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

On day 2 of your leisurely self-drive tour across Italy, you’ll go deep into Bologna, where you'll stay for 2 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 Bologna, and meet locals along the way!

Make a stop at Palazzo Re Enzo. This up-and-coming palace is a must-visit for travelers looking for a unique holiday experience. Make your way to Fountain Of Neptune, Bologna located in Bologna for another exciting encounter.

Next, immerse yourself in the setting of Palazzo Del Podestà, Bologna. Its symbolic features will captivate you. After the palace, continue your tour of the city with a visit to Bologna Cathedral. Visitors usually appreciate the picture-perfect features of this church. Next up is Piazza Maggiore, a highly recommended public square.

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.

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 Bologna, explore the city like a local by trying out the best restaurants in the area.

Treat yourself to an extraordinary dining experience at Ahimè, a Bib Gourmand restaurant offering an incredible country cooking menu. Alternatively, if your taste buds call for something different, I Portici is one of the best restaurants for creative and contemporary cuisine in Bologna. This 1-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Trattoria di Via Serra. As a top-rated establishment with a Bib Gourmand status, it is an ideal choice for emilian cuisine in the city.

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.

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

Raise your glass to celebrate another day of your laid-back and relaxed road trip experience in Italy!

Day 3 of your relaxed road trip through Italy means 24 hours of making the best memories in Bologna. You’ll go sightseeing at famous attractions in Bologna. 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 Bologna!

Check out the interesting monument, Two Towers. Afterward, continue to International Museum And Library Of Music, a museum every traveler should visit. As you explore Bologna’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Piazza Santo Stefano. This intriguing public square is an essential stop.

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.

For an unforgettable shopping experience, visit Via d'Azeglio, the top shopping destination in Bologna. Browse local boutique shops and luxury stores, each offering delightful surprises. Find unique souvenirs or items to take home. After shopping, explore what Via d'Azeglio has to offer, including attractions, essential services, and vibrant community activities.

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.

Enjoy a delicious meal 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.

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 Bologna. The bars in Bologna make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Round off your dining experience by visiting Aurum, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Senza Nome, a bar catering to every mood and preference. Caffè Ristretto likewise offers a unique atmosphere, perfect for a memorable night out.

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

Day 4 of your self-drive tour in Italy offers a chance to experience the country’s diversity. You’ll start your day in Bologna and end it in Siena. You’ll stay in Siena for 2 nights. Along the way, you’ll glimpse local life and explore some of the most remarkable places in Italy.

Palazzo Grassi, Bologna is must-visit palace and a great option for a daytime tour of the area. Continue your journey to San Martino, a frequently visited church, located just a leisurely stroll away. Next, head to La Piccola Venezia, a romantic street, also available for your discovery today.

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

Exploring the food culture in Siena 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 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.

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.

If you’re not ready to end the night just yet, Meet Life Cafè offers a perfect venue to relax and savor a drink. Similarly, Maudit Pub is well-suited for those looking to unwind in a social setting. Bar Impero Siena is another excellent spot to enjoy a nightcap after a delightful meal.

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

Day 5 introduces you to many popular attractions and activities in Siena, further proving that leisurely self-drive tours in Italy are extraordinary.

Tower Of Mangia is must-visit monument and a great option for a daytime tour of the area. Continue your journey to Piazza Del Campo, an astonishing public square, located just a leisurely stroll away. Next, head to Opera Delle Metropolitana, a breathtaking museum, also available for your discovery today.

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

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 delicious dinner at Osteria Quattro Venti, an excellent option for tonight's dining. Looking for something different? Fischi per Fiaschi offers a tantalizing alternative with its diverse menu. And don’t miss Osteria da Divo. Known for great service, it’s a fantastic choice for tonight in Siena.

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

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.

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

On day 6 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.

Start your day at Santuario Di Santa Caterina. This culturally significant church is a beloved place to see in Siena. Then, wander over to Basilica Of San Domenico. If awe-inspiring sites excite you, this church will be right up your alley. Nearby, you’ll also find Fortezza Medicea (siena). This picture-perfect monument is a favorite among visitors.

After a day of exploration, relax at one of the top hotels or accommodations in Rome. Staying in the city gives you a comfortable, welcoming place to recharge during your laid-back road trip in Italy.

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.

Start your culinary exploration in Rome by securing a reservation at La Pergola. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of mediterranean and contemporary cuisine. For another dining delight, visit Il Pagliaccio, celebrated for its delectable creative and innovative menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Enoteca La Torre, a top local spot known for its tantalizing mediterranean and creative menu. With a 2-star Michelin recognition, it guarantees an exceptional dining adventure.

If you feel like it, head out to a bar to celebrate another fantastic day in Rome and take the pulse of the city’s nightlife. Enjoy the night without rushing to fully appreciate it.

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.

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

On day 7 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, where you'll stay for 5 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!

Make time for Trevi Fountain, a wondrous monument that is worthwhile a visit in the city. Nearby, you’ll find Altare Della Patria, enchanting visitors with its picture-perfect appeal. Continue your exploration at Capitoline Hill. This public square is one of the city’s most captivating spots.

Enjoy the freedom of exploring Rome at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Roman Forum. After exploring the archeological site, head to the world-famous Colosseum.

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!

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 RomAntica, 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 Coso Ristorante, 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 DEROMA - Farine Romane, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

If you feel like it, head out to a bar to celebrate another fantastic day in Rome and take the pulse of the city’s nightlife. Enjoy the night without rushing to fully appreciate it.

After your meal, keep the night alive at a bar like Sant' Eustachio Caffè, known for its lively atmosphere. Yellowsquare Rome is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Caffè Portofino offers an excellent atmosphere for those looking to amp up the evening.

Soak in the unique atmosphere of Rome as you commemorate this day of your relaxed road trip with a toast. Cheers to a memorable, leisurely self-drive holiday in Italy!

Day 8 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!

Set aside time today to explore Trastevere, 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.

One of the most well-known attractions included on the itinerary is Largo Di Torre Argentina. This photogenic archeological site will help you start your sightseeing on top. Then, take a leisurely stroll to Pantheon and learn what makes this culturally significant monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the iconic Piazza Navona. After exploring the public square, head to Campo De' Fiori. This astonishing public square is a highlight in Rome.

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.

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

Have a fantastic dining experience at Hotel de Russie, a highly recommended choice for tonight's dinner. If you're looking to mix things up, La Taverna Italiana offers an enticing alternative with its varied menu. Additionally, The Parrot Bar is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

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

Let the evening flow smoothly from dinner to drinks at The Apartment Bar Roma, a top-rated bar in the area. For other recommendations, Hotel Hassler Roma provides a perfect setting for rounding out your night with style and great drinks.

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

At the top of the list of things to do today is to explore Via del Corso, a street that captures the true essence of Rome. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.

Villa Borghese Pinciana is perfect for a self-paced visit during the day. This history-steeped museum is sure to impress. Next on your list is Villa Borghese, another must-visit landmark and impressive park renowned for its detailed 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 Piazza Del Popolo. This history-steeped public square is an essential place to visit for anyone looking for the full Rome experience. We also recommend visiting Castel Sant'angelo, a top-rated castle.

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 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.

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.

If you’re not yet ready to call it a night, head back out to celebrate your vacation with a drink. This is a great time to slow down, look back at your day, and raise a toast to your wonderful holiday in Italy.

A leisurely self-drive holiday in Rome can’t get any better than this! Toast to another amazing day in Italy!

On day 10 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, where you'll stay for 2 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!

Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Make sure to visit Via dei Condotti, a popular street in Rome. Spend some time wandering around the area and soak in its distinctive charm. You’ll also discover that several of the city’s must-see attractions are just around the corner.

Start your day at Orange Garden. This stunning park is a captivating place to see in Rome. Then, wander over to Circus Maximus. If historic sites excite you, this archeological site will be right up your alley. Nearby, you’ll also find Spanish Steps. This culturally significant 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, Piazza Di Spagna is a wondrous spot in the city that will captivate you with its unique charm.

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.

Savor the flavors at Ristorante Va. Do. , a top pick for dinner tonight. Alternatively, Giulia Restaurant beckons with its unique menu offerings. Also, consider L'Archeologia. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

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

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

Day 11 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 Monti today, a must-see neighborhood 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.

Your adventure in Rome is only getting started when you visit Archbasilica Of St. John Lateran, a well-known local hot spot. Another notable attraction to explore is Basilica Di Santa Maria Maggiore. This notable church is known for its breathtaking 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 visually striking concert hall offers a fascinating experience that many visitors find memorable. Foro Italico is also worth visiting.

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!

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.

Don’t miss out on dining at Caffè Antica Roma, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Maccheroni, another top spot with a mouthwatering menu. You might also want to secure a reservation at In Roma - since 1917. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

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.

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

Day 12 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 Arezzo. By evening, drive toward the Arezzo, where you’ll stay at a top-rated hotel of your choice for 2 nights.

Set your GPS to Arezzo and hit the road. Expect a journey of approximately 2 hours 33 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Arezzo beckons with new experiences!

Our first attraction recommendation in Arezzo is The Medici Fortress Park, an intriguing park that draws attention for its enchanting features. Spend some time soaking in the atmosphere before continuing to Piazza Grande, a visually striking public square that stands out in the city.

Time flies when you're having fun! But don't forget to stop for a bit to eat and drink between your adventures. When you're rested and recharged, head to San Francesco, Arezzo, an increasingly popular church that offers a unique experience.

In Arezzo, 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.

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 Arezzo.

Enjoy an outstanding dining experience at Octavin, a 1-star Michelin restaurant offering an exceptional creative menu. 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.

If you’re not yet ready to call it a night, head back out to celebrate your vacation with a drink. This is a great time to slow down, look back at your day, and raise a toast to your wonderful holiday in Italy.

After enjoying a fulfilling meal, continue your evening at Liquid Bar, ideal for those looking to unwind with a drink in a comfortable setting.

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

On day 13 of your relaxed road trip across Italy, you’ll explore the area around Arezzo, where you’ll be staying for another 1 night. With so many fun and inspiring experiences to offer, a tour of Arezzo will make you fall even more in love with the city and uniqueness of Italy.

When you’re ready to jump back into the car and say goodbye to Arezzo, you’ll hit the road in the direction of Sansepolcro. This drive usually takes around 39 min.

Aboca Museum is a worthwhile museum we recommend visiting today. Discover its instagrammable features before continuing your self-guided tour to Museo Civico Di Sansepolcro, a historic museum that’s well-regarded in the area.

Set your GPS to La Verna and hit the road. Expect a journey of approximately 42 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. La Verna beckons with new experiences!

Spend your afternoon discovering La Verna - Franciscan Sanctuary, an intriguing monastery known for its stunning features.

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

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 lovely dining experience at La Nuova Tagliatella, 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 i 3 bicchieri, 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 Il Cantuccio. It’s yet another ideal choice to enhance your time in Arezzo tonight.

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

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.