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.

Piazza Santo Stefano is an ideal stop early in the day. This increasingly popular public square is a must-visit in the city. When you’re ready for your next discovery, continue to Two Towers, which may be one of the most picture-perfect 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 Bologna Cathedral, an underrated church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Fountain Of Neptune, Bologna and Palazzo Del Podestà, Bologna. End your day with a visit to Piazza Maggiore, an extraordinary public square that’s sure to leave a lasting impression.

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.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Bologna, it's often a good idea to reserve a table in advance.

Don’t miss out on dining at Bononia Cafè, a top-rated dining destination in Bologna. If you're in the mood to try something new, consider Via Con Me, another top spot with a mouthwatering menu. You might also want to secure a reservation at Trattoria Pizzeria La Mela. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Bologna this evening.

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.

Relax and look forward to more memorable moments to come!

Dive into day 3 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Florence. At the end of the day, you’ll unwind at one of the finest accommodations in Florence, where you'll spend 2 nights.

When you’ve had your share of Bologna, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Florence. Your travel time is around 1 hour 30 min.

One of our top recommendations for your sightseeing is Piazzale Michelangelo. Spend some time admiring the visually striking features of the observation deck before you continue to your next stop. Then, head to Ponte Vecchio. This globally renowned historical landmark is a traveler-favorite in the city.

If you're keen to see more, continue to Uffizi Gallery. Feed your curiosity by learning something new about the art gallery. Next, take your journey to Palazzo Vecchio, a well-known palace. Conclude your sightseeing at Cathedral Of Santa Maria Del Fiore, known for its history-steeped features.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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 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.

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 fulfilling meal, continue your evening at Manifattura, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Se·sto On Arno Rooftop Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Il Vinile provides an excellent environment for a relaxed and enjoyable evening.

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

On day 4 of your road trip in Italy, you’ll start and end your day in Florence, but spend the day exploring what’s beyond the city. Since you still have 1 night to spend in Florence, there’s no need to rush. Experience Pisa, Lucca, and Greti to the fullest today with this curated day itinerary.

Throughout the day, make sure to take breaks to appreciate the surroundings.

Pisa’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Florence behind. This drive usually takes around 1 hour 16 min. Pisa welcomes you with a multitude of unique vacation experiences.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Piazza Del Duomo, Pisa, a wondrous public square that everyone visiting Pisa should see. Next, head to Leaning Tower Of Pisa. This culturally significant monument is one of the most wondrous attractions in the region.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Lucca may take around 32 min. Upon your arrival in Lucca, you’ll be greeted with the opportunity to do some sightseeing and exploring.

One of our top recommendations for your sightseeing is Guinigi Tower. Spend some time admiring the visually striking features of the monument before you continue to your next stop. Then, head to Piazza Dell'anfiteatro. This well-known public square is a traveler-favorite in the city.

Continue your road trip and head to your next destination, Greti. This car ride takes around 1 hour 20 min.

Set out on a self-guided sightseeing tour at Villa Calcinaia - Conti Capponi and explore the romantic features.

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

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Florence, it's often a good idea to reserve a table in advance.

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.

To truly maximize your evening out, consider visiting Bar 50 Rosso after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bitter Bar, another bar with an inviting ambiance. Similarly, Archea Brewery also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Head back to your accommodation in Florence and get some rest to prepare for another magical day of your road trip in Italy.

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Siena. At the end of the day, you will retreat to the hotel of your choice in Siena, where will spend 1 night.

Embrace the thrill of the open road as you wave goodbye to Florence and set your GPS to Siena. 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 1 hour 10 min. Upon reaching Siena, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

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

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

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.

Siena 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 Siena.

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

Cap off your dinner by heading to Meet Life Cafè, ideal for a leisurely evening with a drink in hand. Maudit Pub is another bar that offers an enjoyable setting. Similarly, Bar Impero Siena is also a popular place to go on a night out, perfect for relaxing and socializing.

Savor another day of unforgettable experiences in Italy!

On day 6 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. San Gimignano are on today's agenda. In the evening, you’ll end up in Bologna, where you will stay for 1 night.

When you’re ready to jump back into the car and say goodbye to Siena, you’ll hit the road in the direction of San Gimignano. This drive usually takes around 43 min.

For a more meaningful self-guided tour of the village's best attractions, visit Porta San Giovanni, an underrated monument that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Sangimignano1300 and admire its heritage-rich features.

When you’re ready, continue to Palazzo Comunale, Pinacoteca, Torre Grossa, an intriguing museum beloved by locals and tourists alike. Don't miss out on Piazza Del Duomo, another highlight of the area that promises a memorable visit. Not far away, you’ll also find Rocca Di Montestaffoli, an enchanting place to see that you won’t regret spending some extra time discovering.

When you’re done exploring for the day, you’ll drive to your hotel in Bologna. 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 Bologna. Enjoy a relaxing evening as you savor delicious local cuisine.

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.

Continue the enjoyment post-dinner at Aurum, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bar Senza Nome offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Caffè Ristretto. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Relax and look forward to more memorable moments to come!