Two-Week Relaxed Italy Self-Drive Road Trip With Itinerary from Bologna to Siena, Rome, and Arezzo

Day 2 introduces you to many popular attractions and activities in Bologna, further proving that leisurely self-drive tours in Italy are extraordinary.

One of the most curiosity-inducing attractions included on the itinerary is Palazzo Re Enzo. This breathtaking palace will help you start your sightseeing on top. Then, take a leisurely stroll to Fountain Of Neptune, Bologna and learn what makes this heritage-rich monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the underrated Palazzo Del Podestà, Bologna. After exploring the palace, head to Bologna Cathedral. This intriguing church is a highlight in Bologna. As your day continues, stop by Piazza Maggiore, known for its respected features.

Make the most of your time in the country by joining activities that let you discover more about Italy. Check out all of the tours you can join this day of your leisurely self-drive holiday in Italy and ensure the experience of a lifetime.

After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Get ready for an unforgettable culinary journey in Bologna by reserving a table at Ahimè. Renowned as a Bib Gourmand restaurant, it offers an exceptional country cooking menu. For a different taste experience, head to I Portici, recognized for its delicious creative and contemporary dishes. This 1-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Trattoria di Via Serra, a local favorite known for its delightful emilian cuisine in Bologna. Nestled in the heart of the city, this Bib Gourmand awardee is an ideal choice for emilian foodies seeking culinary excellence.

Before calling it a day, visit one of the best bars in Bologna. There, you can look back on the highlights of today’s pleasant and invigorating travel experiences, have friendly conversations with locals, and unwind.

Keep the evening going at Lime Bar, a great choice for enjoying the after-dinner hours with a drink. You could also go to Macondo - Cocktail Bar, which offers a similarly pleasant setting and great drinks. Another option is Bar Onda Marina By Night, which provides an inviting environment for unwinding after a busy day out.

Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience in Italy!

On day 3 of your leisurely self-drive tour across Italy, you’ll go deep into Bologna, where you'll stay for 1 night, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Bologna, and meet locals along the way!

Two Towers brings Bologna's character to life. This awe-inspiring monument is a highlight of any visit in the city. Then, enjoy International Museum And Library Of Music, another eye-catching attraction that never fails to captivate visitors. Next, head over to Piazza Santo Stefano, one of the city’s most often recommended attractions, known for its visually striking features.

Italy makes the perfect setting for a calming but fun road trip experience. Aside from amazing sights, Italy also offers plenty of tours to enhance your relaxed road trip experience.

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Bologna, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Don’t miss out on dining at Va Mo Là, a top-rated dining destination in Bologna. If you're in the mood to try something new, consider Trattoria dal Biassanot, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Enoteca da Lucia. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Bologna this evening.

After dinner, it’s time to fall in love with the amazing nightlife in Bologna and unwind at some of the best bars in the city.

Cap off your dinner by heading to Aurum, ideal for a leisurely evening with a drink in hand. Bar Senza Nome is another bar that offers an enjoyable setting. Similarly, Caffè Ristretto is also a popular place to go on a night out, perfect for relaxing and socializing.

Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience in Italy!

Day 4 of your relaxed road trip in Italy will take you on a self-paced journey to more than one incredible place in one day. See some of the best attractions in Italy, taste the most delectable foods and exquisite drinks, and make incredible memories as you go!

To truly experience Bologna, make sure to drop by Palazzo Grassi, Bologna. This curiosity-inducing palace is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is San Martino, one of the city’s best highlights.

Next, check out La Piccola Venezia, one of the most frequently visited places to see in Bologna. This street is a favorite among locals and travelers alike.

You'll be staying in Siena on this laid-back road trip through Italy. You'll stay here for 2 nights.

After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Enjoy a delicious meal 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.

Experience the amazing nightlife in Siena and unwind at the coolest bars in the city.

Continue the enjoyment post-dinner at Meet Life Cafè, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Maudit Pub offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Impero Siena. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Raise your glass and toast to another unforgettable, laid-back road trip adventure in Italy!

Day 5 of your relaxed road trip through Italy means 24 hours of making the best memories in Siena. You’ll go sightseeing at famous attractions in Siena. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Siena!

Visiting Tower Of Mangia is always a good idea. This underrated monument is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Piazza Del Campo, 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 Opera Delle Metropolitana. This curiosity-inducing museum offers an enriching experience. For a change of pace, head to Siena Cathedral, where you can take in romantic features.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Bologna. There are so many fun and eye-opening activities to try out in Bologna that will make your slow-paced self-drive tour in Italy more memorable. Check out all the most recommended and top-rated tour options in the city of Siena to find the best options for you!

Exploring new places makes you hungry. Luckily, Siena has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

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.

Hang out and unwind at some of the top bars in Siena.

Continue your evening by exploring the vibrant nightlife scene at Charlie Mixology Bar Di Aldinucci Riccardo, a prime destination for a thrilling night out. Also, don’t forget to check out Bar Pinacoteca, a bar that offers unique local touches. Likewise, San Paolo Pub provides an excellent alternative for a fun evening.

Look back at an amazing day filled with adventure in Italy. And don’t forget to get some rest so you can continue your relaxed holiday in Italy tomorrow with new energy.

Day 6 of your easy, relaxed road trip through Italy lets you travel at your own pace and visit multiple places in a single day. Begin by exploring the best sights in Siena. By evening, drive toward the Rome, where you’ll stay at a top-rated hotel of your choice for 6 nights.

No visit to Siena is complete without Santuario Di Santa Caterina. This increasingly popular church is one of the top attractions in the city. Proceed to Basilica Of San Domenico, another must-visit attraction.

As you wander through the inviting streets of Siena, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Fortezza Medicea (siena). This underrated monument is a traveler-favorite.

In Rome, you’ll find plenty of places to unwind after a day on the road. Our top recommendations go perfectly with your laid-back road trip in Italy.

Mealtimes are the perfect opportunities to immerse yourself in the local culture of Italy. When you're not appreciating the best places to visit in Rome, explore the city like a local by trying out the best restaurants in the area.

Dive into a culinary adventure like no other in Rome by booking a table at La Pergola. This popular restaurant holds 3 Michelin star and offers an exceptional menu of mediterranean and contemporary cuisine. For another dining option, venture to Il Pagliaccio, celebrated for its delectable creative and innovative menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Enoteca La Torre, a top local restaurant known for its tantalizing mediterranean and creative menu. With a 2-star Michelin recognition, it promises an exceptional dining experience not to be missed.

After dinner, it’s time to fall in love with the amazing nightlife in Rome and unwind at some of the best bars in the city.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, La Botticella Of Poggi Giovanni stands out as an excellent choice for a post-dinner cocktail. Alternatively, Almalu Trastevere offers an ideal atmosphere to enjoy the pleasures of the night. Bar Viminale Di Pepi Maurilio is also a great option that provides a perfect setting for a relaxing evening.

Grab yourself a drink and savor every moment of your relaxed road trip experience in Italy!

Day 7 introduces you to many popular attractions and activities in Rome, further proving that leisurely self-drive tours in Italy are extraordinary.

Start your day at Trevi Fountain. This detailed monument is a timeless place to see in Rome. Then, wander over to Altare Della Patria. If detailed sites excite you, this monument will be right up your alley. Nearby, you’ll also find Capitoline Hill. This enchanting public square is a favorite among visitors.

Rome offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Roman Forum is a globally renowned spot in the city that will captivate you with its unique charm. When you’re done at the archeological site, don’t forget to check out the UNESCO world heritage-designated Colosseum. Take a moment to appreciate the fascinating details of this iconic archeological site.

Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities. Rome offers a wide selection of experiences for every traveler.

Mealtimes are the perfect opportunities to immerse yourself in the local culture of Italy. When you're not appreciating the best places to visit in Rome, explore the city like a local by trying out the best restaurants in the area.

Enjoy a delicious meal at RomAntica, a highly-rated dining destination in Rome. If you're eager to try something different, consider Coso Ristorante, another top spot with a tantalizing menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Rome. The bars in Rome make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Keep the excitement of the evening going by visiting a bar or two. Sant' Eustachio Caffè is an excellent place to start. You could also check out Yellowsquare Rome, offering a different kind of charm. A last recommendation for the day is Caffè Portofino. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Grab yourself a drink and savor every moment of your relaxed road trip experience in Italy!

On day 8 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, where you'll stay for 4 nights, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Rome, and meet locals along the way!

A visit to Trastevere is a must on the agenda today. This neighborhood is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights.

Experience Largo Di Torre Argentina, an interesting archeological site in the city. Then, head to Pantheon and soak in the ambiance of this culturally significant monument.

There are many interesting places to see in Rome, and when you are ready for more, go to Piazza Navona. This is one of the city’s most globally renowned enchanting spots of interest. After exploring the public square, visit the astonishing Campo De' Fiori.

Make the most of your time in the country by joining activities that let you discover more about Italy. Check out all of the tours you can join this day of your leisurely self-drive holiday in Italy and ensure the experience of a lifetime.

When you’re not driving and exploring some of the best places in Italy, it’s time to make your relaxed road trip even more comforting. Sit down for a lovely meal at one of the best restaurants in Rome.

Treat yourself to a delicious dinner at Hotel de Russie, an excellent option for tonight's dining. Looking for something different? La Taverna Italiana offers a tantalizing alternative with its diverse menu. And don’t miss The Parrot Bar. Known for great service, it’s a fantastic choice for tonight in Rome.

A visit to a top-rated local bar is one of the most refreshing ways to cap off a beautiful night in Rome.

To truly maximize your evening out, consider visiting The Apartment Bar Roma after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Hotel Hassler Roma, another bar with an inviting ambiance.

Savor the rest of the night and celebrate another incredible, relaxed road trip adventure in the magical Rome!

Day 9 of your relaxed road trip through Italy means 24 hours of making the best memories in Rome. You’ll go sightseeing at famous attractions in Rome. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Rome!

Don’t miss Via del Corso today, a must-see street that offers a glimpse into the city’s vibrant character. Take your time to explore its best features, and enjoy the convenience of nearby top-rated landmarks.

Check out the captivating museum, Villa Borghese Pinciana. Afterward, continue to Villa Borghese, a park every traveler should visit. As you explore Rome’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Piazza Del Popolo. This famous public square is an essential stop. Following that, head to Castel Sant'angelo, another must-visit site that will enhance your experience.

Italy makes the perfect setting for a calming but fun road trip experience. Aside from amazing sights, Italy also offers plenty of tours to enhance your relaxed road trip experience.

Exploring the food culture in Rome offers you an exciting chance to connect with locals and experience diversity along your relaxed road trip. When you’re ready to eat, we recommend you visit one of the best dining spots in the city.

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

Experience the amazing nightlife in Rome and unwind at the coolest bars in the city.

Free your mind of worries as you enjoy the taste of freedom on your laid-back road trip adventure across Italy.

Day 10 introduces you to many popular attractions and activities in Rome, further proving that leisurely self-drive tours in Italy are extraordinary.

Set aside time today to explore Via dei Condotti, a standout street 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.

Orange Garden is perfect for a self-paced visit during the day. This history-steeped park is sure to impress. Next on your list is Circus Maximus, another must-visit landmark and notable archeological site renowned for its culturally significant features.

While exploring and sightseeing, take time to savor the culture of Rome by sampling some local delicacies. When you’re ready for more sightseeing, head to Spanish Steps. This visually striking public square is an essential place to visit for anyone looking for the full Rome experience. We also recommend visiting Piazza Di Spagna, a wondrous public square.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Bologna. There are so many fun and eye-opening activities to try out in Bologna that will make your slow-paced self-drive tour in Italy more memorable. Check out all the most recommended and top-rated tour options in the city of Rome to find the best options for you!

After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Treat yourself to a wonderful meal at Ristorante Va. Do. , a top-rated dining spot in Rome. If you're in the mood for something new, try Giulia Restaurant, another premier location with a delectable menu. You might also want to book a table at L'Archeologia. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.

As the day is coming to an end, stop at some of Rome’s best bars to celebrate this day of your slow-paced adventure in Italy.

Cherish every minute of your relaxed road trip vacation across Italy.

On day 11 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, where you'll stay for 1 night, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Rome, and meet locals along the way!

A top thing to do today is to explore Monti, a must-see neighborhood in Rome. It's the perfect starting point for touring the top attractions in the area.

Your adventure in Rome is only getting started when you visit Archbasilica Of St. John Lateran, a locally renowned local hot spot. Another notable attraction to explore is Basilica Di Santa Maria Maggiore. This interesting church is known for its historic appeal.

After soaking in the highlights of these sights, take some time to wander Rome's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Auditorium Parco Della Musica. This instagrammable concert hall offers a fascinating experience that many visitors find memorable. Foro Italico is also worth visiting.

Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities. Rome offers a wide selection of experiences for every traveler.

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Rome, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Enjoy a lovely dining experience at Caffè Antica Roma, a popular restaurant in Rome. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Rome at Maccheroni, 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 In Roma - since 1917. It’s yet another ideal choice to enhance your time in Rome tonight.

Take a stroll around the area, head back to your accommodation for the night, or continue your evening at one of the best-rated bars in the city.

Raise your glass and relax after another big day of your leisurely paced road trip in Italy!

On day 12 of your laid-back road trip adventure in Italy, you can visit several remarkable places. With the freedom and flexibility of a self-drive tour, you decide how much time to spend in each, making the most of these memorable destinations.

Your adventure in Rome is only getting started when you visit The Medici Fortress Park, a curiosity-inducing local hot spot. Another notable attraction to explore is Piazza Grande. This notable public square is known for its romantic appeal.

After soaking in the highlights of these sights, take some time to wander Rome's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to San Francesco, Arezzo. This heritage-rich church offers a fascinating experience that many visitors find memorable.

When you’re not exploring beautiful places, you can relax in Arezzo. Here, you can choose from the best hotels and other accommodations as you get to know more about the culture in the city.

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Arezzo, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Prepare for an extraordinary culinary adventure in Arezzo by booking a table at Octavin, a 1-star Michelin restaurant that boasts an exceptional creative menu. If you're eager to try something different, consider La Clandestina, another top spot with a tantalizing menu.

Hang out and unwind at some of the top bars in Arezzo.

Extend your evening after a delightful meal by visiting Liquid Bar, which offers the perfect atmosphere for a night out.

Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience in Italy!

Your relaxed road trip in Italy continues on day 13 with more unforgettable memories to make. Today, you’ll get to know Italy better by exploring the top attractions of Arezzo and beyond. With 1 night left in Arezzo, you’ll still have time to eat and unwind at popular restaurants and bars in the city.

No visit to Arezzo is complete without Aboca Museum. This frequently visited museum is one of the top attractions in the town. Proceed to Museo Civico Di Sansepolcro, another must-visit attraction.

As you wander through the inviting streets of Arezzo, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to La Verna - Franciscan Sanctuary. This up-and-coming monastery is a traveler-favorite.

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

Exploring new places makes you hungry. Luckily, Arezzo has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

Treat yourself to a delicious dinner at La Nuova Tagliatella, an excellent option for tonight's dining. Looking for something different? i 3 bicchieri offers a tantalizing alternative with its diverse menu. And don’t miss Il Cantuccio. Known for great service, it’s a fantastic choice for tonight in Arezzo.

Take a stroll around the area, head back to your accommodation for the night, or continue your evening at one of the best-rated bars in the city.

Look back at an amazing day filled with adventure in Italy. And don’t forget to get some rest so you can continue your relaxed holiday in Italy tomorrow with new energy.