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, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Florence. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

Get ready to discover some of the most iconic wonders in Bologna, including an observation deck, an art gallery, a historical landmark, a church, a public square and much more! Start your day at Piazzale Michelangelo. This symbolic observation deck is a spectacular place to see in Bologna. Then, wander over to Uffizi Gallery. If instagrammable sites excite you, this art gallery will be right up your alley. Nearby, you’ll also find Ponte Vecchio. This romantic historical landmark is a favorite among visitors.

Bologna offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Cathedral Of Santa Maria Del Fiore is an extraordinary spot in the city that will captivate you with its unique charm. When you’re done at the church, don’t forget to check out the detailed Galleria Dell'accademia. Take a moment to appreciate the fascinating details of this captivating art gallery. Wrap up your self-guided tour of Bologna's top attractions with a visit to Piazza Della Signoria.

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.

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 and reflect on the day's adventures.

Enjoy a delicious meal at Ristorante Oliviero 1962, a highly-rated dining destination in Florence. If you're eager to try something different, consider Di Poneta Novoli, another top spot with a tantalizing menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

Continue your lively evening at Manifattura, a perfect place for winding down or revving up the night, depending on which mood you’re in. Se·sto On Arno Rooftop Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Il Vinile ensures a night out tailored to your taste.

Savor another day of unforgettable experiences in Italy!

Wake up to day 3 of your extraordinary road trip in Italy. With 1 night left in Florence, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Today’s route brings fun adventures, breathtaking views, and picturesque spots. The first attraction of today is Knights' Square. This frequently visited public square is a picture-perfect place to see in Florence. Continue your discovery at Leaning Tower Of Pisa, an UNESCO world heritage-listed monument with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Del Duomo, Pisa. This timeless public square offers a historic encounter with Florence. Next, make your way to Pisa Cathedral to add another highlight to your day. After that, visit Mura Di Lucca, an up-and-coming historical landmark that’s sure to impress. 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.

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

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.

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.

Let the evening flow smoothly from dinner to drinks at Bar 50 Rosso, a top-rated bar in the area. For other recommendations, Bitter Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Archea Brewery offers a memorable night with diverse drink options and excellent service.

Raise your glass to another unforgettable day in Italy!

Dive into day 4 of your remarkable road trip in Italy. Today you will explore San Gimignano and Siena, 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 Siena. You’ll stay here for 2 nights.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Parco Della Rocca. This enchanting park is a highlight of any visit in the village. Then, enjoy Fortezza Medicea (siena), another historic attraction that never fails to captivate visitors. Next, head over to Basilica Of San Domenico, one of the village’s most beloved attractions, known for its historic features.

If you’re looking for more, spend time soaking in the atmosphere of Siena Cathedral. This culturally significant church is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Del Campo, a top-rated public square, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Tower Of Mangia before you head back to your hotel.

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

Treat yourself to a wonderful meal at Enoteca I Terzi, a top-rated dining spot in Siena. If you're in the mood for something new, try Ristorante Tar-Tufo, another premier location with a delectable menu. You might also want to book a table at Antica Trattoria Papei. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Meet Life Cafè stands out as an excellent choice for a post-dinner cocktail. Alternatively, Maudit Pub offers an ideal atmosphere to enjoy the pleasures of the night. Bar Impero Siena is also a great option that provides a perfect setting for a relaxing evening.

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.

At the end of the day, you'll drive back to Siena, where you'll stay for 1 night more.

Siena is home to plenty of attractions that offer family-friendly attractions, romantic experiences, and breathtaking views! Start at Abbey Of Sant'antimo, an up-and-coming monastery that is worthwhile a visit in the village. Nearby, you’ll find Fortress Of Montalcino, enchanting visitors with its enchanting appeal. Continue your exploration at Piazza Del Popolo. This public square is one of the village’s most locally appreciated spots.

Enjoy the freedom of exploring Siena at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Palazzo Piccolomini, Pienza. After exploring the palace, head to the frequently visited Chapel Vitaleta. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Cipressi Di San Quirico D'orcia, a place of romantic interest in Siena.

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

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

Treat yourself to a delicious dinner at Osteria Quattro Venti, an excellent option for tonight's dining. Looking for something different? Fischi per Fiaschi offers a tantalizing alternative with its diverse menu. And don’t miss Osteria da Divo. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Charlie Mixology Bar Di Aldinucci Riccardo, a well-loved spot among locals and tourists. Or, head to Bar Pinacoteca. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at San Paolo Pub, another top-rated place in the area.

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

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Rome. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 2 nights.

Today’s route brings family-friendly attractions, scenic views, and photo-friendly spots. The first attraction of today is Colosseum. This timeless archeological site is a historic place to see in Siena. Continue your discovery at Roman Forum, an awe-inspiring archeological site with stories to tell.

As you stroll around Siena, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Trevi Fountain. This timeless monument offers a visually striking encounter with Siena. Next, make your way to Pantheon to add another highlight to your day. After that, visit Piazza Navona, an iconic public square that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Siena.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Rome. Rome 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 Rome's best restaurants.

Make sure to reserve a table at La Bottega Roma, 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 Pasta In Corso, 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 Trattoria Vecchia Roma, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Explore the vibrant nightlife at La Botticella Of Poggi Giovanni after your meal, a hub for lively evenings and memorable moments. Or, head to Almalu Trastevere for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Viminale Di Pepi Maurilio is perfect for those looking to extend their night with a touch of local flavor.

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

On day 7 of your road trip, you’ll start and end your day in Rome, where you'll stay for 1 night more.

Begin your adventure at Vatican Museums. This is a world-famous art museum you should not miss. Another must-see is St. Peter's Basilica, a wondrous major basilica in Rome.

When you’re ready for the next sight, head to Sistine Chapel. From there, take a leisurely stroll to Castel Sant'angelo, another of the city’s impressive attractions. We recommend continuing your self-guided tour at Piazza Di Spagna, a visually striking place of interest in the city. If time allows, add Spanish Steps to your itinerary. This extraordinary public square offers the perfect finishing touch to your day in Rome.

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

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

Don’t miss out on dining at RomAntica, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Coso Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at DEROMA - Farine Romane. 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 Sant' Eustachio Caffè, a perfect place for winding down or revving up the night, depending on which mood you’re in. Yellowsquare Rome is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Caffè Portofino ensures a night out tailored to your taste.

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

Experience an unparalleled adventure on day 8 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Orvieto. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Bologna. You will spend 1 night here for some well-deserved relaxation.

Rome is home to plenty of attractions that offer family-friendly attractions, breathtaking views, and picturesque spots! Start at Well Of St. Patrick, a popular monument that is worthwhile a visit in the village. Nearby, you’ll find Orvieto Cathedral, enchanting visitors with its history-steeped appeal. Continue your exploration at Museo Dell'opera Del Duomo. This museum is one of the village’s most up-and-coming spots.

Enjoy the freedom of exploring Rome at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Orvieto Underground. After exploring the cave system, head to the curiosity-inducing Torre Del Moro Orvieto. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Pozzo Della Cava, a place of photogenic interest in Rome.

At the end of the day, you will drive to Bologna, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

As you explore more of Bologna, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Enjoy a lovely meal at Bononia Cafè, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Via Con Me is another top choice with a popular menu. You could also check for a table at Trattoria Pizzeria La Mela. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Bologna tonight.

Extend your evening after a delightful meal by visiting Lime Bar, which offers the perfect atmosphere for a night out. Moreover, Macondo - Cocktail Bar is another popular option for a drink or two. Likewise, Bar Onda Marina By Night 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!