How to Spend One Magical Week in Tuscany by Car

Why a Road Trip is the Best Way to See Tuscany

Two Itinerary Options Without Florence – With Hidden Gems, Wineries & Driving Tips

Tuscany is made for road trips. Its sun-drenched hills, medieval villages, vineyard-dotted valleys, and hilltop towns are best explored with the freedom of your own car.

Whether you land in Florence or Pisa, this guide gives you two magical one-week road trip routes that skip Florence (you can come back for that later!) and dive straight into the heart of Tuscany’s countryside.

We can’t imagine exploring Tuscany any other way. Sure, we could stick to the train routes and organized tours, but we’d miss so much of what makes this region special.

With a car, we can pull over when we spot that perfect vineyard photo opportunity, follow signs to a tiny village that caught our eye, or spend an extra hour at a winery because the owner’s telling us stories about their family’s history.

Florence deserves its own leisurely visit, so these itineraries begin at either Florence Airport or Pisa Airport, where you’ll pick up your rental car and drive directly into rural Tuscany.

You’ll stay in charming accommodations, sip wine at local vineyards, and discover why Tuscany is one of the most romantic and unforgettable regions in Italy.

Option 1: Tuscany Road Trip Starting from Florence Airport

Route: Florence Airport ➝ Siena ➝ Montepulciano ➝ Pienza ➝ Montalcino ➝ San Quirico ➝ Volterra ➝ Return to Florence

Day 1: Florence Airport ➝ Siena (1.5 hrs)

Pick up your rental car at Florence Airport and head south to Siena, one of Tuscany’s most enchanting medieval cities.

Siena Rich in medieval charm and famed for its Palio horse race, Siena is a city of winding alleys, soaring Gothic architecture, and timeless Tuscan culture. Its fan-shaped Piazza del Campo is one of Italy’s most beautiful squares, perfect for relaxing with a glass of local wine and soaking up the atmosphere.

What to Do:

Stroll through Piazza del Campo, where the Palio horse race is held.
Visit Siena Cathedral – a stunning Gothic masterpiece.
Walk the ancient walls for panoramic countryside views.

Where to Stay in Siena:

Palazzo Ravizza – Classic charm and garden views.
Hotel Athena – Great parking and a short walk to the old town.
La Terrazza Sul Campo – Right on the Piazza, if you want to splurge.

Where to Eat & Drink:

La Taverna di San Giuseppe – Authentic Tuscan with a deep wine cellar.
Enoteca I Terzi – Fantastic for wine tasting and light plates.

Day 2: Siena ➝ Montepulciano (1.5 hrs)

Drive through rolling countryside into the Val di Chiana. Montepulciano is perched dramatically above the vineyards. Montepulciano is a handsome hilltop town known for its noble red wine and long, sloping streets lined with Renaissance palaces.

Visit underground wine cellars, relax in piazzas, and take in views across southern Tuscany. It’s lively but less crowded than other towns, ideal for wine lovers and history buffs.

Things to Do:

Explore the historic center and artisan wine shops.
Sample Vino Nobile di Montepulciano in underground cellars.
Enjoy golden hour views from the fortress.

Where to Stay in Montepulciano:

Villa Cicolina – A countryside villa with infinity pool.
La Terrazza di Montepulciano – Cozy, central and friendly.
Palazzo Carletti – Luxurious suites inside the town walls.

Dining Tip:

Osteria Acquacheta – Known for its steak and handmade pasta.
De’ Ricci Cantine Storiche – Combine a wine tour with your meal.

Day 3: Montepulciano ➝ Pienza (30 min)

A short drive takes you to Pienza, a jewel of the Renaissance. Pienza is Tuscany’s dream in miniature—perfect Renaissance streets, sweeping Val d’Orcia views, and the scent of pecorino cheese.

Built by a pope as an “ideal city,” it’s postcard-perfect and peaceful, with artisan shops, trattorias, and sunset views that will stay with you forever.

Highlights:

Admire the harmonious architecture of Pope Pius II’s ideal town.
Sample Pecorino di Pienza – the town’s signature cheese.
Walk the panoramic paths like Via dell’Amore.

Where to Stay in Pienza:

La Bandita Townhouse – Chic and modern inside a 15th-century building.
Hotel Corsignano – With parking and a rooftop Jacuzzi.
Relais Il Chiostro di Pienza – Elegant with garden views.

Where to Eat:

Sette di Vino – Cozy, with great wine and rustic plates.
La Buca di Enea – Try the pici pasta with wild boar.

Day 4: Pienza ➝ Bagno Vignoni (optional stop) ➝ San Quirico d’Orcia

After a relaxed morning in Pienza, enjoy a scenic drive through the Val d’Orcia.

Along the way, stop in Bagno Vignoni, a unique village where hot thermal water fills an ancient Roman pool in the town square. It’s perfect for a short coffee break or a quick spa visit.

A quiet gem in the Val d’Orcia, San Quirico is often overlooked—but utterly charming. Stroll through its medieval lanes, explore Renaissance gardens, and admire sweeping countryside views.

Arrive in San Quirico d’Orcia by early afternoon and settle into this peaceful stone town. Walk the Via Dante Alighieri, explore the Horti Leonini gardens, and visit Collegiata Church. It’s an ideal place to slow down and absorb Tuscany’s rural soul without crowds.

Where to Stay in San Quirico d’Orcia:

Palazzo del Capitano Wellness & Relais – Romantic with a spa
Hotel Palazzo Pura – Boutique and historic
Villa Liberty Boutique Hotel – This elegant villa offers a blend of classic Tuscan architecture and modern boutique design.

Dinner Tip:
Dine at Trattoria Osenna, a local favorite with outdoor seating and hearty Tuscan dishes under a canopy of vines.

Day 5: San Quirico d’Orcia ➝ Montalcino (25 mins)

Famous for its world-renowned Brunello wine, Montalcino is a hilltop village surrounded by vineyards and golden fields. Wander its cobbled streets, tour medieval fortresses, and enjoy wine tastings with panoramic views.

Start your day with a scenic 25-minute drive from San Quirico to Montalcino, arriving by mid-morning. Explore the Fortezza di Montalcino, stroll the charming historic center, and stop for tastings at Enoteca la Fortezza or nearby estates like Castello Banfi and Poggio Antico.

Spend the night here to fully enjoy the wine country setting.

Where to Stay in Montalcino:

B&B Porta Castellana – Charming and central
Capanna Suites – Modern rooms with vineyard views
Castello di Velona – Luxury with spa and hot springs just outside town

Dinner Tip:

Try Osticcio Ristorante for local dishes and sweeping views, or Re di Macchia for hearty Tuscan fare with a local crowd.

Day 6: Montalcino ➝ Volterra (1.5 hrs)

Volterra offers a quieter, more mysterious slice of Tuscany. With its Etruscan roots, Roman theatre, and alabaster artisans, it’s a treasure trove of history and craftsmanship.

Leave Montalcino after breakfast for a scenic 1.5–2 hour drive through the Tuscan hills to Volterra, passing golden fields, olive groves, and hilltop villages. Volterra feels more untouched than many towns in Tuscany—perfect for a slower, more immersive afternoon.

Walk through the Porta all’Arco, the town’s ancient Etruscan gate, visit the Roman amphitheatre, and explore the Palazzo dei Priori, the oldest town hall in Tuscany. Don’t miss a stop in one of Volterra’s many alabaster workshops—the city is known for this translucent local stone.

Optional stop en route:

If you want a break on the way, Murlo or Radicondoli are tiny, picturesque villages where time seems to stand still.

Where to Stay in Volterra:

Hotel La Locanda – Central with historic ambiance
Albergo Etruria – Friendly and walkable to all major sites
Borgo Pignano – Countryside luxury just outside Volterra

Dinner Tip:
Book a table at Ristorante Enoteca Del Duca for a refined evening meal, or enjoy hearty Tuscan classics at Osteria La Pace—a local favorite tucked into a cozy stone alley.

Day 7: Volterra ➝ Return to Florence (1.5 hrs)

Return your rental car and get ready to explore Florence on foot. You’ll have seen Tuscany’s countryside—now you’re ready for Florence.

Where to Stay in Florence

1. 3-Star Hotel: Hotel Davanzati

Why stay here:
A family-run gem with warm hospitality and a fantastic central location. It’s clean, comfortable, and great value for money.

2. 4-Star Hotel: Hotel Spadai

Why stay here:
One of the top-rated 4-star hotels in Florence, Hotel Spadai combines sleek modern rooms with Renaissance touches.

3. 4-Star Hotel: Hotel Santa Maria Novella

Why stay here:
A historic hotel with elegant interiors and rooftop views. The décor is classic Florentine, and many rooms have frescoed ceilings or antique furnishings.

4. 5-Star Hotel: Portrait Firenze – Lungarno Collection

Why stay here:
Luxury meets intimacy in this stylish all-suite hotel designed by Ferragamo.

5. Apartment: Canto degli Scali – Luxury Apartments

Why stay here:
Perfect for longer stays or travelers seeking space and independence.

Option 2: Tuscany Road Trip Starting from Pisa Airport

Route: Pisa Airport ➝ Lucca ➝ Volterra ➝ San Gimignano ➝ Pienza ➝ Montepulciano ➝ Siena ➝ Return to Florence

This route begins in Pisa, taking you through the charming streets of Lucca, the alabaster town of Volterra, and the turreted skyline of San Gimignano before looping through southern Tuscany’s iconic countryside. You’ll finish your trip in Siena, returning your car before heading to Florence by train for the next leg of your journey.

Day 1: Pisa Airport ➝ Pisa (explore) ➝ Lucca (overnight

Pisa is more than its famous Leaning Tower. It’s lively university scene, riverside cafes, and grand Romanesque buildings make it worth more than just a photo stop.

After landing at Pisa Airport, pick up your rental car and head straight into town (just a 10–15 minute drive).

Spend the morning exploring Pisa’s impressive Piazza dei Miracoli, home to the Leaning Tower, the grand Duomo, and the Baptistery. Walk up the tower for sweeping views over the city and beyond.

Afterward, wander down to the Arno River, browse shops along Borgo Stretto, and grab a coffee or light lunch in the old town. Pisa’s historic core is compact and easily walkable in half a day.

Where to Eat in Pisa (Lunch Ideas):

La Bottega del Parco – Excellent panini and local specialties near the tower
Osteria di Culegna – Cozy, traditional Tuscan lunch spot
Filter Coffee Lab – Perfect for brunch or specialty coffee lovers

Drive to Lucca (approx. 30 minutes)

In the late afternoon, drive to Lucca—a peaceful walled city that’s a perfect base for your first night in Tuscany.

Lucca (our favorite Tuscan Town)

Encircled by perfectly preserved Renaissance walls, Lucca is a peaceful, elegant city that blends art, history, and daily life.

Rent a bike and circle the old town, climb Torre Guinigi for rooftop views, and enjoy leisurely aperitivo in leafy piazzas lined with locals, not crowds.

What to Do in Lucca:

Cycle or walk around the 4 km Renaissance city walls.
Visit Piazza dell’Anfiteatro, built over a Roman amphitheater.
Climb Torre Guinigi for panoramic views (with a tree on top!).

Where to Stay in Lucca:

Hotel Ilaria – Comfortable and close to the historic center.
Palazzo Dipinto – Modern style inside an old-world building.
Albergo San Martino – Quiet and centrally located.

Where to Eat:

Trattoria da Leo – Classic Lucca comfort food.
Ristorante Giglio – Upscale dining with a lovely courtyard.

Day 2: Lucca ➝ Volterra (1.5 hrs)

Wind your way through the countryside to Volterra, known for its Etruscan roots and artisan alabaster. Perched on a windswept ridge, Volterra blends Etruscan, Roman, and medieval history.

Famed for its dramatic views, quiet lanes, and ancient ruins. Far less touristy than its neighbors, it’s a rewarding stop for history lovers and travelers seeking authentic Tuscan character.

Highlights:

Discover the Etruscan Arch and ruins of the Roman Theater.
Visit the Alabaster Ecomuseum and artisan shops.
Stroll the medieval lanes and city walls.

Where to Stay in Volterra:

La Locanda – A boutique hotel with character.
Hotel Volterra In – Friendly and in the historic center.
Podere San Lorenzo – Agriturismo with views and pool.

Day 3: Volterra ➝ San Gimignano (1 hr)

With its soaring medieval towers, San Gimignano is Tuscany’s skyline superstar. Walk the walled town, sip Vernaccia white wine, and admire frescoed churches and panoramic views. Though popular, it’s absolutely magical in the early morning or evening when day-trippers fade and golden light settles in.

Things to Do:

Climb Torre Grossa for sweeping views.
Wander the cobbled lanes and artisan shops.
Try Vernaccia di San Gimignano, Tuscany’s famous white wine.

Where to Stay in San Gimignano:

Hotel L’Antico Pozzo – Elegant and well-located.
Relais Santa Chiara – With a pool overlooking the valley.
Fattoria San Donato – Agriturismo with wine tastings.

Dining Tip:

Cum Quibus – Michelin-starred dining in a cozy setting.
La Mandragola – A hidden gem with garden seating.

Day 4: San Gimignano ➝ Pienza (1.5 hr)

Drive south into the heart of the Val d’Orcia. Pienza is Tuscany’s dream in miniature—perfect Renaissance streets, sweeping Val d’Orcia views, and the scent of pecorino cheese.

Built by a pope as an “ideal city,” it’s postcard-perfect and peaceful, with artisan shops, trattorias, and sunset views that will stay with you forever.

Highlights:

Admire the harmonious architecture of Pope Pius II’s ideal town.
Sample Pecorino di Pienza – the town’s signature cheese.
Walk the panoramic paths like Via dell’Amore.

Where to Stay in Pienza:

La Bandita Townhouse – Chic and modern inside a 15th-century building.
Hotel Corsignano – With parking and a rooftop Jacuzzi.
Relais Il Chiostro di Pienza – Elegant with garden views.

Where to Eat:

Sette di Vino – Cozy, with great wine and rustic plates.
La Buca di Enea – Try the pici pasta with wild boar.

Day 5: Pienza ➝ Montepulciano (30 min)

Another short and scenic hop to Montepulciano for rich wines and charming streets.

Montepulciano is a handsome hilltop town known for its noble red wine and long, sloping streets lined with Renaissance palaces.

Visit underground wine cellars, relax in piazzas, and take in views across southern Tuscany. It’s lively but less crowded than other towns, ideal for wine lovers and history buffs.

Things to Do:

Explore the historic center and artisan wine shops.
Sample Vino Nobile di Montepulciano in underground cellars.
Enjoy golden hour views from the fortress.

Where to Stay in Montepulciano:

Villa Cicolina – A countryside villa with infinity pool.
La Terrazza di Montepulciano – Cozy, central and friendly.
Palazzo Carletti – Luxurious suites inside the town walls.

Dining Tip:

Osteria Acquacheta – Known for its steak and handmade pasta.
De’ Ricci Cantine Storiche – Combine a wine tour with your meal.

Day 6: Montepulciano ➝ Siena (1.5 hrs)

End your road trip with a stay in Siena. Wander its brick lanes and imagine the medieval rivalries that once shaped this city.

Siena’s medieval magic lies in its red-brick buildings, winding alleys, and the vast, fan-shaped Piazza del Campo.

Known for the dramatic Palio horse race and its striking striped cathedral, Siena blends art, drama, and deep local pride. It’s the perfect place to end your Tuscan drive.