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.

Immerse yourself in Bologna’s rich culture with today's sightseeing itinerary. Start your journey at Palazzo Re Enzo. This instagrammable palace is sure to ignite your curiosity. Next, dive into the symbolic features of Fountain Of Neptune, Bologna, a must-visit monument in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Palazzo Del Podestà, Bologna, a curiosity-inducing palace. For a change of scene, check out Bologna Cathedral, known for its symbolic 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 Bologna 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.

Prepare for an extraordinary culinary adventure in Bologna by booking a table at Ahimè, a Bib Gourmand restaurant that boasts an exceptional country cooking menu. For a different flavor experience, head to I Portici, renowned for its delectable creative and contemporary dishes. This 1-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Trattoria di Via Serra, a local gem known for its delightful emilian cuisine in Bologna. Nestled in the city's heart, this Bib Gourmand-awardee is a perfect choice for discerning restaurant-goers seeking a new experience.

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.

Unwind after your meal by stepping into Lime Bar. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Macondo - Cocktail Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Onda Marina By Night, another top-rated bar 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!

Today's adventure in Bologna promises more breathtaking discoveries and enriching experiences! Begin at Two Towers. This culturally significant monument is a highlight of any visit in the city. Then, enjoy International Museum And Library Of Music, another photogenic attraction that never fails to captivate visitors. Next, head over to Piazza Santo Stefano, one of the city’s most up-and-coming attractions, known for its history-steeped features.

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 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.

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 feel like it, head out to a bar to celebrate another fantastic day in Bologna 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, Aurum offers a perfect venue to relax and savor a drink. Similarly, Bar Senza Nome is well-suited for those looking to unwind in a social setting. Caffè Ristretto 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 4 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Siena 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.

Get ready for a day filled with family-friendly attractions, photo-friendly spots, and history-rich sites in the charming city of Bologna. Your adventure starts at Palazzo Grassi, Bologna, a frequently visited local hot spot. Another notable attraction to explore is San Martino.

After soaking in the highlights of these sights, take some time to wander Bologna's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to La Piccola Venezia. This visually striking street offers a fascinating experience that many visitors find memorable.

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.

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

Dine in style at Enoteca I Terzi, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante Tar-Tufo boasts a menu that's sure to impress. Also, be sure to check out Antica Trattoria Papei. Known as a local hotspot, it’s a great choice for tonight in Siena.

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.

Keep the evening going at Meet Life Cafè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Maudit Pub, which offers a similarly pleasant setting and great drinks. Another option is Bar Impero Siena, 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!

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’s route brings family-friendly attractions, scenic views, and photo-friendly spots. The first attraction of today is Tower Of Mangia. This curiosity-inducing monument is an UNESCO world heritage-designated place to see in Siena. Continue your discovery at Piazza Del Campo, an awe-inspiring public square with stories to tell.

As you stroll around Siena, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Opera Delle Metropolitana. This beloved museum offers a breathtaking encounter with Siena. Siena Cathedral is the last of our recommendations for today. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Siena.

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 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.

Have a fantastic dining experience at Osteria Quattro Venti, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Fischi per Fiaschi offers an enticing alternative with its varied menu. Additionally, Osteria da Divo is worth considering. Renowned for satisfying diners, it’s an ideal option 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.

Round off your dining experience by visiting Charlie Mixology Bar Di Aldinucci Riccardo, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Pinacoteca, a bar catering to every mood and preference. San Paolo Pub likewise offers a unique atmosphere, perfect for a memorable night out.

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

Day 6 of your relaxed road trip across Italy promises an exciting agenda full of discovery. You’ll start your day in the city of Siena and drive in the direction of the city of Rome for some laid-back sightseeing. You’ll end your day in the city of Rome, where you’ll stay for 6 nights.

Today’s route brings family-friendly attractions, photo-friendly spots, and historic treasures. The first attraction of today is Santuario Di Santa Caterina. This locally appreciated church is a photogenic place to see in Siena. Continue your discovery at Basilica Of San Domenico, a stunning church with stories to tell.

As you stroll around Siena, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Fortezza Medicea (siena). This up-and-coming monument offers a historic encounter with Siena.

In the city of Rome, 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.

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 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.

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.

Explore the vibrant nightlife at La Botticella Of Poggi Giovanni after your meal, a hub for lively evenings and memorable moments. Or, head to Almalu Trastevere for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Viminale Di Pepi Maurilio is perfect for those looking to extend their night with a touch of local flavor.

Raise your glass and toast to another unforgettable, laid-back road trip adventure 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.

Enjoy the perfect balance of relaxation and exploration in Rome today. One of the most wondrous attractions included on the itinerary is Trevi Fountain. This noteworthy monument will help you start your sightseeing on top. Then, take a leisurely stroll to Altare Della Patria and learn what makes this remarkable monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the popular Capitoline Hill. After exploring the public square, head to Roman Forum. This globally renowned archeological site is a highlight in Rome. Lastly, don’t forget to check out the iconic Colosseum. Enjoy exploring this incredible archeological site at your own pace.

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.

Enjoy a lovely meal at RomAntica, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Coso Ristorante is another top choice with a popular menu. You could also check for a table at DEROMA - Farine Romane. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

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 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.

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!

Trastevere is a neighborhood 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.

Today’s agenda in Rome includes an archeological site, a monument, and a public square. Largo Di Torre Argentina is must-visit archeological site and a great starting point for the day. Next, continue your journey to Pantheon, a globally renowned monument, located just a leisurely stroll away. Next, head to Piazza Navona, a heritage-rich public square, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Rome. If you’re looking for more, Campo De' Fiori is also a widely recognized attraction that is worthwhile a visit.

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!

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 Hotel de Russie, a top-rated dining destination in Rome. If you're in the mood to try something new, consider La Taverna Italiana, another top spot with a mouthwatering menu. You might also want to secure a reservation at The Parrot Bar. 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.

After your meal, keep the night alive at a bar like The Apartment Bar Roma, known for its lively atmosphere. Hotel Hassler Roma is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance.

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.

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!

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

Get ready to discover some of the most iconic wonders in Rome, including a museum, a park, a public square, a castle and much more! Start your day at Villa Borghese Pinciana. This remarkable museum is a captivating place to see in Rome. Then, wander over to Villa Borghese. If idyllic sites excite you, this park will be right up your alley. Nearby, you’ll also find Piazza Del Popolo. This romantic 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, Castel Sant'angelo is a spectacular 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.

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.

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

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

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

Day 10 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 dei Condotti, 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.

Prepare for a day full of family-friendly attractions, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Orange Garden. This locally renowned park is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Circus Maximus, one of the city’s most promising highlights.

Next, check out Spanish Steps, one of the most spectacular places to see in Rome. This public square is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Piazza Di Spagna. Wander around and soak in the romantic atmosphere this public square offers.

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.

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.

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

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

One of the most iconic places you can visit today in Rome is Monti. Allow yourself some time to leisurely explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Start by visiting Archbasilica Of St. John Lateran, a prime spot to begin your journey. This historic church is sure to impress. Next on your list is Basilica Di Santa Maria Maggiore, another must-visit landmark and interesting church renowned for its respected features.

While exploring and sightseeing, take time to savor the ambiance of Rome by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to Auditorium Parco Della Musica. This instagrammable concert hall is a remarkable attraction that offers a unique experience. Foro Italico also adds charm to your journey.

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.

Treat yourself to a delightful dinner at Caffè Antica Roma, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Maccheroni? It's another excellent option with a diverse menu. Consider reserving a table at In Roma - since 1917 as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

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.

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

Day 12 of your leisurely self-drive tour in Italy is another opportunity for an in-depth travel experience in the country. You’ll stay in Arezzo for 2 nights.

Discover a day packed with fun adventures, romantic experiences, and breathtaking views in Rome. Begin your sightseeing with The Medici Fortress Park. This increasingly popular park is one of the top attractions in the city. Proceed to Piazza Grande, another must-visit attraction that enhances the city’s allure.

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 San Francesco, Arezzo. This intriguing church is a traveler-favorite.

You’ll be staying at the incredible city of Arezzo in this laid-back road trip in Italy. You'll stay here for 2 nights.

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.

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

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Liquid Bar stands out as an excellent choice for a post-dinner cocktail.

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.

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.

Get ready for an exciting day in Arezzo. Today’s sightseeing agenda includes a museum and a monastery. Begin your adventure at Aboca Museum. This is an underrated museum you should not miss. Another must-see is Museo Civico Di Sansepolcro, an up-and-coming museum in Arezzo.

When you’re ready for the next sight, head to La Verna - Franciscan Sanctuary.

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

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.

Make sure to reserve a table at La Nuova Tagliatella, an iconic dining spot in Arezzo. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of i 3 bicchieri, a popular restaurant in Arezzo. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Il Cantuccio, a hidden gem nestled in Arezzo. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Experience the amazing nightlife in Arezzo 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, relaxed road trip adventure across Italy.