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.

Enjoy all that Two Towers has to offer. This is a well-known monument you should not miss. Another must-see is Piazza Santo Stefano, a frequently visited public square in Bologna.

When you’re ready for the next sight, head to Basilica Of San Domenico.

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.

For an unforgettable shopping experience, visit Quadrilatero, the top shopping destination in Bologna. Browse local boutique shops and stores, each offering delightful surprises. Find unique souvenirs or items to take home. After shopping, explore what Quadrilatero has to offer, including attractions, essential services, and vibrant community activities.

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 Bononia Cafè, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Via Con Me? It's another excellent option with a diverse menu. Consider reserving a table at Trattoria Pizzeria La Mela as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Bologna.

Continue your evening by exploring the vibrant nightlife scene at Lime Bar, a prime destination for a thrilling night out. Also, don’t forget to check out Macondo - Cocktail Bar, a bar that offers unique local touches. Likewise, Bar Onda Marina By Night provides an excellent alternative for a fun evening.

Raise your glass to another unforgettable day 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.

Piazzale Michelangelo brings Bologna's character to life. This romantic observation deck is a highlight of any visit in the city. Then, enjoy Ponte Vecchio, another grand attraction that never fails to captivate visitors. Next, head over to Uffizi Gallery, one of the city’s most famous attractions, known for its romantic features.

If you’re looking for more, spend time soaking in the atmosphere of Basilica Of Santa Croce In Florence. This culturally significant church is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Della Signoria, an astonishing public square, and take a stroll around the area.

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.

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.

Don’t miss out on dining 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 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.

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

On day 4 of your road trip, you’ll start and end your day in Florence, where you have 1 night left to stay.

Your adventure in Florence is only getting started when you visit Piazza Del Duomo, Pisa, a wondrous local hot spot. Another notable attraction to explore is Leaning Tower Of Pisa. This globally renowned monument is known for its stunning appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Galleria Dell'accademia. This respected art gallery offers a fascinating experience that many visitors find memorable. Cathedral Of Santa Maria Del Fiore is also worth visiting, along with Basilica Di Santa Maria Novella, Firenze (fi). These standout landmarks offer unique experiences that add to the day’s enjoyment.

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.

Enjoy a lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Florence tonight.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar 50 Rosso stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bitter Bar offers an ideal atmosphere to enjoy the pleasures of the night. Archea Brewery is also a great option that provides a perfect setting for a relaxing evening.

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

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Siena. When you’re not sightseeing, take time to relax at your chosen hotel in Siena, where you’ll be staying for 2 nights.

Make a stop at Basilica Of San Domenico. This locally appreciated church is a must-visit for travelers looking for a unique holiday experience. Make your way to Piccolomini Library located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Siena Cathedral. Its inviting features will captivate you. After the church, continue your tour of the city with a visit to Piazza Del Campo. Visitors usually appreciate the history-steeped features of this public square. Next up is Tower Of Mangia, a highly recommended monument.

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.

Indulge in a memorable dining experience at one of Siena's most popular restaurants, and connect with friendly locals for a true cultural experience.

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.

Following your dinner, dive into the local bar culture at Meet Life Cafè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Maudit Pub, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Impero Siena provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Wake up to day 6 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Pievasciata, San Regolo, and Castellina in Chianti. With 1 night to stay in Siena, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Parco Sculture Del Chianti brings Siena's character to life. This romantic sculpture garden is a highlight of any visit in the hamlet. Then, enjoy Castello Di Brolio, another romantic attraction that never fails to captivate visitors. Next, head over to Rocca Di Castellina In Chianti, one of the hamlet’s most underrated attractions, known for its awe-inspiring features.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Siena. Enjoy a relaxing evening as you savor delicious local cuisine.

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.

Keep the evening going at Charlie Mixology Bar Di Aldinucci Riccardo, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bar Pinacoteca, which offers a similarly pleasant setting and great drinks. Another option is San Paolo Pub, which provides an inviting environment for unwinding after a busy day out.

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

Day 8 offers an itinerary packed with the best things to see in Rome. You’ll stay in Rome for 1 night more, offering you enough time to explore at a relaxed pace.

Rome is brimming with adventures.

Make time for Colosseum, a wondrous archeological site that is worthwhile a visit in the city. Nearby, you’ll find Roman Forum, enchanting visitors with its picture-perfect appeal. Continue your exploration at Trevi Fountain. This monument is one of the city’s most wondrous 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 Pantheon. After exploring the monument, head to the world-famous Piazza Navona. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Castel Sant'angelo, a place of grand interest in Rome.

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

Enjoy a delicious meal at RomAntica, a highly-rated dining destination in Rome. If you're eager to try something different, consider Coso Ristorante, another top spot with a tantalizing menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

To truly maximize your evening out, consider visiting Sant' Eustachio Caffè after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Yellowsquare Rome, another bar with an inviting ambiance. Similarly, Caffè Portofino also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Head back to your accommodation in Rome and get some rest to prepare for another magical day of your road trip in Italy.

On day 9 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Orvieto are on today's agenda. In the evening, you’ll end up in Bologna, where you will stay for 1 night.

Enjoy all that Well Of St. Patrick has to offer. This is an interesting monument you should not miss. Another must-see is Orvieto Cathedral, a locally renowned church in Rome.

When you’re ready for the next sight, head to Museo Dell'opera Del Duomo. From there, take a leisurely stroll to Orvieto Underground, another of the village’s underrated attractions. We recommend continuing your self-guided tour at Torre Del Moro Orvieto, a standout place of interest in the village. If time allows, add Pozzo Della Cava to your itinerary. This beloved cave offers the perfect finishing touch to your day 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 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.

Enjoy a lovely dining experience at Va Mo Là, 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 Trattoria dal Biassanot, 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 Ristorante Enoteca da Lucia. It’s yet another ideal choice to enhance your time in Bologna tonight.

If you’re not ready to end the night just yet, Aurum offers a perfect venue to relax and savor a drink. Similarly, Bar Senza Nome is well-suited for those looking to unwind in a social setting. Caffè Ristretto is another excellent spot to enjoy a nightcap after a delightful meal.

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.