9-Day Italy Self-Drive Road Trip With Itinerary from Rimini traveling west to Bologna, Florence, Siena, and Arezzo

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 place, which are Bologna. At the end of the day, you will retreat to the hotel of your choice in Bologna, where will spend 1 night.

Fasten your seatbelt and make your way to your next stop — Bologna, home to many well-known sights in the region. Keep in mind that your travel time from Rimini to Bologna may take around 1 hour 27 min without traffic disruptions. Upon arrival in Bologna, we highly recommend checking out some of the top attractions.

When you're ready for some sights, head to Piazza Santo Stefano, an increasingly popular public square in Bologna. Explore its history-steeped features at your own pace before you continue your journey to your next attraction, Two Towers. This locally renowned monument is a top recommendation in the area.

When you’re ready to explore more, Bologna Cathedral is an excellent choice. Spend some time discovering what some claim to be the most picture-perfect church in the region. Next, continue your sightseeing at the intriguing Palazzo Re Enzo and discover what makes this palace unique. If you’re up for one more stop in the city, head to Fountain Of Neptune, Bologna, a symbolic monument many travelers find the visit worthwhile.

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.

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

Enjoy a lovely dining experience at Ristorante Ciacco, 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 Ristorante Ballarini, 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 Sfoglia Rina. It’s yet another ideal choice to enhance your time in Bologna tonight.

Round off your dining experience by visiting Bar Al Bricco D'oro, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Freud E Squisito, a bar catering to every mood and preference. Osteria Del Sole likewise offers a unique atmosphere, perfect for a memorable night out.

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.

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

Embrace the thrill of the open road as you wave goodbye to Bologna and set your GPS to Florence. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 1 hour 35 min. Upon reaching Florence, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

For a more meaningful self-guided tour of the city's best attractions, visit Central Market, a captivating food market 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 Cathedral Of Santa Maria Del Fiore and admire its history-steeped features.

When you’re ready, continue to Florence Baptistery, an often recommended church beloved by locals and tourists alike. Don't miss out on Ponte Vecchio, another highlight of the area that promises a memorable visit. Not far away, you’ll also find Uffizi Gallery, a romantic 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.

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.

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.

After enjoying a fulfilling meal, continue your evening at Manifattura, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Se·sto On Arno Rooftop Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Il Vinile provides an excellent environment for a relaxed and enjoyable evening.

Say good night to Florence and look forward to another great day 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.

One of the most iconic spots you can visit today is Oltrarno. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Make time for Basilica Of Santa Croce In Florence, a well-known church that is worthwhile a visit in the city. Nearby, you’ll find Piazzale Michelangelo, enchanting visitors with its history-steeped appeal.

After soaking in Florence’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Pisa. Expect your car journey to take a minimum of 1 hour 16 min. When you arrive in Pisa, it's time to take a break from the road.

One of our top recommendations for your sightseeing is Piazza Del Duomo, Pisa. Spend some time admiring the UNESCO world heritage-listed features of the public square before you continue to your next stop. Then, head to Leaning Tower Of Pisa. This iconic monument is a traveler-favorite in the city.

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

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.

Treat yourself to a delicious dinner at Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. Known for great service, it’s a fantastic choice for tonight in Florence.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bar 50 Rosso, a well-loved spot among locals and tourists. Or, head to Bitter Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Archea Brewery, another top-rated place in the area.

Savor another day of unforgettable experiences in Italy!

Your itinerary for day 5 of your road trip in Italy includes 1 stop and features some of the highlights of Siena. At the end of the day, enjoy the comforts of a top-rated hotel in Siena, where you'll spend 2 nights.

After soaking in Florence’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Siena. Expect your car journey to take a minimum of 1 hour 8 min. When you arrive in Siena, it's time to take a break from the road.

Set out on a self-guided sightseeing tour at Basilica Of San Domenico and explore the picture-perfect features. Next, make your way to Piazza Del Duomo, another highlight in Siena. When you’re done exploring the public square, continue to Siena Cathedral, a visually striking church.

Nearby, you will also find Pubblico Palace. This worthwhile palace is a top place to see in the area. Lastly, head to Piazza Del Campo, a respected public square that is perfect for some final exploring in the city.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Siena. Siena offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

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.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Meet Life Cafè, a well-loved spot among locals and tourists. Or, head to Maudit Pub. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Bar Impero Siena, another top-rated place in the area.

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

On day 6 of your road trip, you'll get the chance to experience San Gimignano and Siena. At the end of the day, you'll drive back to Siena, where you still have 1 night left to stay.

Fortezza Medicea (siena) makes a great addition to your morning plans. This locally appreciated monument is a breathtaking place to see in 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.

Set your GPS to San Gimignano and hit the road. Expect a journey of approximately 43 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. San Gimignano beckons with new experiences!

Set out on a self-guided sightseeing tour at Porta San Giovanni and explore the culturally significant features. Next, make your way to Piazza Del Duomo, another highlight in San Gimignano. When you’re done exploring the public square, continue to Rocca Di Montestaffoli, an UNESCO world heritage-designated castle.

Nearby, you will also find Parco Della Rocca. This frequently visited park is a top place to see in the area. Lastly, head to Chiesa Di Sant'agostino, a respected church that is perfect for some final exploring in the village.

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

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.

Don’t miss out on dining at Osteria Quattro Venti, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Fischi per Fiaschi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

Continue your lively evening at Charlie Mixology Bar Di Aldinucci Riccardo, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Pinacoteca is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, San Paolo Pub ensures a night out tailored to your taste.

Relax and look forward to more memorable moments to come!

On day 7 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Arezzo. When you’re not sightseeing, take time to relax at your chosen hotel in Arezzo, where you’ll be staying for 1 night.

Set your GPS to Arezzo and hit the road. Expect a journey of approximately 1 hour 10 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Arezzo beckons with new experiences!

Spend your afternoon discovering Casa Vasari, an up-and-coming museum known for its eye-catching features. Next, continue your sightseeing at The Medici Fortress Park, an often recommended park.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Piazza Grande and uncover the details of this enchanting public square. Make sure to also explore Santa Maria Della Pieve, a frequently visited church. For your last stop, consider San Francesco, Arezzo, a culturally significant church that many travelers find worth the detour.

At the end of the day, you will drive to Arezzo, 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 Arezzo. Enjoy a relaxing evening as you savor delicious local cuisine.

Treat yourself to a delicious dinner at Il Covo dei Briganti, an excellent option for tonight's dining. Looking for something different? La Clandestina offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Logge Vasari. Known for great service, it’s a fantastic choice for tonight in Arezzo.

Let the evening flow smoothly from dinner to drinks at Liquid Bar, a top-rated bar in the area.

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

On day 8 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Urbino are on today's agenda. In the evening, you’ll end up in Rimini, where you will stay for 1 night.

When you’ve had your share of Arezzo, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Urbino. Your travel time is around 2 hours 1 min.

One of our top recommendations for your sightseeing is Palazzo Ducale. Spend some time admiring the breathtaking features of the palace before you continue to your next stop. Then, head to Galleria Nazionale Delle Marche. This often recommended museum is a traveler-favorite in the town.

If you're keen to see more, continue to Oratory Of St John The Baptist, Urbino. Feed your curiosity by learning something new about the church. Next, take your journey to Casa Santi, an underrated museum. Conclude your sightseeing at Fortezza Albornoz, known for its stunning features.

When you’re done exploring for the day, you’ll drive to your hotel in Rimini. 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 Rimini, it's often a good idea to reserve a table in advance.

Enjoy a lovely meal at Osteria Brodo di Giuggiole, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Hotel Touring is another top choice with a popular menu. You could also check for a table at Ristorante Lo Zodiaco Rimini. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Rimini tonight.

After savoring a delicious meal, step into the vibrant nightlife at Hobo's, where the evening is just getting started. In the same way, Sunflower City Backpacker offers a unique charm perfect for experiencing the local bar scene in Rimini. Bar Capogiro 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.