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

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.

Your adventure in Bologna is only getting started when you visit Two Towers, a popular local hot spot. Another notable attraction to explore is Piazza Santo Stefano. This intriguing public square is known for its picture-perfect appeal.

After soaking in the highlights of these sights, take some time to wander Bologna's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Basilica Of San Domenico. This noteworthy church offers a fascinating experience that many visitors find memorable.

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.

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.

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

Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Florence.

After soaking in Bologna’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Florence. Expect your car journey to take a minimum of 1 hour 30 min. When you arrive in Florence, it's time to take a break from the road.

Savor the day by heading to Piazzale Michelangelo, an impressive observation deck that draws visitors from near and far. When you're done, continue to Ponte Vecchio, where you can soak in the visually striking surroundings.

Next, explore Uffizi Gallery, yet another widely recognized place to see in the area. After the art gallery, make time to go to Basilica Of Santa Croce In Florence. This photogenic church is well worth the visit. Lastly, head to Piazza Della Signoria, a widely recognized public square you won’t want to miss.

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.

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 delicious meal 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.

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.

Relax and look forward to more memorable moments to come!

Greet day 4 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night to stay in Florence, 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 Pisa and Florence.

Whether you decide to explore Pisa on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

One of the most popular attractions included on the itinerary is Galleria Dell'accademia. This heritage-rich art gallery will help you start your sightseeing on top. Then, take a leisurely stroll to Cathedral Of Santa Maria Del Fiore and learn what makes this inviting church unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the captivating Basilica Di Santa Maria Novella, Firenze (fi).

When you’re ready to jump back into the car and say goodbye to Florence, you’ll hit the road in the direction of Pisa. This drive usually takes around 1 hour 16 min.

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 world-famous public square that everyone visiting Pisa should see. Next, head to Leaning Tower Of Pisa. This noteworthy monument is one of the most iconic attractions in the region.

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

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.

Enjoy a delicious meal at Ditta Artigianale, a highly-rated dining destination in Florence. If you're eager to try something different, consider Trattoria Da Burde, another top spot with a tantalizing menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

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.

Raise your glass and celebrate another amazing day 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 2 nights.

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 8 min. Upon reaching Siena, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

For a more meaningful self-guided tour of the city's best attractions, visit Basilica Of San Domenico, an underrated church 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 Piccolomini Library and admire its historic features.

When you’re ready, continue to Siena Cathedral, a captivating church beloved by locals and tourists alike. Don't miss out on Piazza Del Campo, another highlight of the area that promises a memorable visit. Not far away, you’ll also find Tower Of Mangia, an UNESCO world heritage-listed 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 Siena. Check in and relax 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 Siena. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Dine in style at Enoteca I Terzi, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante Tar-Tufo boasts a menu that's sure to impress. Also, be sure to check out Antica Trattoria Papei. Known as a local hotspot, it’s a great choice for tonight in Siena.

To truly maximize your evening out, consider visiting Meet Life Cafè after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Maudit Pub, another bar with an inviting ambiance. Similarly, Bar Impero Siena also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

On day 6 of your road trip, you’ll start and end your day in Siena, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate city, including Pievasciata, San Regolo, and Castellina in Chianti.

Pievasciata’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Siena behind. This drive usually takes around 26 min. Pievasciata welcomes you with a multitude of unique vacation experiences.

When you're ready for some sights, head to Parco Sculture Del Chianti, an often recommended sculpture garden in Pievasciata. Explore its visually striking features at your own pace before you continue your journey.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to San Regolo may take around 21 min. Upon your arrival in San Regolo, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Our first attraction recommendation in San Regolo is Castello Di Brolio, an intriguing castle that draws attention for its enchanting features.

After soaking in San Regolo’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Castellina in Chianti. Expect your car journey to take a minimum of 43 min. When you arrive in Castellina in Chianti, it's time to take a break from the road.

Spend your afternoon discovering Rocca Di Castellina In Chianti, an up-and-coming castle known for its history-steeped 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.

Savor the flavors at Osteria Quattro Venti, a top pick for dinner tonight. Alternatively, Fischi per Fiaschi beckons with its unique menu offerings. Also, consider Osteria da Divo. With its consistent customer satisfaction, it’s an excellent option for dining in Siena tonight.

After savoring a delicious meal, step into the vibrant nightlife at Charlie Mixology Bar Di Aldinucci Riccardo, where the evening is just getting started. In the same way, Bar Pinacoteca offers a unique charm perfect for experiencing the local bar scene in Siena. San Paolo Pub is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Raise your glass to another unforgettable day in Italy!

Day 8 of your road trip across Italy promises a magnificent time exploring what to see in Rome. You have 1 night left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

No visit to Rome is complete without Colosseum. This wondrous archeological site is one of the top attractions in the city. Proceed to Roman Forum, 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 Trevi Fountain. This iconic monument is a traveler-favorite. Not far away, you’ll find Pantheon, another key site on your sightseeing itinerary. Piazza Navona is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers. Conclude your day at Castel Sant'angelo and uncover why it's recognized as one of the city's most extraordinary attractions.

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

Enjoy a lovely dining experience at RomAntica, a popular restaurant in Rome. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Rome at Coso Ristorante, 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 DEROMA - Farine Romane. It’s yet another ideal choice to enhance your time in Rome tonight.

After your meal, keep the night alive at a bar like Sant' Eustachio Caffè, known for its lively atmosphere. Yellowsquare Rome is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Caffè Portofino offers an excellent atmosphere for those looking to amp up the evening.

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

Dive into day 9 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Orvieto. At the end of the day, you’ll unwind at one of the finest accommodations in Bologna, where you'll spend 1 night.

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.

One of our top recommendations for your sightseeing is Well Of St. Patrick. Spend some time admiring the historic features of the monument before you continue to your next stop.

When you’ve had your share of Rome, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Orvieto. Your travel time is around 1 hour 35 min.

Our first attraction recommendation in Orvieto is Orvieto Cathedral, a popular church that draws attention for its enchanting 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 up-and-coming 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, an eye-catching 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.

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

Savor the flavors at Va Mo Là, a top pick for dinner tonight. Alternatively, Trattoria dal Biassanot beckons with its unique menu offerings. Also, consider Ristorante Enoteca da Lucia. With its consistent customer satisfaction, it’s an excellent option for dining in Bologna tonight.

After savoring a delicious meal, step into the vibrant nightlife at Aurum, where the evening is just getting started. In the same way, Bar Senza Nome offers a unique charm perfect for experiencing the local bar scene in Bologna. Caffè Ristretto is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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