7-Day Italy Self-Drive Road Trip With Itinerary from Bologna to Florence and San Gimignano

On day 2 of your road trip, you will have an entire day to explore Bologna. You’ll stay in Bologna for 1 night and discover all the best things to see and do in the area.

Bologna is brimming with adventures. Today’s wonderful stops include an art gallery, a monument, a public square, a church and much more! Begin your sightseeing adventure at the locally appreciated Pinacoteca Nazionale Di Bologna and allow yourself time to explore. Just a short distance away you'll find your next stop, Two Towers, a historic monument that draws visitors from far and near.

Continue your journey to Piazza Santo Stefano, one of the city’s most up-and-coming spots that you shouldn’t miss. Another great site to visit is the astonishing Piazza Maggiore. When you're finished at the public square, Bologna Cathedral awaits your visit. This church is a respected highlight on today's itinerary. Last up is a monument - the often recommended Fountain Of Neptune, 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.

After a day of adventure, treat yourself to an exquisite dinner at one of Bologna's best restaurants.

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.

Unwind after your meal by stepping into Lime Bar. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Macondo - Cocktail Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Onda Marina By Night, another top-rated bar in the area.

Raise your glass and celebrate another amazing 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 Florence. You will spend 1 night here for some well-deserved relaxation.

Immerse yourself in Bologna’s rich culture with today's sightseeing itinerary. Start your journey at Piazzale Michelangelo. This romantic observation deck is sure to ignite your curiosity. Next, dive into the heritage-rich features of Basilica Of Santa Croce In Florence, 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 Uffizi Gallery, a widely recognized art gallery. For a change of scene, check out Ponte Vecchio, known for its culturally significant features. We also recommend visiting Palazzo Vecchio. This palace is a must for anyone looking to experience the city to the fullest. Lastly, end your day with a visit to Cathedral Of Santa Maria Del Fiore, yet another impressive attraction in 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.

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

Don’t miss out on dining 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.

Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile likewise offers a unique atmosphere, perfect for a memorable night out.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Siena and San Gimignano. At the end of the day, you will enjoy the comforts of a top-rated hotel in San Gimignano, which will be your home away from home for 1 night.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Fortezza Medicea (siena). This curiosity-inducing monument provides an insightful glimpse into the city's identity. Next, discover Basilica Of San Domenico, a picture-perfect church, promising a delightful encounter.

Continue your sightseeing with a visit to Tower Of Mangia, a worthwhile monument. When you’re done, don’t forget to make a stop at the famous Piazza Del Campo. Not far away from the public square, you will find the romantic Piazza Del Duomo, perfect for a quick visit. Round off your day at Siena Cathedral, another gem in Florence with history-steeped features to discover.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in San Gimignano. San Gimignano offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in San Gimignano. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

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

Dive into day 5 of your remarkable road trip in Italy. Today you will explore Pisa and Lucca, 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.

Get ready for an exciting day in San Gimignano. Today’s sightseeing agenda includes a church, a public square, a monument, a historical landmark and much more! Begin your adventure at Pisa Cathedral. This is an often recommended church you should not miss. Another must-see is Piazza Del Duomo, Pisa, an iconic public square in San Gimignano.

When you’re ready for the next sight, head to Leaning Tower Of Pisa. From there, take a leisurely stroll to Mura Di Lucca, another of the city’s underrated attractions. We recommend continuing your self-guided tour at Piazza Dell'anfiteatro, a romantic place of interest in the city.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. 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 Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

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.

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