Tuscany, Italy

Scenic Road Trip with Tuscany & Umbria

4.9/5 341 Latest reviews
Tour Code: ODY-ITA-013
Destination: Italy
  • Duration 8 Days
  • Tour Type Self-Drive
  • Tour Style Classic

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


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 Bologna - 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

Suggested Itinerary


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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

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.

  • B D
  • Siena

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

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

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

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.

  • B
  • Treviso

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."

  • B
  • Treviso

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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What's Included in Your Private Tour


  • A dedicated travel expert will work with you to design and arrange your itinerary based on your interests, travel style, schedule, and budget. Your trip can be adjusted as your plans take shape.
  • Accommodation is selected based on location, quality, your preferences, and budget. Depending on the destination and itinerary, options may include international hotel chains, boutique hotels, and locally distinctive properties.
  • Local guides are arranged in each destination, with strong language skills and in-depth local knowledge. Your guide will help you make the most of each destination while sharing local history, culture, and everyday life.

    Guide arrangements may vary depending on your destination and itinerary. Please refer to your Tour Program for the specific guide arrangements for your trip.

    If you have any special requirements for your guide, such as in-depth historical and cultural interpretation or expertise in a particular industry or subject, please let us know in advance so we can take your preferences into consideration when arranging your trip.
    • Private air-conditioned vehicle with a dedicated driver, as specified in the itinerary
    • Domestic trains as specified in the itinerary
    • Domestic flights as specified in the itinerary
    • International flights for selected multi-country tours, as specified in the itinerary.

    Transportation arrangements can be adjusted to suit your itinerary and travel needs.

    *As each trip is tailor-made, transportation arrangements may vary by itinerary and destination. The final arrangements will be detailed in your Tour Program.

    *International flights to and from your home country are normally not included in the initial Tour Program. If you would like, your travel expert can also help arrange these flights upon request.

    • Breakfast (B), lunch (L), and dinner (D) as specified in the itinerary
    • Additional meals can be arranged upon request
    • Vegetarian and vegan options are available upon request

Your Travel Partner Every Step of the Way


  • Before You Travel
    • Personalized itinerary planning
    • Professional advice from local experts
    • Smooth booking support from start to finish
    Every great journey starts with thoughtful planning. From the moment you contact us, we take the time to understand your travel style, interests, and expectations. Whether you’re looking for iconic highlights, local experiences, or a more relaxed pace, we help design a trip that truly fits you.
  • While You Travel
    • Expert local guides with deep knowledge
    • 24/7 support for any on-the-go needs
    • Flexible arrangements to suit your pace
    Once your trip begins, we're right there with you behind the scenes. Our local guides, trusted partners, and support team work together to make your journey smooth, comfortable, and worry-free. From airport pickups to flexible day-to-day arrangements, we help you travel with confidence and ease.
  • After You Return Home
    • We welcome and value your feedback
    • A travel team you can return to anytime
    • Special benefits for your next journey
    For us, the journey doesn’t simply end when the trip is over. We love staying connected with our travelers, hearing your feedback, and learning more about your experience. Your insights help us continue improving our services while also inspiring future travelers. Many of our guests travel with us again, or recommend us to family and friends, and that’s something we truly value.

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