About This Trip
Pick up your rental car in Rome before making your way up to Siena with a stopover in the mountain town of Orvieto and Perugia, the chocolate heaven of Umbria. Taste wine and olive oil in Chianti of Tuscany. Head to Florence and Bologna to visit their historic squares, cathedrals, and museums. You’ll have some free time to leisurely explore the palaces and canals in Treviso and Venice before ending your Italy tour.
Itinerary Summary
- DAYPLACE
- 1Rome - Siena
- 2Siena
- 3Siena - Chianti - Florence
- 4Florence
- 5Bologna
- 6Bologna - Ferrara - Treviso
- 7Treviso
- 8Treviso - Venice
Itinerary
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Day 1: Self-drive Route: Rome - Orvieto - Perugia - Siena (300 km)
Begin your adventure by picking up your rental car at Fiumicino Airport or Termini Station. Travel towards the captivating hill town of Orvieto, where you can explore the awe-inspiring Orvieto Cathedral and St. Patrick's Well. Continue to Perugia, the chocolate heaven of Umbria. Roam freely around the medieval alleys of the city center to discover its rich history, or step into a local workshop to create your own tempered chocolate bar.
At the end of the day, reach your accommodation in the Siena area to rest.
- Siena
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Day 2: Self-drive Route: Siena - Val d'Orcia - Siena (150 km)
Embark on a full-day journey through Val d'Orcia to relish in its sprawling and scenic countryside. With verdant hills with rolling vineyards, picturesque villages with quaint churches, and cypresses outlining the endless fields, it is considered the jewel in Tuscany's crown.
Among the many villages, Montalcino and Montepulciano with world-class winemaking traditions, Bagno Vignoni around a great pool of thermal water, and Pienza full of Renaissance masterpieces are some that can't be missed. Return to hotel and overnight stay.
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- Siena
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Day 3: Self-drive Route: Siena - Chianti - Florence (120 km)
It's recommended to take some time strolling around the Siena's shell-shaped Piazza to feel its well-preserved medieval image.
Later, drive through the picturesque Chianti region with its winding hills and fortified villages to Florence. Optionally stop at one of the many villages, such as Monteriggioni, Radda, and Greve, for a pleasant walk. Make sure to arrive at San Casciano Val di Pesa in the afternoon, where wine and olive oil tasting awaits you.
Arrive in Florence in the late afternoon and settle into the hotel.
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- Florence
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Day 4: Self-drive Route: Florence - Bologna (110 km)
Discover the birthplace of the Renaissance with a morning walking tour of Florence's Historic Center, checking out the symbols of the city, like Ponte Vecchio. You can also combine a visit to the Accademia Gallery or Uffizi Gallery after the walk.
In the late afternoon, move on to Bologna for the night.
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- Bologna
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Day 5: Self-drive Route: Bologna - Modena - Bologna (210 km)
In the heart of Bologna, red brick walls, literary twin towers, and well-preserved medieval buildings will bring history to your eyes. It's also known as the Learned City since it is home to the oldest university in the world and the Fat City for its rich cuisine. Following a local guide, stroll under the arched colonnades of the buildings along the street to take in its unique charm.
Before getting back to the hotel, visit an acetaia in Modena with a balsamic vinegar-tasting experience.
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- Bologna
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Day 6: Self-drive Route: Bologna - Ferrara - Treviso (190 km)
Journey forwards Treviso, making a stop in the UNESCO-listed Ferrara. Here, the Middle Ages and the Renaissance co-exist, bounded by Viale Cavour. Along with a local guide, you will walk through its historic center and admire the Cathedral with its outstanding façade, the imposing Estense Castle, the magnificent Palazzo dei Diamanti, and so on.
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- Treviso
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Day 7: Treviso, Day at Leisure
Today is yours to discover the city or surroundings at your own pace.
Treviso, though not as well-known as the nearby Venice, is still a stunning location of its own, featuring a number of old palaces, medieval walls, a network of exquisite canals, and winding cobblestone alleyways. You can kill time within the city center, hanging out around and stopping wherever you like. Alternatively, venture to Venice for a private guided walking tour, discovering the allure of the "City of Canals."
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- Treviso
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Day 8: Self-drive Route: Treviso - Venice (40 km), Departure
Enjoy some free time until driving to the Venice Airport, about half an hour away. Return the rental car and board your homebound flight.
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