11-Day Italy Self-Drive Road Trip With Itinerary from Florence to Siena, Perugia, and Orvieto

Day 2 of your road trip across Italy promises a magnificent time exploring what to see in Florence. You have 2 nights left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Awaiting your discovery is the widely recognized Piazzale Michelangelo, an enchanting observation deck in Florence. Next, go to Basilica Of Santa Croce In Florence.

After visiting Piazzale Michelangelo and Basilica Of Santa Croce In Florence, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Piazza Della Signoria. This remarkable public square offers a unique experience. Palazzo Vecchio is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Uffizi Gallery, one of the most picture-perfect places to visit in Florence. If you still have some time left for sightseeing, we also recommend stopping by Ponte Vecchio.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

After a day of adventure, treat yourself to an exquisite dinner at one of Florence's best restaurants.

Treat yourself to a delicious dinner at Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. Known for great service, it’s a fantastic choice for tonight in Florence.

After your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

As the sun sets, rest up and recharge for the next leg of your road trip in Italy.

Wake up to day 3 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Pisa and Lucca. With 1 night to stay in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Whether you decide to explore Pisa on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Whatever your travel style is, Piazza Del Duomo, Pisa is an essential stop in Florence. This world-famous public square provides an insightful glimpse into the city's identity. Next, discover Leaning Tower Of Pisa, a noteworthy monument, promising a delightful encounter.

Continue your sightseeing with a visit to Guinigi Tower, a locally appreciated monument. When you’re done, don’t forget to make a stop at the locally appreciated San Michele In Foro. Round off your day at Mura Di Lucca, another gem in Florence with history-steeped features to discover.

When you’re done exploring for the day, you’ll return to Florence and your accommodation.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine.

Treat yourself to a delightful dinner at Ristorante Buca Mario, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Agricola Toscana? It's another excellent option with a diverse menu. Consider reserving a table at Eataly Firenze as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

Following your dinner, dive into the local bar culture at Gosh*. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Antico Caffè Del Moro - Art Bar Firenze, the perfect place for those looking to experience the best of the nightlife. Similarly, Quelo Bar provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Raise your glass to another unforgettable day in Italy!

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Siena. When you’re not sightseeing, take time to relax at your chosen hotel in Siena, where you’ll be staying for 3 nights.

To truly experience Florence, make sure to drop by Fortezza Medicea (siena). This frequently visited monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Basilica Of San Domenico, one of the city’s best highlights.

Next, check out Siena Cathedral, one of the most notable places to see in Florence. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza Del Campo. Wander around and soak in the romantic atmosphere this public square offers. Then, head to Pubblico Palace, a top-rated palace that adds another dimension to your day. Finally, visit the locally appreciated Porta Romana, the last of our attraction recommendations for today.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Siena. Siena offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

Siena is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Siena.

Treat yourself to a delicious dinner at Enoteca I Terzi, an excellent option for tonight's dining. Looking for something different? Ristorante Tar-Tufo offers a tantalizing alternative with its diverse menu. And don’t miss Antica Trattoria Papei. Known for great service, it’s a fantastic choice for tonight in Siena.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Meet Life Cafè, known for its inviting atmosphere. Maudit Pub is another great option if you’re looking for a place to get the night started. Similarly, Bar Impero Siena provides a great setting to enjoy the night away.

Head back to your accommodation in Siena and get some rest to prepare for another magical day of your road trip in Italy.

Greet day 5 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 2 nights to stay in Siena, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in San Gimignano and Volterra.

San Gimignano is brimming with adventures.

Look forward to a unique sightseeing adventure at the underrated Piazza Del Duomo and allow yourself time to explore. Just a short distance away you'll find your next stop, Palazzo Comunale, Pinacoteca, Torre Grossa, a culturally significant museum that draws visitors from far and near.

Continue your journey to Parco Della Rocca, one of the village’s most curiosity-inducing spots that you shouldn’t miss. Another great site to visit is the often recommended Etruscan Museum "mario Guarnacci". When you're finished at the museum, Palazzo Incontri Viti awaits your visit. This palace is a historic highlight on today's itinerary. Last up is a church - the beloved Baptistery Of San Giovanni Battista.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Siena.

Siena is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Siena.

Make sure to reserve a table at Osteria Quattro Venti, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Fischi per Fiaschi, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Osteria da Divo, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

If you’re not ready to end the night just yet, Charlie Mixology Bar Di Aldinucci Riccardo offers a perfect venue to relax and savor a drink. Similarly, Bar Pinacoteca is well-suited for those looking to unwind in a social setting. San Paolo Pub is another excellent spot to enjoy a nightcap after a delightful meal.

Relax and recharge in preparation for another adventurous day in Italy!

On day 6 of your road trip, you’ll start and end your day in Siena, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate city, including Castellina in Chianti, Greve in Chianti, and San Regolo.

Let Rocca Di Castellina In Chianti set the tone for the day. Spend some time admiring this visually striking castle before continuing your journey. Poggio Amorelli is your next stop. This curiosity-inducing winery is one of the best-rated sights in Siena.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Il Molino Di Grace. This majestic winery is a sight to behold. To round off your sightseeing experience, visit Castello Di Brolio.

When you’re done exploring for the day, you’ll return to Siena and your accommodation.

After a day of adventure, treat yourself to an exquisite dinner at one of Siena's best restaurants.

Treat yourself to a wonderful meal at Ristorante San Desiderio, a top-rated dining spot in Siena. If you're in the mood for something new, try Osteria Le Logge, another premier location with a delectable menu. You might also want to book a table at Ristorante Taverna Di Cecco. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

Savor another day of unforgettable experiences in Italy!

Dive into day 7 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Santa Maria degli Angeli and Perugia. At the end of the day, you’ll unwind at one of the finest accommodations in Perugia, where you'll spend 1 night.

Basilica Of San Francesco D'assisi leaves a lasting impression. This church is one of the most well-known places to visit in Siena. Next, head to Rocca Maggiore, a worthwhile castle, known for its culturally significant features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Etruscan Arch. This culturally significant historical landmark is a highly recommended experience. Nearby, you'll also find Perugia Cathedral and Piazza Iv Novembre. Visit these for an interesting touch to your journey. Finish the day with a visit to The Fontana Maggiore, a breathtaking monument in Siena.

When you’re done exploring for the day, you’ll drive to your hotel in Perugia. Check in and relax before you head out to tour the city.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Perugia. Enjoy a relaxing evening as you savor delicious local cuisine.

Dine in style at Ristorante Settimo Sigillo, a top recommendation for dinner tonight. Or, for a change of pace, Caffè Baglioni boasts a menu that's sure to impress. Also, be sure to check out Bar Pellas. Known as a local hotspot, it’s a great choice for tonight in Perugia.

Round off your dining experience by visiting Tommi Bar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Valentina, a bar catering to every mood and preference. Caffe Dal Perugino likewise offers a unique atmosphere, perfect for a memorable night out.

Savor another day of unforgettable experiences in Italy!

On day 8 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Orvieto are on today's agenda. In the evening, you’ll end up in Orvieto, where you will stay for 2 nights.

Check out the captivating monument, Well Of St. Patrick. Afterward, continue to Orvieto Cathedral, a church every traveler should visit. As you explore Perugia’s charming streets, take in the lively atmosphere and get to know the character of the village.

Next, make your way to Museo Dell'opera Del Duomo. This frequently visited museum is an essential stop. Following that, head to Orvieto Underground, another must-visit site that will enhance your experience. Don’t forget to stop by Torre Del Moro Orvieto, a frequently visited monument in the village. Finally, end your day with a visit to Pozzo Della Cava, a photogenic cave that offers the perfect conclusion to your sightseeing of the day.

At the end of the day, you will drive to Orvieto, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

After a day of adventure, treat yourself to an exquisite dinner at one of Orvieto's best restaurants.

If you’re not ready to end the night just yet, Bar Duomo offers a perfect venue to relax and savor a drink.

Raise your glass and celebrate another amazing day of your road trip in Italy!

On day 9 of your road trip, you’ll start and end your day in Orvieto, where you have 1 night left to stay.

Colosseum brings Orvieto's character to life. This UNESCO world heritage-listed archeological site is a highlight of any visit in the city. Then, enjoy Roman Forum, another breathtaking attraction that never fails to captivate visitors. Next, head over to Trevi Fountain, one of the city’s most wondrous attractions, known for its history-steeped features.

If you’re looking for more, spend time soaking in the atmosphere of Pantheon. This culturally significant monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Navona, a timeless public square, and take a stroll around the area.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Orvieto.

Indulge in a memorable dining experience at one of Orvieto's most popular restaurants, and connect with friendly locals for a true cultural experience.

Relax and look forward to more memorable moments to come!

Experience an unparalleled adventure on day 10 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Cortona. At the end of the day, you will retreat to the hotel of your choice in Florence, where will spend 1 night.

Catch Parterre before the crowds roll in. This enchanting park is sure to ignite your curiosity. Next, dive into the picture-perfect features of Basilica Of Saint Margaret Of Cortona, a must-visit church in the town.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Hermitage "le Celle", a beloved monastery.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Florence. Florence offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Florence, it's often a good idea to reserve a table in advance.

Savor the flavors at Tijuana, a top pick for dinner tonight. Alternatively, Djària - American Bar beckons with its unique menu offerings. Also, consider The Florence Irish Pub. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

Relax and recharge in preparation for another adventurous day in Italy!