Embark on a captivating Tuscany road trip 10 days, where rolling vineyards, timeless villages, and Renaissance masterpieces await at every turn. From the bustling streets of Florence to the serene hills of Val d’Orcia, this immersive itinerary is your ultimate guide to experiencing the very best of this Italian gem.
Day 1-2: Florence – The Renaissance Cradle
Start your Tuscan journey in Florence, the city that gave birth to the Renaissance. Spend two days soaking in its historic charm.
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Visit the Duomo, with its iconic red-tiled dome by Brunelleschi.
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Admire the Uffizi Gallery, home to Botticelli’s Birth of Venus and da Vinci’s Annunciation.
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Walk across the Ponte Vecchio, a medieval bridge lined with artisan jewelry shops.
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Don’t miss Michelangelo’s David at the Accademia Gallery.
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For panoramic views, hike up to Piazzale Michelangelo.
Savor a Florentine steak at Trattoria Zà Zà, and stay in a centrally located boutique hotel like Hotel L’Orologio.
Day 3: Florence to San Gimignano (Distance: 60 km / 37 miles)
Depart Florence and head towards San Gimignano, the “Medieval Manhattan” of Tuscany.
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En route, stop at a winery in Chianti for a wine tasting session.
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Once in San Gimignano, wander through the cobbled streets and explore Piazza della Cisterna.
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Climb the Torre Grossa for sweeping views of the Tuscan countryside.
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Indulge in award-winning gelato from Gelateria Dondoli.
Overnight at a charming farmhouse such as Fattoria San Donato, surrounded by vineyards and olive groves.
Day 4: Volterra – A Journey into Etruscan Times
Just 40 minutes from San Gimignano lies Volterra, a hidden treasure with deep Etruscan and Roman roots.
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Discover the Etruscan Museum (Guarnacci) and Roman Theatre ruins.
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Watch artisans craft intricate alabaster sculptures.
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Visit the Palazzo dei Priori, Tuscany’s oldest town hall.
Volterra’s authenticity and fewer crowds make it a refreshing stop. Stay at Hotel Etruria for a comfortable and scenic experience.
Day 5-6: Siena – Gothic Grandeur and Timeless Alleys
Next, drive to Siena, a medieval masterpiece steeped in tradition and pageantry.
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Marvel at the striped Siena Cathedral, featuring frescoes by Pinturicchio.
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Stroll the Piazza del Campo, home to the world-famous Palio horse race.
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Climb the Torre del Mangia for a bird’s-eye view of the city.
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Enjoy local delicacies like pici cacio e pepe and ricciarelli almond cookies.
Spend two nights in Palazzo Ravizza, a historic residence with spectacular garden views over the countryside.
Day 7: Montepulciano – The Noble Wine Hilltop Town
Drive south to Montepulciano, renowned for its Vino Nobile wines and Renaissance architecture.
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Tour the Contucci Winery inside the city walls.
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Visit Piazza Grande, surrounded by elegant palazzos and the town hall.
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Take a guided tasting tour of the underground wine cellars carved into the hillside.
Dine at Osteria Acquacheta, famous for its bistecca alla fiorentina. Overnight at Etruria Resort & Natural Spa for a wellness retreat.
Day 8: Pienza – The Ideal Renaissance City
Only 20 minutes from Montepulciano, Pienza is a UNESCO World Heritage Site and a showcase of Renaissance urban planning.
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Walk along Via dell’Amore for picturesque countryside views.
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Try pecorino cheese, for which Pienza is famous, at La Bottega del Naturista.
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Visit Palazzo Piccolomini and its terraced gardens.
Stay at Relais Il Chiostro di Pienza, housed in a former 15th-century convent with panoramic vistas.
Day 9: Montalcino – Brunello Wine Paradise
Continue to Montalcino, where the prestigious Brunello di Montalcino wine is born.
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Explore the Fortezza di Montalcino and its wine shop offering tastings.
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Visit Abbey of Sant’Antimo, a Romanesque masterpiece nestled in a quiet valley.
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Take a scenic drive through rolling hills carpeted with vineyards.
Spend the night in Castello Banfi – Il Borgo, a luxury wine resort offering immersive wine experiences.
Day 10: Val d’Orcia – Tuscany’s Most Iconic Landscape
Conclude your Tuscan journey in Val d’Orcia, a UNESCO-protected valley that epitomizes the essence of the region.
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Drive the SR2 road from San Quirico d’Orcia to Pienza for the most scenic route.
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Photograph the iconic Cypress Tree Roads and rolling golden hills.
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Visit the Chapel of the Madonna di Vitaleta, one of Tuscany’s most photographed sites.
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Relax in the thermal waters of Bagno Vignoni, a unique spa village with hot springs flowing through its main square.
Have your final meal at Osteria La Porta in Monticchiello, known for its spectacular views and authentic cuisine.
Tips for a Memorable Tuscany Road Trip
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Best Time to Visit: April to June and September to October for mild weather and fewer crowds.
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Driving: Rent a small car for easier navigation on narrow village streets.
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Parking: Use designated parking areas outside town centers (ZTL zones are strictly monitored).
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Local Experiences: Book cooking classes, truffle hunting tours, or olive oil tastings to enrich your itinerary.
A 10-day road trip from Florence to Val d’Orcia is more than a vacation—it’s a deeply enriching experience through art, food, history, and some of the most photogenic landscapes on Earth. Follow this detailed itinerary and let the heart of Tuscany reveal itself, one hilltop village and vineyard at a time.
Dreaming of a Tuscany road trip in 10 days without breaking the bank? Discover the charm of rolling hills, medieval villages, and world-class wine with Classic Tuscany’s affordable Tuscany travel packages. Whether you’re craving culture, countryside, or cuisine, we make your Italian adventure unforgettable. Ready to explore Tuscany in 10 days on a budget? Let Classic Tuscany plan your perfect road trip!
- Discover Tuscany in 10 Days: A Scenic Road Trip from Florence to Val d’Orcia
- Explore Tuscany in 10 days with a scenic road trip from Florence to Val d’Orcia. Discover hilltop towns, vineyards, and hidden gems along the way.
- Tuscany road trip 10 days, Tuscany travel Packages
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