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

Day 2 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.

Whatever your travel style is, Basilica Of Santa Croce In Florence is an essential stop in Florence. This captivating church provides an insightful glimpse into the city's identity. Next, discover Piazza Della Signoria, a visually striking public square, promising a delightful encounter.

Continue your sightseeing with a visit to Palazzo Vecchio, a well-known palace. When you’re done, don’t forget to make a stop at the astonishing Uffizi Gallery. Not far away from the art gallery, you will find the romantic The Boboli Gardens, perfect for a quick visit. Round off your day at Ponte Vecchio, another gem in Florence with romantic features to discover.

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.

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 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.

To truly maximize your evening out, consider visiting Bar 50 Rosso after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bitter Bar, another bar with an inviting ambiance. Similarly, Archea Brewery also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Greet day 3 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night to stay in Florence, 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 Pisa and Lucca.

Visiting Battistero Di San Giovanni is always a good idea. This frequently visited church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the stunning wonders of Piazza Del Duomo, Pisa, a must-see public square in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Leaning Tower Of Pisa. This world-famous monument offers an enriching experience. For a change of pace, head to Guinigi Tower, where you can take in visually striking features. Conclude your self-guided sightseeing tour with a visit to San Michele In Foro and Mura Di Lucca These sights offer a fulfilling end to a perfect day.

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.

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

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.

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

Experience an unparalleled adventure on day 4 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Siena. At the end of the day, you will retreat to the hotel of your choice in Siena, where will spend 3 nights.

Basilica Of San Domenico leaves a lasting impression. This church is one of the most intriguing places to visit in Florence. Next, head to Siena Cathedral, a well-known church, known for its romantic 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 Facciatone. This enchanting observation deck is a highly recommended experience. Nearby, you'll also find Pubblico Palace and Piazza Del Campo Visit these for an interesting touch to your journey.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Unwind after your meal by stepping into Meet Life Cafè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Maudit Pub offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Impero Siena, another top-rated bar in the area.

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

Wake up to day 5 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of San Gimignano and Volterra. With 2 nights to stay in Siena, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Whether you decide to explore San Gimignano on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Piazza Del Duomo brings Siena's character to life. This symbolic 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 up-and-coming attractions, known for its history-steeped 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 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. If you are looking to dine at a popular restaurant in Siena, it's often a good idea to reserve a table in advance.

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. Known for great service, it’s a fantastic choice for tonight in Siena.

After enjoying a fulfilling meal, continue your evening at Charlie Mixology Bar Di Aldinucci Riccardo, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bar Pinacoteca offers a welcoming atmosphere for easing into the nightlife. Similarly, San Paolo Pub provides an excellent environment for a relaxed and enjoyable evening.

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

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

Bargino is brimming with adventures.

Make a stop at Antinori Nel Chianti Classico. This curiosity-inducing winery is a must-visit for travelers looking for a unique holiday experience. Make your way to Il Molino Di Grace located in Siena for another exciting encounter.

Next, immerse yourself in the setting of Castello Di Brolio. Its enchanting features will captivate you.

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

Siena 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 Siena.

Enjoy a lovely dining experience at Ristorante San Desiderio, 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 Osteria Le Logge, 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 Ristorante Taverna Di Cecco. It’s yet another ideal choice to enhance your time in Siena tonight.

Raise your glass to another unforgettable day in Italy!

Your itinerary for day 7 of your road trip in Italy includes 2 stops and features some of the highlights of Santa Maria degli Angeli and Perugia. At the end of the day, enjoy the comforts of a top-rated hotel in Perugia, where you'll spend 3 nights.

Check out the interesting church, Basilica Of San Francesco D'assisi. Afterward, continue to Etruscan Well, an archeological site every traveler should visit. As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the town.

Next, make your way to Perugia Cathedral. This beloved church is an essential stop. Following that, head to Piazza Iv Novembre, another must-visit site that will enhance your experience. Don’t forget to stop by The Fontana Maggiore, a worthwhile monument in the town.

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.

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

Treat yourself to a delicious dinner at Ristorante Settimo Sigillo, an excellent option for tonight's dining. Looking for something different? Caffè Baglioni offers a tantalizing alternative with its diverse menu. And don’t miss Bar Pellas. Known for great service, it’s a fantastic choice for tonight in Perugia.

Keep the excitement of the evening going by visiting a bar or two. Tommi Bar is an excellent place to start. You could also check out Valentina, offering a different kind of charm. A last recommendation for the day is Caffe Dal Perugino. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

On day 8 of your road trip, you’ll start and end your day in Perugia, where you have 2 nights left to stay.

Look forward to a unique sightseeing adventure at the interesting Well Of St. Patrick and allow yourself time to explore. Just a short distance away you'll find your next stop, Orvieto Cathedral, a visually striking church that draws visitors from far and near.

Continue your journey to Museo Dell'opera Del Duomo, one of the village’s most curiosity-inducing spots that you shouldn’t miss. Another great site to visit is the increasingly popular Orvieto Underground. When you're finished at the cave system, Torre Del Moro Orvieto awaits your visit. This monument is a historic highlight on today's itinerary. Last up is a cave - the curiosity-inducing Pozzo Della Cava.

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

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

Dine in style at La Taverna, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante del Sole boasts a menu that's sure to impress. Also, be sure to check out Al Mangiar Bene. Known as a local hotspot, it’s a great choice for tonight in Perugia.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Caffè Fortebraccio stands out as an excellent choice for a post-dinner cocktail. Alternatively, Caffe Del Banco offers an ideal atmosphere to enjoy the pleasures of the night. Dempsey's Perugia is also a great option that provides a perfect setting for a relaxing evening.

Savor another day of unforgettable experiences 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 still have 1 night to spend in Perugia, there’s no need to rush. Experience Il Mulino and Arezzo to the fullest today with this curated day itinerary.

Make time for Melone Secondo Del Sodo, a locally appreciated archeological site that is worthwhile a visit in the hamlet. Nearby, you’ll find San Francesco, Arezzo, enchanting visitors with its culturally significant appeal. Continue your exploration at Santa Maria Della Pieve. This church is one of the hamlet’s most beloved 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 Piazza Grande.

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 delightful dinner at Perugia Plaza Hotel, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Elfo Pub Perugia? It's another excellent option with a diverse menu. Consider reserving a table at Sangallo Palace Hotel as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Perugia.

Continue your evening by exploring the vibrant nightlife scene at Il Birrino, a prime destination for a thrilling night out. Also, don’t forget to check out Quei Bravi Ragazzi, a bar that offers unique local touches. Likewise, Lo Chalet - Lounge Bar provides an excellent alternative for a fun evening.

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

On day 10 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Bologna. When you’re not sightseeing, take time to relax at your chosen hotel in Bologna, where you’ll be staying for 1 night.

Pinacoteca Nazionale Di Bologna is an ideal stop early in the day. This increasingly popular art gallery is a must-visit in the city. When you’re ready for your next discovery, continue to Two Towers, which may be one of the most standout places you will experience today.

One of the best things about exploring Perugia 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 Bologna Cathedral, a curiosity-inducing church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Fountain Of Neptune, Bologna and Piazza Maggiore.

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

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

Savor the flavors at Ristorante Ciacco, a top pick for dinner tonight. Alternatively, Ristorante Ballarini beckons with its unique menu offerings. Also, consider Sfoglia Rina. With its consistent customer satisfaction, it’s an excellent option for dining in Bologna tonight.

Round off your dining experience by visiting Bar Al Bricco D'oro, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Freud E Squisito, a bar catering to every mood and preference. Osteria Del Sole likewise offers a unique atmosphere, perfect for a memorable night out.

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

Dive into day 11 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Modena. At the end of the day, you’ll unwind at one of the finest accommodations in Florence, where you'll spend 1 night.

Enzo Ferrari Museum makes a great addition to your morning plans. This notable museum is an eye-catching place to see in Bologna. Continue your discovery at Torre Civica - Ghirlandina, an UNESCO world heritage-listed monument with stories to tell.

As you stroll around Bologna, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Duomo Di Modena. This popular church offers an UNESCO world heritage-designated encounter with Bologna. Next, make your way to Piazza Duomo to add another highlight to your day. After that, visit Piazza Grande, a beloved public square that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Bologna.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

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.

Treat yourself to a wonderful meal at Tijuana, a top-rated dining spot in Florence. If you're in the mood for something new, try Djària - American Bar, another premier location with a delectable menu. You might also want to book a table at The Florence Irish Pub. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

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