Tuscany Itinerary Map

Exploring Tuscany through a well-planned itinerary is one of the most rewarding road trips in Italy. With its rolling hills, medieval towns, cypress trees, and world-class wines, this amazing region captures the essence of central Italy. This article is one of several suggested itineraries for exploring Tuscany, helping you plan your journey through this iconic region. This Tuscany itinerary map can also be part of a broader Italy road trip itinerary, making it easy to connect Tuscany with other must-see Italian destinations. This Tuscany itinerary map will guide you through Florence, Siena, the Chianti wine region, and southern Tuscany’s countryside — all the way to the walled city of Lucca and the famous leaning tower of Pisa.

Whether you travel by rental car or combine public transportation and bus service, this route lets you experience the best of Tuscany Italy, from UNESCO World Heritage Sites to authentic Italian cities and charming hill towns. Use this map to visit Tuscany and discover the perfect Tuscany adventure, filled with unforgettable landscapes, charming towns, and renowned wineries.

This map is designed to help you create the perfect Tuscany experience.

Introduction to Tuscany

Tuscany, nestled in the heart of central Italy, is an amazing region where rolling hills dotted with cypress trees stretch as far as the eye can see. This UNESCO World Heritage Site is celebrated for its breathtaking Tuscan countryside, rich history, and a tapestry of medieval towns and hilltop villages that seem frozen in time. From the iconic skyline of San Gimignano to the charming cobbled streets of many hilltop towns, Tuscany invites you to step into a world where every corner tells a story.

Exploring Tuscany means wandering through picturesque landscapes, discovering the allure of smaller towns, and marveling at architectural wonders like the famous leaning tower of Pisa. The region’s vibrant culture is deeply rooted in its past, with each medieval town offering a glimpse into centuries-old traditions and artistry. Whether you’re drawn to the historic city walls, the bustling piazzas, or the tranquil surrounding countryside, there’s something here for every traveler.

To truly experience the best of Tuscany, consider renting a car. While public transportation connects the main towns, a rental car gives you the freedom to explore hidden gems and enjoy wine tastings at local vineyards nestled among the hills. Savor world-class wines such as Vino Nobile di Montepulciano and Brunello di Montalcino, and indulge in the region’s renowned cuisine, from delicious pizza to artisanal cheeses.

Whether you’re planning to visit the medieval towers of San Gimignano, take in the views from a hilltop town, or simply relax with a glass of wine in the sun-drenched countryside, Tuscany promises an unforgettable journey through one of Italy’s most beautiful and storied landscapes.

Day 1: Arrive in Florence (sleep in Florence)

Fly into Florence Airport, the capital city of Tuscany and the cradle of the Renaissance. Spend your first evening wandering the cobblestone streets, admiring the Duomo, and enjoying a delicious pizza or a glass of Chianti wine on a terrace near the Piazza della Signoria.

Day 2–4: Florence (sleep in Florence)

Spend three full days discovering Florence’s historic buildings, churches, and museums. Don’t miss the Uffizi Gallery, Ponte Vecchio, and the bell tower of Giotto for panoramic views. The city is a UNESCO World Heritage Site, packed with Renaissance art, medieval architecture, and countless tourist attractions.

Florence's train station provides easy access for day trips to other Tuscan towns, making it convenient to explore the region without overnight stays. Use this time to rest before starting your Tuscany road trip, as Florence can be explored easily on foot or via a short train ride to nearby towns.

Day 5: Bus to Siena (sleep in Siena)

Take a bus from Florence to Siena (1.5 hours). Siena is one of Italy’s most beautiful medieval towns, famous for its Piazza del Campo — one of Europe’s most impressive squares — and the Siena Cathedral (Santa Maria Assunta). The Town Hall and Civic Museum display fascinating details of Siena’s rich history.

Enjoy the narrow streets, climb the bell tower, and have dinner in a main street trattoria, sipping local red wine before heading to your hotel. To fully experience Siena’s attractions and atmosphere without feeling rushed, it is recommended to spend at least two nights in the city.

Day 6: Siena (sleep in Siena)

Spend a full day exploring Siena’s walled city atmosphere. Visit small churches, admire Gothic architecture, and wander through quiet alleys filled with tour buses and local life. Siena’s layout is compact — everything is within a few hours’ walk.

If you have time, visit a nearby vineyard in the Chianti region to enjoy wine tastings and learn about local wine production.

Spending several days in Tuscany, including Siena, allows you to truly experience the region’s charm and explore destinations like Val d'Orcia and San Gimignano at a relaxed pace. Avoid trying to visit too many major attractions in the same day to make the most of your time and not feel rushed.

Day 7: Rent Car – Crete Senesi Route to Montepulciano (sleep in Montepulciano)

Pick up your rental car in Siena, where you'll find a good selection of rental cars available, and start your Tuscany road trip itinerary through the Crete Senesi, an area of gorgeous landscapes with clay hills, winding narrow roads, and cypress trees. Stop at small hilltop towns for photos, and by late afternoon arrive in Montepulciano, one of Tuscany’s most beautiful towns. There are convenient car parks located outside the town center, making it easy to park before exploring Montepulciano on foot.

Spend the evening drinking wine and enjoying Vino Nobile di Montepulciano, one of Italy’s most prestigious reds.

Day 8: “Heart of Tuscany Drive” with a Stop in Pienza (sleep in Montepulciano)

This day Tuscany itinerary is structured to help you make the most of your time, with each day planned for optimal sightseeing and memorable experiences.

Follow the scenic Heart of Tuscany Drive, a perfect way to explore Tuscany at your own pace. Stop in Pienza, known for its pecorino cheese and Renaissance layout designed by Pope Pius II. While in the region, take the opportunity to sample local white wine, such as the renowned Vernaccia di San Gimignano, a unique specialty that stands out among Tuscany's celebrated wines. The surrounding countryside is a photographer’s dream — classic Tuscan countryside views with rolling hills and stone farmhouses.

Day 9: “Brunello Wine Country Drive” with Wine Tasting (sleep in Montepulciano)

Dedicate this day to Brunello di Montalcino, one of the top wines in the world. Drive south toward Montalcino and enjoy wine tasting at local wineries. For an immersive tasting experience, consider joining a wine tour in the Montalcino area to explore renowned wineries and learn about the region's winemaking traditions. Visit Bagni San Filippo, where you can relax in natural hot springs.

This area of southern Tuscany is known for its gorgeous landscapes and authentic small towns with cobbled streets and historic buildings.

Day 10: San Gimignano and Volterra (sleep in Volterra)

Leave Montepulciano early and drive toward San Gimignano, a UNESCO World Heritage Site famous for its medieval towers and skyline. Stroll the main street, have a gelato in the Piazza della Cisterna, and take time to appreciate how San Gimignano’s squares, much like the traditional Piazza Grande found in many Tuscan towns, serve as vibrant centers for local culture and architecture. Continue to Volterra, another ancient hilltop town.

Volterra’s city walls and Etruscan origins make it one of Tuscany’s most fascinating destinations, with a historical significance that extends across the Italian Peninsula.

Day 11: Volterra (sleep in Volterra)

Spend a relaxed day exploring the small town of Volterra, known for its unique character, as you wander its narrow streets and visit the Town Hall and Etruscan Museum. The walled city atmosphere and stone architecture give you a real sense of Tuscany’s medieval charm.

Day 12: Drive to Lucca, Drop Off Car (sleep in Lucca)

Drive north toward Lucca, drop off your car, and start walking or biking along the city walls that circle the town. Lucca is known for its civic buildings, quiet cobblestone streets, and relaxed pace — a great way to unwind after your road trip.

Day 13: Day Trip to Pisa (sleep in Lucca)

Take a short train ride or bus to Pisa. Spend a few hours visiting the famous Leaning Tower, Piazza dei Miracoli, and Cathedral of Santa Maria Assunta. Despite being full of tourists, Pisa is worth visiting for its iconic architecture and rich history. Many travelers who have visited Tuscany consider Pisa a must-see destination for its unique landmarks and vibrant atmosphere. Return to Lucca for your final evening in Tuscany.

Day 14: Fly Home

From Lucca, reach Florence Airport or another major Italian city for your flight home. Early summer is a particularly beautiful time to visit Tuscany, when the scenery is lush and green. After one week or two weeks exploring beautiful Tuscany, you’ll return with unforgettable memories of wine tours, medieval towns, and gorgeous landscapes.