7-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling south to Florence and Siena

On day 2 of your road trip, you will have an entire day to explore Bologna. You’ll stay in Bologna for 1 night and discover all the best things to see and do in the area.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and breathtaking views. Whether you decide to explore Bologna on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Piazza Santo Stefano is the first of them. Spend some time admiring this history-steeped public square before continuing your journey. Two Towers is your next stop. This locally renowned monument is one of the best-rated sights in Bologna.

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 Bologna Cathedral. This awe-inspiring church is a sight to behold. To round off your sightseeing experience, visit Fountain Of Neptune, Bologna and Palazzo Del Podestà, Bologna. If time allows, end your day with Piazza Maggiore, an enchanting public square that offers a memorable conclusion to your exploration.

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.

Bring home unique finds from Bologna's bustling shopping hub, Via d'Azeglio. Enjoy a leisurely exploration of unique boutiques and high-end stores where locals shop. Don’t forget to browse souvenirs and local specialties that make perfect gifts for your loved ones. Beyond shopping, Via d'Azeglio offers plenty of options, including primary services, unique landmarks, and community events.

As dinnertime approaches, it's time to head out for a bite to eat in Bologna. 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 dining experience at Bononia Cafè, 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 Via Con Me, 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 Trattoria Pizzeria La Mela. It’s yet another ideal choice to enhance your time in Bologna tonight.

After savoring a delicious meal, step into the vibrant nightlife at Lime Bar, where the evening is just getting started. In the same way, Macondo - Cocktail Bar offers a unique charm perfect for experiencing the local bar scene in Bologna. Bar Onda Marina By Night is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 2 nights.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Bologna allows for both. Start by heading to Piazzale Michelangelo. This famous observation deck provides an insightful glimpse into the city's identity. Next, discover Ponte Vecchio, a culturally significant historical landmark, promising a delightful encounter.

Continue your sightseeing with a visit to Uffizi Gallery, a famous art gallery. When you’re done, don’t forget to make a stop at the notable Palazzo Vecchio. Not far away from the palace, you will find the history-steeped Piazza Della Signoria, perfect for a quick visit. Round off your day at Cathedral Of Santa Maria Del Fiore, another gem in Bologna with history-steeped features to discover.

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.

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.

Savor the flavors at Ristorante Oliviero 1962, a top pick for dinner tonight. Alternatively, Di Poneta Novoli beckons with its unique menu offerings. Also, consider Caffe San Firenze. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

After savoring a delicious meal, step into the vibrant nightlife at Manifattura, where the evening is just getting started. In the same way, Se·sto On Arno Rooftop Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Il Vinile is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Savor another day of unforgettable experiences 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 will return to Florence for 1 night more, there’s no need to rush. Experience Pisa, Lucca, and Greti to the fullest today with this curated day itinerary!

Start by visiting Piazza Del Duomo, Pisa, a prime spot to begin your journey. This grand public square is sure to impress. Next on your list is Leaning Tower Of Pisa, another must-visit landmark and timeless monument renowned for its historic 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 Guinigi Tower. This enchanting monument is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Piazza Dell'anfiteatro, a captivating public square. Nearby, you'll also find Villa Calcinaia - Conti Capponi, ready to add charm to your journey.

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

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.

Continue the enjoyment post-dinner at Bar 50 Rosso, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bitter Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Archea Brewery. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Take some time to reflect on your day and savor another beautiful night 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 1 vibrant destinations - Siena. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Siena. You will spend 1 night here for some well-deserved relaxation.

Today’s route brings family-friendly attractions, scenic views, and picturesque spots. The first attraction of today is Fortezza Medicea (siena). This up-and-coming monument is a culturally significant place to see in Florence. Continue your discovery at Basilica Of San Domenico, a grand church with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Siena Cathedral. This locally renowned church offers a visually striking encounter with Florence. Next, make your way to Pubblico Palace to add another highlight to your day. After that, visit Piazza Del Campo, a top-rated public square that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Tower Of Mangia, a curiosity-inducing monument in the city. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Florence.

At the end of the day, you will drive to Siena, 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 Siena. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Dine in style at Enoteca I Terzi, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante Tar-Tufo boasts a menu that's sure to impress. Also, be sure to check out Antica Trattoria Papei. Known as a local hotspot, it’s a great choice for tonight in Siena.

Cap off your dinner by heading to Meet Life Cafè, ideal for a leisurely evening with a drink in hand. Maudit Pub is another bar that offers an enjoyable setting. Similarly, Bar Impero Siena is also a popular place to go on a night out, perfect for relaxing and socializing.

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

Dive into day 6 of your remarkable road trip in Italy. Today you will explore San Gimignano, 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 Bologna. You’ll stay here for 1 night.

A blend of fun adventures, breathtaking views, and picturesque spots await you in Siena on today’s itinerary. First up is the up-and-coming monument, Porta San Giovanni. Afterward, continue to Sangimignano1300, a museum every traveler should visit.

As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the village. Next, make your way to Palazzo Comunale, Pinacoteca, Torre Grossa. This frequently visited museum is an essential stop. Following that, head to Piazza Del Duomo, another must-visit site that will enhance your experience. Don’t forget to stop by Rocca Di Montestaffoli, a curiosity-inducing castle in the village. Finally, end your day with a visit to Chiesa Di Sant'agostino, a heritage-rich church that offers the perfect conclusion to your sightseeing of the day.

When you’re done exploring for the day, you’ll drive to your hotel in Bologna. 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 Bologna. 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 wonderful meal at Va Mo Là, a top-rated dining spot in Bologna. If you're in the mood for something new, try Trattoria dal Biassanot, another premier location with a delectable menu. You might also want to book a table at Ristorante Enoteca da Lucia. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Bologna.

If you’re not ready to end the night just yet, Aurum offers a perfect venue to relax and savor a drink. Similarly, Bar Senza Nome is well-suited for those looking to unwind in a social setting. Caffè Ristretto is another excellent spot to enjoy a nightcap after a delightful meal.

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.