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

On day 2 of your road trip, you will have an entire day to discover what to see in Bologna. You’ll stay in Bologna for 1 night.

Experience Two Towers, a well-known monument in the city. Then, head to Piazza Santo Stefano and soak in the ambiance of this inviting public square.

There are many interesting places to see in Bologna, and when you are ready for more, go to Basilica Of San Domenico. This is one of the city’s most underrated monumental spots of interest.

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.

Bring home unique finds from Bologna's bustling shopping hub, Via d'Azeglio. Enjoy a leisurely exploration of unique boutiques and high-end stores where locals shop. Don’t forget to browse souvenirs and local specialties that make perfect gifts for your loved ones. Beyond shopping, Via d'Azeglio offers plenty of options, including primary services, unique landmarks, and community events.

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.

Treat yourself to a wonderful meal at Bononia Cafè, a top-rated dining spot in Bologna. If you're in the mood for something new, try Via Con Me, another premier location with a delectable menu. You might also want to book a table at Trattoria Pizzeria La Mela. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Bologna.

Cap off your dinner by heading to Lime Bar, ideal for a leisurely evening with a drink in hand. Macondo - Cocktail Bar is another bar that offers an enjoyable setting. Similarly, Bar Onda Marina By Night is also a popular place to go on a night out, perfect for relaxing and socializing.

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

Your itinerary for day 3 of your road trip in Italy includes 1 stop and features some of the highlights of Florence. At the end of the day, enjoy the comforts of a top-rated hotel in Florence, where you'll spend 2 nights.

Continue your road trip and head to your next destination, Florence. This car ride takes around 1 hour 30 min.

For a more meaningful self-guided tour of the city's best attractions, visit Piazzale Michelangelo, an astonishing observation deck that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Ponte Vecchio and admire its visually striking features.

When you’re ready, continue to Uffizi Gallery, a spectacular art gallery beloved by locals and tourists alike. Don't miss out on Basilica Of Santa Croce In Florence, another highlight of the area that promises a memorable visit. Not far away, you’ll also find Piazza Della Signoria, an enchanting place to see that you won’t regret spending some extra time discovering.

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

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

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.

Keep the excitement of the evening going by visiting a bar or two. Manifattura is an excellent place to start. You could also check out Se·sto On Arno Rooftop Bar, offering a different kind of charm. A last recommendation for the day is Il Vinile. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Raise your glass to another unforgettable day in Italy!

On day 4 of your road trip, you'll get the chance to experience Pisa and Florence. At the end of the day, you'll drive back to Florence, where you still have 1 night left to stay.

Pisa is brimming with adventures.

To truly experience Florence, make sure to drop by Galleria Dell'accademia. This captivating art gallery is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Cathedral Of Santa Maria Del Fiore, one of the city’s best highlights.

Next, check out Basilica Di Santa Maria Novella, Firenze (fi), one of the most popular places to see in Florence. This church is a favorite among locals and travelers alike.

When you’re ready to jump back into the car and say goodbye to Florence, you’ll hit the road in the direction of Pisa. This drive usually takes around 1 hour 16 min.

Our first attraction recommendation in Pisa is Piazza Del Duomo, Pisa, a world-famous public square that draws attention for its breathtaking features. Spend some time soaking in the atmosphere before continuing to Leaning Tower Of Pisa, a culturally significant monument that stands out in the city.

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.

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.

Continue your lively evening at Bar 50 Rosso, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bitter Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Archea Brewery ensures a night out tailored to your taste.

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

Throughout the day, make sure to take breaks to appreciate the surroundings.

When you’re ready to jump back into the car and say goodbye to Florence, you’ll hit the road in the direction of Siena. This drive usually takes around 1 hour 8 min.

Basilica Of San Domenico is a beloved church we recommend visiting today. Discover its breathtaking features before continuing your self-guided tour to Piccolomini Library, a history-steeped library that’s well-regarded in the area.

Next, stop by Siena Cathedral, an inviting church. While you’re nearby, don’t forget to visit Piazza Del Campo, a romantic and truly unique public square. End your sightseeing at Tower Of Mangia, a worthwhile monument that’s highly recommended by travelers passing through the city.

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.

Siena 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 Siena.

Enjoy a lovely dining experience at Enoteca I Terzi, a popular restaurant in Siena. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Siena at Ristorante Tar-Tufo, 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 Antica Trattoria Papei. It’s yet another ideal choice to enhance your time in Siena tonight.

If you’re not ready to end the night just yet, Meet Life Cafè offers a perfect venue to relax and savor a drink. Similarly, Maudit Pub is well-suited for those looking to unwind in a social setting. Bar Impero Siena 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!

On day 6 of your road trip in Italy, you’ll start and end your day in Siena, but spend the day exploring what’s beyond the city. Since you still have 1 night to spend in Siena, there’s no need to rush. Experience Pievasciata, San Regolo, and Castellina in Chianti to the fullest today with this curated day itinerary.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Pievasciata may take around 26 min. Upon your arrival in Pievasciata, you’ll be greeted with the opportunity to do some sightseeing and exploring.

One of our top recommendations for your sightseeing is Parco Sculture Del Chianti. Spend some time admiring the romantic features of the sculpture garden before you continue to your next stop.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in San Regolo. This drive usually takes around 21 min, without any stops or traffic disruptions.

Our first attraction recommendation in San Regolo is Castello Di Brolio, a locally appreciated castle that draws attention for its romantic features.

When you’re ready to jump back into the car and say goodbye to San Regolo, you’ll hit the road in the direction of Castellina in Chianti. This drive usually takes around 43 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Rocca Di Castellina In Chianti, a worthwhile castle that everyone visiting Castellina in Chianti should see.

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.

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.

After savoring a delicious meal, step into the vibrant nightlife at Charlie Mixology Bar Di Aldinucci Riccardo, where the evening is just getting started. In the same way, Bar Pinacoteca offers a unique charm perfect for experiencing the local bar scene in Siena. San Paolo Pub is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Day 8 of your road trip will take you to the best attractions Rome has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Rome.

Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Whatever your travel style is, Colosseum is an essential stop in Rome. This world-famous archeological site provides an insightful glimpse into the city's identity. Next, discover Roman Forum, a respected archeological site, promising a delightful encounter.

Continue your sightseeing with a visit to Trevi Fountain, an iconic monument. When you’re done, don’t forget to make a stop at the globally renowned Pantheon. Not far away from the monument, you will find the visually striking Castel Sant'angelo, perfect for a quick visit. Round off your day at Piazza Navona, another gem in Rome with noteworthy features to discover.

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.

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.

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.

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

Experience an unparalleled adventure on day 9 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Orvieto. At the end of the day, you will retreat to the hotel of your choice in Bologna, where will spend 1 night.

Orvieto’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Rome behind. This drive usually takes around 1 hour 35 min. Orvieto welcomes you with a multitude of unique vacation experiences.

Savor the day by heading to Well Of St. Patrick, a locally renowned monument that draws visitors from near and far.

When you’re ready to jump back into the car and say goodbye to Rome, you’ll hit the road in the direction of Orvieto. This drive usually takes around 1 hour 35 min.

Savor the day by heading to Orvieto Cathedral, a popular church that draws visitors from near and far. When you're done, continue to Museo Dell'opera Del Duomo, where you can soak in the photogenic surroundings.

Next, explore Orvieto Underground, yet another beloved place to see in the area. After the cave system, make time to go to Torre Del Moro Orvieto. This historic monument is well worth the visit. Lastly, head to Pozzo Della Cava, an often recommended cave you won’t want to miss.

When you’re done exploring for the day, you’ll drive to your hotel in Bologna. Check in and relax before you head out to tour the city.

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

Treat yourself to a delicious dinner at Va Mo Là, an excellent option for tonight's dining. Looking for something different? Trattoria dal Biassanot offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Enoteca da Lucia. Known for great service, it’s a fantastic choice for tonight in Bologna.

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

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