10-Day Italy Self-Drive Road Trip With Itinerary from Bologna to Florence, San Gimignano, Perugia, and Rome

Day 3 offers an itinerary packed with the best things to see in Florence. You’ll stay in Florence for 2 nights more, offering you enough time to explore at a relaxed pace.

Florence is brimming with adventures.

To truly experience Florence, make sure to drop by Basilica Of Santa Croce In Florence. This notable church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Uffizi Gallery, one of the city’s best highlights.

Next, check out Ponte Vecchio, one of the most wondrous places to see in Florence. This historical landmark is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Palazzo Vecchio. Wander around and soak in the visually striking atmosphere this palace offers. Then, head to Piazza Della Signoria, a top-rated public square that adds another dimension to your day. Finally, visit the famous Cathedral Of Santa Maria Del Fiore, the last of our attraction recommendations for today.

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.

Have a fantastic dining experience at Ditta Artigianale, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria Da Burde offers an enticing alternative with its varied menu. Additionally, Casa Toscana is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

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.

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

On day 4 of your road trip in Italy, you’ll start and end your day in Florence, but spend the day exploring what’s beyond the city. Since you still have 1 night to spend in Florence, there’s no need to rush. Experience Pisa and Lucca to the fullest today with this curated day itinerary.

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.

Make time for Piazza Del Duomo, Pisa, a world-famous public square that is worthwhile a visit in the city. Nearby, you’ll find Pisa Cathedral, enchanting visitors with its historic appeal. Continue your exploration at Leaning Tower Of Pisa. This monument is one of the city’s most iconic spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Mura Di Lucca. After exploring the historical landmark, head to the notable Piazza Dell'anfiteatro.

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 delicious dinner at Ristorante Buca Mario, an excellent option for tonight's dining. Looking for something different? Agricola Toscana offers a tantalizing alternative with its diverse menu. And don’t miss Eataly Firenze. Known for great service, it’s a fantastic choice for tonight in Florence.

Let the evening flow smoothly from dinner to drinks at Gosh*, a top-rated bar in the area. For other recommendations, Antico Caffè Del Moro - Art Bar Firenze provides a perfect setting for rounding out your night with style and great drinks. Likewise, Quelo Bar offers a memorable night with diverse drink options and excellent service.

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

On day 5 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Siena and San Gimignano are on today's agenda. In the evening, you’ll end up in San Gimignano, where you will stay for 2 nights.

Experience Santuario Di Santa Caterina, a frequently visited church in the city. Then, head to Pubblico Palace and soak in the ambiance of this UNESCO world heritage-listed palace.

There are many interesting places to see in Florence, and when you are ready for more, go to Tower Of Mangia. This is one of the city’s most underrated awe-inspiring spots of interest. After exploring the monument, visit the top-rated Piazza Del Campo. Not far away, you'll also find Siena Cathedral. This church is a history-steeped highlight in Florence. Before wrapping up your self-guided sightseeing tour, head to Porta San Giovanni, a worthwhile monument in the city.

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

Say good night to San Gimignano and look forward to another great day of your road trip in Italy!

Wake up to day 6 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of San Regolo and San Gimignano. With 1 night to stay in San Gimignano, we encourage you to seize the day and discover the unexplored beauty of the village’s surroundings!

Make a stop at Castello Di Brolio. This up-and-coming castle is a must-visit for travelers looking for a unique holiday experience. Make your way to Chiesa Di Sant'agostino located in San Gimignano for another exciting encounter.

Next, immerse yourself in the setting of Piazza Del Duomo. Its culturally significant features will captivate you. After the public square, continue your tour of the hamlet with a visit to Palazzo Comunale, Pinacoteca, Torre Grossa. Visitors usually appreciate the UNESCO world heritage-listed features of this museum. Next up is Sangimignano1300, a highly recommended museum.

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

San Gimignano 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 San Gimignano.

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.

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

Make a stop at Basilica Of San Francesco D'assisi. This captivating church is a must-visit for travelers looking for a unique holiday experience. Make your way to Rocca Maggiore located in San Gimignano for another exciting encounter.

Next, immerse yourself in the setting of Rocca Paolina. Its photogenic features will captivate you. After the historical landmark, continue your tour of the town with a visit to Perugia Cathedral. Visitors usually appreciate the culturally significant features of this church. Next up is Piazza Iv Novembre, a highly recommended public square. For a change of pace, head to The Fontana Maggiore. As one of the most beloved attractions in San Gimignano, this monument is the perfect place to end your self-guided sightseeing tour.

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.

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.

Make sure to reserve a table at Ristorante Settimo Sigillo, an iconic dining spot in Perugia. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Caffè Baglioni, a popular restaurant in Perugia. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Bar Pellas, a hidden gem nestled in Perugia. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

Raise your glass to another unforgettable day in Italy!

Dive into day 8 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Orvieto and Rome. At the end of the day, you’ll unwind at one of the finest accommodations in Rome, where you'll spend 1 night.

Catch Orvieto Cathedral before the crowds roll in. This visually striking church is sure to ignite your curiosity. Next, dive into the heritage-rich features of Orvieto Underground, a must-visit cave system 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 Pozzo Della Cava, an underrated cave. For a change of scene, check out Piazza Navona, known for its culturally significant features. We also recommend visiting Pantheon. This monument is a must for anyone looking to experience the town to the fullest. Lastly, end your day with a visit to Trevi Fountain, yet another world-famous attraction in Perugia.

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.

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

Have a fantastic dining experience at La Bottega Roma, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Pasta In Corso offers an enticing alternative with its varied menu. Additionally, Trattoria Vecchia Roma is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

Extend your evening after a delightful meal by visiting La Botticella Of Poggi Giovanni, which offers the perfect atmosphere for a night out. Moreover, Almalu Trastevere is another popular option for a drink or two. Likewise, Bar Viminale Di Pepi Maurilio also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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