10 Day Tuscany Road Trip Itinerary: Explore the Heart of Italy

Few places in the world capture the soul of travel like Tuscany. From the sun-soaked vineyards of Chianti to the Renaissance magic of Florence and the serene valleys of Val d’Orcia, Tuscany offers an intoxicating mix of history, flavor, and scenery. A 10 Day Tuscany road trip itinerary gives you the perfect amount of time to see the highlights and hidden gems, while still savoring the slow rhythm that defines Italian life.

This itinerary will take you on a loop through Tuscany’s most beautiful towns, vineyards, and hillscapes — blending culture, food, and adventure into one unforgettable Italian experience.

Overview

Starting and ending in Florence, this itinerary covers Tuscany’s most picturesque regions, from wine country to medieval hill towns and the Tyrrhenian coast. The route combines leisurely drives, breathtaking views, and authentic local 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 – Renaissance Beginnings

Your journey begins in the cradle of the Renaissance. As you arrive in Florence, the city greets you with its terracotta rooftops and artistic energy. Spend your first day getting oriented with its historical core — everything is walkable and beautifully preserved.
Things to do:

• Climb the Duomo di Firenze for panoramic city views
• Explore the Uffizi Gallery to see Botticelli’s Birth of Venus
• Stroll along the Ponte Vecchio at sunset
• Enjoy dinner at a local trattoria like Trattoria ZaZa

Day 2: Florence – Art, Views, and the Local Side

Dedicate a second day to Florence’s quieter side. Cross the Arno River to explore the Oltrarno district, where local artisans craft jewelry, leather, and ceramics by hand. Climb to Piazzale Michelangelo for an incredible sunrise or sunset view — it’s one of the best in Italy.
Things to do:

• Visit Basilica di Santa Croce and Michelangelo’s tomb
• Discover hidden shops in Via Romana and Santo Spirito
• Take a short drive to Fiesole for hilltop views and Roman ruins

Day 3: Chianti Wine Region – Vineyards and Rolling Hills

Leave Florence behind and drive into the heart of Chianti, a region that embodies the Tuscan countryside. Winding roads lead through vineyards and olive groves where every turn offers a postcard-worthy view. The day is best spent wine tasting, exploring small towns, and relaxing at a countryside villa.
Things to do:

• Visit Greve in Chianti, the region’s charming wine capital
• Stop for tastings at Castello di Verrazzano or Antinori nel Chianti Classico
• Explore Radda in Chianti for boutique shopping and cafés
• Stay overnight at a vineyard agriturismo

Day 4: Siena – Medieval Elegance

Drive about an hour south to Siena, one of Tuscany’s most enchanting cities. Its medieval architecture and shell-shaped square make it feel frozen in time. Spend the day walking through narrow streets, admiring the Gothic cathedrals, and soaking in the atmosphere of La Dolce Vita.
Things to do:

• Admire the magnificent Siena Cathedral (Duomo di Siena)
• Relax in Piazza del Campo, home of the Palio horse race
• Climb Torre del Mangia for sweeping city views
• Try the almond pastry ricciarelli with espresso

Day 5: San Gimignano – The Town of Towers

Depart Siena and head to San Gimignano, about 45 minutes away. This hilltop town, known for its medieval towers, looks like something out of a fairytale. Wander through narrow alleys, sample gelato, and admire the surrounding vineyards stretching to the horizon.
Things to do:

• Visit the Torre Grossa, the tallest tower in town
• Sample local Vernaccia wine at a vineyard nearby
• Enjoy gelato from the famous Gelateria Dondoli
• Visit Volterra for a quieter evening and sunset views

Day 6: Val d’Orcia – The Soul of Tuscany

Today’s drive is one of the most beautiful in Italy. The Val d’Orcia unfolds in soft golden hills dotted with cypress trees, stone farmhouses, and castles. This UNESCO-listed region is the heart of Tuscany’s scenic charm and a photographer’s dream.
Things to do:

• Visit Pienza, known for Pecorino cheese and Renaissance charm
• Explore Montalcino, famous for Brunello wine
• Stop for photos along the iconic cypress road near La Foce
• Enjoy sunset views over the rolling landscape

Day 7: Montepulciano & Bagno Vignoni – Wine and Wellness

Spend your day discovering the elegance of Montepulciano, a hill town where wine and history flow together. Then unwind in Bagno Vignoni, a nearby spa village built around natural hot springs — a perfect mid-trip recharge.
Things to do:

• Visit Cantina Contucci or Avignonesi Winery for tastings
• Stroll through Montepulciano’s old town and artisan shops
• Soak in the thermal waters of Bagno Vignoni
• Dinner at a countryside restaurant overlooking the valley

Day 8: Lucca – Renaissance Walls and Italian Charm

Head north to Lucca, a charming city surrounded by intact Renaissance walls. The drive takes about 2.5 hours, offering a scenic shift from rural valleys to lush lowlands. Lucca’s calm energy is a welcome contrast to busier Tuscan towns.
Things to do:

• Bike or walk along Lucca’s ancient city walls
• Visit San Michele in Foro and Piazza dell’Anfiteatro
• Explore antique shops and cafés in the historic center
• Enjoy dinner at Trattoria da Leo, a local favorite

Day 9: Pisa & The Tuscan Coast – From Landmarks to the Sea

Start your morning in Pisa, just 30 minutes from Lucca, to see the world-famous Leaning Tower. Afterward, head to the Tuscan coast for a day by the sea — a side of Tuscany many travelers overlook. Relax, enjoy fresh seafood, and watch the sunset dip over the Tyrrhenian horizon.
Things to do:

• Visit Piazza dei Miracoli and climb the Leaning Tower of Pisa
• Explore Castiglione della Pescaia or Viareggio beaches
• Have a seaside dinner at a trattoria overlooking the water

Day 10: Return to Florence – Farewell to Tuscany

Your road trip comes full circle as you drive back to Florence. Stop in Prato or Empoli for one last espresso before returning your car. Reflect on your journey through one of the most timeless regions in the world.
Things to do:

• Last-minute shopping in Florence’s artisan markets
• Visit a local café for one final cappuccino
• Enjoy a farewell dinner with a view of the Arno River

Best Times to Go

The best times for a Tuscany road trip are April–June and September–October, when the weather is warm but comfortable and the landscapes are most vibrant.

• Spring: Blooming wildflowers and fresh air ideal for exploring countryside drives.
• Autumn: Wine harvest season and golden light across Val d’Orcia.
• Summer: Great for coastal days but can be hot inland.
• Winter: Quieter travel with fewer tourists and cozy atmospheres.

Packing List

• Comfortable walking shoes for city and hill towns
• Lightweight clothing and a light jacket
• Sunglasses, sunscreen, and hat
• Reusable water bottle
• Power adapter and camera
• Swimwear (for coastal or hot spring days)
• Travel documents and international driver’s permit

Where to Stay

Location	Check Hotels
Florence	Check Hotels
Chianti	Check Hotels
Siena	Check Hotels
Val d’Orcia	Check Hotels
Lucca	Check Hotels
Tuscan Coast	Check Hotels

Fun Facts

• Tuscany has over 120 nature reserves, making it one of Italy’s greenest regions.
• The Leaning Tower of Pisa began tilting during construction in the 12th century.
• Tuscany was the birthplace of the Italian Renaissance, home to Da Vinci and Michelangelo.
• The black rooster symbol on Chianti wine bottles guarantees its authenticity.

7 Things to Know Before a Tuscany Road Trip

1. Plan for Scenic Drives – Tuscany’s countryside is filled with winding roads and hilltop towns, so allow extra time between destinations like Siena, San Gimignano, and Montepulciano.
2. Rent a Small Car – Roads in medieval villages are narrow, and parking spots are limited. A compact vehicle makes navigating much easier.
3. Avoid ZTL Zones – Town centers often have restricted driving zones. Entering them without a local permit can result in expensive fines.
4. Stay Overnight in the Countryside – Agriturismos (farm stays) offer the best mix of charm, comfort, and authentic Tuscan hospitality.
5. Watch for Fuel Stops – Gas stations can be scarce in rural areas, so top off your tank before long scenic stretches.
6. Carry Cash for Tolls and Cafés – Many small businesses still prefer euros over cards, especially in the countryside.
7. Protect Your Connection on the Road – When using hotel or café Wi-Fi to plan routes or book stays, stay secure with NordVPN. It keeps your data private and your travel browsing safe while exploring Italy online.

Final Thoughts

A 10-day Tuscany road trip isn’t just a vacation, it’s a love letter to Italy. Every hill, vineyard, and cobblestone street tells a story, from the art of Florence to the quiet beauty of the countryside. Take your time, savor the food and wine, and let Tuscany show you why it’s one of the most captivating places on Earth.

Try This 14 Day Italy Road Trip Itinerary Planner