By Tuscany is a dream destination for anyone who wants to experience the true essence of Italy. With its charming medieval towns, rolling hills dotted with vineyards, historic landmarks, and incredible food and wine, Tuscany offers a captivating blend of culture, history, and natural beauty. This 10-day road trip itinerary will guide you through the heart of the region, giving you plenty of time to savor its delights, from the iconic sights to the hidden gems.
Overview
Starting and ending in Florence, this 10-day road trip will take you on a scenic loop through Tuscany’s most beautiful towns and landscapes. You’ll explore world-renowned wine regions, ancient hill towns, and stunning coastal villages, all while enjoying leisurely drives and the region’s authentic experiences.
Suggested Route:
Florence → Chianti → Siena → San Gimignano → Val d’Orcia → Montepulciano → Montalcino → Pienza → Lucca → Pisa → Tuscan Coast → Florence
Day-by-Day Itinerary
Day 1: Arrival in Florence – The Renaissance Awaits
Your journey begins in Florence, the cradle of the Renaissance. This vibrant city welcomes you with its stunning architecture, world-class museums, and rich history. Start your exploration by wandering through the historical center, where every street offers something unique.
- Things to do:
- Climb the Duomo for panoramic views of the city.
- Visit the Uffizi Gallery to see masterpieces like Botticelli’s Birth of Venus.
- Stroll along the Ponte Vecchio at sunset.
- Have dinner at a traditional trattoria such as Trattoria ZaZa.
Day 2: Florence – Art, Views, and Hidden Treasures
On your second day, explore Florence’s quieter side. Cross the Arno River to the Oltrarno district, known for its artisanal shops and local charm. For breathtaking views, head up to Piazzale Michelangelo, especially at sunrise or sunset.
- Things to do:
- Visit Basilica di Santa Croce, where Michelangelo is buried.
- Discover unique shops in Via Romana and Santo Spirito.
- Take a short drive to Fiesole for views of Florence and Roman ruins.
Day 3: Chianti – Wine and Vineyards
Leave Florence behind and head into the picturesque Chianti region. With rolling hills covered in vineyards and olive groves, this area is a paradise for wine lovers. Spend the day tasting Chianti wines and exploring quaint villages.
- Things to do:
- Visit Greve in Chianti, the heart of the wine region.
- Tour wineries like Castello di Verrazzano or Antinori nel Chianti Classico.
- Wander around Radda in Chianti for boutique shopping and a relaxing café break.
- Stay overnight at a vineyard agriturismo for an authentic Tuscan experience.
Day 4: Siena – Medieval Charm
Drive south to Siena, a city that exudes medieval elegance. With its narrow streets and beautiful piazzas, Siena feels like a living history book. Spend the day soaking in the city’s rich heritage.
- Things to do:
- Visit the stunning Siena Cathedral (Duomo di Siena).
- Relax in Piazza del Campo, the site of the famous Palio horse race.
- Climb Torre del Mangia for panoramic views of Siena’s red rooftops.
- Try ricciarelli, the city’s famous almond pastry.
Day 5: San Gimignano – Towers and Vineyards
Next, head to San Gimignano, a hilltop town known for its medieval towers. This UNESCO World Heritage site is a great place to wander through cobblestone streets and take in the views.
- Things to do:
- Climb Torre Grossa, the tallest tower in the town.
- Sample local Vernaccia wine at nearby vineyards.
- Enjoy gelato from Gelateria Dondoli, one of Italy’s best.
- Visit Volterra for a peaceful evening and stunning sunset views.
Day 6: Val d’Orcia – Tuscany’s Scenic Heart
Today, you’ll drive through Val d’Orcia, one of the most visually striking landscapes in Italy. With its rolling hills, cypress-lined roads, and picturesque villages, it’s no wonder this area is a UNESCO World Heritage site.
- Things to do:
- Explore Pienza, famous for its Pecorino cheese and Renaissance architecture.
- Visit Montalcino, known for its world-class Brunello wine.
- Take photos of the iconic cypress-lined road near La Foce.
- Enjoy sunset views over the golden fields.
Day 7: Montepulciano & Bagno Vignoni – Wine and Wellness
Spend the day in Montepulciano, a charming hill town known for its fine wines. Afterward, relax in Bagno Vignoni, a spa village built around natural hot springs, perfect for a rejuvenating break.
- Things to do:
- Visit wineries like Cantina Contucci or Avignonesi for tastings.
- Stroll through Montepulciano’s old town and artisan shops.
- Soak in the thermal waters of Bagno Vignoni.
- Have dinner at a countryside restaurant overlooking the valley.
Day 8: Lucca – Walled Beauty
Head north to Lucca, a city surrounded by well-preserved Renaissance walls. Lucca offers a peaceful contrast to the busier Tuscan towns, with its cobblestone streets and charming squares.
- Things to do:
- Bike or walk along Lucca’s ancient city walls.
- Visit San Michele in Foro and the Piazza dell’Anfiteatro.
- Explore the local antique shops and cafés.
- Dine at Trattoria da Leo, a local favorite.
Day 9: Pisa & The Tuscan Coast – Landmarks and Seaside Relaxation
Start the day with a visit to Pisa, where you can see the famous Leaning Tower. Afterward, enjoy a relaxing afternoon on the Tuscan coast, away from the usual crowds, with a day by the sea.
- Things to do:
- Visit Piazza dei Miracoli and climb the Leaning Tower of Pisa.
- Head to Castiglione della Pescaia or Viareggio for a beachside escape.
- Savor fresh seafood at a seaside trattoria.
Day 10: Return to Florence – Farewell to Tuscany
Your journey concludes as you return to Florence. On the way back, stop in Prato or Empoli for one last espresso and reflect on your Tuscan adventure.
- Things to do:
- Shop for artisanal souvenirs in Florence’s markets.
- Have a final cappuccino in a local café.
- Enjoy a farewell dinner with a view of the Arno River.
Best Times to Go
The best times for a Tuscany road trip are in the spring (April–June) and fall (September–October), when the weather is mild and the landscapes are vibrant. Summer can be quite hot inland, but it’s perfect for coastal days. Winter is a quieter time to visit, ideal for those seeking a more peaceful experience.
Packing List
- Comfortable walking shoes for city and hill town exploration
- Lightweight clothing with a light jacket for evenings
- Sunglasses, sunscreen, and a hat
- Reusable water bottle
- Camera and power adapter
- Swimwear for coastal and thermal spring days
- Travel documents and international driver’s permit
Final Thoughts
A 10-day Tuscany road trip is the perfect way to immerse yourself in the beauty of one of Italy’s most iconic regions. From the art and architecture of Florence to the rolling hills of Chianti, the medieval charm of Siena, and the tranquil landscapes of Val d’Orcia, Tuscany offers an unforgettable journey. Take your time, savor every moment, and let this magical region leave a lasting impression.
