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.

Start by visiting Basilica Of Santa Croce In Florence, a prime spot to begin your journey. This instagrammable church is sure to impress. Next on your list is Piazza Della Signoria, another must-visit landmark and impressive public square renowned for its noteworthy features.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Palazzo Vecchio. This romantic palace is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Uffizi Gallery, a top-rated art gallery. Nearby, you'll also find Ponte Vecchio, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at The Boboli Gardens and wrap up your day with its detailed appeal.

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 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.

Enjoy a delicious meal 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 excitement of the evening going by visiting a bar or two. Bar 50 Rosso is an excellent place to start. You could also check out Bitter Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Raise your glass to another unforgettable day in Italy!

Wake up to day 3 of your extraordinary road trip in Italy. With 1 night left in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Get ready for a day filled with family-friendly attractions, breathtaking views, and photo-friendly spots in the charming city of Florence. Your adventure starts at Battistero Di San Giovanni, an underrated local hot spot. Another notable attraction to explore is Piazza Del Duomo, Pisa. This timeless public square is known for its UNESCO world heritage-listed appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Leaning Tower Of Pisa. This historic monument offers a fascinating experience that many visitors find memorable. Guinigi Tower is also worth visiting, along with San Michele In Foro. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Mura Di Lucca. This intriguing historical landmark provides a fitting finale to your sightseeing.

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.

Have a fantastic dining experience at Ristorante Buca Mario, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Agricola Toscana offers an enticing alternative with its varied menu. Additionally, Eataly Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

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

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Siena. At the end of the day, you will enjoy the comforts of a top-rated hotel in Siena, which will be your home away from home for 3 nights.

Florence is brimming with adventures. Today’s wonderful stops include a church, an observation deck, a palace, a public square and much more! Begin your sightseeing adventure at the beloved Basilica Of San Domenico and allow yourself time to explore. Just a short distance away you'll find your next stop, Siena Cathedral, a grand church that draws visitors from far and near.

Continue your journey to Facciatone, one of the city’s most worthwhile spots that you shouldn’t miss. Another great site to visit is the increasingly popular Pubblico Palace. When you're finished at the palace, Piazza Del Campo awaits your visit. This public square is an UNESCO world heritage-listed highlight on today's itinerary.

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.

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 and reflect on the day's adventures.

Enjoy a delicious meal at Enoteca I Terzi, a highly-rated dining destination in Siena. If you're eager to try something different, consider Ristorante Tar-Tufo, another top spot with a tantalizing menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

Extend your evening after a delightful meal by visiting Meet Life Cafè, which offers the perfect atmosphere for a night out. Moreover, Maudit Pub is another popular option for a drink or two. Likewise, Bar Impero Siena also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Say good night to Siena and look forward to another great day 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 will return to Siena for 2 nights more, there’s no need to rush. Experience San Gimignano and Volterra to the fullest today with this curated day itinerary!

Today, you'll explore some of the most beautiful places in Siena, including a public square, a museum, and a park. Start your day with a visit to Piazza Del Duomo. This frequently visited public square is a must-visit in the village. When you’re ready for your next discovery, continue to Sangimignano1300, which may be one of the most standout 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 Parco Della Rocca, a curiosity-inducing park in the village. If you’re up for more discoveries, don’t forget to reserve some time for Etruscan Museum "mario Guarnacci".

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.

Enjoy a lovely dining experience at Osteria Quattro Venti, 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 Fischi per Fiaschi, 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 Osteria da Divo. It’s yet another ideal choice to enhance your time in Siena tonight.

If you’re not ready to end the night just yet, Charlie Mixology Bar Di Aldinucci Riccardo offers a perfect venue to relax and savor a drink. Similarly, Bar Pinacoteca is well-suited for those looking to unwind in a social setting. San Paolo Pub is another excellent spot to enjoy a nightcap after a delightful meal.

Celebrate another amazing day of your road trip adventure 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.

Set out on a day brimming with fun adventures, romantic experiences, and scenic views. Start at the locally appreciated Antinori Nel Chianti Classico, a romantic winery in Siena. Next, go to Il Molino Di Grace.

After visiting Antinori Nel Chianti Classico and Il Molino Di Grace, have a stroll along Siena's streets and take in the local charm. Continue your sightseeing by heading to Castello Di Brolio. This romantic castle offers a unique experience.

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

As dinnertime approaches, it's time to head out for a bite to eat in Siena. 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.

Enjoy a lovely meal at Ristorante San Desiderio, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Osteria Le Logge is another top choice with a popular menu. You could also check for a table at Ristorante Taverna Di Cecco. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

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

Dive into day 7 of your remarkable road trip in Italy. Today you will explore Santa Maria degli Angeli and Perugia, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Perugia. You’ll stay here for 3 nights.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Siena allows for both. Start by heading to Basilica Of San Francesco D'assisi. This popular church provides an insightful glimpse into the town's identity. Next, discover Etruscan Well, a visually striking archeological site, promising a delightful encounter.

Continue your sightseeing with a visit to Perugia Cathedral, an often recommended church. When you’re done, don’t forget to make a stop at the often recommended Piazza Iv Novembre. Round off your day at The Fontana Maggiore, another gem in Siena with breathtaking features to discover.

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 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.

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.

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

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 8 of your road trip, you’ll start and end your day in Perugia, where you'll stay for 2 nights more.

A blend of fun adventures, scenic views, and photo-friendly spots await you in Perugia on today’s itinerary. First up is the well-known monument, Well Of St. Patrick. Afterward, continue to Orvieto Cathedral, a church every traveler should visit.

As you explore Perugia’s charming streets, take in the lively atmosphere and get to know the character of the village. Next, make your way to Museo Dell'opera Del Duomo. This up-and-coming museum is an essential stop. Following that, head to Orvieto Underground, another must-visit site that will enhance your experience. Don’t forget to stop by Torre Del Moro Orvieto, a frequently visited monument in the village. Finally, end your day with a visit to Pozzo Della Cava, an eye-catching cave that offers the perfect conclusion to your sightseeing of the day.

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

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.

Treat yourself to a delicious dinner at La Taverna, an excellent option for tonight's dining. Looking for something different? Ristorante del Sole offers a tantalizing alternative with its diverse menu. And don’t miss Al Mangiar Bene. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Perugia.

After your meal, keep the night alive at a bar like Caffè Fortebraccio, known for its lively atmosphere. Caffe Del Banco is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Dempsey's Perugia offers an excellent atmosphere for those looking to amp up the 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.

Greet day 9 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 1 night 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 Il Mulino and Arezzo.

Today’s well-planned self-sightseeing route offers several fun adventures, scenic views, and picturesque spots. Whether you decide to explore Perugia on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Melone Secondo Del Sodo is the first of them. Spend some time admiring this awe-inspiring archeological site before continuing your journey. San Francesco, Arezzo is your next stop. This beloved church is one of the best-rated sights in Perugia.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Santa Maria Della Pieve. This romantic church is a sight to behold. To round off your sightseeing experience, visit Piazza Grande.

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

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.

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

To truly maximize your evening out, consider visiting Il Birrino after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Quei Bravi Ragazzi, another bar with an inviting ambiance. Similarly, Lo Chalet - Lounge Bar also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

A blend of fun adventures, photo-friendly spots, and historic treasures await you in Perugia on today’s itinerary. First up is the locally appreciated art gallery, Pinacoteca Nazionale Di Bologna. Afterward, continue to Two Towers, a monument every traveler should visit.

As you explore Perugia’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Bologna Cathedral. This increasingly popular church is an essential stop. Following that, head to Fountain Of Neptune, Bologna, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Maggiore, a famous public square in the city.

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

Enjoy a lovely dining experience at Ristorante Ciacco, a popular restaurant in Bologna. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Bologna at Ristorante Ballarini, 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 Sfoglia Rina. It’s yet another ideal choice to enhance your time in Bologna tonight.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar Al Bricco D'oro, a well-loved spot among locals and tourists. Or, head to Bar Freud E Squisito. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Osteria Del Sole, another top-rated place in the area.

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

On day 11 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Modena. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 1 night.

Set out on a day brimming with family-friendly attractions, picturesque spots, and history-rich sites. Start at the locally renowned Enzo Ferrari Museum, a historic museum in Bologna. Next, go to Torre Civica - Ghirlandina.

After visiting Enzo Ferrari Museum and Torre Civica - Ghirlandina, have a stroll along Bologna's streets and take in the local charm. Continue your sightseeing by heading to Duomo Di Modena. This enchanting church offers a unique experience. Piazza Duomo is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazza Grande, one of the most enchanting places to visit in Bologna.

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 dinnertime approaches, it's time to head out for a bite to eat in Florence. 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.

Treat yourself to a delightful dinner at Tijuana, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Djària - American Bar? It's another excellent option with a diverse menu. Consider reserving a table at The Florence Irish Pub as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

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