Ultimate 13-Day Tuscany Italy Road Trip Itinerary: From Florence to Val d'Orcia

Day 1: Florence Introduction

Florence, Italy on August 8, 2025

9:00am

Piazza del Duomo

Start your trip at Florence’s Cathedral complex featuring Brunelleschi's Dome, Giotto's Campanile, and the Baptistery. It's a remarkable showcase of Renaissance art and architecture.
EUR18, 2h0m

11:30am

Galleria degli Uffizi

Explore one of the most famous art museums in the world, housing masterpieces by Botticelli and Michelangelo. Booking tickets in advance is highly recommended.
EUR20, 2h30m

2:00pm

Lunch at Trattoria Mario

Enjoy classic Tuscan dishes in this popular Florence spot known for its hearty ribollita and bistecca alla Fiorentina.
EUR25, 1h0m

3:30pm

Ponte Vecchio

Walk across this medieval stone bridge famous for its jewelry shops and lovely views of the Arno River.
Free, 0h45m

4:30pm

Piazzale Michelangelo

Drive or walk up to this panoramic viewpoint that offers the best sunset views of Florence.
Free, 1h0m

7:00pm

Dinner at La Giostra

Dine in a charming restaurant serving refined Tuscan cuisine with a romantic ambiance.
EUR40, 1h30m
View Hotel Availability

Day 2: Siena Classics

Siena, Italy on August 9, 2025

8:30am

Drive to Siena

Take a scenic 1.5-hour drive south from Florence to Siena, passing through the beautiful Chianti wine region.
EUR0 (transport cost varies), 1h30m

10:00am

Piazza del Campo

Visit Siena's famed main square, known for its unique shell shape and the site of the historic Palio horse race.
Free, 1h0m

11:15am

Siena Cathedral (Duomo di Siena)

Marvel at this stunning Gothic cathedral famous for its intricate marble floors and Piccolomini Library.
EUR15, 1h30m

1:00pm

Lunch at Osteria La Chiacchera

Taste authentic local Sienese flavors like pici pasta and wild boar sauce in this cozy eatery.
EUR30, 1h0m

2:30pm

Walk the Medieval Streets

Explore Siena’s historic center with narrow streets, artisan shops, and quaint piazzas.
Free, 2h0m

5:00pm

Visit Pinacoteca Nazionale

Discover a rich collection of Sienese art from the 12th to 17th centuries housed in a former monastery.
EUR7, 1h0m

7:30pm

Dinner at Antica Trattoria Papei

Relax with classic Tuscan dishes like ribollita and truffle pasta in a traditional setting.
EUR35, 1h30m
View Hotel Availability

Day 3: Medieval Towns

San Gimignano & Volterra, Italy on August 10, 2025

8:00am

Drive to San Gimignano

Travel a scenic 45-minute drive from Siena to San Gimignano, known as the ‘Medieval Manhattan’ for its tower houses.
EUR0 (transport cost varies), 0h45m

9:00am

Piazza della Cisterna

Explore this picturesque square lined with medieval buildings and towers.
Free, 1h0m

10:30am

Visit Torre Grossa

Climb the tallest tower in San Gimignano for breathtaking views across the Tuscan countryside.
EUR9, 1h0m

12:00pm

Lunch at Cum Quibus

Savor gourmet dishes in a charming atmosphere; reservations recommended for this Michelin-recommended restaurant.
EUR50, 1h30m

2:00pm

Drive to Volterra

Take a short, scenic 40-minute drive southwest to the ancient Etruscan town of Volterra.
EUR0 (transport cost varies), 0h40m

3:00pm

Explore Volterra’s Roman Theatre and Etruscan Walls

Visit these historical landmarks showcasing the town’s ancient roots and panoramic hilltop views.
EUR12, 1h30m

5:00pm

Wander Volterra’s Historic Centre

Stroll through cobbled streets, artisan shops, and admire alabaster craftsmanship.
Free, 1h0m

7:30pm

Dinner at La Carabaccia

Dine on traditional Tuscan fare with an emphasis on local ingredients in Volterra’s heart.
EUR30, 1h30m
View Hotel Availability

Day 4: Pisa & Lucca

Pisa & Lucca, Italy on August 11, 2025

8:30am

Drive to Pisa

Depart Volterra early for a 1-hour drive to Pisa to beat the crowds.
EUR0 (transport cost varies), 1h0m

9:30am

Piazza dei Miracoli

Visit the iconic Leaning Tower of Pisa, the Cathedral, Baptistery, and Camposanto Monumentale. Climbing the tower requires advance tickets.
EUR25, 2h0m

12:00pm

Lunch at Osteria dei Cavalieri

Enjoy fresh Tuscan dishes and local seafood in this popular spot near the Piazza.
EUR30, 1h0m

1:30pm

Drive to Lucca

A short 30-minute drive from Pisa to Lucca, a charming Renaissance town famous for its intact city walls.
EUR0 (transport cost varies), 0h30m

2:00pm

Cycle or Walk Lucca’s City Walls

Rent a bike or stroll atop the wide, tree-lined Renaissance walls for excellent views of Lucca’s historic center.
EUR8, 1h30m

3:45pm

Piazza dell’Anfiteatro

Visit this unique oval-shaped piazza that sits on the site of an ancient Roman amphitheater, now lined with cafes and shops.
Free, 0h45m

5:00pm

Torre Guinigi

Climb this iconic tower crowned with oak trees for panoramic views of the city.
EUR5, 0h45m

7:30pm

Dinner at Ristorante Giglio

Taste traditional Lucchese dishes served in a historic building in central Lucca.
EUR35, 1h30m
View Hotel Availability

Day 5: Val d'Orcia Beauty

Montepulciano, Pienza, Montalcino, Italy on August 12, 2025

8:30am

Drive to Montepulciano

From Lucca, embark on a longer 2.5-hour drive to Montepulciano, a medieval hill town famous for Vino Nobile wine.
EUR0 (transport cost varies), 2h30m

11:00am

Wine Tasting at Cantina Contucci

Taste renowned local wines in one of Montepulciano’s historic cellars.
EUR20, 1h0m

12:30pm

Lunch at Osteria Acquacheta

Relish rustic Tuscan fare and bistecca alla Fiorentina in a cozy atmosphere.
EUR30, 1h0m

2:00pm

Drive to Pienza

A short 30-minute drive to Pienza, known as the ‘ideal Renaissance town’ and famed for pecorino cheese.
EUR0 (transport cost varies), 0h30m

2:30pm

Piazza Pio II & Cathedral

Explore Pienza’s beautiful main square and cathedral, exemplary Renaissance urban planning.
Free, 1h0m

3:30pm

Pecorino Cheese Tasting

Visit a local shop to sample and buy the famous sheep’s milk cheese.
EUR10, 0h30m

4:30pm

Drive to Montalcino

Drive about 40 minutes to Montalcino, famed for its Brunello wine and stunning views.
EUR0 (transport cost varies), 0h40m

5:15pm

Visit Fortress of Montalcino

Tour this impressive medieval fortress offering scenic views and historical insights.
EUR5, 1h0m

7:30pm

Dinner at Osteria Le Logge

Enjoy refined Tuscan cuisine paired with local Brunello wines in an elegant setting.
EUR45, 1h30m
View Hotel Availability

Day 6: Thermal Springs & Hill Towns

Bagno Vignoni & Cortona, Italy on August 13, 2025

9:00am

Drive to Bagno Vignoni

Take a 25-minute scenic drive to Bagno Vignoni, a quaint village famous for its hot thermal springs in the main square.
EUR0 (transport cost varies), 0h25m

9:30am

Relax at Thermal Spa

Enjoy a refreshing morning soak in the thermal pools (open 9am-8pm), perfect for relaxation.
EUR40, 2h0m

11:30am

Light Lunch at La Bottega del Moro

Sample light local snacks and pastries alongside excellent coffee or wine.
EUR15, 0h45m

1:00pm

Drive to Cortona

Head approximately 35 minutes east to the charming hilltop town of Cortona.
EUR0 (transport cost varies), 0h35m

2:00pm

Explore Cortona Old Town

Walk through narrow streets, visit Piazza della Repubblica, and enjoy panoramic views of the Val di Chiana.
Free, 2h0m

4:30pm

Visit Museo Diocesano

See religious art and Renaissance masterpieces presented in a historic building.
EUR5, 1h0m

7:00pm

Dinner at La Bucaccia da Romano

Dine on traditional Tuscan dishes in a cozy, rustic setting well-loved by locals.
EUR35, 1h30m
View Hotel Availability

Day 7: Arezzo & Return

Arezzo & Florence, Italy on August 14, 2025

8:30am

Drive to Arezzo

From Cortona, drive 30 minutes north to Arezzo, a city rich in art and antiques.
EUR0 (transport cost varies), 0h30m

9:00am

Visit Piazza Grande

Arezzo’s central square is famous for its medieval architecture and the historic monthly antiques fair.
Free, 1h0m

10:30am

Basilica of San Francesco

See Piero della Francesca’s famous fresco cycle 'The Legend of the True Cross'.
EUR5, 1h0m

12:00pm

Lunch at Trattoria La Torre

Enjoy Tuscan classics in a charming restaurant overlooking the Piazza Grande.
EUR30, 1h0m

1:30pm

Drive Back to Florence

Return to Florence in roughly an hour to conclude your trip or continue further travel.
EUR0 (transport cost varies), 1h0m

3:00pm

Relax at Boboli Gardens

Stroll through Florence’s grand Renaissance gardens, open until 7pm, a perfect end to your trip.
EUR10, 1h30m

6:00pm

Farewell Dinner at Il Palagio

Celebrate your Tuscan adventure with a luxurious dinner at the Four Seasons Florence's Michelin-starred restaurant.
EUR80, 2h0m
View Hotel Availability