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 Bologna. You’ll stay in Florence for 2 nights more, offering you enough time to explore at a relaxed pace.

Enjoy all that Basilica Of Santa Croce In Florence has to offer. This is an interesting church you should not miss. Another must-see is Uffizi Gallery, an impressive art gallery in Florence.

When you’re ready for the next sight, head to Ponte Vecchio. From there, take a leisurely stroll to Palazzo Vecchio, another of the city’s locally renowned attractions. We recommend continuing your self-guided tour at Piazza Della Signoria, a masterful place of interest in the city. If time allows, add Cathedral Of Santa Maria Del Fiore to your itinerary. This extraordinary church 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.

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 lovely dining experience at Ditta Artigianale, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Trattoria Da Burde, 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 Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar 50 Rosso stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bitter Bar offers an ideal atmosphere to enjoy the pleasures of the night. Archea Brewery is also a great option that provides a perfect setting for a relaxing evening.

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, you’ll start and end your day in Florence, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate city, including Pisa and Lucca.

As you explore Pisa’s charming streets, take in the lively atmosphere and get to know the character of the city.

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.

Savor the day by heading to Piazza Del Duomo, Pisa, an iconic public square that draws visitors from near and far. When you're done, continue to Pisa Cathedral, where you can soak in the historic surroundings.

Next, explore Leaning Tower Of Pisa, yet another timeless place to see in the area.

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

Our first attraction recommendation in Lucca is Mura Di Lucca, an underrated historical landmark that draws attention for its visually striking features. Spend some time soaking in the atmosphere before continuing to Piazza Dell'anfiteatro, an instagrammable public square that stands out in the city.

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.

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.

Raise your glass to another unforgettable day in Italy!

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 places, which are Siena and San Gimignano. At the end of the day, you will retreat to the hotel of your choice in San Gimignano, where will spend 2 nights.

When you’ve had your share of Florence, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Siena. Your travel time is around 1 hour 12 min.

Savor the day by heading to Santuario Di Santa Caterina, a locally appreciated church that draws visitors from near and far. When you're done, continue to Pubblico Palace, where you can soak in the UNESCO world heritage-listed surroundings.

Next, explore Tower Of Mangia, yet another increasingly popular place to see in the area. After the monument, make time to go to Piazza Del Campo. This UNESCO world heritage-listed public square is well worth the visit. Lastly, head to Siena Cathedral, a popular church you won’t want to miss.

When you’re ready to jump back into the car and say goodbye to Siena, you’ll hit the road in the direction of San Gimignano. This drive usually takes around 42 min.

Set out on a self-guided sightseeing tour at Porta San Giovanni and explore the awe-inspiring features.

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.

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.

Savor another day of unforgettable experiences 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 San Gimignano, 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 Regolo and San Gimignano.

Chiesa Di Sant'agostino leaves a lasting impression. This church is one of the most worthwhile places to visit in San Gimignano. Next, head to Piazza Del Duomo, an underrated public square, known for its symbolic 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 Palazzo Comunale, Pinacoteca, Torre Grossa. This breathtaking museum is a highly recommended experience. Nearby, you'll also find Sangimignano1300 Visit these for an interesting touch to your journey.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in San Regolo. This drive usually takes around 1 hour 11 min, without any stops or traffic disruptions.

One of our top recommendations for your sightseeing is Castello Di Brolio. Spend some time admiring the awe-inspiring features of the castle before you continue to your next stop.

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

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

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.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Santa Maria degli Angeli. This drive usually takes around 2 hours 8 min, without any stops or traffic disruptions.

Our first attraction recommendation in Santa Maria degli Angeli is Basilica Of San Francesco D'assisi, a popular church that draws attention for its picture-perfect features. Spend some time soaking in the atmosphere before continuing to Rocca Maggiore, a history-steeped castle that stands out in the town.

Continue your road trip and head to your next destination, Perugia. This car ride takes around 31 min.

Rocca Paolina is an often recommended historical landmark we recommend visiting today. Discover its symbolic features before continuing your self-guided tour to Perugia Cathedral, a photogenic church that’s well-regarded in the area.

Next, stop by Piazza Iv Novembre, an enchanting public square. While you’re nearby, don’t forget to visit The Fontana Maggiore, a culturally significant and truly unique 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 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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Tommi Bar, known for its inviting atmosphere. Valentina is another great option if you’re looking for a place to get the night started. Similarly, Caffe Dal Perugino provides a great setting to enjoy the night away.

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

On day 8 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Orvieto and Rome are on today's agenda. In the evening, you’ll end up in Rome, where you will stay 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 19 min. Upon reaching Orvieto, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Orvieto Cathedral is a locally renowned church we recommend visiting today. Discover its visually striking features before continuing your self-guided tour to Orvieto Underground, a photogenic cave system that’s well-regarded in the area.

Next, stop by Pozzo Della Cava, a heritage-rich cave.

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 31 min. Rome welcomes you with a multitude of unique vacation experiences.

One of our top recommendations for your sightseeing is Piazza Navona. Spend some time admiring the enchanting features of the public square before you continue to your next stop. Then, head to Pantheon. This wondrous monument is a traveler-favorite in the town.

If you're keen to see more, continue to Trevi Fountain. Feed your curiosity by learning something new about the monument.

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

Make sure to reserve a table at La Bottega Roma, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Pasta In Corso, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Trattoria Vecchia Roma, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Continue the enjoyment post-dinner at La Botticella Of Poggi Giovanni, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Almalu Trastevere offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Viminale Di Pepi Maurilio. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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