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

Experience an unparalleled adventure on day 2 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 Florence. You will spend 1 night here for some well-deserved relaxation.

Prepare for a day full of family-friendly attractions, scenic views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Palazzo D'accursio. This frequently visited 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 frequently visited 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 up-and-coming 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.

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

Have a fantastic dining experience at Ristorante Oliviero 1962, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Di Poneta Novoli offers an enticing alternative with its varied menu. Additionally, Caffe San Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Following your dinner, dive into the local bar culture at Manifattura. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Se·sto On Arno Rooftop Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Il Vinile provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

On day 3 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 Florence. In the evening, you’ll end up in Siena, where you will stay for 1 night.

Discover a day packed with fun adventures, romantic experiences, and breathtaking views in Florence. Begin your sightseeing with Piazza Della Signoria. This famous public square is one of the top attractions in the city. Proceed to Cathedral Of Santa Maria Del Fiore, another must-visit attraction.

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 Ponte Vecchio. This iconic historical landmark is a traveler-favorite. Not far away, you’ll find Uffizi Gallery, another key site on your sightseeing itinerary. Basilica Of Santa Croce In Florence is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Piazzale Michelangelo and uncover why it's recognized as one of the city's most famous attractions.

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

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.

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.

Keep the excitement of the evening going by visiting a bar or two. Meet Life Cafè is an excellent place to start. You could also check out Maudit Pub, offering a different kind of charm. A last recommendation for the day is Bar Impero Siena. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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 3 stops and experience some of the highlights of Siena, San Gimignano, and Pisa. At the end of the day, you will enjoy the comforts of a top-rated hotel in Bologna, which will be your home away from home for 1 night.

A blend of family-friendly attractions, romantic experiences, and breathtaking views await you in Siena on today’s itinerary. First up is the famous public square, Piazza Del Campo. Afterward, continue to Siena Cathedral, a church every traveler should visit.

As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Porta San Giovanni. This worthwhile monument is an essential stop. Following that, head to Piazza Del Duomo, Pisa, another must-visit site that will enhance your experience. Don’t forget to stop by Leaning Tower Of Pisa, a wondrous monument 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 delicious meal at Bononia Cafè, a highly-rated dining destination in Bologna. If you're eager to try something different, consider Via Con Me, another top spot with a tantalizing menu. You might also want to secure a reservation at Trattoria Pizzeria La Mela. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Bologna this evening.

Let the evening flow smoothly from dinner to drinks at Lime Bar, a top-rated bar in the area. For other recommendations, Macondo - Cocktail Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Onda Marina By Night offers a memorable night with diverse drink options and excellent service.

Raise your glass to another unforgettable day in Italy!