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

On day 2 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 Bologna. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Prepare for a day full of fun adventures, breathtaking views, and photo-friendly spots. When you’re ready, kick off your sightseeing adventure at Palazzo D'accursio. This intriguing palace is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazza Maggiore, one of the city’s best highlights.

Next, check out Biblioteca Salaborsa, one of the most curiosity-inducing places to see in Bologna. This library is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Bologna Cathedral. Wander around and soak in the picture-perfect atmosphere this church offers. Then, head to Fountain Of Neptune, Bologna, a top-rated monument that adds another dimension to your day. Finally, visit the locally appreciated Palazzo Re Enzo, the last of our attraction recommendations for today.

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.

Enjoy a delicious meal at Ristorante Oliviero 1962, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Di Poneta Novoli, another top spot with a mouthwatering menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

Keep the evening going at Manifattura, a great choice for enjoying the after-dinner hours with a drink. You could also go to Se·sto On Arno Rooftop Bar, which offers a similarly pleasant setting and great drinks. Another option is Il Vinile, which provides an inviting environment for unwinding after a busy day out.

Raise your glass to another unforgettable day in Italy!

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. 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 1 night.

A blend of fun adventures, romantic experiences, and scenic views await you in Florence on today’s itinerary. First up is the astonishing public square, Piazza Della Signoria. Afterward, continue to Cathedral Of Santa Maria Del Fiore, a church every traveler should visit.

As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Ponte Vecchio. This wondrous historical landmark is an essential stop. Following that, head to Uffizi Gallery, another must-visit site that will enhance your experience. Don’t forget to stop by Basilica Of Santa Croce In Florence, a captivating church in the city. Finally, end your day with a visit to Piazzale Michelangelo, a romantic observation deck that offers the perfect conclusion to your sightseeing of the day.

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 explore more of Siena, 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.

Treat yourself to a wonderful meal at Enoteca I Terzi, a top-rated dining spot in Siena. If you're in the mood for something new, try Ristorante Tar-Tufo, another premier location with a delectable menu. You might also want to book a table at Antica Trattoria Papei. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Meet Life Cafè stands out as an excellent choice for a post-dinner cocktail. Alternatively, Maudit Pub offers an ideal atmosphere to enjoy the pleasures of the night. Bar Impero Siena 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 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 3 destinations, Siena, San Gimignano, and Pisa. When you’re not sightseeing, take time to relax at your selected hotel in Bologna, where you’ll be staying for 1 night.

Today’s route brings fun adventures, romantic experiences, and scenic views. The first attraction of today is Piazza Del Campo. This impressive public square is a respected place to see in Siena. Continue your discovery at Siena Cathedral, a history-steeped church with stories to tell.

As you stroll around Siena, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Porta San Giovanni. This worthwhile monument offers an UNESCO world heritage-designated encounter with Siena. Next, make your way to Piazza Del Duomo, Pisa to add another highlight to your day. After that, visit Leaning Tower Of Pisa, an iconic monument 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 Siena.

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.

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.

Treat yourself to a delicious dinner at Bononia Cafè, an excellent option for tonight's dining. Looking for something different? Via Con Me offers a tantalizing alternative with its diverse menu. And don’t miss Trattoria Pizzeria La Mela. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Bologna.

Following your dinner, dive into the local bar culture at Lime Bar. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Macondo - Cocktail Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Onda Marina By Night provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Head back to your accommodation in Bologna and get some rest in preparation for another magical day of your road trip in Italy!