12-Day Italy Self-Drive Road Trip With Itinerary from Florence to Siena, Perugia, and Bologna and surrounding area

On day 2 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 2 nights and discover all the best things to see and do in the area.

Florence is brimming with adventures. Today’s wonderful stops include a church, a public square, a palace, an art gallery, a historical landmark, a botanical garden and much more! Begin your sightseeing adventure at the locally renowned Basilica Of Santa Croce In Florence. Just a short distance away is Piazza Della Signoria, a romantic public square that draws visitors from far and near.

Continue your journey to Palazzo Vecchio, one of the city’s most interesting spots that you shouldn’t miss. Another great site to visit is the impressive Uffizi Gallery. Last up on today’s itinerary is a historical landmark. Make your way to Ponte Vecchio for some final sightseeing. Each attraction will leave you with lasting memories and a deeper appreciation for the rich heritage of Florence.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

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

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.

Let the evening flow smoothly from dinner to drinks at Bar 50 Rosso, a top-rated bar in the area. For other recommendations, Bitter Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Archea Brewery offers a memorable night with diverse drink options and excellent service.

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

At the end of the day, you'll drive back to Florence, where you'll stay for 1 night more.

Today’s agenda in Florence includes a church, a public square, a monument, a historical landmark and much more! Battistero Di San Giovanni is must-visit church and a great starting point for the day. Next, continue your journey to Piazza Del Duomo, Pisa, a world-famous public square, located just a leisurely stroll away. Next, head to Leaning Tower Of Pisa, an UNESCO world heritage-listed monument, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Florence. If you’re looking for more, Guinigi Tower is also a curiosity-inducing attraction that is worthwhile a visit. Lastly, don’t miss San Michele In Foro, a locally appreciated gem to see in the city.

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

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 and reflect on the day's adventures.

Enjoy a lovely dining experience at Ristorante Buca Mario, 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 Agricola Toscana, 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 Eataly Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

If you’re not ready to end the night just yet, Gosh* offers a perfect venue to relax and savor a drink. Similarly, Antico Caffè Del Moro - Art Bar Firenze is well-suited for those looking to unwind in a social setting. Quelo Bar is another excellent spot to enjoy a nightcap after a delightful meal.

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

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Siena. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 3 nights.

Discover a day packed with fun adventures, scenic views, and picturesque spots in Florence. Begin your sightseeing with Basilica Of San Domenico. This underrated church is one of the top attractions in the city. Proceed to Siena Cathedral, another must-visit attraction that enhances the city’s allure.

As you wander through the inviting streets of Florence, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Facciatone. This intriguing observation deck is a traveler-favorite. Not far away, you’ll find Pubblico Palace, another key site on your sightseeing itinerary. Conclude your day at Piazza Del Campo and uncover why it's recognized as one of the city's most top-rated attractions.

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

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

Enjoy a lovely dining experience at Enoteca I Terzi, 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 Ristorante Tar-Tufo, 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 Antica Trattoria Papei. It’s yet another ideal choice to enhance your time in Siena tonight.

Continue your lively evening at Meet Life Cafè, a perfect place for winding down or revving up the night, depending on which mood you’re in. Maudit Pub is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Impero Siena ensures a night out tailored to your taste.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

Wake up to day 5 of your extraordinary road trip in Italy. With 2 nights left in Siena, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Today's adventure in Siena promises more breathtaking discoveries and enriching experiences! Begin at Piazza Del Duomo. This romantic public square is a highlight of any visit in the village. Then, enjoy Sangimignano1300, another heritage-rich attraction that never fails to captivate visitors. Next, head over to Parco Della Rocca, one of the village’s most locally appreciated attractions, known for its romantic features.

If you’re looking for more, spend time soaking in the atmosphere of Etruscan Museum "mario Guarnacci". This photogenic museum is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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

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 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. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Charlie Mixology Bar Di Aldinucci Riccardo stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar Pinacoteca offers an ideal atmosphere to enjoy the pleasures of the night. San Paolo Pub is also a great option that provides a perfect setting for a relaxing evening.

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

On day 6 of your road trip, you’ll start and end your day in Siena, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Bargino, Greve in Chianti, and San Regolo. You still have 1 night left in Siena.

Start by visiting Antinori Nel Chianti Classico, a prime spot to begin your journey. This gorgeous winery is sure to impress. Next on your list is Il Molino Di Grace, another must-visit landmark and intriguing winery renowned for its eye-catching features.

While exploring and sightseeing, take time to savor the ambiance of Siena by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to Castello Di Brolio. This visually striking castle is a remarkable attraction 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 an authentic adventure.

Enjoy a delicious meal at Ristorante San Desiderio, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Osteria Le Logge, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Taverna Di Cecco. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

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

On day 7 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Santa Maria degli Angeli and Perugia. In the evening, you’ll end up in Perugia, where you will stay for 3 nights.

Today, you'll explore some of the most beautiful places in Siena, including a church, an archeological site, a public square, a monument and much more! Start your day with a visit to Basilica Of San Francesco D'assisi. This captivating church is a must-visit in the town. When you’re ready for your next discovery, continue to Etruscan Well, which may be one of the most historic places you will experience today.

One of the best things about exploring Siena on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Perugia Cathedral, a worthwhile church in the town. If you’re up for more discoveries, don’t forget to reserve some time for Piazza Iv Novembre and The Fontana Maggiore.

When you’re done exploring for the day, you’ll drive to your hotel in Perugia. Check in and spend some time relaxing before you head out to tour the city.

As dinnertime approaches, it's time to head out for a bite to eat in Perugia. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

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.

Continue the enjoyment post-dinner at Tommi Bar, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Valentina offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Caffe Dal Perugino. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Savor another day of unforgettable experiences in Italy!

Greet day 8 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Perugia for your remaining 2 nights in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in Orvieto.

Perugia is home to plenty of attractions that offer fun adventures, breathtaking views, and picturesque spots! Start at Well Of St. Patrick, an interesting monument that is worthwhile a visit in the village. Nearby, you’ll find Orvieto Cathedral, enchanting visitors with its romantic appeal. Continue your exploration at Museo Dell'opera Del Duomo. This museum is one of the village’s most up-and-coming spots.

Enjoy the freedom of exploring Perugia at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Orvieto Underground. After exploring the cave system, head to the frequently visited Torre Del Moro Orvieto. This monument will wrap up today’s self-guided sightseeing tour in the village.

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

As you explore more of Perugia, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Make sure to reserve a table at La Taverna, 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 Ristorante del Sole, 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 Al Mangiar Bene, a hidden gem nestled in Perugia. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Explore the vibrant nightlife at Caffè Fortebraccio after your meal, a hub for lively evenings and memorable moments. Or, head to Caffe Del Banco for a great selection of flavorful drinks and a charming setting. Furthermore, Dempsey's Perugia is perfect for those looking to extend their night with a touch of local flavor.

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

On day 9 of your road trip in Italy, you’ll start and end your day in Perugia, but spend the day exploring what’s beyond the city. Since you will return to Perugia for 1 night more, there’s no need to rush. Experience Il Mulino and Arezzo to the fullest today with this curated day itinerary!

Get ready to discover some of the most iconic wonders in Perugia, including an archeological site, a church, and a public square. Start your day at Melone Secondo Del Sodo. This historic archeological site is a curiosity-inducing place to see in Perugia. Then, wander over to San Francesco, Arezzo. If culturally significant sites excite you, this church will be right up your alley. Nearby, you’ll also find Santa Maria Della Pieve. This inviting church is a favorite among visitors.

Perugia offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Piazza Grande is a well-known spot in the hamlet that will captivate you with its unique charm.

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

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

Savor the flavors at Perugia Plaza Hotel, a top pick for dinner tonight. Alternatively, Elfo Pub Perugia beckons with its unique menu offerings. Also, consider Sangallo Palace Hotel. With its consistent customer satisfaction, it’s an excellent option for dining in Perugia tonight.

Keep the evening going at Il Birrino, a great choice for enjoying the after-dinner hours with a drink. You could also go to Quei Bravi Ragazzi, which offers a similarly pleasant setting and great drinks. Another option is Lo Chalet - Lounge Bar, which provides an inviting environment for unwinding after a busy day out.

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 vibrant destinations - Bologna. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Bologna. You will spend 1 night here for some well-deserved relaxation.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Perugia allows for both. Start by heading to Pinacoteca Nazionale Di Bologna. This often recommended art gallery provides an insightful glimpse into the city's identity. Next, discover Two Towers, a breathtaking monument, promising a delightful encounter.

Continue your sightseeing with a visit to Bologna Cathedral, a locally appreciated church. When you’re done, don’t forget to make a stop at the increasingly popular Fountain Of Neptune, Bologna. Round off your day at Piazza Maggiore, another gem in Perugia with majestic features to discover.

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

Treat yourself to a delightful dinner at Ristorante Ciacco, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante Ballarini? It's another excellent option with a diverse menu. Consider reserving a table at Sfoglia Rina as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Bologna.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar Al Bricco D'oro stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar Freud E Squisito offers an ideal atmosphere to enjoy the pleasures of the night. Osteria Del Sole is also a great option that provides a perfect setting for a relaxing evening.

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

Embark on another extraordinary experience on day 11 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Modena. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 1 night.

Get ready for an exciting day in Bologna. Today’s sightseeing agenda includes a museum, a monument, a church, a public square and much more! Begin your adventure at Enzo Ferrari Museum. This is a well-known museum you should not miss. Another must-see is Torre Civica - Ghirlandina, a locally appreciated monument in Bologna.

When you’re ready for the next sight, head to Duomo Di Modena. From there, take a leisurely stroll to Piazza Duomo, another of the city’s curiosity-inducing attractions. We recommend continuing your self-guided tour at Piazza Grande, a romantic place of interest in the city.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Florence. Florence 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 Florence. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Don’t miss out on dining at Tijuana, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Djària - American Bar, another top spot with a mouthwatering menu. You might also want to secure a reservation at The Florence Irish Pub. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

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