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

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

Piazza Santo Stefano makes a great addition to your morning plans. This underrated public square is a symbolic place to see in Rimini. Continue your discovery at Two Towers, an instagrammable monument with stories to tell.

As you stroll around Rimini, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Bologna Cathedral. This beloved church offers a picture-perfect encounter with Rimini. Next, make your way to Palazzo Re Enzo to add another highlight to your day. After that, visit Fountain Of Neptune, Bologna, an underrated monument that’s sure to impress. If you’re up for more, end your self-guided sightseeing tour at Piazza Maggiore, an impressive public square in the city. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Rimini.

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.

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.

Treat yourself to a delicious dinner at Ristorante Ciacco, an excellent option for tonight's dining. Looking for something different? Ristorante Ballarini offers a tantalizing alternative with its diverse menu. And don’t miss Sfoglia Rina. Known for great service, it’s a fantastic choice for tonight in Bologna.

Cap off your dinner by heading to Bar Al Bricco D'oro, ideal for a leisurely evening with a drink in hand. Bar Freud E Squisito is another bar that offers an enjoyable setting. Similarly, Osteria Del Sole is also a popular place to go on a night out, perfect for relaxing and socializing.

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.

Whatever your travel style is, Central Market is an essential stop in Bologna. This well-known food market provides an insightful glimpse into the city's identity. Next, discover Cathedral Of Santa Maria Del Fiore, a visually striking church, promising a delightful encounter.

Continue your sightseeing with a visit to Florence Baptistery, a worthwhile church. When you’re done, don’t forget to make a stop at the iconic Ponte Vecchio. Not far away from the historical landmark, you will find the history-steeped Piazza Della Signoria, perfect for a quick visit. Round off your day at Uffizi Gallery, another gem in Bologna with romantic features to discover.

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. If you are looking to dine at a popular restaurant in Florence, it's often a good idea to reserve a table in advance.

Have a fantastic dining experience at Ristorante Oliviero 1962, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Di Poneta Novoli offers an enticing alternative with its varied menu. Additionally, Caffe San Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option 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 Manifattura, a well-loved spot among locals and tourists. Or, head to Se·sto On Arno Rooftop Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Il Vinile, another top-rated place in the area.

Savor another day of unforgettable experiences 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.

Oltrarno is a fantastic place you can explore today in Pisa. This neighborhood is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Pisa-way-of-life and visit all the nearby sights.

Visiting Piazza Del Duomo, Pisa is always a good idea. This iconic public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the noteworthy wonders of Leaning Tower Of Pisa, a must-see monument in the city.

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 Basilica Of Santa Croce In Florence. This interesting church offers an enriching experience. For a change of pace, head to Piazzale Michelangelo, where you can take in visually striking features.

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.

Enjoy a lovely dining experience at Ditta Artigianale, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Trattoria Da Burde, 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 Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

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.

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

Enjoy all that Basilica Of San Domenico has to offer. This is an increasingly popular church you should not miss. Another must-see is Piazza Del Duomo, an increasingly popular public square in Florence.

When you’re ready for the next sight, head to Siena Cathedral. From there, take a leisurely stroll to Pubblico Palace, another of the city’s often recommended attractions. We recommend continuing your self-guided tour at Piazza Del Campo, an enchanting place of interest in the city. If time allows, add Tower Of Mangia to your itinerary. This up-and-coming monument offers the perfect finishing touch to your day in Florence.

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.

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 Enoteca I Terzi, 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 Ristorante Tar-Tufo, 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 Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Explore the vibrant nightlife at Meet Life Cafè after your meal, a hub for lively evenings and memorable moments. Or, head to Maudit Pub for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Impero Siena 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!

On day 6 of your road trip, you’ll start and end your day in Siena, where you still have 1 night left. You'll spend part of the day exploring places of interest outside the immediate city, including San Gimignano and Siena.

Porta San Giovanni is an ideal stop early in the day. This curiosity-inducing monument is a must-visit in the village. When you’re ready for your next discovery, continue to Piazza Del Duomo, which may be one of the most UNESCO world heritage-listed places you will experience today.

One of the best things about exploring Siena 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 Rocca Di Montestaffoli, a beloved castle in the village. If you’re up for more discoveries, don’t forget to reserve some time for Parco Della Rocca and Chiesa Di Sant'agostino. End your day with a visit to Fortezza Medicea (siena), an intriguing monument that’s sure to leave a lasting impression.

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.

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.

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.

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.

Casa Vasari leaves a lasting impression. This museum is one of the most underrated places to visit in Siena. Next, head to The Medici Fortress Park, a worthwhile park, known for its majestic 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 Piazza Grande. This romantic public square is a highly recommended experience. Nearby, you'll also find Santa Maria Della Pieve and San Francesco, Arezzo Visit these for an interesting touch to your journey.

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

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

Savor the flavors at Il Covo dei Briganti, a top pick for dinner tonight. Alternatively, La Clandestina beckons with its unique menu offerings. Also, consider Ristorante Logge Vasari. With its consistent customer satisfaction, it’s an excellent option for dining in Arezzo tonight.

Keep the evening going at Liquid Bar, a great choice for enjoying the after-dinner hours with a drink.

Relax and look forward to more memorable moments to come!

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

Palazzo Ducale brings Arezzo's character to life. This UNESCO world heritage-listed palace is a highlight of any visit in the town. Then, enjoy Galleria Nazionale Delle Marche, another UNESCO world heritage-designated attraction that never fails to captivate visitors. Next, head over to Oratory Of St John The Baptist, Urbino, one of the town’s most underrated attractions, known for its respected features.

If you’re looking for more, spend time soaking in the atmosphere of Casa Santi. This instagrammable museum is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Fortezza Albornoz, a beloved castle, and take a stroll around the area.

At the end of the day, you will drive to Rimini, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

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

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.

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

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