and browsing artisan shops. The Etruscan Academy Museum houses fascinating artifacts from the area’s ancient past.

Savoring Tuscany’s Bounties
Tuscany is a feast for the senses, especially when it comes to food and wine. I’ve found that exploring the region’s culinary treasures is an essential part of any road trip here.
Wine Tasting in Tuscany’s Famed Vineyards
I love starting my wine journey in the Chianti region, where rolling hills are covered with vineyards. Many wineries offer tours and tastings, giving me a chance to try the famous Chianti Classico.
In Montalcino, I always make time for Brunello di Montalcino. This rich red wine is a true Tuscan gem. The views from the hilltop town are breathtaking too.
Montepulciano is another must-visit for wine lovers. I’ve sipped Vino Nobile di Montepulciano in ancient cellars beneath the town. It’s an unforgettable experience.

Culinary Delights: From Pecorino to Tuscan Cuisine
Tuscan food is simple but bursting with flavor. In Pienza, I always pick up some Pecorino cheese. The town is famous for this sharp sheep’s milk cheese.
The Val d’Orcia region offers amazing farm-to-table experiences. I’ve enjoyed hearty ribollita soup and pici pasta in tiny trattorias here.
Florence’s Mercato Centrale is a food lover’s paradise. I love wandering the stalls, tasting local specialties like lampredotto sandwiches and fresh pasta.
Taking Part in a Traditional Cooking Class
Learning to cook Tuscan dishes is one of my favorite activities. I’ve taken classes in farmhouses, where we picked ingredients from the garden.
In these classes, I’ve learned to make perfect pici pasta by hand. We’ve also prepared classic dishes like pappa al pomodoro and bistecca alla fiorentina.
Cooking with local nonnas (grandmothers) is always special. They’ve shared family recipes and secret tips that I now use in my own kitchen.

Leisure and Pleasure Beyond the Road
A Tuscany road trip offers more than just scenic drives. I’ve found countless ways to relax and soak in the region’s rich culture between destinations.
Unwinding in Thermal Springs
I love taking breaks at Tuscany’s natural thermal springs. The warm, mineral-rich waters of Saturnia are a must-visit. These cascading pools in Southern Tuscany offer a free and rejuvenating experience.
For a more luxurious soak, I head to Chianciano Terme. This spa town has modern facilities built around ancient Etruscan and Roman baths. The healing waters here are said to help with digestion and stress relief.
On chilly days, nothing beats the steamy outdoor pools of Bagno Vignoni. This tiny village has a large central pool that’s been used since Roman times. It’s a unique sight and a great place to warm up.
Exploring Arts and Crafts in Tuscan Villages
San Gimignano is my go-to for traditional crafts. This walled town is famous for its medieval towers and local artisans. I love watching potters shape clay and glassblowers create delicate pieces.
In Volterra, I always stop to admire the intricate alabaster carvings. This soft stone has been worked here for centuries. Local shops offer everything from small figurines to elaborate vases.
Arezzo is a treasure trove for antique hunters. Its monthly fair fills the streets with vendors selling unique finds. I’ve picked up vintage ceramics and old prints that make perfect souvenirs.
Engaging with Local History and Culture
Tuscany’s smaller towns bring its rich history to life. In Poppi, I explore the well-preserved Castello dei Conti Guidi. This medieval fortress offers stunning views of the Casentino Valley.
The Crete Senesi area south of Siena feels like stepping into a Renaissance painting. I love visiting the Abbey of Monte Oliveto Maggiore to see its beautiful frescoes.
For a taste of island life, I take a ferry to Elba. Napoleon’s exile home is now a museum, offering a glimpse into a different side of Tuscan history.
In Florence, I always make time for the Boboli Gardens. These grand green spaces behind the Pitti Palace are perfect for a peaceful stroll among sculptures and fountains.