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

Day 2 of your road trip across Italy promises a magnificent time exploring what to see in Bologna. You have 1 night left in Bologna. Take the opportunity to experience more of the best attractions and activities in the city.

Two Towers is an ideal stop early in the day. This popular monument is a must-visit in the city. When you’re ready for your next discovery, continue to Piazza Santo Stefano, which may be one of the most romantic places you will experience today.

One of the best things about exploring Bologna on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Basilica Of San Domenico, an up-and-coming church in the city.

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.

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.

To truly maximize your evening out, consider visiting Lime Bar after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Macondo - Cocktail Bar, another bar with an inviting ambiance. Similarly, Bar Onda Marina By Night also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Dive into day 3 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Florence. At the end of the day, you’ll unwind at one of the finest accommodations in Florence, where you'll spend 2 nights.

One of the most extraordinary attractions included on the itinerary is Piazzale Michelangelo. This visually striking observation deck will help you start your sightseeing on top. Then, take a leisurely stroll to Ponte Vecchio and learn what makes this symbolic historical landmark unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the extraordinary Uffizi Gallery. After exploring the art gallery, head to Basilica Of Santa Croce In Florence. This interesting church is a highlight in Bologna. As your day continues, stop by Piazza Della Signoria, known for its history-steeped features.

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.

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.

After savoring a delicious meal, step into the vibrant nightlife at Manifattura, where the evening is just getting started. In the same way, Se·sto On Arno Rooftop Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Il Vinile is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.

On day 4 of your road trip, you’ll start and end your day in Florence, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate city, including Pisa and Florence.

Whatever your travel style is, Piazza Del Duomo, Pisa is an essential stop in Florence. This globally renowned public square provides an insightful glimpse into the city's identity. Next, discover Leaning Tower Of Pisa, a culturally significant monument, promising a delightful encounter.

Continue your sightseeing with a visit to Galleria Dell'accademia, a captivating art gallery. When you’re done, don’t forget to make a stop at the astonishing Cathedral Of Santa Maria Del Fiore. Round off your day at Basilica Di Santa Maria Novella, Firenze (fi), another gem in Florence with enchanting features to discover.

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

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.

Treat yourself to a delightful dinner at Ditta Artigianale, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria Da Burde? It's another excellent option with a diverse menu. Consider reserving a table at Casa Toscana as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

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.

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

On day 5 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Siena are on today's agenda. In the evening, you’ll end up in Siena, where you will stay for 2 nights.

Basilica Of San Domenico leaves a lasting impression. This church is one of the most beloved places to visit in Florence. Next, head to Piccolomini Library, a beloved library, known for its eye-catching features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Siena Cathedral. This grand church is a highly recommended experience. Nearby, you'll also find Piazza Del Campo and Tower Of Mangia Visit these for an interesting touch to your journey.

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.

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.

Extend your evening after a delightful meal by visiting Meet Life Cafè, which offers the perfect atmosphere for a night out. Moreover, Maudit Pub is another popular option for a drink or two. Likewise, Bar Impero Siena also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

Greet day 6 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 Pievasciata, San Regolo, and Castellina in Chianti.

Parco Sculture Del Chianti makes a great addition to your morning plans. This curiosity-inducing sculpture garden is a visually striking place to see in Siena. Continue your discovery at Castello Di Brolio, an awe-inspiring castle with stories to tell.

As you stroll around Siena, take in the distinct atmosphere and learn what makes this hamlet so unique. Maximize your sightseeing with a visit to Rocca Di Castellina In Chianti. This intriguing castle offers a visually striking encounter with Siena. 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.

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

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

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 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.

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

On day 8 of your road trip, you will have an entire day to discover what to see in Rome. You’ll stay in Rome for 1 night.

Colosseum brings Rome's character to life. This UNESCO world heritage-listed archeological site is a highlight of any visit in the city. Then, enjoy Roman Forum, another culturally significant attraction that never fails to captivate visitors. Next, head over to Trevi Fountain, one of the city’s most wondrous attractions, known for its history-steeped features.

If you’re looking for more, spend time soaking in the atmosphere of Pantheon. This culturally significant monument is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Navona, a timeless public square, and take a stroll around the area. If you want to extend your self-guided sightseeing tour, go check out Castel Sant'angelo before you head back to your hotel.

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 Rome's most popular restaurants, and connect with friendly locals for a true cultural experience.

Enjoy a lovely meal at RomAntica, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Coso Ristorante is another top choice with a popular menu. You could also check for a table at DEROMA - Farine Romane. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Rome tonight.

Explore the vibrant nightlife at Sant' Eustachio Caffè after your meal, a hub for lively evenings and memorable moments. Or, head to Yellowsquare Rome for a great selection of flavorful drinks and a charming setting. Furthermore, Caffè Portofino is perfect for those looking to extend their night with a touch of local flavor.

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

Your itinerary for day 9 of your road trip in Italy includes 1 stop and features some of the highlights of Orvieto. At the end of the day, enjoy the comforts of a top-rated hotel in Bologna, where you'll spend 1 night.

Visiting Well Of St. Patrick is always a good idea. This captivating monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the visually striking 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 worthwhile museum offers an enriching experience. For a change of pace, head to Orvieto Underground, where you can take in standout 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.

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

Treat yourself to a delightful dinner at Va Mo Là, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria dal Biassanot? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Enoteca da Lucia as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Bologna.

Keep the evening going at Aurum, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bar Senza Nome, which offers a similarly pleasant setting and great drinks. Another option is Caffè Ristretto, which provides an inviting environment for unwinding after a busy day out.

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