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.

Enjoy all that Piazzale Michelangelo has to offer. This is a spectacular observation deck you should not miss. Another must-see is Basilica Of Santa Croce In Florence, a popular church in Florence.

When you’re ready for the next sight, head to Piazza Della Signoria. From there, take a leisurely stroll to Palazzo Vecchio, another of the city’s interesting attractions. We recommend continuing your self-guided tour at Uffizi Gallery, a romantic place of interest in the city. If time allows, add Ponte Vecchio to your itinerary. This world-famous historical landmark offers the perfect finishing touch to your day in Florence.

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 long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

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

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.

Set your GPS to Pisa and hit the road. Expect a journey of approximately 1 hour 16 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Pisa 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 Piazza Del Duomo, Pisa, a wondrous public square that everyone visiting Pisa should see. Next, head to Leaning Tower Of Pisa. This breathtaking monument is one of the most world-famous attractions in the region.

After soaking in Pisa’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Lucca. Expect your car journey to take a minimum of 32 min. When you arrive in Lucca, it's time to take a break from the road.

Guinigi Tower is an often recommended monument we recommend visiting today. Discover its visually striking features before continuing your self-guided tour to San Michele In Foro, a breathtaking church that’s well-regarded in the area.

Next, stop by Mura Di Lucca, a romantic historical landmark.

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

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.

Dine in style at Ristorante Buca Mario, a top recommendation for dinner tonight. Or, for a change of pace, Agricola Toscana boasts a menu that's sure to impress. Also, be sure to check out Eataly Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.

Continue the enjoyment post-dinner at Gosh*, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Antico Caffè Del Moro - Art Bar Firenze offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Quelo Bar. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Take some time to reflect on your day and savor another beautiful night 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.

Siena’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Florence behind. This drive usually takes around 1 hour 10 min. Siena 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 Fortezza Medicea (siena), a beloved monument that everyone visiting Siena should see. Next, head to Basilica Of San Domenico. This stunning church is one of the most up-and-coming attractions in the region.

If you're keen to see more, don’t miss out on Siena Cathedral, a majestic church popular among locals as well as travelers. Piazza Del Campo is an excellent attraction to visit next. Spend some time learning more about this impressive public square before you continue your journey. Lastly, visit Pubblico Palace, a picture-perfect palace and a top attraction in the city.

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

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

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 savoring a delicious meal, step into the vibrant nightlife at Meet Life Cafè, where the evening is just getting started. In the same way, Maudit Pub offers a unique charm perfect for experiencing the local bar scene in Siena. Bar Impero Siena is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

On day 5 of your road trip in Italy, you’ll start and end your day in Siena, but spend the day exploring what’s beyond the city. Since you still have 2 nights to spend in Siena, there’s no need to rush. Experience San Gimignano and Volterra to the fullest today with this curated day itinerary.

Fasten your seatbelt and make your way to your next stop — San Gimignano, home to many well-known sights in the region. Keep in mind that your travel time from Siena to San Gimignano may take around 51 min without traffic disruptions. Upon arrival in San Gimignano, we highly recommend checking out some of the top attractions.

One of our top recommendations for your sightseeing is Piazza Del Duomo. Spend some time admiring the enchanting features of the public square before you continue to your next stop. Then, head to Palazzo Comunale, Pinacoteca, Torre Grossa. This intriguing museum is a traveler-favorite in the village.

If you're keen to see more, continue to Parco Della Rocca. Feed your curiosity by learning something new about the park.

Continue your road trip and head to your next destination, Volterra. This car ride takes around 38 min.

Our first attraction recommendation in Volterra is Etruscan Museum "mario Guarnacci", a locally appreciated museum that draws attention for its photogenic features. Spend some time soaking in the atmosphere before continuing to Palazzo Incontri Viti, a standout palace that stands out in the village.

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 Baptistery Of San Giovanni Battista, an intriguing church that offers a unique experience.

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

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

Treat yourself to a delicious dinner at Osteria Quattro Venti, an excellent option for tonight's dining. Looking for something different? Fischi per Fiaschi offers a tantalizing alternative with its diverse menu. And don’t miss Osteria da Divo. Known for great service, it’s a fantastic choice for tonight in Siena.

Keep the evening going at Charlie Mixology Bar Di Aldinucci Riccardo, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bar Pinacoteca, which offers a similarly pleasant setting and great drinks. Another option is San Paolo Pub, which provides an inviting environment for unwinding after a busy day out.

Savor another day of unforgettable experiences 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.

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.

Set out on a self-guided sightseeing tour at Rocca Di Castellina In Chianti and explore the romantic features. Next, make your way to Poggio Amorelli, another highlight in Castellina in Chianti.

Set your GPS to Greve in Chianti and hit the road. Expect a journey of approximately 13 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Greve in Chianti beckons with new 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!

When you're ready for some sights, head to Castello Di Brolio, a curiosity-inducing castle in San Regolo. Explore its enchanting features at your own pace before you continue your journey.

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 lovely dining experience at Ristorante San Desiderio, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Osteria Le Logge, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Ristorante Taverna Di Cecco. It’s yet another ideal choice to enhance your time in Siena tonight.

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

On day 7 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Santa Maria degli Angeli and Perugia are on today's agenda. In the evening, you’ll end up in Perugia, where you will stay for 1 night.

Continue your road trip and head to your next destination, Santa Maria degli Angeli. This car ride takes around 1 hour 36 min.

Basilica Of San Francesco D'assisi is a well-known church we recommend visiting today. Discover its breathtaking features before continuing your self-guided tour to Rocca Maggiore, a visually striking castle that’s well-regarded in the area.

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.

Spend your afternoon discovering Etruscan Arch, a locally appreciated historical landmark known for its breathtaking features. Next, continue your sightseeing at Perugia Cathedral, a beloved church.

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 Piazza Iv Novembre and uncover the details of this romantic public square. Make sure to also explore The Fontana Maggiore, an up-and-coming monument.

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.

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

Don’t miss out on dining 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.

To truly maximize your evening out, consider visiting Tommi Bar after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Valentina, another bar with an inviting ambiance. Similarly, Caffe Dal Perugino also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.

Your itinerary for day 8 of your road trip in Italy includes 1 stop and features some of the highlights of Orvieto. At the end of the day, enjoy the comforts of a top-rated hotel in Orvieto, where you'll spend 2 nights.

Fasten your seatbelt and make your way to your next stop — Orvieto, home to many well-known sights in the region. Keep in mind that your travel time from Perugia to Orvieto may take around 1 hour 17 min without traffic disruptions. Upon arrival in Orvieto, we highly recommend checking out some of the top attractions.

When you're ready for some sights, head to Well Of St. Patrick, a popular monument in Orvieto. Explore its picture-perfect features at your own pace before you continue your journey.

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.

One of our top recommendations for your sightseeing is Orvieto Cathedral. Spend some time admiring the symbolic features of the church before you continue to your next stop. Then, head to Museo Dell'opera Del Duomo. This often recommended museum is a traveler-favorite in the village.

If you're keen to see more, continue to Orvieto Underground. Feed your curiosity by learning something new about the cave system. Next, take your journey to Torre Del Moro Orvieto, a beloved monument. Conclude your sightseeing at Pozzo Della Cava, known for its heritage-rich features.

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.

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.

After your meal, keep the night alive at a bar like Bar Duomo, known for its lively atmosphere.

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

Wake up to day 9 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Rome. With 1 night to stay in Orvieto, we encourage you to seize the day and discover the unexplored beauty of the town’s surroundings!

Continue your road trip and head to your next destination, Rome. This car ride takes around 1 hour 37 min.

For a more meaningful self-guided tour of the city's best attractions, visit Colosseum, a world-famous archeological site 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 Roman Forum and admire its historic features.

When you’re ready, continue to Trevi Fountain, a globally renowned monument beloved by locals and tourists alike. Don't miss out on Pantheon, another highlight of the area that promises a memorable visit. Not far away, you’ll also find Piazza Navona, a noteworthy place to see that you won’t regret spending some extra time discovering.

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

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.

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

When you’re ready to jump back into the car and say goodbye to Orvieto, you’ll hit the road in the direction of Cortona. This drive usually takes around 1 hour 11 min.

One of our top recommendations for your sightseeing is Parterre. Spend some time admiring the enchanting features of the park before you continue to your next stop. Then, head to Basilica Of Saint Margaret Of Cortona. This curiosity-inducing church is a traveler-favorite in the town.

If you're keen to see more, continue to Hermitage "le Celle". Feed your curiosity by learning something new about the monastery.

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

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

Enjoy a delicious meal at Tijuana, a highly-rated dining destination in Florence. If you're eager to try something different, consider Djària - American Bar, another top spot with a tantalizing menu. You might also want to secure a reservation at The Florence Irish Pub. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

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