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

Dive into day 2 of your remarkable road trip in Italy. Today you will explore Bologna, 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 Florence. You’ll stay here for 1 night.

Today, you'll explore some of the most beautiful places in Bologna, including a public square, a monument, and a church. Start your day with a visit to Piazza Maggiore. This top-rated public square is a must-visit in the city. When you’re ready for your next discovery, continue to Piazza Santo Stefano, which may be one of the most visually striking places you will experience today.

One of the best things about exploring Bologna 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 Two Towers, one of the city’s most locally renowned monument. If you’re up for more discoveries, don’t forget to reserve some time for Bologna Cathedral and Fountain Of Neptune, Bologna.

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.

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 and reflect on the day's adventures.

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.

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

Today’s itinerary in Florence covers several incredible sights, including a public square, a church, a historical landmark, an art gallery, an observation deck and much more! Start your adventure at Piazza Della Signoria. This impressive public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the history-steeped wonders of Cathedral Of Santa Maria Del Fiore, a must-see church 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 Ponte Vecchio. This wondrous historical landmark offers an enriching experience. For a change of pace, head to Uffizi Gallery, where you can take in its instagrammable features. Conclude your self-guided sightseeing tour with a visit to Piazzale Michelangelo. This awe-inspiring observation deck offers a fulfilling end to a perfect day.

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.

Enjoy a lovely meal at Enoteca I Terzi, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante Tar-Tufo is another top choice with a popular menu. You could also check for a table at Antica Trattoria Papei. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

Keep the evening going at Meet Life Cafè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Maudit Pub, which offers a similarly pleasant setting and great drinks. Another option is Bar Impero Siena, which provides an inviting environment for unwinding after a busy day out.

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

On day 4 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 Siena, San Gimignano, and Pisa. In the evening, you’ll end up in Bologna, where you will stay for 1 night.

Bring your curiosity for today’s adventure around Siena. Some of the city’s most loved attractions await. Siena Cathedral is the perfect place to start. This church is one of the most notable places to visit in Siena.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in San Gimignano. This drive usually takes around 46 min, without any stops or traffic disruptions.

Your self-guided tour starts at Piazza Del Duomo, an underrated public square that is sure to impress. Take in the surroundings and enjoy the freedom of exploring before you continue your journey.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Pisa. This drive usually takes around 1 hour 19 min, without any stops or traffic disruptions.

Spend your afternoon discovering Piazza Del Duomo, Pisa, a globally renowned public square known for its picture-perfect features. After taking in the atmosphere, continue to Leaning Tower Of Pisa, a wondrous monument that is a must-see for anyone visiting the region.

After soaking up all the sights of today's itinerary, you'll be ready to hit the road in the direction of your accommodation in Bologna. Bologna offers plenty of top-rated hotels and other places to stay on any travel budget. Take some time to relax before you head out to explore.

As you explore more of Bologna, 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 delightful dinner at Bononia Cafè, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Via Con Me? It's another excellent option with a diverse menu. Consider reserving a table at Trattoria Pizzeria La Mela as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Bologna.

Round off your dining experience by visiting Lime Bar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Macondo - Cocktail Bar, a bar catering to every mood and preference. Bar Onda Marina By Night likewise offers a unique atmosphere, perfect for a memorable night out.

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