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!

Brace yourself for today’s incredible lineup of attractions in Bologna, featuring family-friendly attractions, scenic views, and photo-friendly spots. Start at Palazzo Re Enzo, a curiosity-inducing palace in the city. Then, head to Fountain Of Neptune, Bologna and soak in the ambiance of this noteworthy monument.

There are many interesting places to see in Bologna, and when you are ready for more, go to Palazzo Del Podestà, Bologna. This is one of the city’s most beloved heritage-rich spots of interest. After exploring the palace, visit the intriguing Bologna Cathedral. Not far away, you'll also find Piazza Maggiore. This public square is a grand highlight in Bologna.

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, Bologna has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

Begin 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.

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

Continue the enjoyment post-dinner at Lime Bar, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Macondo - Cocktail Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Onda Marina By Night. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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 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!

Bologna is home to plenty of attractions that offer fun adventures, breathtaking views, and picturesque spots! Start at Two Towers, a popular monument that is worthwhile a visit in the city. Nearby, you’ll find International Museum And Library Of Music, enchanting visitors with its heritage-rich appeal. Continue your exploration at Piazza Santo Stefano. This public square is one of the city’s most locally appreciated spots.

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.

Bring home unique finds from Bologna's bustling shopping hub, Quadrilatero. Enjoy a leisurely exploration of unique boutiques and stores where locals shop. Don’t forget to browse souvenirs and local specialties that make perfect gifts for your loved ones. Beyond shopping, Quadrilatero offers plenty of options, including primary services, unique landmarks, and community events.

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.

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.

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.

Continue your evening by exploring the vibrant nightlife scene at Aurum, a prime destination for a thrilling night out. Also, don’t forget to check out Bar Senza Nome, a bar that offers unique local touches. Likewise, Caffè Ristretto provides an excellent alternative for a fun evening.

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

Day 4 of your easy and relaxed road trip through Italy gives you the opportunity to travel leisurely and experience more than one place in one day. You will start your day by exploring some of the best sights in the city of Bologna. By the end of the day, you’ll drive in the direction of the city of Siena, where you’ll stay at a top-rated hotel of your choice for 2 nights.

Discover a day packed with family-friendly attractions, picturesque spots, and historic treasures in Bologna. Begin your sightseeing with Palazzo Grassi, Bologna. This curiosity-inducing palace is one of the top attractions in the city. Proceed to San Martino, 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 La Piccola Venezia. This frequently visited street is a traveler-favorite.

After a day of exploration, relax at one of the top hotels or accommodations in Siena. 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 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.

Treat yourself to a wonderful meal at Enoteca I Terzi, a top-rated dining spot in Siena. If you're in the mood for something new, try Ristorante Tar-Tufo, another premier location with a delectable menu. You might also want to book a table at Antica Trattoria Papei. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

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.

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.

Grab a drink and enjoy every passing minute of this night 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.

Get ready for an exciting day in Siena. Today’s sightseeing agenda includes a monument, a public square, a museum, a church and much more! Begin your adventure at Tower Of Mangia. This is an up-and-coming monument you should not miss. Another must-see is Piazza Del Campo, a top-rated public square in Siena.

When you’re ready for the next sight, head to Opera Delle Metropolitana. From there, take a leisurely stroll to Siena Cathedral, another of the city’s notable attractions.

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.

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 delicious meal at Osteria Quattro Venti, a highly-rated dining destination in Siena. If you're eager to try something different, consider Fischi per Fiaschi, another top spot with a tantalizing menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena 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 Siena. The bars in Siena make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

To truly maximize your evening out, consider visiting Charlie Mixology Bar Di Aldinucci Riccardo after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Pinacoteca, another bar with an inviting ambiance. Similarly, San Paolo Pub also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Day 6 of your leisurely self-drive tour in Italy is another opportunity for an in-depth travel experience in the country. You’ll stay in Rome for 6 nights.

Get ready for a day filled with family-friendly attractions, picturesque spots, and historic treasures in the charming city of Siena. Your adventure starts at Santuario Di Santa Caterina, a beloved local hot spot. Another notable attraction to explore is Basilica Of San Domenico. This curiosity-inducing church is known for its standout appeal.

After soaking in the highlights of these sights, take some time to wander Siena's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Fortezza Medicea (siena). This culturally significant monument offers a fascinating experience that many visitors find memorable.

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.

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.

Experience a harmony of flavors at La Pergola in Rome by securing a reservation in advance. Known for its 3-star Michelin status, La Pergola offers a delightful variety of dishes highlighting its delicious mediterranean and contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Il Pagliaccio, a highly recommended restaurant known for its enticing creative and innovative cuisine. This popular 2-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Enoteca La Torre, a highly acclaimed restaurant celebrated for its exceptional mediterranean and creative menu.

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 La Botticella Of Poggi Giovanni, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Almalu Trastevere offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Viminale Di Pepi Maurilio provides an excellent environment for a relaxed and enjoyable evening.

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

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!

Get ready for a day filled with family-friendly attractions, romantic experiences, and breathtaking views in the charming city of Rome. Your adventure starts at Trevi Fountain, a globally renowned local hot spot. Another notable attraction to explore is Altare Della Patria. This interesting monument is known for its enchanting 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 Capitoline Hill. This enchanting public square offers a fascinating experience that many visitors find memorable. Roman Forum is also worth visiting, along with Colosseum. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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!

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 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.

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

Explore the vibrant nightlife at Sant' Eustachio Caffè after your meal, a hub for lively evenings and memorable moments. Or, head to Yellowsquare Rome for a great selection of flavorful drinks and a charming setting. Furthermore, Caffè Portofino is perfect for those looking to extend their night with a touch of local flavor.

Free your mind of worries as you enjoy the taste of freedom on your laid-back, relaxed road trip adventure across 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!

Make sure to visit Trastevere, 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.

Today’s route brings fun adventures, picturesque spots, and historic treasures. The first attraction of today is Largo Di Torre Argentina. This well-known archeological site is a photogenic place to see in Rome. Continue your discovery at Pantheon, a culturally significant monument with stories to tell.

As you stroll around Rome, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Navona. This iconic public square offers a culturally significant encounter with Rome. Next, make your way to Campo De' Fiori to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day 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.

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 wonderful meal at Hotel de Russie, a top-rated dining spot in Rome. If you're in the mood for something new, try La Taverna Italiana, another premier location with a delectable menu. You might also want to book a table at The Parrot Bar. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening 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.

Cap off your dinner by heading to The Apartment Bar Roma, ideal for a leisurely evening with a drink in hand. Hotel Hassler Roma is another bar that offers an enjoyable setting.

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

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

A visit to Via del Corso in Rome is a must on the agenda today. This street 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.

Discover a day packed with fun adventures, romantic experiences, and scenic views in Rome. Begin your sightseeing with Villa Borghese Pinciana. This well-known museum is one of the top attractions in the city. Proceed to Villa Borghese, another must-visit attraction.

As you wander through the inviting streets of Rome, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Piazza Del Popolo. This widely recognized public square is a traveler-favorite. Not far away, you’ll find Castel Sant'angelo, another key site on your sightseeing itinerary.

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.

Treat yourself to a delicious dinner at Sofitel Roma Villa Borghese, an excellent option for tonight's dining. Looking for something different? Centro offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Tema. With its reputation for pleasing customers, 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.

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

Via dei Condotti is a street that stands out as one of the must-see places in Rome. Take a moment to explore its distinct atmosphere, and don’t miss the popular sightseeing spots just a short walk away.

A blend of family-friendly attractions, romantic experiences, and breathtaking views await you in Rome on today’s itinerary. First up is the notable park, Orange Garden. Afterward, continue to Circus Maximus, an archeological site 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 Spanish Steps. This spectacular public square is an essential stop. Following that, head to Piazza Di Spagna, another must-visit site that will enhance your experience.

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.

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.

Make sure to reserve a table at Ristorante Va. Do. , 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 Giulia Restaurant, 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 L'Archeologia, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

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

At the top of the list of things to do today is to explore Monti, a neighborhood 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.

Today, you'll explore some of the most beautiful places in Rome, including a church, a concert hall, and a sport complex. Start your day with a visit to Archbasilica Of St. John Lateran. This well-known church is a must-visit in the city. When you’re ready for your next discovery, continue to Basilica Di Santa Maria Maggiore, which may be one of the most heritage-rich places you will experience today.

One of the best things about exploring Rome 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 Auditorium Parco Della Musica, a locally renowned concert hall in the city. If you’re up for more discoveries, don’t forget to reserve some time for Foro Italico.

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.

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.

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.

Toast to another unforgettable and relaxing road trip adventure in Italy!

Day 12 of your relaxed road trip across the beautiful country of 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!

Start by visiting The Medici Fortress Park, a prime spot to begin your journey. This romantic park is sure to impress. Next on your list is Piazza Grande, another must-visit landmark and captivating public square renowned for its stunning 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 San Francesco, Arezzo. This culturally significant church is an essential place to visit for anyone looking for the full Rome experience.

Continue your laid-back road trip exploration of the best attractions in Italy at Arezzo. Select from top hotels and accommodations in the city to recharge and rejuvenate.

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.

Set out on a gastronomic journey in Arezzo by reserving a table at Octavin. Renowned for its 1-star Michelin recognition, this restaurant presents an outstanding menu of creative cuisine. Looking for something different? La Clandestina offers a tantalizing alternative with its diverse menu. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Arezzo.

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

After savoring a delicious meal, step into the vibrant nightlife at Liquid Bar, where the evening is just getting started.

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

Your laid-back and relaxed road trip in Italy continues on day 13, allowing you to create more unforgettable memories. Today’s travel plan offers you the chance to have a more in-depth understanding of Italy and its people by visiting the offerings and top attractions of Arezzo and beyond. With 1 night left in Arezzo, you’ll have enough time to eat and unwind at popular restaurants and bars in the city.

Arezzo is home to plenty of attractions that offer family-friendly attractions, photo-friendly spots, and historic treasures! Start at Aboca Museum, an underrated museum that is worthwhile a visit in the town. Nearby, you’ll find Museo Civico Di Sansepolcro, enchanting visitors with its standout appeal. Continue your exploration at La Verna - Franciscan Sanctuary. This monastery is one of the town’s most up-and-coming spots.

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

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.

Savor the flavors at La Nuova Tagliatella, a top pick for dinner tonight. Alternatively, i 3 bicchieri beckons with its unique menu offerings. Also, consider Il Cantuccio. With its consistent customer satisfaction, it’s an excellent option for dining in Arezzo 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!