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.

Brace yourself for today’s incredible lineup of attractions in Bologna, featuring family-friendly attractions, breathtaking views, and photo-friendly spots. Start at Palazzo D'accursio, a curiosity-inducing palace in the city. Then, head to Piazza Maggiore and soak in the ambiance of this enchanting public square.

There are many interesting places to see in Bologna, and when you are ready for more, go to Biblioteca Salaborsa. This is one of the city’s most locally appreciated photogenic spots of interest. After exploring the library, visit the curiosity-inducing Bologna Cathedral. Not far away, you'll also find Fountain Of Neptune, Bologna. This monument is a photogenic highlight in Bologna. Before wrapping up your self-guided sightseeing tour, head to Palazzo Re Enzo, a curiosity-inducing palace in the city.

At the end of the day, you will drive to Florence, 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 Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Treat yourself to a delightful dinner at Ristorante Oliviero 1962, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Di Poneta Novoli? It's another excellent option with a diverse menu. Consider reserving a table at Caffe San Firenze as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

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.

Savor another day of unforgettable experiences in Italy!

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.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Piazza Della Signoria. This majestic public square is sure to ignite your curiosity. Next, dive into the visually striking features of Cathedral Of Santa Maria Del Fiore, a must-visit church in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Ponte Vecchio, a world-famous historical landmark. For a change of scene, check out Uffizi Gallery, known for its historic features. We also recommend visiting Basilica Of Santa Croce In Florence. This church is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Piazzale Michelangelo, yet another impressive attraction in Florence.

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 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.

Have a fantastic dining experience at Enoteca I Terzi, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante Tar-Tufo offers an enticing alternative with its varied menu. Additionally, Antica Trattoria Papei is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.

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.

Raise your glass to another unforgettable day 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.

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and breathtaking views. Whether you decide to explore Siena on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Piazza Del Campo is the first of them. Spend some time admiring this enchanting public square before continuing your journey. Siena Cathedral is your next stop. This interesting church is one of the best-rated sights in Siena.

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 Porta San Giovanni. This awe-inspiring monument is a sight to behold. To round off your sightseeing experience, visit Piazza Del Duomo, Pisa and Leaning Tower Of Pisa.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Bologna. Bologna 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 Bologna's best restaurants.

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.

If you’re not ready to end the night just yet, Lime Bar offers a perfect venue to relax and savor a drink. Similarly, Macondo - Cocktail Bar is well-suited for those looking to unwind in a social setting. Bar Onda Marina By Night is another excellent spot to enjoy a nightcap after a delightful meal.

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