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

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

Get ready for an exciting day in Bologna. Today’s sightseeing agenda includes an observation deck, an art gallery, a historical landmark, a church, a public square and much more! Begin your adventure at Piazzale Michelangelo. This is an astonishing observation deck you should not miss. Another must-see is Uffizi Gallery, a spectacular art gallery in Bologna.

When you’re ready for the next sight, head to Ponte Vecchio. From there, take a leisurely stroll to Cathedral Of Santa Maria Del Fiore, another of the city’s top-rated attractions. We recommend continuing your self-guided tour at Galleria Dell'accademia, a noteworthy place of interest in the city. If time allows, add Piazza Della Signoria to your itinerary. This spectacular public square offers the perfect finishing touch to your day in Bologna.

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

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 your meal, keep the night alive at a bar like Manifattura, known for its lively atmosphere. Se·sto On Arno Rooftop Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Il Vinile offers an excellent atmosphere for those looking to amp up the evening.

Savor another day of unforgettable experiences in Italy!

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

Set out on a day brimming with family-friendly attractions, scenic views, and picturesque spots. Start at the underrated Knights' Square, an awe-inspiring public square in Florence. Next, go to Leaning Tower Of Pisa.

After visiting Knights' Square and Leaning Tower Of Pisa, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Piazza Del Duomo, Pisa. This picture-perfect public square offers a unique experience. Pisa Cathedral is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Mura Di Lucca, one of the most culturally significant places to visit in Florence.

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

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

Enjoy a delicious meal 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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar 50 Rosso, known for its inviting atmosphere. Bitter Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery provides a great setting to enjoy the night away.

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

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, San Gimignano and Siena. When you’re not sightseeing, take time to relax at your selected hotel in Siena, where you’ll be staying for 2 nights.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, romantic experiences, and breathtaking views. Start at Parco Della Rocca, an increasingly popular park in the village. Then, head to Fortezza Medicea (siena) and soak in the ambiance of this historic monument.

There are many interesting places to see in Florence, and when you are ready for more, go to Basilica Of San Domenico. This is one of the village’s most locally appreciated breathtaking spots of interest. After exploring the church, visit the interesting Siena Cathedral. Not far away, you'll also find Piazza Del Campo. This public square is an UNESCO world heritage-designated highlight in Florence. Before wrapping up your self-guided sightseeing tour, head to Tower Of Mangia, a worthwhile monument in the village.

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

Don’t miss out on dining 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.

Keep the excitement of the evening going by visiting a bar or two. Meet Life Cafè is an excellent place to start. You could also check out Maudit Pub, offering a different kind of charm. A last recommendation for the day is Bar Impero Siena. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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, where you'll stay for 1 night more.

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and breathtaking views. Whether you decide to explore Siena on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Abbey Of Sant'antimo is the first of them. Spend some time admiring this inviting monastery before continuing your journey. Fortress Of Montalcino is your next stop. This up-and-coming castle is one of the best-rated sights in Siena.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Piazza Del Popolo. This romantic public square is a sight to behold. To round off your sightseeing experience, visit Palazzo Piccolomini, Pienza and Chapel Vitaleta. If time allows, end your day with Cipressi Di San Quirico D'orcia, an awe-inspiring rock formation that offers a memorable conclusion to your exploration.

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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Charlie Mixology Bar Di Aldinucci Riccardo stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar Pinacoteca offers an ideal atmosphere to enjoy the pleasures of the night. San Paolo Pub is also a great option that provides a perfect setting for a relaxing evening.

Raise your glass to another unforgettable day in Italy!

Embark on another extraordinary experience on day 6 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Rome. At the end of the day, you will enjoy the comforts of a top-rated hotel in Rome, which will be your home away from home for 2 nights.

A blend of family-friendly attractions, breathtaking views, and picturesque spots await you in Siena on today’s itinerary. First up is the timeless archeological site, Colosseum. Afterward, continue to Roman Forum, an archeological site every traveler should visit.

As you explore Siena’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Trevi Fountain. This timeless monument is an essential stop. Following that, head to Pantheon, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Navona, an iconic public square 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.

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

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.

After enjoying a fulfilling meal, continue your evening at La Botticella Of Poggi Giovanni, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Almalu Trastevere offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Viminale Di Pepi Maurilio provides an excellent environment for a relaxed and enjoyable evening.

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

Greet day 7 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Rome for your remaining 1 night in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in Vatican City and Rome.

Get ready for a day filled with fun adventures, romantic experiences, and scenic views in the charming city of Rome. Your adventure starts at Vatican Museums, an iconic local hot spot. Another notable attraction to explore is St. Peter's Basilica.

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 Sistine Chapel. Castel Sant'angelo is also worth visiting, along with Piazza Di Spagna. These standout landmarks offer unique experiences that add to the day’s enjoyment. End your day at Spanish Steps. This spectacular public square provides a fitting finale to your sightseeing.

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

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

Dine in style at RomAntica, a top recommendation for dinner tonight. Or, for a change of pace, Coso Ristorante boasts a menu that's sure to impress. Also, be sure to check out DEROMA - Farine Romane. Known as a local hotspot, it’s a great choice for tonight in Rome.

Keep the excitement of the evening going by visiting a bar or two. Sant' Eustachio Caffè is an excellent place to start. You could also check out Yellowsquare Rome, offering a different kind of charm. A last recommendation for the day is Caffè Portofino. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Celebrate another amazing day of your road trip adventure 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.

Today’s itinerary in Rome covers several incredible sights, including a monument, a church, a museum, a cave system, a cave and much more! Start your adventure at Well Of St. Patrick. This captivating monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Orvieto Cathedral, a must-see church 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 Museo Dell'opera Del Duomo. This often recommended museum offers an enriching experience. For a change of pace, head to Orvieto Underground, where you can take in photogenic features. Conclude your self-guided sightseeing tour with a visit to Torre Del Moro Orvieto and Pozzo Della Cava. These sights offer a fulfilling end to a perfect day.

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.

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

Dine in style at Bononia Cafè, a top recommendation for dinner tonight. Or, for a change of pace, Via Con Me boasts a menu that's sure to impress. Also, be sure to check out Trattoria Pizzeria La Mela. Known as a local hotspot, it’s a great choice for tonight in Bologna.

If you’re not ready to end the night just yet, Lime Bar offers a perfect venue to relax and savor a drink. Similarly, Macondo - Cocktail Bar is well-suited for those looking to unwind in a social setting. Bar Onda Marina By Night is another excellent spot to enjoy a nightcap after a delightful meal.

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