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

Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 2 nights here for some well-deserved relaxation.

Start by visiting Piazzale Michelangelo, a prime spot to begin your journey. This history-steeped observation deck is sure to impress. Next on your list is Uffizi Gallery, another must-visit landmark and spectacular art gallery renowned for its standout features.

While exploring and sightseeing, take time to savor the culture of Bologna by sampling some local delicacies. When you’re ready for more sightseeing, head to Ponte Vecchio. This romantic historical landmark is an essential place to visit for anyone looking for the full Bologna experience. We also recommend visiting Cathedral Of Santa Maria Del Fiore, an impressive church. Nearby, you'll also find Galleria Dell'accademia, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Piazza Della Signoria and wrap up your day with its enchanting appeal.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and spend some time relaxing before you head out to tour the city.

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

Dine in style at Ristorante Oliviero 1962, a top recommendation for dinner tonight. Or, for a change of pace, Di Poneta Novoli boasts a menu that's sure to impress. Also, be sure to check out Caffe San Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.

Cap off your dinner by heading to Manifattura, ideal for a leisurely evening with a drink in hand. Se·sto On Arno Rooftop Bar is another bar that offers an enjoyable setting. Similarly, Il Vinile 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!

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!

Florence is home to plenty of attractions that offer family-friendly attractions, scenic views, and picturesque spots! Start at Knights' Square, an intriguing public square that is worthwhile a visit in the city. Nearby, you’ll find Leaning Tower Of Pisa, enchanting visitors with its culturally significant appeal. Continue your exploration at Piazza Del Duomo, Pisa. This public square is one of the city’s most timeless spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Pisa Cathedral. After exploring the church, head to the intriguing Mura Di Lucca.

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 an authentic adventure.

Don’t miss out on dining at Ditta Artigianale, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Trattoria Da Burde, another top spot with a mouthwatering menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

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.

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.

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 itinerary in Florence covers several incredible sights, including a park, a monument, a church, a public square and much more! Start your adventure at Parco Della Rocca. This beloved park is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the picture-perfect wonders of Fortezza Medicea (siena), a must-see monument in the village.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Basilica Of San Domenico. This beloved church offers an enriching experience. For a change of pace, head to Siena Cathedral, where you can take in majestic features. Conclude your self-guided sightseeing tour with a visit to Piazza Del Campo and Tower Of Mangia. These sights offer a fulfilling end to a perfect day.

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.

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.

Keep the evening going at Meet Life Cafè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Maudit Pub, which offers a similarly pleasant setting and great drinks. Another option is Bar Impero Siena, which provides an inviting environment for unwinding after a busy day out.

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

On day 5 of your road trip, you’ll start and end your day in Siena, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Castelnuovo dell'Abate, Montalcino, Pienza, and San Quirico d'Orcia. You still have 1 night left in Siena.

Today’s agenda in Siena includes a monastery, a castle, a public square, a palace, a church, a rock formation and much more! Abbey Of Sant'antimo is must-visit monastery and a great starting point for the day. Next, continue your journey to Fortress Of Montalcino, a beloved castle, located just a leisurely stroll away. Next, head to Piazza Del Popolo, a visually striking public square, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Siena. When you're ready, let your sightseeing route take you to the often recommended Palazzo Piccolomini, Pienza. If you’re looking for more, Chapel Vitaleta is also a worthwhile attraction that is worthwhile a visit. Lastly, don’t miss Cipressi Di San Quirico D'orcia, a place of stunning interest in the village.

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.

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.

Following your dinner, dive into the local bar culture at Charlie Mixology Bar Di Aldinucci Riccardo. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar Pinacoteca, the perfect place for those looking to experience the best of the nightlife. Similarly, San Paolo Pub provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Get ready for an exciting day in Siena. Today’s sightseeing agenda includes an archeological site, a monument, and a public square. Begin your adventure at Colosseum. This is an iconic archeological site you should not miss. Another must-see is Roman Forum, a globally renowned archeological site in Siena.

When you’re ready for the next sight, head to Trevi Fountain. From there, take a leisurely stroll to Pantheon, another of the city’s timeless attractions. We recommend continuing your self-guided tour at Piazza Navona, a visually striking place of interest in the city.

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.

As you explore more of Rome, 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.

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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to La Botticella Of Poggi Giovanni, known for its inviting atmosphere. Almalu Trastevere is another great option if you’re looking for a place to get the night started. Similarly, Bar Viminale Di Pepi Maurilio 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!

On day 7 of your road trip in Italy, you’ll start and end your day in Rome, but spend the day exploring what’s beyond the city. Since you will return to Rome for 1 night more, there’s no need to rush. Experience Vatican City and Rome to the fullest today with this curated day itinerary!

Bring your curiosity for today’s adventure around Rome. Some of the city’s most loved attractions await! Vatican Museums is the perfect place to start. This art museum is one of the most wondrous places to visit in Rome.

Nearby, you'll also find Castel Sant'angelo and Piazza Di Spagna. Visit these for an interesting touch to your journey. Finish the day with a visit to Spanish Steps, an enchanting public square in Rome.

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

As you explore more of Rome, 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 delicious meal 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.

Keep the evening going at Sant' Eustachio Caffè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Yellowsquare Rome, which offers a similarly pleasant setting and great drinks. Another option is Caffè Portofino, which provides an inviting environment for unwinding after a busy day out.

Say good night to Rome and look forward to another great day of your road trip in Italy!

Embark on another extraordinary experience on day 8 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Orvieto. At the end of the day, you will enjoy the comforts of a top-rated hotel in Bologna, which will be your home away from home for 1 night.

Get ready for a day filled with family-friendly attractions, scenic views, and photo-friendly spots in the charming village of Rome. Your adventure starts at Well Of St. Patrick, a notable local hot spot. Another notable attraction to explore is Orvieto Cathedral. This notable church is known for its culturally significant appeal.

After soaking in the highlights of these sights, take some time to wander Rome's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Museo Dell'opera Del Duomo. This noteworthy museum offers a fascinating experience that many visitors find memorable. Orvieto Underground is also worth visiting, along with Torre Del Moro Orvieto. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Pozzo Della Cava. This often recommended cave provides a fitting finale to your sightseeing.

When you’re done exploring for the day, you’ll drive to your hotel in Bologna. Check in and spend some time relaxing 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 and reflect on the day's adventures.

Enjoy a lovely dining experience at Bononia Cafè, 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 Via Con Me, 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 Trattoria Pizzeria La Mela. It’s yet another ideal choice to enhance your time 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.

Head back to your accommodation in Bologna and get some rest in preparation for another magical day of your road trip in Italy!