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

Dive into day 2 of your remarkable road trip in Italy. Today you will explore Bologna, 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 Bologna. You’ll stay here for 1 night.

Enjoy the perfect balance of relaxation and exploration in Rimini today. One of the most underrated attractions included on the itinerary is Piazza Santo Stefano. This symbolic public square will help you start your sightseeing on top. Then, take a leisurely stroll to Two Towers and learn what makes this picture-perfect monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the beloved Bologna Cathedral. After exploring the church, head to Palazzo Re Enzo. This intriguing palace is a highlight in Rimini. As your day continues, stop by Fountain Of Neptune, Bologna, known for its heritage-rich features. Lastly, don’t forget to check out the spectacular Piazza Maggiore. Enjoy exploring this incredible public square at your own pace.

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

Make sure to reserve a table at Ristorante Ciacco, an iconic dining spot in Bologna. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Ballarini, a popular restaurant in Bologna. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Sfoglia Rina, a hidden gem nestled in Bologna. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Explore the vibrant nightlife at Bar Al Bricco D'oro after your meal, a hub for lively evenings and memorable moments. Or, head to Bar Freud E Squisito for a great selection of flavorful drinks and a charming setting. Furthermore, Osteria Del Sole is perfect for those looking to extend their night with a touch of local flavor.

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

Experience an unparalleled adventure on day 3 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 2 nights here for some well-deserved relaxation.

Prepare for a day full of family-friendly attractions, picturesque spots, and budget-friendly activities. When you’re ready, kick off your sightseeing adventure at Central Market. This notable food market 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 Florence Baptistery, one of the most up-and-coming places to see in Bologna. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Ponte Vecchio. Wander around and soak in the history-steeped atmosphere this historical landmark offers. Then, head to Uffizi Gallery, a top-rated art gallery that adds another dimension to your day. Finally, visit the top-rated Piazza Della Signoria, the last of our attraction recommendations for today.

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

As dinnertime approaches, it's time to head out for a bite to eat in Florence. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Treat yourself to a delicious dinner at Ristorante Oliviero 1962, an excellent option for tonight's dining. Looking for something different? Di Poneta Novoli offers a tantalizing alternative with its diverse menu. And don’t miss Caffe San Firenze. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

To truly maximize your evening out, consider visiting Manifattura after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Se·sto On Arno Rooftop Bar, another bar with an inviting ambiance. Similarly, Il Vinile also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

At the end of the day, you'll drive back to Florence, where you'll stay for 1 night more.

Oltrarno is one of the highlights of today. Take your time exploring this iconic neighborhood in Pisa, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city.

Today’s itinerary in Florence covers several incredible sights, including a public square, a monument, a church, an observation deck and much more! Start your adventure at Piazza Del Duomo, Pisa. This timeless public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the UNESCO world heritage-listed 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 locally renowned church offers an enriching experience. For a change of pace, head to Piazzale Michelangelo, where you can take in visually striking features. These sights offer a fulfilling end to a perfect day.

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

As you explore more of Florence, 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.

Have a fantastic dining experience at Ditta Artigianale, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria Da Burde offers an enticing alternative with its varied menu. Additionally, Casa Toscana is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

Keep the excitement of the evening going by visiting a bar or two. Bar 50 Rosso is an excellent place to start. You could also check out Bitter Bar, offering a different kind of charm. A last recommendation for the day is Archea Brewery. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

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

Today’s itinerary in Florence covers several incredible sights, including a church, a public square, a palace, a monument and much more! Start your adventure at Basilica Of San Domenico. This intriguing church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Piazza Del Duomo, a must-see public square 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 Siena Cathedral. This well-known church offers an enriching experience. For a change of pace, head to Pubblico Palace, where you can take in respected features. Conclude your self-guided sightseeing tour with a visit to Piazza Del Campo and Tower Of Mangia. These sights offer a fulfilling end to a perfect day.

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.

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

Have a fantastic dining experience at Enoteca I Terzi, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante Tar-Tufo offers an enticing alternative with its varied menu. Additionally, Antica Trattoria Papei is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Siena.

After enjoying a fulfilling meal, continue your evening at Meet Life Cafè, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Maudit Pub offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Impero Siena provides an excellent environment for a relaxed and enjoyable evening.

Savor another day of unforgettable experiences in Italy!

Wake up to day 6 of your extraordinary road trip in Italy. With 1 night left in Siena, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Today’s well-planned self-sightseeing route offers several family-friendly attractions, breathtaking views, and picturesque spots. Whether you decide to explore Siena on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Porta San Giovanni is the first of them. Spend some time admiring this UNESCO world heritage-designated monument before continuing your journey. Piazza Del Duomo is your next stop. This frequently visited public square is one of the best-rated sights in Siena.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Rocca Di Montestaffoli. This visually striking castle is a sight to behold. To round off your sightseeing experience, visit Parco Della Rocca and Chiesa Di Sant'agostino. If time allows, end your day with Fortezza Medicea (siena), a culturally significant monument that offers a memorable conclusion to your exploration.

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.

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.

Say good night to Siena and look forward to another great day of your road trip in Italy!

Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Arezzo. At the end of the day, you will enjoy the comforts of a top-rated hotel in Arezzo, which will be your home away from home for 1 night.

Today’s route brings fun adventures, picturesque spots, and history-rich sites. The first attraction of today is Casa Vasari. This frequently visited museum is a heritage-rich place to see in Siena. Continue your discovery at The Medici Fortress Park, an awe-inspiring park with stories to tell.

As you stroll around Siena, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Grande. This captivating public square offers an instagrammable encounter with Siena. Next, make your way to Santa Maria Della Pieve to add another highlight to your day. After that, visit San Francesco, Arezzo, an increasingly popular church 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 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 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 and reflect on the day's adventures.

Enjoy a lovely dining experience at Il Covo dei Briganti, a popular restaurant in Arezzo. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Arezzo at La Clandestina, 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 Logge Vasari. It’s yet another ideal choice to enhance your time in Arezzo tonight.

Continue the enjoyment post-dinner at Liquid Bar, a cherished local gathering spot renowned for its welcoming atmosphere.

Say good night to Arezzo and look forward to another great day of your road trip in Italy!

On day 8 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 Urbino. In the evening, you’ll end up in Rimini, where you will stay for 1 night.

Get ready for a day filled with fun adventures, breathtaking views, and photo-friendly spots in the charming town of Arezzo. Your adventure starts at Palazzo Ducale, a locally renowned local hot spot. Another notable attraction to explore is Galleria Nazionale Delle Marche. This up-and-coming museum is known for its historic appeal.

After soaking in the highlights of these sights, take some time to wander Arezzo's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Oratory Of St John The Baptist, Urbino. This heritage-rich church offers a fascinating experience that many visitors find memorable. Casa Santi is also worth visiting, along with Fortezza Albornoz. These standout landmarks offer unique experiences that add to the day’s enjoyment.

When you’re done exploring for the day, you’ll drive to your hotel in Rimini. Check in and spend some time relaxing before you head out to tour the city.

As you explore more of Rimini, 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.

Treat yourself to a delightful dinner at Osteria Brodo di Giuggiole, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Hotel Touring? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Lo Zodiaco Rimini as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rimini.

Cap off your dinner by heading to Hobo's, ideal for a leisurely evening with a drink in hand. Sunflower City Backpacker is another bar that offers an enjoyable setting. Similarly, Bar Capogiro is also a popular place to go on a night out, perfect for relaxing and socializing.

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