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, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Bologna. In the evening, you’ll end up in Bologna, where you will stay for 1 night.

Rimini is home to plenty of attractions that offer fun adventures, romantic experiences, and scenic views! Start at Piazza Santo Stefano, a beloved public square that is worthwhile a visit in the city. Nearby, you’ll find Two Towers, enchanting visitors with its stunning appeal. Continue your exploration at Bologna Cathedral. This church is one of the city’s most intriguing spots.

Enjoy the freedom of exploring Rimini at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Palazzo Re Enzo. After exploring the palace, head to the frequently visited Fountain Of Neptune, Bologna. Lastly, wrap up today’s self-guided sightseeing tour with a visit to Piazza Maggiore, a place of history-steeped interest in Rimini.

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

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 delightful dinner at Ristorante Ciacco, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante Ballarini? It's another excellent option with a diverse menu. Consider reserving a table at Sfoglia Rina as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Bologna.

To truly maximize your evening out, consider visiting Bar Al Bricco D'oro after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Freud E Squisito, another bar with an inviting ambiance. Similarly, Osteria Del Sole also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Florence. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 2 nights.

Brace yourself for today’s incredible lineup of attractions in Bologna, featuring fun adventures, photo-friendly spots, and budget-friendly activities. Start at Central Market, a well-known food market in the city. Then, head to Cathedral Of Santa Maria Del Fiore and soak in the ambiance of this romantic church.

There are many interesting places to see in Bologna, and when you are ready for more, go to Florence Baptistery. This is one of the city’s most worthwhile inviting spots of interest. After exploring the church, visit the iconic Ponte Vecchio. Not far away, you'll also find Uffizi Gallery. This art gallery is a history-steeped highlight in Bologna. Before wrapping up your self-guided sightseeing tour, head to Piazza Della Signoria, an astonishing public square in the city.

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.

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

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.

Continue your evening by exploring the vibrant nightlife scene at Manifattura, a prime destination for a thrilling night out. Also, don’t forget to check out Se·sto On Arno Rooftop Bar, a bar that offers unique local touches. Likewise, Il Vinile provides an excellent alternative for a fun evening.

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

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

Set aside time today to explore Oltrarno, a standout neighborhood that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Piazza Del Duomo, Pisa. This stunning public square is a highlight of any visit in the city. Then, enjoy Leaning Tower Of Pisa, another breathtaking attraction that never fails to captivate visitors. Next, head over to Basilica Of Santa Croce In Florence, one of the city’s most interesting attractions, known for its monumental features.

If you’re looking for more, spend time soaking in the atmosphere of Piazzale Michelangelo. This visually striking observation deck is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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.

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. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

Round off your dining experience by visiting Bar 50 Rosso, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bitter Bar, a bar catering to every mood and preference. Archea Brewery likewise offers a unique atmosphere, perfect for a memorable night out.

Savor another day of unforgettable experiences in Italy!

Embark on another extraordinary experience on day 5 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Siena. At the end of the day, you will enjoy the comforts of a top-rated hotel in Siena, which will be your home away from home for 2 nights.

Start by visiting Basilica Of San Domenico, a prime spot to begin your journey. This symbolic church is sure to impress. Next on your list is Piazza Del Duomo, another must-visit landmark and underrated public square renowned for its culturally significant features.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Siena Cathedral. This visually striking church is an essential place to visit for anyone looking for the full Florence experience. We also recommend visiting Pubblico Palace, an increasingly popular palace. Nearby, you'll also find Piazza Del Campo, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Tower Of Mangia and wrap up your day with its picture-perfect appeal.

When you’re done exploring for the day, you’ll drive to your hotel in Siena. Check in and spend some time relaxing 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 an authentic adventure.

Enjoy a lovely meal at Enoteca I Terzi, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante Tar-Tufo is another top choice with a popular menu. You could also check for a table at Antica Trattoria Papei. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

After your meal, keep the night alive at a bar like Meet Life Cafè, known for its lively atmosphere. Maudit Pub is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Bar Impero Siena offers an excellent atmosphere for those looking to amp up the evening.

Raise your glass to another unforgettable day in Italy!

Greet day 6 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Siena for your remaining 1 night in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in San Gimignano and Siena.

Brace yourself for today’s incredible lineup of attractions in Siena, featuring fun adventures, breathtaking views, and photo-friendly spots. Start at Porta San Giovanni, a frequently visited monument in the village. Then, head to Piazza Del Duomo and soak in the ambiance of this romantic public square.

There are many interesting places to see in Siena, and when you are ready for more, go to Rocca Di Montestaffoli. This is one of the village’s most beloved UNESCO world heritage-designated spots of interest. After exploring the castle, visit the beloved Parco Della Rocca. Not far away, you'll also find Chiesa Di Sant'agostino. This church is a respected highlight in Siena. Before wrapping up your self-guided sightseeing tour, head to Fortezza Medicea (siena), an up-and-coming monument in the village.

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 and reflect on the day's adventures.

Enjoy a lovely dining experience at Osteria Quattro Venti, 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 Fischi per Fiaschi, 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 Osteria da Divo. It’s yet another ideal choice to enhance your time in Siena tonight.

Extend your evening after a delightful meal by visiting Charlie Mixology Bar Di Aldinucci Riccardo, which offers the perfect atmosphere for a night out. Moreover, Bar Pinacoteca is another popular option for a drink or two. Likewise, San Paolo Pub also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise your glass to another unforgettable day in Italy!

Experience an unparalleled adventure on day 7 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Arezzo. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Arezzo. You will spend 1 night here for some well-deserved relaxation.

Set out on a day brimming with family-friendly attractions, photo-friendly spots, and history-rich sites. Start at the beloved Casa Vasari, a history-steeped museum in Siena. Next, go to The Medici Fortress Park.

After visiting Casa Vasari and The Medici Fortress Park, have a stroll along Siena's streets and take in the local charm. Continue your sightseeing by heading to Piazza Grande. This standout public square offers a unique experience. Santa Maria Della Pieve is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to San Francesco, Arezzo, one of the most culturally significant places to visit in Siena.

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

As you explore more of Arezzo, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Don’t miss out on dining at Il Covo dei Briganti, a top-rated dining destination in Arezzo. If you're in the mood to try something new, consider La Clandestina, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Logge Vasari. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Arezzo this evening.

If you’re not ready to end the night just yet, Liquid Bar offers a perfect venue to relax and savor a drink.

Head back to your accommodation in Arezzo and get some rest in preparation for another magical day of your road trip in Italy!

Dive into day 8 of your remarkable road trip in Italy. Today you will explore Urbino, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Rimini. You’ll stay here for 1 night.

Today’s route brings family-friendly attractions, breathtaking views, and photo-friendly spots. The first attraction of today is Palazzo Ducale. This captivating palace is a standout place to see in Arezzo. Continue your discovery at Galleria Nazionale Delle Marche, an UNESCO world heritage-listed museum with stories to tell.

As you stroll around Arezzo, take in the distinct atmosphere and learn what makes this town so unique. Maximize your sightseeing with a visit to Oratory Of St John The Baptist, Urbino. This beloved church offers an instagrammable encounter with Arezzo. Next, make your way to Casa Santi to add another highlight to your day. After that, visit Fortezza Albornoz, a beloved castle that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Arezzo.

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.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Rimini. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy a delicious meal at Osteria Brodo di Giuggiole, a highly-rated dining destination in Rimini. If you're eager to try something different, consider Hotel Touring, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante Lo Zodiaco Rimini. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rimini this evening.

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

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!