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

On day 2 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Florence are on today's agenda. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

When you’re ready to jump back into the car and say goodbye to Bologna, you’ll hit the road in the direction of Florence. This drive usually takes 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 Uffizi Gallery. This extraordinary art gallery is a traveler-favorite in the city.

If you're keen to see more, continue to Ponte Vecchio. Feed your curiosity by learning something new about the historical landmark. Next, take your journey to Cathedral Of Santa Maria Del Fiore, a widely recognized church. Conclude your sightseeing at Galleria Dell'accademia, known for its heritage-rich 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.

Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, Se·sto On Arno Rooftop Bar is another popular option for a drink or two. Likewise, Il Vinile also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

Wake up to day 3 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Pisa and Lucca. With 1 night to stay in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Embrace the thrill of the open road as you wave goodbye to Florence and set your GPS to Pisa. 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 17 min. Upon reaching Pisa, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

When you're ready for some sights, head to Knights' Square, a locally appreciated public square in Pisa. Explore its breathtaking features at your own pace before you continue your journey to your next attraction, Leaning Tower Of Pisa. This timeless monument is a top recommendation in the area.

When you’re ready to explore more, Piazza Del Duomo, Pisa is an excellent choice. Spend some time discovering what some claim to be the most picture-perfect public square in the region. Next, continue your sightseeing at the frequently visited Pisa Cathedral and discover what makes this church unique.

When you’re ready to jump back into the car and say goodbye to Pisa, you’ll hit the road in the direction of Lucca. This drive usually takes around 30 min.

Mura Di Lucca is an often recommended historical landmark we recommend visiting today. Discover its visually striking features before continuing your self-guided tour.

When you’re done exploring for the day, you’ll return to Florence and your accommodation.

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

Savor the flavors at Ditta Artigianale, a top pick for dinner tonight. Alternatively, Trattoria Da Burde beckons with its unique menu offerings. Also, consider Casa Toscana. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

After savoring a delicious meal, step into the vibrant nightlife at Bar 50 Rosso, where the evening is just getting started. In the same way, Bitter Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Archea Brewery is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Experience an unparalleled adventure on day 4 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 places, which are San Gimignano and Siena. At the end of the day, you will retreat to the hotel of your choice in Siena, where will spend 2 nights.

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

When you're ready for some sights, head to Parco Della Rocca, a worthwhile park in San Gimignano. Explore its stunning features at your own pace before you continue your journey.

Embrace the thrill of the open road as you wave goodbye to San Gimignano 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 43 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), an up-and-coming monument that draws visitors from near and far. When you're done, continue to Basilica Of San Domenico, where you can soak in the grand surroundings.

Next, explore Siena Cathedral, yet another notable place to see in the area. After the church, make time to go to Piazza Del Campo. This visually striking public square is well worth the visit. Lastly, head to Tower Of Mangia, a locally appreciated monument 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.

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

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.

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.

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

Greet day 5 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night to stay in Siena, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Castelnuovo dell'Abate, Montalcino, Pienza, and San Quirico d'Orcia.

Castelnuovo dell'Abate’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Siena behind. This drive usually takes around 1 hour 4 min. Castelnuovo dell'Abate welcomes you with a multitude of unique vacation experiences.

One of our top recommendations for your sightseeing is Abbey Of Sant'antimo. Spend some time admiring the inviting features of the monastery before you continue to your next stop.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Montalcino. This drive usually takes around 12 min, without any stops or traffic disruptions.

One of our top recommendations for your sightseeing is Fortress Of Montalcino. Spend some time admiring the romantic features of the castle before you continue to your next stop. Then, head to Piazza Del Popolo. This curiosity-inducing public square is a traveler-favorite in the village.

After soaking in Montalcino’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Pienza. Expect your car journey to take a minimum of 31 min. When you arrive in Pienza, it's time to take a break from the road.

Our first attraction recommendation in Pienza is Palazzo Piccolomini, Pienza, an intriguing palace that draws attention for its UNESCO world heritage-listed features.

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

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 Siena, it's often a good idea to reserve a table in advance.

Make sure to reserve a table at Osteria Quattro Venti, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Fischi per Fiaschi, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Osteria da Divo, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Extend your evening after a delightful meal by visiting Charlie Mixology Bar Di Aldinucci Riccardo, which offers the perfect atmosphere for a night out. Moreover, Bar Pinacoteca is another popular option for a drink or two. Likewise, San Paolo Pub also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Get a good night's sleep and look forward to another great day on the road in Italy!

Your itinerary for day 6 of your road trip in Italy includes 1 stop and features some of the highlights of Rome. At the end of the day, enjoy the comforts of a top-rated hotel in Rome, where you'll spend 2 nights.

Rome’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Siena behind. This drive usually takes around 2 hours 42 min. Rome welcomes you with a multitude of unique vacation experiences.

Colosseum is an iconic archeological site we recommend visiting today. Discover its UNESCO world heritage-listed features before continuing your self-guided tour to Roman Forum, a historic archeological site that’s well-regarded in the area.

Next, stop by Trevi Fountain, a romantic monument. While you’re nearby, don’t forget to visit Pantheon, a culturally significant and truly unique monument. End your sightseeing at Piazza Navona, an iconic public square that’s highly recommended by travelers passing through the city.

At the end of the day, you will drive to Rome, 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 Rome's most popular restaurants, and connect with friendly locals for a true cultural experience.

Enjoy a delicious meal at La Bottega Roma, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Pasta In Corso, another top spot with a mouthwatering menu. You might also want to secure a reservation at Trattoria Vecchia Roma. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

Continue your lively evening at La Botticella Of Poggi Giovanni, a perfect place for winding down or revving up the night, depending on which mood you’re in. Almalu Trastevere is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Viminale Di Pepi Maurilio ensures a night out tailored to your taste.

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

On day 7 of your road trip, you'll get the chance to experience Vatican City and Rome. At the end of the day, you'll drive back to Rome, where you still have 1 night left to stay.

No visit to Rome is complete without Castel Sant'angelo. This famous castle is one of the top attractions in the city. Proceed to Piazza Di Spagna, another must-visit attraction.

As you wander through the inviting streets of Rome, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Spanish Steps. This top-rated public square is a traveler-favorite.

Fasten your seatbelt and make your way to your next stop — Vatican City, home to many well-known sights in the region. Keep in mind that your travel time from Rome to Vatican City may take around 12 min without traffic disruptions. Upon arrival in Vatican City, we highly recommend checking out some of the top attractions.

Vatican Museums is a globally renowned art museum we recommend visiting today.

When you’re done exploring for the day, you’ll return to Rome and your accommodation.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Rome. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Make sure to reserve a table at RomAntica, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Coso Ristorante, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of DEROMA - Farine Romane, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Cap off your dinner by heading to Sant' Eustachio Caffè, ideal for a leisurely evening with a drink in hand. Yellowsquare Rome is another bar that offers an enjoyable setting. Similarly, Caffè Portofino is also a popular place to go on a night out, perfect for relaxing and socializing.

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

On day 8 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Orvieto. When you’re not sightseeing, take time to relax at your chosen hotel in Bologna, where you’ll be staying for 1 night.

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

Fasten your seatbelt and make your way to your next stop — Orvieto, home to many well-known sights in the region. Keep in mind that your travel time from Rome to Orvieto may take around 1 hour 35 min without traffic disruptions. Upon arrival in Orvieto, we highly recommend checking out some of the top attractions.

Spend your afternoon discovering Well Of St. Patrick, a popular monument known for its picture-perfect features.

Fasten your seatbelt and make your way to your next stop — Orvieto, home to many well-known sights in the region. Keep in mind that your travel time from Rome to Orvieto may take around 1 hour 35 min without traffic disruptions. Upon arrival in Orvieto, we highly recommend checking out some of the top attractions.

Our first attraction recommendation in Orvieto is Orvieto Cathedral, a well-known church that draws attention for its romantic features. Spend some time soaking in the atmosphere before continuing to Museo Dell'opera Del Duomo, a photogenic 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 Orvieto Underground, an underrated cave system that offers a unique experience. Be sure to also explore Torre Del Moro Orvieto, a nearby monument, highly recommended by other travelers. End your self-guided tour at Pozzo Della Cava, a heritage-rich cave and the perfect final attraction in Orvieto.

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.

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.

Have a fantastic dining experience at Bononia Cafè, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Via Con Me offers an enticing alternative with its varied menu. Additionally, Trattoria Pizzeria La Mela is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Bologna.

Round off your dining experience by visiting Lime Bar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Macondo - Cocktail Bar, a bar catering to every mood and preference. Bar Onda Marina By Night likewise offers a unique atmosphere, perfect for a memorable night out.

Raise your glass to another unforgettable day in Italy!