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

Day 2 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!

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Bologna allows for both. Start by heading to Palazzo Re Enzo. This often recommended palace provides an insightful glimpse into the city's identity. Next, discover Fountain Of Neptune, Bologna, a symbolic monument, promising a delightful encounter.

Continue your sightseeing with a visit to Palazzo Del Podestà, Bologna, a locally appreciated palace. When you’re done, don’t forget to make a stop at the up-and-coming Bologna Cathedral. Round off your day at Piazza Maggiore, another gem in Bologna with visually striking features to discover.

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.

Dive into a culinary adventure like no other in Bologna by booking a table at Ahimè. This popular restaurant holds a Bib Gourmand award and offers an exceptional menu of country cooking cuisine. For another culinary dining option, venture to I Portici, celebrated for its delectable creative and contemporary menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Trattoria di Via Serra, a top local restaurant known for its tantalizing emilian menu. With a Bib Gourmand recognition, it promises an exceptional dining experience not to be missed.

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

After enjoying a fulfilling meal, continue your evening at Lime Bar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Macondo - Cocktail Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Onda Marina By Night 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 3 introduces you to many popular attractions and activities in Bologna, further proving that leisurely self-drive tours in Italy are extraordinary.

Get ready for a day filled with family-friendly attractions, scenic views, and picturesque spots in the charming city of Bologna. Your adventure starts at Two Towers, an interesting local hot spot. Another notable attraction to explore is International Museum And Library Of Music. This increasingly popular museum is known for its picture-perfect appeal.

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 Piazza Santo Stefano. This enchanting public square offers a fascinating experience that many visitors find memorable.

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!

Visit Quadrilatero in Bologna for an unforgettable shopping experience. Browse unique boutiques and stores, each offering delightful surprises. Find unique souvenirs or items to take home. After shopping, explore what Quadrilatero has to offer, including attractions, essential services, and vibrant community activities.

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.

Enjoy a lovely meal at Va Mo Là, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria dal Biassanot is another top choice with a popular menu. You could also check for a table at Ristorante Enoteca da Lucia. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Bologna tonight.

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

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

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

Day 4 of your relaxed road trip across Italy promises an exciting agenda full of discovery. You’ll start your day in the city of Bologna and drive in the direction of the city of Siena for some laid-back sightseeing. You’ll end your day in the city of Siena, where you’ll stay for 2 nights.

Brace yourself for today’s incredible lineup of attractions in Bologna, featuring family-friendly attractions, photo-friendly spots, and historic treasures. Start at Palazzo Grassi, Bologna, a beloved palace in the city. Then, head to San Martino and soak in the ambiance of this respected church.

There are many interesting places to see in Bologna, and when you are ready for more, go to La Piccola Venezia. This is one of the city’s most worthwhile instagrammable spots of interest.

When you’re not exploring beautiful places, you’ll have a relaxed time at Siena. Here, you can choose from the best selection of hotels and places to stay as you get to know more about this spectacular city.

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

Enjoy a delicious meal at Enoteca I Terzi, a highly-rated dining destination in Siena. If you're eager to try something different, consider Ristorante Tar-Tufo, another top spot with a tantalizing menu. You might also want to secure a reservation at Antica Trattoria Papei. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Siena this evening.

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.

Continue your evening by exploring the vibrant nightlife scene at Meet Life Cafè, a prime destination for a thrilling night out. Also, don’t forget to check out Maudit Pub, a bar that offers unique local touches. Likewise, Bar Impero Siena provides an excellent alternative for a fun evening.

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

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 increasingly popular monument is a culturally significant place to see in Siena. Continue your discovery at Piazza Del Campo, a romantic 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 underrated museum offers an awe-inspiring encounter with Siena. Next, make your way to Siena Cathedral 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 Siena.

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.

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 Siena.

Treat yourself to a wonderful meal at Osteria Quattro Venti, a top-rated dining spot in Siena. If you're in the mood for something new, try Fischi per Fiaschi, another premier location with a delectable menu. You might also want to book a table at Osteria da Divo. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Siena.

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

Following your dinner, dive into the local bar culture at Charlie Mixology Bar Di Aldinucci Riccardo. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar Pinacoteca, the perfect place for those looking to experience the best of the nightlife. Similarly, San Paolo Pub provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Day 6 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!

Bring your curiosity for today’s adventure around Siena. Some of the city’s most loved attractions await! Santuario Di Santa Caterina is the perfect place to start. This church is one of the most intriguing places to visit in Siena. Next, head to Basilica Of San Domenico, an often recommended church, known for its historic 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 Fortezza Medicea (siena). This respected monument is a highly recommended experience. Visit these for an interesting touch to your journey.

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

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 an outstanding dining experience at La Pergola, a 3-star Michelin restaurant offering an exceptional mediterranean and contemporary menu. Alternatively, if you're in the mood for something different, consider the nearby 2-star Michelin-awardee, Il Pagliaccio, known for its delicious creative and innovative cuisine. Another highly-recommended place to eat in Rome is Enoteca La Torre, a renowned restaurant with a 2-star Guide Michelin recognition and a delicious mediterranean and creative menu.

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 savoring a delicious meal, step into the vibrant nightlife at La Botticella Of Poggi Giovanni, where the evening is just getting started. In the same way, Almalu Trastevere offers a unique charm perfect for experiencing the local bar scene in Rome. Bar Viminale Di Pepi Maurilio is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Day 7 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!

Today’s agenda in Rome includes a monument, a public square, and an archeological site. Trevi Fountain is must-visit monument and a great starting point for the day. Next, continue your journey to Altare Della Patria, a notable monument, located just a leisurely stroll away. Next, head to Capitoline Hill, a majestic 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. When you're ready, let your sightseeing route take you to the globally renowned Roman Forum. If you’re looking for more, Colosseum is also a globally renowned attraction that is worthwhile a visit.

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 RomAntica, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Coso Ristorante? It's another excellent option with a diverse menu. Consider reserving a table at DEROMA - Farine Romane as well. Known for its consistent customer satisfaction, it’s an ideal pick 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.

Extend your evening after a delightful meal by visiting Sant' Eustachio Caffè, which offers the perfect atmosphere for a night out. Moreover, Yellowsquare Rome is another popular option for a drink or two. Likewise, Caffè Portofino also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

Day 8 introduces you to many popular attractions and activities in Rome, further proving that leisurely self-drive tours in Italy are extraordinary.

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

Brace yourself for today’s incredible lineup of attractions in Rome, featuring fun adventures, picturesque spots, and historic treasures. Start at Largo Di Torre Argentina, a locally renowned archeological site in the city. Then, head to Pantheon and soak in the ambiance of this culturally significant monument.

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

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

Make sure to reserve a table at Hotel de Russie, 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 La Taverna Italiana, 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 The Parrot Bar, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

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

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!

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.

Start by visiting Villa Borghese Pinciana, a prime spot to begin your journey. This history-steeped museum is sure to impress. Next on your list is Villa Borghese, another must-visit landmark and top-rated park renowned for its remarkable 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 culturally significant public square is an essential place to visit for anyone looking for the full Rome experience. We also recommend visiting Castel Sant'angelo, a famous castle.

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!

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

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

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

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

Day 10 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!

Via dei Condotti 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.

Today’s itinerary in Rome covers several incredible sights, including a park, an archeological site, and a public square. Start your adventure at Orange Garden. This well-known park is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the standout wonders of Circus Maximus, a must-see archeological site in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Spanish Steps. This top-rated public square offers an enriching experience. For a change of pace, head to Piazza Di Spagna, where you can take in history-steeped features. These sights offer a fulfilling end to a perfect day.

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.

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.

Have a fantastic dining experience at Ristorante Va. Do. , a highly recommended choice for tonight's dinner. If you're looking to mix things up, Giulia Restaurant offers an enticing alternative with its varied menu. Additionally, L'Archeologia is worth considering. Renowned for satisfying diners, it’s an ideal option 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.

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

Day 11 introduces you to many popular attractions and activities in Rome, further proving that leisurely self-drive tours in Italy are extraordinary.

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

Enjoy the perfect balance of relaxation and exploration in Rome today. One of the most captivating attractions included on the itinerary is Archbasilica Of St. John Lateran. This culturally significant church will help you start your sightseeing on top. Then, take a leisurely stroll to Basilica Di Santa Maria Maggiore and learn what makes this culturally significant church unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the popular Auditorium Parco Della Musica. After exploring the concert hall, head to Foro Italico. This locally renowned sports complex 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 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 Caffè Antica Roma, an excellent option for tonight's dining. Looking for something different? Maccheroni offers a tantalizing alternative with its diverse menu. And don’t miss In Roma - since 1917. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.

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.

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 family-friendly attractions, romantic experiences, and scenic views await you in Rome on today’s itinerary. First up is the intriguing 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 often recommended 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.

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

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.

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.

Following your dinner, dive into the local bar culture at Liquid Bar. Enjoy this evening's relaxed ambiance with delightful 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.

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.

Brace yourself for today’s incredible lineup of attractions in Arezzo, featuring fun adventures, picturesque spots, and history-rich sites. Start at Aboca Museum, a curiosity-inducing museum in the town. Then, head to Museo Civico Di Sansepolcro and soak in the ambiance of this photogenic 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 often recommended historic spots of interest.

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

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.

Treat yourself to a wonderful meal at La Nuova Tagliatella, a top-rated dining spot in Arezzo. If you're in the mood for something new, try i 3 bicchieri, another premier location with a delectable menu. You might also want to book a table at Il Cantuccio. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Arezzo.

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

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