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.

Discover a day packed with fun adventures, breathtaking views, and picturesque spots in Bologna. Begin your sightseeing with Palazzo Re Enzo. This locally appreciated palace is one of the top attractions in the city. Proceed to Fountain Of Neptune, Bologna, another must-visit attraction.

As you wander through the inviting streets of Bologna, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Palazzo Del Podestà, Bologna. This frequently visited palace is a traveler-favorite. Not far away, you’ll find Bologna Cathedral, another key site on your sightseeing itinerary. Piazza Maggiore is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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

Exploring the food culture in Bologna 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.

Start your culinary exploration in Bologna by securing a reservation at Ahimè. This renowned restaurant holds a Bib Gourmand award and offers an exceptional menu of country cooking cuisine. For another dining delight, visit I Portici, celebrated for its delectable creative and contemporary menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Trattoria di Via Serra, a top local spot known for its tantalizing emilian menu. With a Bib Gourmand recognition, it guarantees an exceptional dining adventure.

Experience the amazing nightlife in Bologna and unwind at the coolest 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.

Grab a drink and enjoy every passing minute of this night of your 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!

Savor the day by visiting some of the best places to see in Bologna, including a monument, a museum, and a public square. Start your adventure at Two Towers. This popular monument is a must-visit for travelers looking for a unique holiday experience. Make your way to International Museum And Library Of Music located in Bologna for another exciting encounter.

Next, immerse yourself in the setting of Piazza Santo Stefano. Its romantic features will captivate you.

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

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.

Make sure to reserve a table at Va Mo Là, 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 Trattoria dal Biassanot, 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 Ristorante Enoteca da Lucia, a hidden gem nestled in Bologna. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

Keep the evening going at Aurum, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bar Senza Nome, which offers a similarly pleasant setting and great drinks. Another option is Caffè Ristretto, which provides an inviting environment for unwinding after a busy day out.

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

Day 4 of your leisurely self-drive tour in Italy is another opportunity for an in-depth travel experience in the country. You’ll stay in Siena for 2 nights.

Start your day with a visit to Palazzo Grassi, Bologna. This often recommended palace is a must-visit in the city. When you’re ready for your next discovery, continue to San Martino, which may be one of the most heritage-rich places you will experience today.

One of the best things about exploring Bologna 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 La Piccola Venezia, a worthwhile street in the city.

In the city of Siena, you’ll find plenty of stay options that will accommodate your need for rest and relaxation after spending your day on the road. Our top recommendations perfectly complement your relaxed road trip vacation 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 Siena, 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 Enoteca I Terzi, 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 Ristorante Tar-Tufo, 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 Antica Trattoria Papei. It’s yet another ideal choice to enhance your time in Siena tonight.

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

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

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

On day 5 of your leisurely self-drive tour across Italy, you’ll go deep into Siena, 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 Siena, and meet locals along the way!

Today, you'll explore some of the most beautiful places in Siena, including a monument, a public square, a museum, a church and much more! Start your day with a visit to Tower Of Mangia. This intriguing monument is a must-visit in the city. When you’re ready for your next discovery, continue to Piazza Del Campo, which may be one of the most history-steeped 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 Opera Delle Metropolitana, a frequently visited museum in the city. If you’re up for more discoveries, don’t forget to reserve some time for Siena Cathedral.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Siena. There are so many fun and eye-opening activities to try out in Siena 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!

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 Siena, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

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.

After dinner, you can choose between heading back to your hotel to recharge, taking a leisurely stroll, or going out to a bar for a relaxed drink in great company.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Charlie Mixology Bar Di Aldinucci Riccardo, known for its inviting atmosphere. Bar Pinacoteca is another great option if you’re looking for a place to get the night started. Similarly, San Paolo Pub provides a great setting to enjoy the night away.

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

On day 6 of your laid-back and relaxed road trip adventure, you’ll have the chance to visit more than one remarkable area in Italy. Since this self-drive tour offers freedom and flexibility, you can decide how much time you want to spend in each place to enjoy the memorable travel destinations in Italy.

Set out on a day brimming with family-friendly attractions, photo-friendly spots, and historic treasures. Start at the increasingly popular Santuario Di Santa Caterina, a culturally significant church in Siena. Next, go to Basilica Of San Domenico.

After visiting Santuario Di Santa Caterina and Basilica Of San Domenico, have a stroll along Siena's streets and take in the local charm. Continue your sightseeing by heading to Fortezza Medicea (siena). This picture-perfect monument offers a unique experience.

You’ll be staying at the incredible city of Rome in this laid-back road trip in Italy. You'll stay here for 6 nights.

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 an extraordinary dining experience at La Pergola, a 3-star Michelin restaurant offering an incredible mediterranean and contemporary menu. Alternatively, if your taste buds call for something different, Il Pagliaccio is one of the best restaurants for creative and innovative cuisine in Rome. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Enoteca La Torre. As a top-rated establishment with 2 Michelin star, it is an ideal choice for mediterranean and creative cuisine in the city.

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.

If you’re not ready to end the night just yet, La Botticella Of Poggi Giovanni offers a perfect venue to relax and savor a drink. Similarly, Almalu Trastevere is well-suited for those looking to unwind in a social setting. Bar Viminale Di Pepi Maurilio 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 7 introduces you to many popular attractions and activities in Rome, further proving that leisurely self-drive tours in Italy are extraordinary.

Set out on a day brimming with family-friendly attractions, romantic experiences, and breathtaking views. Start at the wondrous Trevi Fountain, a history-steeped monument in Rome. Next, go to Altare Della Patria.

After visiting Trevi Fountain and Altare Della Patria, have a stroll along Rome's streets and take in the local charm. Continue your sightseeing by heading to Capitoline Hill. This romantic public square offers a unique experience. Roman Forum is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Colosseum, one of the most UNESCO world heritage-designated places to visit 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.

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

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

After enjoying a fulfilling meal, continue your evening at Sant' Eustachio Caffè, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Yellowsquare Rome offers a welcoming atmosphere for easing into the nightlife. Similarly, Caffè Portofino provides an excellent environment for a relaxed and enjoyable evening.

Raise your glass in celebration of your freedom and relaxed road trip adventure 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.

Rome is home to plenty of attractions that offer fun adventures, photo-friendly spots, and historic treasures! Start at Largo Di Torre Argentina, a well-known archeological site that is worthwhile a visit in the city. Nearby, you’ll find Pantheon, enchanting visitors with its photogenic appeal. Continue your exploration at Piazza Navona. This public square is one of the city’s most world-famous 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 Campo De' Fiori.

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 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 delightful dinner at Hotel de Russie, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try La Taverna Italiana? It's another excellent option with a diverse menu. Consider reserving a table at The Parrot Bar as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

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.

Continue your evening by exploring the vibrant nightlife scene at The Apartment Bar Roma, a prime destination for a thrilling night out. Also, don’t forget to check out Hotel Hassler Roma, a bar that offers unique local touches.

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

On day 9 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, where you'll stay for 3 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!

Via del Corso is a fantastic place you can explore today in Rome. This street 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 Rome-way-of-life and visit all the nearby sights.

Bring your curiosity for today’s adventure around Rome. Some of the city’s most loved attractions await! Villa Borghese Pinciana is the perfect place to start. This museum is one of the most popular places to visit in Rome. Next, head to Villa Borghese, an impressive park, known for its noteworthy 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 Del Popolo. This noteworthy public square is a highly recommended experience. Nearby, you'll also find Castel Sant'angelo. Visit these for an interesting touch to your journey.

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

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 Sofitel Roma Villa Borghese, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Centro, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Tema. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

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

Free your mind of worries as you enjoy the taste of freedom on your laid-back, relaxed 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.

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

Rome is brimming with adventures. Today’s wonderful stops include a park, an archeological site, and a public square. Begin your sightseeing adventure at the notable Orange Garden and allow yourself time to explore. Just a short distance away you'll find your next stop, Circus Maximus, a breathtaking archeological site that draws visitors from far and near.

Continue your journey to Spanish Steps, one of the city’s most widely recognized spots that you shouldn’t miss. Another great site to visit is the globally renowned Piazza Di Spagna.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Rome. There are so many fun and eye-opening activities to try out in Rome 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.

Treat yourself to a delicious dinner at Ristorante Va. Do. , an excellent option for tonight's dining. Looking for something different? Giulia Restaurant offers a tantalizing alternative with its diverse menu. And don’t miss L'Archeologia. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

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.

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

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!

Make sure to visit Monti, a popular neighborhood 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 by visiting Archbasilica Of St. John Lateran, a prime spot to begin your journey. This stunning church is sure to impress. Next on your list is Basilica Di Santa Maria Maggiore, another must-visit landmark and popular church renowned for its heritage-rich 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 Auditorium Parco Della Musica. This romantic concert hall is an essential place to visit for anyone looking for the full Rome experience. We also recommend visiting Foro Italico, a locally renowned sports complex.

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

Enjoy a lovely meal at Caffè Antica Roma, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Maccheroni is another top choice with a popular menu. You could also check for a table at In Roma - since 1917. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

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.

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 12 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Arezzo for 2 nights. Along the route of your relaxed road trip, you can get a glimpse of the locals’ way of life and visit some of the most amazing locations in Italy.

A blend of fun adventures, romantic experiences, and breathtaking views await you in Rome on today’s itinerary. First up is the often recommended park, The Medici Fortress Park. Afterward, continue to Piazza Grande, a public square 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 San Francesco, Arezzo. This locally appreciated church is an essential stop.

After a day of exploration, relax at one of the top hotels or accommodations in Arezzo. Staying in the city enhances your laid-back road trip experience in Italy by offering a comfortable and welcoming environment to recharge in this charming destination.

Exploring the food culture in Arezzo 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.

Experience a harmony of flavors at Octavin in Arezzo by securing a reservation in advance. Known for its 1-star Michelin status, Octavin offers a delightful variety of dishes highlighting its delicious creative menu. If you're looking to mix things up, La Clandestina offers an enticing alternative with its varied menu.

After dinner, you can choose between heading back to your hotel to recharge, taking a leisurely stroll, or going out to a bar for a relaxed drink in great company.

To truly maximize your evening out, consider visiting Liquid Bar after dinner. This bar is known for offering some of the best drinks and vibes in the city.

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

On day 13 of your relaxed road trip, you’ll start your self-paced adventure in Arezzo and visit amazing attractions in Sansepolcro and La Verna destinations, just outside of the city. You still have 1 night left in Arezzo. This means today is also another excellent opportunity to dine at some of the top-rated restaurants and bars in the area.

Brace yourself for today’s incredible lineup of attractions in Arezzo, featuring fun adventures, photo-friendly spots, and historic treasures. Start at Aboca Museum, an up-and-coming museum in the town. Then, head to Museo Civico Di Sansepolcro and soak in the ambiance of this heritage-rich museum.

There are many interesting places to see in Arezzo, and when you are ready for more, go to La Verna - Franciscan Sanctuary. This is one of the town’s most worthwhile stunning spots of interest.

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

Exploring the food culture in Arezzo 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.

Enjoy a delicious meal at La Nuova Tagliatella, a highly-rated dining destination in Arezzo. If you're eager to try something different, consider i 3 bicchieri, another top spot with a tantalizing menu. You might also want to secure a reservation at Il Cantuccio. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Arezzo this evening.

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

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