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

Day 2 offers an itinerary packed with the best things to see in Bologna. You’ll stay in Bologna for 1 night more, offering you enough time to explore at a relaxed pace.

Look forward to a unique sightseeing adventure at the frequently visited Piazza Santo Stefano and allow yourself time to explore. Just a short distance away you'll find your next stop, Two Towers, a breathtaking monument that draws visitors from far and near.

Continue your journey to Bologna Cathedral, one of the city’s most intriguing spots that you shouldn’t miss. Another great site to visit is the up-and-coming Fountain Of Neptune, Bologna. When you're finished at the monument, Palazzo Del Podestà, Bologna awaits your visit. This palace is a heritage-rich highlight on today's itinerary. Last up is a public square - the extraordinary Piazza Maggiore.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

Indulge in a memorable dining experience at one of Bologna's most popular restaurants, and connect with friendly locals for a true cultural experience.

Make sure to reserve a table at Bononia Cafè, 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 Via Con Me, 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 Trattoria Pizzeria La Mela, a hidden gem nestled in Bologna. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Lime Bar, known for its inviting atmosphere. Macondo - Cocktail Bar is another great option if you’re looking for a place to get the night started. Similarly, Bar Onda Marina By Night provides a great setting to enjoy the night away.

Get a good night's sleep and look forward to another great day on the road 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 place, which are Florence. At the end of the day, you will retreat to the hotel of your choice in Florence, where will spend 2 nights.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Florence. This drive usually takes around 1 hour 30 min, without any stops or traffic disruptions.

When you're ready for some sights, head to Piazzale Michelangelo, an extraordinary observation deck in Florence. Explore its visually striking features at your own pace before you continue your journey to your next attraction, Ponte Vecchio. This world-famous historical landmark is a top recommendation in the area.

When you’re ready to explore more, Uffizi Gallery is an excellent choice. Spend some time discovering what some claim to be the most historic art gallery in the region. Next, continue your sightseeing at the popular Palazzo Vecchio and discover what makes this palace unique. If you’re up for one more stop in the city, head to Cathedral Of Santa Maria Del Fiore, an enchanting church many travelers find the visit worthwhile.

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.

Florence is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Florence.

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.

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

Wake up to day 4 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Pisa, Lucca, and Greti. With 1 night to stay in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Continue your road trip and head to your next destination, Pisa. This car ride takes around 1 hour 16 min.

Savor the day by heading to Piazza Del Duomo, Pisa, a world-famous public square that draws visitors from near and far. When you're done, continue to Leaning Tower Of Pisa, where you can soak in the culturally significant surroundings.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Lucca. This drive usually takes around 32 min, without any stops or traffic disruptions.

Spend your afternoon discovering Guinigi Tower, a beloved monument known for its culturally significant features. Next, continue your sightseeing at Piazza Dell'anfiteatro, a captivating public square.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Greti may take around 1 hour 20 min. Upon your arrival in Greti, you’ll be greeted with the opportunity to do some sightseeing and exploring.

When you're ready for some sights, head to Villa Calcinaia - Conti Capponi, an often recommended winery in Greti. Explore its visually striking features at your own pace before you continue your journey.

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.

Enjoy a lovely dining experience at Ditta Artigianale, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Trattoria Da Burde, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

Continue your lively evening at Bar 50 Rosso, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bitter Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Archea Brewery ensures a night out tailored to your taste.

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

Your itinerary for day 5 of your road trip in Italy includes 1 stop and features some of the highlights of Siena. At the end of the day, enjoy the comforts of a top-rated hotel in Siena, where you'll spend 1 night.

Fasten your seatbelt and make your way to your next stop — Siena, home to many well-known sights in the region. Keep in mind that your travel time from Florence to Siena may take around 1 hour 10 min without traffic disruptions. Upon arrival in Siena, we highly recommend checking out some of the top attractions.

Savor the day by heading to Fortezza Medicea (siena), an increasingly popular monument that draws visitors from near and far. When you're done, continue to Basilica Of San Domenico, where you can soak in the monumental surroundings.

Next, explore Siena Cathedral, yet another interesting place to see in the area. After the church, make time to go to Pubblico Palace. This picture-perfect palace is well worth the visit. Lastly, head to Piazza Del Campo, a famous public square you won’t want to miss.

When you’re done exploring for the day, you’ll drive to your hotel in Siena. Check in and relax before you head out to tour the city.

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.

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 consistently gains high praises from customers, it’s an ideal choice in Siena tonight.

Continue your evening by exploring the vibrant nightlife scene at Meet Life Cafè, a prime destination for a thrilling night out. Also, don’t forget to check out Maudit Pub, a bar that offers unique local touches. Likewise, Bar Impero Siena provides an excellent alternative for a fun evening.

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

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including San Gimignano. When you’re not sightseeing, take time to relax at your chosen hotel in Bologna, where you’ll be staying for 1 night.

Embrace the thrill of the open road as you wave goodbye to Siena and set your GPS to San Gimignano. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 43 min. Upon reaching San Gimignano, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Our first attraction recommendation in San Gimignano is Porta San Giovanni, a curiosity-inducing monument that draws attention for its historic features. Spend some time soaking in the atmosphere before continuing to Sangimignano1300, a heritage-rich museum that stands out in the village.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to Palazzo Comunale, Pinacoteca, Torre Grossa, a frequently visited museum that offers a unique experience. Be sure to also explore Piazza Del Duomo, a nearby public square, highly recommended by other travelers. End your self-guided tour at Rocca Di Montestaffoli, a romantic castle and the perfect final attraction in San Gimignano.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Bologna. Bologna 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 Bologna's most popular restaurants, and connect with friendly locals for a true cultural experience.

Enjoy a lovely dining experience at Va Mo Là, a popular restaurant in Bologna. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Bologna at Trattoria dal Biassanot, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Ristorante Enoteca da Lucia. It’s yet another ideal choice to enhance your time in Bologna tonight.

Round off your dining experience by visiting Aurum, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Senza Nome, a bar catering to every mood and preference. Caffè Ristretto likewise offers a unique atmosphere, perfect for a memorable night out.

Take some time to reflect on your day and savor another beautiful night in Italy.