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

Day 2 of your road trip will take you to the best attractions Bologna has to offer. Cherish the 1 night you have left in Bologna by discovering the best things there are to see and do in the city.

Today’s route brings family-friendly attractions, romantic experiences, and scenic views. The first attraction of today is Piazza Santo Stefano. This locally appreciated public square is a romantic place to see in Bologna. Continue your discovery at Two Towers, a breathtaking monument 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 Bologna Cathedral. This beloved church offers a stunning encounter with Bologna. Next, make your way to Fountain Of Neptune, Bologna to add another highlight to your day. After that, visit Palazzo Del Podestà, Bologna, an up-and-coming palace that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Piazza Maggiore, an extraordinary public square 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.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

Experience shopping bliss at Bologna as you explore Galleria Cavour. Take a leisurely stroll through unique and high-end shops, where local treasures are waiting to be found. Beyond shopping, Galleria Cavour offers more options, including unique attractions, key services, and vibrant events.

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.

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.

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.

Savor another day of unforgettable experiences in Italy!

On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 2 nights.

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

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.

Savor the flavors at Ristorante Oliviero 1962, a top pick for dinner tonight. Alternatively, Di Poneta Novoli beckons with its unique menu offerings. Also, consider Caffe San Firenze. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

Unwind after your meal by stepping into Manifattura. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Se·sto On Arno Rooftop Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Il Vinile, another top-rated bar in the area.

As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.

At the end of the day, you'll drive back to Florence, where you'll stay for 1 night more.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Piazza Del Duomo, Pisa. This culturally significant public square is a highlight of any visit in the city. Then, enjoy Leaning Tower Of Pisa, another detailed attraction that never fails to captivate visitors. Next, head over to Guinigi Tower, one of the city’s most worthwhile attractions, known for its culturally significant features.

If you’re looking for more, spend time soaking in the atmosphere of Piazza Dell'anfiteatro. This romantic public square is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Villa Calcinaia - Conti Capponi, a curiosity-inducing winery, and take a stroll around the area.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.

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.

Dine in style at Ditta Artigianale, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria Da Burde boasts a menu that's sure to impress. Also, be sure to check out Casa Toscana. Known as a local hotspot, it’s a great choice for tonight in Florence.

After enjoying a fulfilling meal, continue your evening at Bar 50 Rosso, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bitter Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Archea Brewery provides an excellent environment for a relaxed and enjoyable evening.

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

On day 5 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. In the evening, you’ll end up in Siena, where you will stay for 1 night.

Florence is home to plenty of attractions that offer family-friendly attractions, scenic views, and photo-friendly spots! Start at Fortezza Medicea (siena), an up-and-coming monument that is worthwhile a visit in the city. Nearby, you’ll find Basilica Of San Domenico, enchanting visitors with its breathtaking appeal. Continue your exploration at Siena Cathedral. This church is one of the city’s most locally renowned spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Pubblico Palace. After exploring the palace, head to the astonishing Piazza Del Campo. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Tower Of Mangia, a place of respected interest in Florence.

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 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 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.

Let the evening flow smoothly from dinner to drinks at Meet Life Cafè, a top-rated bar in the area. For other recommendations, Maudit Pub provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Impero Siena offers a memorable night with diverse drink options and excellent service.

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

Experience an unparalleled adventure on day 6 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - San Gimignano. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Bologna. You will spend 1 night here for some well-deserved relaxation.

Bring your curiosity for today’s adventure around Siena. Some of the village’s most loved attractions await! Porta San Giovanni is the perfect place to start. This monument is one of the most intriguing places to visit in Siena. Next, head to Sangimignano1300, a frequently visited museum, known for its heritage-rich features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Palazzo Comunale, Pinacoteca, Torre Grossa. This breathtaking museum is a highly recommended experience. Nearby, you'll also find Piazza Del Duomo and Rocca Di Montestaffoli. Visit these for an interesting touch to your journey. Finish the day with a visit to Chiesa Di Sant'agostino, an instagrammable church in Siena.

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.

Make sure to reserve a table at Va Mo Là, an iconic dining spot in Bologna. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Trattoria dal Biassanot, a popular restaurant in Bologna. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante Enoteca da Lucia, a hidden gem nestled in Bologna. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Following your dinner, dive into the local bar culture at Aurum. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar Senza Nome, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffè Ristretto provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Head back to your accommodation in Bologna and get some rest in preparation for another magical day of your road trip in Italy!