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.

Make a stop at Piazzale Michelangelo. This impressive observation deck is a must-visit for travelers looking for a unique holiday experience. Make your way to Basilica Of Santa Croce In Florence located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Piazza Della Signoria. Its detailed features will captivate you. After the public square, continue your tour of the city with a visit to Palazzo Vecchio. Visitors usually appreciate the romantic features of this palace. Next up is Uffizi Gallery, a highly recommended art gallery. For a change of pace, head to Ponte Vecchio. As one of the most world-famous attractions in Florence, this historical landmark is the perfect place to end your self-guided sightseeing tour.

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.

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.

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.

If you’re not ready to end the night just yet, Bar 50 Rosso offers a perfect venue to relax and savor a drink. Similarly, Bitter Bar is well-suited for those looking to unwind in a social setting. Archea Brewery is another excellent spot to enjoy a nightcap after a delightful meal.

Celebrate another amazing day of your road trip adventure in Italy!

On day 3 of your road trip, you’ll start and end your day in Florence, where you have 1 night left to stay.

After soaking in Florence’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Pisa. Expect your car journey to take a minimum of 1 hour 16 min. When you arrive in Pisa, it's time to take a break from the road.

When you're ready for some sights, head to Piazza Del Duomo, Pisa, a globally renowned public square in Pisa. Explore its picture-perfect features at your own pace before you continue your journey to your next attraction, Leaning Tower Of Pisa. This world-famous monument is a top recommendation in the area.

Embrace the thrill of the open road as you wave goodbye to Pisa and set your GPS to Lucca. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 32 min. Upon reaching Lucca, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Our first attraction recommendation in Lucca is Guinigi Tower, an up-and-coming monument that draws attention for its enchanting features. Spend some time soaking in the atmosphere before continuing to San Michele In Foro, a stunning church that stands out in the city.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Mura Di Lucca, an up-and-coming historical landmark that offers a unique experience.

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

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

Treat yourself to a wonderful meal at Ristorante Buca Mario, a top-rated dining spot in Florence. If you're in the mood for something new, try Agricola Toscana, another premier location with a delectable menu. You might also want to book a table at Eataly Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Gosh*, known for its inviting atmosphere. Antico Caffè Del Moro - Art Bar Firenze is another great option if you’re looking for a place to get the night started. Similarly, Quelo Bar provides a great setting to enjoy the night away.

Savor another day of unforgettable experiences in Italy!

Dive into day 4 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Siena. At the end of the day, you’ll unwind at one of the finest accommodations in Siena, where you'll spend 3 nights.

Continue your road trip and head to your next destination, Siena. This car ride takes around 1 hour 10 min.

Savor the day by heading to Fortezza Medicea (siena), an often recommended monument that draws visitors from near and far. When you're done, continue to Basilica Of San Domenico, where you can soak in the respected surroundings.

Next, explore Siena Cathedral, yet another well-known place to see in the area. After the church, make time to go to Piazza Del Campo. This enchanting public square is well worth the visit. Lastly, head to Pubblico Palace, an often recommended palace you won’t want to miss.

At the end of the day, you will drive to Siena, 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 Siena's best restaurants.

Dine in style at Enoteca I Terzi, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante Tar-Tufo boasts a menu that's sure to impress. Also, be sure to check out Antica Trattoria Papei. Known as a local hotspot, it’s a great choice for tonight in Siena.

Keep the excitement of the evening going by visiting a bar or two. Meet Life Cafè is an excellent place to start. You could also check out Maudit Pub, offering a different kind of charm. A last recommendation for the day is Bar Impero Siena. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Get a good night's sleep and look forward to another great day on the road in Italy!

Wake up to day 5 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of San Gimignano and Volterra. With 2 nights to stay in Siena, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Throughout the day, make sure to take breaks to appreciate the surroundings.

Set your GPS to San Gimignano and hit the road. Expect a journey of approximately 51 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. San Gimignano beckons with new experiences!

Piazza Del Duomo is an underrated public square we recommend visiting today. Discover its majestic features before continuing your self-guided tour to Palazzo Comunale, Pinacoteca, Torre Grossa, a picture-perfect museum that’s well-regarded in the area.

Next, stop by Parco Della Rocca, a stunning park.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Volterra. This drive usually takes around 38 min, without any stops or traffic disruptions.

For a more meaningful self-guided tour of the village's best attractions, visit Etruscan Museum "mario Guarnacci", a locally appreciated museum that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Palazzo Incontri Viti and admire its visually striking features.

When you’re ready, continue to Baptistery Of San Giovanni Battista, a locally appreciated church beloved by locals and tourists alike.

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

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

Enjoy a delicious meal at Osteria Quattro Venti, a highly-rated dining destination in Siena. If you're eager to try something different, consider Fischi per Fiaschi, another top spot with a tantalizing menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

After your meal, keep the night alive at a bar like Charlie Mixology Bar Di Aldinucci Riccardo, known for its lively atmosphere. Bar Pinacoteca is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, San Paolo Pub offers an excellent atmosphere for those looking to amp up the evening.

Get a good night's sleep and look forward to another great day on the road in Italy!

Greet day 6 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night 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 Castellina in Chianti, Greve in Chianti, and San Regolo.

When you’ve had your share of Siena, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Castellina in Chianti. Your travel time is around 31 min.

For a more meaningful self-guided tour of the village's best attractions, visit Rocca Di Castellina In Chianti, a worthwhile castle that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Poggio Amorelli and admire its enchanting features.

Greve in Chianti’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Castellina in Chianti behind. This drive usually takes around 13 min. Greve in Chianti welcomes you with a multitude of unique vacation experiences.

When you're ready for some sights, head to Il Molino Di Grace, a locally appreciated winery in Greve in Chianti. Explore its romantic features at your own pace before you continue your journey.

Set your GPS to San Regolo and hit the road. Expect a journey of approximately 34 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. San Regolo beckons with new experiences!

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Castello Di Brolio, a frequently visited castle that everyone visiting San Regolo should see.

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

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 Siena, it's often a good idea to reserve a table in advance.

Have a fantastic dining experience at Ristorante San Desiderio, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Osteria Le Logge offers an enticing alternative with its varied menu. Additionally, Ristorante Taverna Di Cecco is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.

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

Your itinerary for day 7 of your road trip in Italy includes 2 stops and features some of the highlights of Santa Maria degli Angeli and Perugia. At the end of the day, enjoy the comforts of a top-rated hotel in Perugia, where you'll spend 1 night.

After soaking in Siena’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Santa Maria degli Angeli. Expect your car journey to take a minimum of 1 hour 36 min. When you arrive in Santa Maria degli Angeli, it's time to take a break from the road.

One of our top recommendations for your sightseeing is Basilica Of San Francesco D'assisi. Spend some time admiring the majestic features of the church before you continue to your next stop. Then, head to Rocca Maggiore. This worthwhile castle is a traveler-favorite in the town.

Perugia’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Santa Maria degli Angeli behind. This drive usually takes around 34 min. Perugia welcomes you with a multitude of unique vacation experiences.

For a more meaningful self-guided tour of the town's best attractions, visit Etruscan Arch, an intriguing historical landmark that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Perugia Cathedral and admire its monumental features.

When you’re ready, continue to Piazza Iv Novembre, an up-and-coming public square beloved by locals and tourists alike. Don't miss out on The Fontana Maggiore, another highlight of the area that promises a memorable visit.

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

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

Enjoy a delicious meal at Ristorante Settimo Sigillo, a top-rated dining destination in Perugia. If you're in the mood to try something new, consider Caffè Baglioni, another top spot with a mouthwatering menu. You might also want to secure a reservation at Bar Pellas. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Perugia this evening.

After enjoying a fulfilling meal, continue your evening at Tommi Bar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Valentina offers a welcoming atmosphere for easing into the nightlife. Similarly, Caffe Dal Perugino provides an excellent environment for a relaxed and enjoyable evening.

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

On day 8 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Orvieto. When you’re not sightseeing, take time to relax at your chosen hotel in Orvieto, where you’ll be staying for 2 nights.

Orvieto’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Perugia behind. This drive usually takes around 1 hour 17 min. Orvieto welcomes you with a multitude of unique vacation experiences.

Our first attraction recommendation in Orvieto is Well Of St. Patrick, an interesting monument that draws attention for its culturally significant features.

When you’ve had your share of Perugia, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Orvieto. Your travel time is around 1 hour 17 min.

Spend your afternoon discovering Orvieto Cathedral, a captivating church known for its inviting features. Next, continue your sightseeing at Museo Dell'opera Del Duomo, a frequently visited museum.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Orvieto Underground and uncover the details of this photogenic cave system. Make sure to also explore Torre Del Moro Orvieto, a beloved monument. For your last stop, consider Pozzo Della Cava, a visually striking cave that many travelers find worth the detour.

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

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 Orvieto, it's often a good idea to reserve a table in advance.

Explore the vibrant nightlife at Bar Duomo after your meal, a hub for lively evenings and memorable moments.

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

On day 9 of your road trip, you'll get the chance to experience Rome. At the end of the day, you'll drive back to Orvieto, where you still have 1 night left to stay.

Rome’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Orvieto behind. This drive usually takes around 1 hour 37 min. Rome welcomes you with a multitude of unique vacation experiences.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Colosseum, a globally renowned archeological site that everyone visiting Rome should see. Next, head to Roman Forum. This historic archeological site is one of the most timeless attractions in the region.

If you're keen to see more, don’t miss out on Trevi Fountain, a remarkable monument popular among locals as well as travelers. Pantheon is an excellent attraction to visit next. Spend some time learning more about this world-famous monument before you continue your journey. Lastly, visit Piazza Navona, a masterful public square and a top attraction in the city.

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

Orvieto 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 Orvieto.

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

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.

Set your GPS to Cortona and hit the road. Expect a journey of approximately 1 hour 11 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Cortona beckons with new experiences!

For a more meaningful self-guided tour of the town's best attractions, visit Parterre, an underrated park that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Basilica Of Saint Margaret Of Cortona and admire its picture-perfect features.

When you’re ready, continue to Hermitage "le Celle", a locally appreciated monastery beloved by locals and tourists alike.

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

Florence 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 Florence.

Have a fantastic dining experience at Tijuana, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Djària - American Bar offers an enticing alternative with its varied menu. Additionally, The Florence Irish Pub is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

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