- 4.9/5 341 Latest reviews
- Destination: Italy
- Duration: 8 Days
- Tour Type: Self-Drive
- Tour Style: Classic
About This Trip
This Tuscany Umbria scenic road trip is the perfect way to experience Italy at your own pace, combining the rolling vineyards of Tuscany with the timeless hill towns of Umbria. Designed as an 8-day self-drive journey, this itinerary takes you through some of Central Italy’s most iconic landscapes, historic cities, and gastronomic regions. From Renaissance masterpieces in Florence to medieval streets in Siena and Perugia, every day delivers a new and unforgettable Italian experience.
Driving through Tuscany Umbria, you will discover postcard-perfect countryside, world-famous wine regions like Chianti and Val d’Orcia, and charming towns steeped in history. Enjoy authentic wine and olive oil tastings, explore UNESCO-listed cities such as Ferrara, and soak in the cultural richness of Bologna, Italy’s culinary capital. With the freedom of a rental car, this scenic Italy road trip blends culture, cuisine, and countryside, making it ideal for travelers seeking a classic yet immersive Tuscany Umbria self-drive tour.
Summary
DAY
PLACE
HIGHLIGHTS
1
Rome - Siena
Pick Up Your Rental Car, Orvieto Cathedral, St. Patrick's Well, Chocolate Town Perugia
2
Siena
Val d'Orcia with Wine Tasting
3
Siena - Chianti - Florence
Wine and Olive Oil Tasting in Chianti
4
Florence
City Highlights Tour
5
Bologna
Bologna Guided Walking Tour, Modena Vinegar Tasting
6
ChiantiBologna - Ferrara - Treviso
Estense Castle, Palazzo dei Diamanti, Cathedral of Ferrara
7
Treviso
Explore the Nearby Venice before Departure
8
Treviso - Venice
Return the Rental Car
Itinerary
- Day 1: Rome – Orvieto – Perugia – Siena
Your Tuscany Umbria scenic road trip begins in Rome, where you pick up your rental car and leave the capital behind, driving north through changing landscapes of valleys, farmland, and hill towns. As you enter Umbria, the scenery becomes greener and more dramatic, leading you to Orvieto, a spectacular town rising above volcanic cliffs.
Spend time admiring the breathtaking Orvieto Cathedral, one of Italy’s finest Gothic masterpieces, famous for its golden façade and fresco-filled interiors. Descend into St. Patrick’s Well, an architectural wonder built to supply water during sieges. Continue your journey to Perugia, the vibrant capital of Umbria, where medieval streets, ancient arches, and lively piazzas reveal the region’s rich past.
Perugia is also known for its chocolate heritage—an irresistible stop during your Tuscany Umbria itinerary. After exploring, cross into Tuscany and arrive in the peaceful countryside near Siena, where vineyards and rolling hills welcome you to your first Tuscan evening.
Highlights: Tuscany Umbria road trip begins, Orvieto Cathedral, St. Patrick’s Well, Perugia medieval center, Umbria chocolate tradition, scenic drive to Siena countryside
- Siena
- Day 2: Siena – Val d’Orcia – Siena
Today is fully dedicated to the iconic landscapes that define Tuscany Umbria. Drive through the UNESCO-listed Val d’Orcia, a region celebrated worldwide for its cinematic scenery of rolling hills, cypress-lined roads, vineyards, and golden fields. This is Tuscany at its most romantic and photogenic.
Along the way, explore charming towns such as Montalcino, birthplace of the prestigious Brunello wine, and Montepulciano, renowned for its elegant hilltop setting and noble red wines. Visit Pienza, a Renaissance jewel designed as the “ideal city,” and sample local pecorino cheese. Pause in Bagno Vignoni, famous for its unique thermal pool set right in the main square, before returning to Siena.
This day perfectly captures the soul of a Tuscany Umbria scenic road trip, blending nature, wine, and timeless villages.
Highlights: Tuscany Umbria countryside, Val d’Orcia UNESCO views, Montalcino wine town, Montepulciano vineyards, Pienza Renaissance city, Bagno Vignoni thermal square
- B , D
- Siena
- Day 3: Siena – Chianti – Florence
Begin the day exploring Siena’s historic center, including the iconic Piazza del Campo, where the famous Palio horse race takes place. The city’s medieval atmosphere offers a striking contrast to Florence’s Renaissance grandeur later in the day.
Continue your Tuscany Umbria self-drive tour through the heart of the Chianti region, one of Italy’s most celebrated wine areas. Drive along winding roads flanked by vineyards, olive groves, and stone farmhouses. Stop in picturesque villages such as Monteriggioni, Greve in Chianti, and Radda in Chianti for coffee, photos, or a leisurely walk.
In the afternoon, enjoy a wine and olive oil tasting at a traditional Chianti estate, learning about local production methods passed down through generations. Arrive in Florence by evening, where art, architecture, and history come together in spectacular fashion.
Highlights: Tuscany Umbria wine route, Siena Piazza del Campo, Chianti scenic drive, Monteriggioni village, wine and olive oil tasting, Florence arrival
- B
- Florence
- Day 4: Florence – Bologna
Spend your morning discovering Florence, the artistic heart of Tuscany Umbria. A guided walking tour reveals iconic landmarks such as the Florence Cathedral, Piazza della Signoria, and the romantic Ponte Vecchio. Art lovers may choose to visit the Uffizi Gallery or Accademia Gallery to admire Renaissance masterpieces, including Michelangelo’s David.
In the afternoon, drive north toward Bologna, leaving Tuscany and entering Emilia-Romagna. Bologna’s elegant porticoes, medieval towers, and vibrant student life create a lively yet historic atmosphere. Known as one of Italy’s great food cities, Bologna adds a rich culinary dimension to your journey.
Highlights: Tuscany Umbria cultural heritage, Florence Renaissance landmarks, Duomo and Ponte Vecchio, optional Uffizi or Accademia, scenic drive to Bologna
- B
- Bolonga
- Day 5: Bologna – Modena – Bologna
Explore Bologna with a guided walking tour through its historic streets and arcaded walkways. Discover the famous Two Towers, grand churches, and Europe’s oldest university. Often called Italy’s culinary capital, Bologna is a highlight of any Tuscany Umbria road trip for food lovers.
Later, drive to Modena, home of traditional balsamic vinegar. Visit a family-run acetaia to learn about the long aging process and enjoy a tasting of this prized local specialty. Return to Bologna in the evening for dinner at a traditional trattoria, savoring authentic regional cuisine.
Highlights: Tuscany Umbria culinary experience, Bologna walking tour, Two Towers, Italy food capital, Modena balsamic vinegar tasting
- B
- Bolonga
- Day 6: Bologna – Ferrara – Treviso
Continue your journey north with a stop in Ferrara, a UNESCO World Heritage city admired for its Renaissance urban planning. Walk through the historic center and admire architectural gems such as the Estense Castle, Palazzo dei Diamanti, and Ferrara Cathedral.
After Ferrara, drive toward Treviso, a charming canal town often overlooked by travelers heading straight to Venice. With its medieval walls, waterways, and relaxed pace, Treviso offers an authentic and peaceful atmosphere—an ideal conclusion to your Tuscany Umbria scenic road trip.
Highlights: Tuscany Umbria to Veneto route, Ferrara UNESCO city, Estense Castle, Palazzo dei Diamanti, Treviso canal town
- B
- Treviso
- Day 7: Treviso – Venice (Optional Excursion)
Enjoy a leisurely day exploring Treviso’s historic center, wandering along canals, elegant squares, and cobblestone streets. Stop at local cafés to soak in the laid-back lifestyle or explore nearby villages and countryside.
Alternatively, take an optional excursion to Venice, one of the world’s most iconic cities. A guided walking tour reveals famous squares, bridges, and hidden corners of the City of Canals, adding a memorable highlight to your Tuscany Umbria itinerary.
Highlights: Tuscany Umbria leisure day, Treviso old town, canal-lined streets, optional Venice guided tour, City of Canals experience
- B
- Treviso
- Day 8: Treviso – Venice – Departure
Enjoy free time before driving to Venice Airport. Return your rental car and conclude your unforgettable Tuscany Umbria self-drive holiday, filled with scenic countryside, historic cities, wine regions, and authentic Italian experiences.
Highlights: End of Tuscany Umbria itinerary, scenic drive to Venice Airport, rental car return, Italy road trip finale
- B
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