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

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

Today’s route brings fun adventures, breathtaking views, and picturesque spots. The first attraction of today is Palazzo D'accursio. This worthwhile palace is a stunning place to see in Bologna. Continue your discovery at Piazza Maggiore, a culturally significant public square with stories to tell.

As you stroll around Bologna, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Biblioteca Salaborsa. This up-and-coming library offers a heritage-rich encounter with Bologna. Next, make your way to Bologna Cathedral to add another highlight to your day. After that, visit Fountain Of Neptune, Bologna, an up-and-coming monument that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Palazzo Re Enzo, a beloved palace 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 Bologna.

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.

Indulge in a memorable dining experience at one of Florence's most popular restaurants, and connect with friendly locals for an authentic adventure.

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.

If you’re not ready to end the night just yet, Manifattura offers a perfect venue to relax and savor a drink. Similarly, Se·sto On Arno Rooftop Bar is well-suited for those looking to unwind in a social setting. Il Vinile is another excellent spot to enjoy a nightcap after a delightful meal.

Raise your glass to another unforgettable day in Italy!

Experience an unparalleled adventure on day 3 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Florence. 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 well-planned self-sightseeing route offers several fun adventures, romantic experiences, and scenic views. Whether you decide to explore Florence on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Piazza Della Signoria is the first of them. Spend some time admiring this masterful public square before continuing your journey. Cathedral Of Santa Maria Del Fiore is your next stop. This impressive church is one of the best-rated sights in Florence.

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 Ponte Vecchio. This visually striking historical landmark is a sight to behold. To round off your sightseeing experience, visit Uffizi Gallery and Basilica Of Santa Croce In Florence. If time allows, end your day with Piazzale Michelangelo, a history-steeped observation deck that offers a memorable conclusion to your exploration.

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.

Treat yourself to a delightful dinner at Enoteca I Terzi, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante Tar-Tufo? It's another excellent option with a diverse menu. Consider reserving a table at Antica Trattoria Papei as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Siena.

Unwind after your meal by stepping into Meet Life Cafè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Maudit Pub offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Impero Siena, another top-rated bar in the area.

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

Dive into day 4 of your remarkable road trip in Italy. Today you will explore Siena, San Gimignano, and Pisa, 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.

Today’s agenda in Siena includes a public square, a church, and a monument. Piazza Del Campo is must-visit public square and a great starting point for the day. Next, continue your journey to Siena Cathedral, a popular church, located just a leisurely stroll away. Next, head to Porta San Giovanni, an enchanting monument, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Siena. If you’re looking for more, Piazza Del Duomo, Pisa is also a wondrous attraction that is worthwhile a visit. Lastly, don’t miss Leaning Tower Of Pisa, a timeless gem to see in the city.

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 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.

Savor the flavors at Bononia Cafè, a top pick for dinner tonight. Alternatively, Via Con Me beckons with its unique menu offerings. Also, consider Trattoria Pizzeria La Mela. With its consistent customer satisfaction, it’s an excellent option for dining in Bologna tonight.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Lime Bar stands out as an excellent choice for a post-dinner cocktail. Alternatively, Macondo - Cocktail Bar offers an ideal atmosphere to enjoy the pleasures of the night. Bar Onda Marina By Night is also a great option that provides a perfect setting for a relaxing evening.

Raise your glass and celebrate another amazing day of your road trip in Italy!