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.

Today, you'll explore some of the most beautiful places in Bologna, including a palace, a public square, a library, a church, a monument and much more! Start your day with a visit to Palazzo D'accursio. This intriguing palace is a must-visit in the city. When you’re ready for your next discovery, continue to Piazza Maggiore, which may be one of the most romantic 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 Biblioteca Salaborsa, an often recommended library in the city. If you’re up for more discoveries, don’t forget to reserve some time for Bologna Cathedral and Fountain Of Neptune, Bologna. End your day with a visit to Palazzo Re Enzo, an intriguing palace that’s sure to leave a lasting impression.

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.

Make sure to reserve a table at Ristorante Oliviero 1962, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Di Poneta Novoli, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Caffe San Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Manifattura, a well-loved spot among locals and tourists. Or, head to Se·sto On Arno Rooftop Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Il Vinile, another top-rated place in the area.

Say good night to Florence and look forward to another great day of your road trip 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.

Set out on a day brimming with family-friendly attractions, romantic experiences, and scenic views. Start at the impressive Piazza Della Signoria, a masterful public square in Florence. Next, go to Cathedral Of Santa Maria Del Fiore.

After visiting Piazza Della Signoria and Cathedral Of Santa Maria Del Fiore, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Ponte Vecchio. This romantic historical landmark offers a unique experience. Uffizi Gallery is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Basilica Of Santa Croce In Florence, one of the most photogenic places to visit in Florence. If you still have some time left for sightseeing, we also recommend stopping by Piazzale Michelangelo.

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.

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

Enjoy a delicious meal at Enoteca I Terzi, a highly-rated dining destination in Siena. If you're eager to try something different, consider Ristorante Tar-Tufo, another top spot with a tantalizing menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

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.

Raise your glass and celebrate another amazing day of your road trip 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 itinerary in Siena covers several incredible sights, including a public square, a church, and a monument. Start your adventure at Piazza Del Campo. This astonishing public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the enchanting wonders of Siena Cathedral, 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 Porta San Giovanni. This up-and-coming monument offers an enriching experience. For a change of pace, head to Piazza Del Duomo, Pisa, where you can take in picture-perfect features. Conclude your self-guided sightseeing tour with a visit to Leaning Tower Of Pisa. These sights offer a fulfilling end to a perfect day.

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 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.

After your meal, keep the night alive at a bar like Lime Bar, known for its lively atmosphere. Macondo - Cocktail Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Onda Marina By Night offers an excellent atmosphere for those looking to amp up the evening.

Savor another day of unforgettable experiences in Italy!