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!

Enjoy the perfect balance of relaxation and exploration in Bologna today. One of the most increasingly popular attractions included on the itinerary is Palazzo Re Enzo. This gorgeous palace will help you start your sightseeing on top. Then, take a leisurely stroll to Fountain Of Neptune, Bologna and learn what makes this photogenic monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the curiosity-inducing Palazzo Del Podestà, Bologna. After exploring the palace, head to Bologna Cathedral. This underrated church is a highlight in Bologna. Lastly, don’t forget to check out the extraordinary Piazza Maggiore. Enjoy exploring this incredible public square at your own pace.

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.

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.

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 Lime Bar. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Macondo - Cocktail Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Onda Marina By Night provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

On day 3 of your leisurely self-drive tour across Italy, you’ll go deep into Bologna, 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 Bologna, and meet locals along the way!

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

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.

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

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

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

Bologna is home to plenty of attractions that offer fun adventures, photo-friendly spots, and history-rich sites! Start at Palazzo Grassi, Bologna, an increasingly popular palace that is worthwhile a visit in the city. Nearby, you’ll find San Martino, enchanting visitors with its standout appeal. Continue your exploration at La Piccola Venezia. This street is one of the city’s most locally appreciated spots.

You’ll be staying at the incredible city of Siena 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 Siena, 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 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, it’s time to fall in love with the amazing nightlife in Siena and unwind at some of the best bars in the city.

Let the evening flow smoothly from dinner to drinks at Meet Life Cafè, a top-rated bar in the area. For other recommendations, Maudit Pub provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Impero Siena offers a memorable night with diverse drink options and excellent service.

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

Today’s agenda in Siena includes a monument, a public square, a museum, a church and much more! Tower Of Mangia is must-visit monument and a great starting point for the day. Next, continue your journey to Piazza Del Campo, a spectacular public square, located just a leisurely stroll away. Next, head to Opera Delle Metropolitana, an UNESCO world heritage-designated museum, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Siena. If you’re looking for more, Siena Cathedral is also a notable 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.

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

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.

Toast to another unforgettable and relaxing 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!

Siena is brimming with adventures. Today’s wonderful stops include a church and a monument. Begin your sightseeing adventure at the often recommended Santuario Di Santa Caterina. Just a short distance away is Basilica Of San Domenico, a picture-perfect church that draws visitors from far and near.

Continue your journey to Fortezza Medicea (siena), one of the city’s most underrated spots that you shouldn’t miss.

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

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.

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

If you’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 lively evening at La Botticella Of Poggi Giovanni, a perfect place for winding down or revving up the night, depending on which mood you’re in. Almalu Trastevere is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Viminale Di Pepi Maurilio ensures a night out tailored to your taste.

Cherish every minute of your relaxed road trip vacation across 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!

Prepare for a day full of fun adventures, romantic experiences, and breathtaking views. When you’re ready, kick off your sightseeing adventure at Trevi Fountain. This wondrous monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Altare Della Patria, one of the city’s most promising highlights.

Next, check out Capitoline Hill, one of the most interesting 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, Roman Forum. Wander around and soak in the UNESCO world heritage-designated atmosphere this archeological site offers. Finally, take the path to the timeless Colosseum, the last of our attraction recommendations for today.

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.

Have a fantastic dining experience at RomAntica, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Coso Ristorante offers an enticing alternative with its varied menu. Additionally, DEROMA - Farine Romane is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

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.

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

On day 8 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, where you'll stay for 4 nights, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Rome, and meet locals along the way!

Make 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 itinerary in Rome covers several incredible sights, including an archeological site, a monument, and a public square. Start your adventure at Largo Di Torre Argentina. This notable archeological site is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the culturally significant wonders of Pantheon, a must-see monument 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 Piazza Navona. This timeless public square offers an enriching experience. For a change of pace, head to Campo De' Fiori, where you can take in its historic features.

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.

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.

After dinner, it’s time to fall in love with the amazing nightlife in Rome and unwind at some of the best bars in the city.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, The Apartment Bar Roma stands out as an excellent choice for a post-dinner cocktail. Alternatively, Hotel Hassler Roma offers an ideal atmosphere to enjoy the pleasures of the night.

Grab yourself a drink and savor every moment 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.

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

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 captivating places to visit in Rome. Next, head to Villa Borghese, a top-rated park, known for its mesmerizing 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 history-steeped public square offers a unique experience that is highly recommended. Meanwhile, Castel Sant'angelo adds its own distinct charm to your journey.

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.

Savor the flavors at Sofitel Roma Villa Borghese, a top pick for dinner tonight. Alternatively, Centro beckons with its unique menu offerings. Also, consider Ristorante Tema. With its consistent customer satisfaction, it’s an excellent option for dining 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.

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 take advantage of the nearby must-see sights located nearby.

Brace yourself for today’s incredible lineup of attractions in Rome, featuring family-friendly attractions, romantic experiences, and scenic views. Start at Orange Garden, a well-known park in the city. Then, head to Circus Maximus and soak in the ambiance of this historic archeological site.

There are many interesting places to see in Rome and when you are ready for more, go to Spanish Steps. This is one of the city’s most widely recognized spots. After exploring the public square, visit the timeless Piazza Di Spagna.

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.

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.

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

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

On day 11 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, 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 Rome, and meet locals along the way!

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 popular 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, one of the city’s most captivating concert hall. If you’re up for more discoveries, don’t forget to reserve some time for Foro Italico.

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 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 delicious meal at Caffè Antica Roma, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Maccheroni, another top spot with a mouthwatering menu. You might also want to secure a reservation at In Roma - since 1917. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

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

Day 12 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 Arezzo. By the end of the day, you’ll drive in the direction of the city of Arezzo, where you’ll stay at a top-rated hotel of your choice for 2 nights.

Immerse yourself in Arezzo’s rich culture with today's sightseeing itinerary.

Embrace the thrill of the open road as you wave goodbye to Rome and set your GPS to Arezzo. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 2 hours 33 min. Upon reaching Arezzo, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Spend your afternoon discovering The Medici Fortress Park, a curiosity-inducing park known for its romantic features. After taking in the atmosphere, continue to Piazza Grande, a locally renowned public square that is a must-see for anyone visiting the region. Next, stop by San Francesco, Arezzo and uncover the details of this culturally significant church.

When you’re not exploring beautiful places, you’ll have a relaxed time at Arezzo. 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 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.

Discover the culinary delights of Arezzo by securing a reservation at Octavin. Esteemed for its 1-star Guide Michelin recognition, this restaurant offers a remarkable selection of creative cuisine. Alternatively, La Clandestina beckons with its unique menu offerings.

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.

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.

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

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.

Embrace the thrill of the open road as you wave goodbye to Arezzo and set your GPS to Sansepolcro. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 39 min. Upon reaching Sansepolcro, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Take your self-guided tour to Aboca Museum, an increasingly popular museum that everyone visiting Sansepolcro should see. Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Next, head to Museo Civico Di Sansepolcro. This history-steeped museum is one of the most beloved attractions in the region.

Continue your road trip and head to your next destination, La Verna. This car ride takes around 42 min.

La Verna - Franciscan Sanctuary is an underrated monastery we recommend making time to visit today. Discover its instagrammable features before continuing your self-guided tour.

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

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.

After dinner, it’s time to fall in love with the amazing nightlife in Arezzo and unwind at some of the best 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.