11-Day Italy Self-Drive Road Trip With Itinerary from Florence traveling south to San Gimignano, Perugia, Orvieto, and Rome

On day 2 of your road trip, you will have an entire day to discover what to see in Florence. You’ll stay in Florence for 2 nights.

Start your day at Cathedral Of Santa Maria Del Fiore. This visually striking church is an extraordinary place to see in Florence. Then, wander over to Piazza Della Signoria. If history-steeped sites excite you, this public square will be right up your alley. Nearby, you’ll also find Ponte Vecchio. This visually striking historical landmark is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Uffizi Gallery is a famous spot in the city that will captivate you with its unique charm. When you’re done at the art gallery, don’t forget to check out the romantic Piazzale Michelangelo. Take a moment to appreciate the fascinating details of this top-rated observation deck.

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 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.

Don’t miss out on dining at Ditta Artigianale, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Trattoria Da Burde, another top spot with a mouthwatering menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

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.

Celebrate another amazing day of your road trip adventure 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.

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!

Spend your afternoon discovering Piazza Del Duomo, Pisa, a wondrous public square known for its stunning features. Next, continue your sightseeing at Pisa Cathedral, a curiosity-inducing 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 Leaning Tower Of Pisa and uncover the details of this UNESCO world heritage-designated monument.

Fasten your seatbelt and make your way to your next stop — Lucca, home to many well-known sights in the region. Keep in mind that your travel time from Pisa to Lucca may take around 32 min without traffic disruptions. Upon arrival in Lucca, we highly recommend checking out some of the top attractions.

One of our top recommendations for your sightseeing is Guinigi Tower. Spend some time admiring the majestic features of the monument before you continue to your next stop. Then, head to Piazza Dell'anfiteatro. This interesting public square is a traveler-favorite in the city.

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

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.

Enjoy a delicious meal at Ristorante Buca Mario, a highly-rated dining destination in Florence. If you're eager to try something different, consider Agricola Toscana, another top spot with a tantalizing menu. You might also want to secure a reservation at Eataly Firenze. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

After savoring a delicious meal, step into the vibrant nightlife at Gosh*, where the evening is just getting started. In the same way, Antico Caffè Del Moro - Art Bar Firenze offers a unique charm perfect for experiencing the local bar scene in Florence. Quelo Bar is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Your itinerary for day 4 of your road trip in Italy includes 2 stops and features some of the highlights of Siena and San Gimignano. At the end of the day, enjoy the comforts of a top-rated hotel in San Gimignano, where you'll spend 2 nights.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Siena may take around 1 hour 10 min. Upon your arrival in Siena, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Our first attraction recommendation in Siena is Fortezza Medicea (siena), an increasingly popular monument that draws attention for its culturally significant features. Spend some time soaking in the atmosphere before continuing to Piazza Del Campo, an enchanting public square 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 Siena Cathedral, an interesting church that offers a unique experience.

Embrace the thrill of the open road as you wave goodbye to Siena and set your GPS to San Gimignano. 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 42 min. Upon reaching San Gimignano, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Porta San Giovanni, a beloved monument that everyone visiting San Gimignano should see. Next, head to Piazza Del Duomo. This visually striking public square is one of the most often recommended attractions in the region.

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

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

Savor another day of unforgettable experiences in Italy!

On day 5 of your road trip in Italy, you’ll start and end your day in San Gimignano, but spend the day exploring what’s beyond the village. Since you still have 1 night to spend in San Gimignano, there’s no need to rush. Experience Castellina in Chianti to the fullest today with this curated day itinerary.

Castellina in Chianti is brimming with adventures.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Castellina in Chianti. This drive usually takes around 47 min, without any stops or traffic disruptions.

Our first attraction recommendation in Castellina in Chianti is Poggio Amorelli, a frequently visited winery that draws attention for its enchanting features. Spend some time soaking in the atmosphere before continuing to Tumulo Di Montecalvario, a symbolic archeological site 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 Rocca Di Castellina In Chianti, an often recommended castle that offers a unique experience.

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

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

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

On day 6 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.

Set your GPS to Santa Maria degli Angeli and hit the road. Expect a journey of approximately 2 hours 8 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Santa Maria degli Angeli beckons with new experiences!

When you're ready for some sights, head to Basilica Of San Francesco D'assisi, an interesting church in Santa Maria degli Angeli. Explore its UNESCO world heritage-listed features at your own pace before you continue your journey to your next attraction, Piazza Del Comune. This increasingly popular public square is a top recommendation in the area.

When you’re ready to explore more, Basilica Di Santa Chiara is an excellent choice. Spend some time discovering what some claim to be the most stunning church in the region.

Continue your road trip and head to your next destination, Perugia. This car ride takes around 29 min.

When you're ready for some sights, head to Rocca Paolina, an increasingly popular historical landmark in Perugia. Explore its culturally significant features at your own pace before you continue your journey to your next attraction, Piazza Iv Novembre. This increasingly popular public square is a top recommendation in the area.

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

Perugia 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 Perugia.

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 delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Tommi Bar, a well-loved spot among locals and tourists. Or, head to Valentina. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Caffe Dal Perugino, another top-rated place in the area.

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

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Orvieto and Bolsena. When you’re not sightseeing, take time to relax at your chosen hotel in Orvieto, where you’ll be staying for 1 night.

Embrace the thrill of the open road as you wave goodbye to Perugia and set your GPS to Orvieto. 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 1 hour 17 min. Upon reaching Orvieto, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Well Of St. Patrick, a notable monument that everyone visiting Orvieto should see.

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.

Savor the day by heading to Orvieto Cathedral, a notable church that draws visitors from near and far. When you're done, continue to Torre Del Moro Orvieto, where you can soak in the picture-perfect surroundings.

Fasten your seatbelt and make your way to your next stop — Bolsena, home to many well-known sights in the region. Upon arrival in Bolsena, we highly recommend checking out some of the top attractions.

One of our top recommendations for your sightseeing is Basilica Of Santa Cristina, Bolsena. Spend some time admiring the stunning features of the church before you continue to your next stop.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Orvieto. Orvieto 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 Orvieto, it's often a good idea to reserve a table in advance.

To truly maximize your evening out, consider visiting Bar Duomo after dinner. This bar is known for offering some of the best drinks and vibes in the city.

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

Experience an unparalleled adventure on day 8 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Rome. At the end of the day, you will retreat to the hotel of your choice in Rome, where will spend 2 nights.

When you’re ready to jump back into the car and say goodbye to Orvieto, you’ll hit the road in the direction of Rome. This drive usually takes around 1 hour 33 min.

One of our top recommendations for your sightseeing is Piazza Di Spagna. Spend some time admiring the visually striking features of the public square before you continue to your next stop. Then, head to Trevi Fountain. This timeless monument is a traveler-favorite in the city.

If you're keen to see more, continue to Piazza Navona. Feed your curiosity by learning something new about the public square. Next, take your journey to Pantheon, a timeless monument.

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

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

Treat yourself to a delicious dinner at La Bottega Roma, an excellent option for tonight's dining. Looking for something different? Pasta In Corso offers a tantalizing alternative with its diverse menu. And don’t miss Trattoria Vecchia Roma. Known for great service, it’s a fantastic choice for tonight in Rome.

Cap off your dinner by heading to La Botticella Of Poggi Giovanni, ideal for a leisurely evening with a drink in hand. Almalu Trastevere is another bar that offers an enjoyable setting. Similarly, Bar Viminale Di Pepi Maurilio is also a popular place to go on a night out, perfect for relaxing and socializing.

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

Dive into day 10 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Tivoli. At the end of the day, you’ll unwind at one of the finest accommodations in Florence, where you'll spend 1 night.

Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Tivoli.

When you’ve had your share of Rome, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Tivoli. Your travel time is around 49 min.

Savor the day by heading to Villa D'este, a notable palace that draws visitors from near and far. When you're done, continue to Fontana Dell'organo, where you can soak in the history-steeped surroundings.

Next, explore Fontana Dell'ovato (o Di Tivoli), yet another frequently visited place to see in the area. After the monument, make time to go to Villa Gregoriana. This standout park is well worth the visit.

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.

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.

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.

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