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!

Today’s itinerary in Bologna covers several incredible sights, including a palace, a monument, a church, a public square and much more! Start your adventure at Palazzo Re Enzo. This curiosity-inducing palace is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the noteworthy wonders of Fountain Of Neptune, Bologna, 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 Palazzo Del Podestà, Bologna. This curiosity-inducing palace offers an enriching experience. For a change of pace, head to Bologna Cathedral, where you can take in stunning features. Conclude your self-guided sightseeing tour with a visit to Piazza Maggiore and Piazza Maggiore. These sights offer a fulfilling end to a perfect day.

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 Bologna.

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

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

Cap off your dinner by heading to Lime Bar, ideal for a leisurely evening with a drink in hand. Macondo - Cocktail Bar is another bar that offers an enjoyable setting. Similarly, Bar Onda Marina By Night is also a popular place to go on a night out, perfect for relaxing and socializing.

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

Immerse yourself in Bologna’s rich culture with today's sightseeing itinerary. Start your journey at Two Towers. This awe-inspiring monument is sure to ignite your curiosity. Next, dive into the heritage-rich features of International Museum And Library Of Music, a must-visit museum 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 Piazza Santo Stefano, a curiosity-inducing public square.

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.

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

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 a delightful dinner at Va Mo Là, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria dal Biassanot? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Enoteca da Lucia as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Bologna.

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 your meal, keep the night alive at a bar like Aurum, known for its lively atmosphere. Bar Senza Nome is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Caffè Ristretto offers an excellent atmosphere for those looking to amp up the evening.

Toast to another unforgettable and relaxing 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.

Start your day at Palazzo Grassi, Bologna. Then, wander over to San Martino. If culturally significant sites excite you, this church will be right up your alley. Nearby, you’ll also find La Piccola Venezia. This awe-inspiring street is a favorite among visitors.

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 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.

Make sure to reserve a table at Enoteca I Terzi, an iconic dining spot in Siena. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Ristorante Tar-Tufo, a popular restaurant in Siena. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Antica Trattoria Papei, a hidden gem nestled in Siena. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Siena. The bars in Siena make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Cap off your dinner by heading to Meet Life Cafè, ideal for a leisurely evening with a drink in hand. Maudit Pub is another bar that offers an enjoyable setting. Similarly, Bar Impero Siena is also a popular place to go on a night out, perfect for relaxing and socializing.

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

Siena is brimming with adventures. Today’s wonderful stops include a monument, a public square, a museum, a church and much more! Begin your sightseeing adventure at the often recommended Tower Of Mangia. Just a short distance away is Piazza Del Campo, a visually striking public square that draws visitors from far and near.

Continue your journey to Opera Delle Metropolitana, one of the city’s most often recommended spots that you shouldn’t miss. Another great site to visit is the notable Siena Cathedral.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Siena. There are so many fun and eye-opening activities to try out in Siena that will make your slow-paced self-drive tour in Italy more memorable. Check out all the most recommended and top-rated tour options in the city of Siena to find the best options for you!

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.

Don’t miss out on dining at Osteria Quattro Venti, a top-rated dining destination in Siena. If you're in the mood to try something new, consider Fischi per Fiaschi, another top spot with a mouthwatering menu. You might also want to secure a reservation at Osteria da Divo. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Siena this evening.

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

Continue your lively evening at Charlie Mixology Bar Di Aldinucci Riccardo, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Pinacoteca is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, San Paolo Pub ensures a night out tailored to your taste.

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

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.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Siena allows for both. Start by heading to Santuario Di Santa Caterina. This up-and-coming church provides an insightful glimpse into the city's identity. Next, discover Basilica Of San Domenico, a monumental church, promising a delightful encounter.

Continue your sightseeing with a visit to Fortezza Medicea (siena), an intriguing monument.

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

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 symphony of flavors at La Pergola in Rome by securing a reservation in advance. Renowned for its 3-star Michelin distinction, La Pergola delights its guests with its exceptional variety of meals showcasing delicious mediterranean and contemporary cuisine. For a palate-pleasing alternative, make sure to dine at Il Pagliaccio, acclaimed for its delectable creative and innovative specialties. This local 2-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Enoteca La Torre, a top-rated restaurant known for its outstanding menu. Known as a top-rated 2-star Michelin establishment, it's a top choice for mediterranean and creative cuisine in the city.

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

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.

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!

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 route brings fun adventures, romantic experiences, and breathtaking views. The first attraction of today is Trevi Fountain. This timeless monument is a visually striking place to see in Rome. Continue your discovery at Altare Della Patria, 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 Capitoline Hill. This interesting public square offers a detailed encounter with Rome. Next, make your way to Roman Forum to add another highlight to your day. After that, visit Colosseum, a globally renowned archeological site that’s sure to impress. 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.

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.

Enjoy a lovely dining experience at RomAntica, a popular restaurant in Rome. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Rome at Coso Ristorante, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated DEROMA - Farine Romane. It’s yet another ideal choice to enhance your time in Rome tonight.

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

Following your dinner, dive into the local bar culture at Sant' Eustachio Caffè. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Yellowsquare Rome, the perfect place for those looking to experience the best of the nightlife. Similarly, Caffè Portofino provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Raise your glass to celebrate another day of your laid-back and 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.

Set aside time today to explore Trastevere, a standout neighborhood that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, photo-friendly spots, and history-rich sites. Whether you decide to explore Rome on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Largo Di Torre Argentina is the first of them. Spend some time admiring this standout archeological site before continuing your journey. Pantheon is your next stop. This iconic monument is one of the best-rated sights in Rome.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Piazza Navona. This romantic public square is a sight to behold. To round off your sightseeing experience, visit Campo De' Fiori.

Make the most of your time in the country by joining activities that let you discover more about Italy. Check out all of the tours you can join this day of your leisurely self-drive holiday in Italy and ensure the experience of a lifetime.

Mealtimes are the perfect opportunities to immerse yourself in the local culture of Italy. When you're not appreciating the best places to visit in Rome, explore the city like a local by trying out the best restaurants in the area.

Enjoy a 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.

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.

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

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

On day 9 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, where you'll stay for 3 nights, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Rome, and meet locals along the way!

A top thing to do today is to explore Via del Corso, a must-see street in Rome. It's the perfect starting point for touring the top attractions in the area.

Set out on a day brimming with fun adventures, romantic experiences, and scenic views. Start at the notable Villa Borghese Pinciana, a history-steeped museum in Rome. Next, go to Villa Borghese.

After visiting Villa Borghese Pinciana and Villa Borghese, take time to explore Rome's streets and absorb its charm. Continue your sightseeing by heading to Piazza Del Popolo. This symbolic public square offers a unique experience. Castel Sant'angelo is another noteworthy stop.

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.

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.

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 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!

Make sure to visit Via dei Condotti, a popular street 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.

Discover a day packed with family-friendly attractions, romantic experiences, and breathtaking views in Rome. Begin your sightseeing with Orange Garden. This popular park is one of the top attractions in the city. Proceed to Circus Maximus, 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 Spanish Steps. This famous public square is a traveler-favorite. Not far away, you’ll find Piazza Di Spagna, another key site on your sightseeing itinerary.

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 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.

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.

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.

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

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

A visit to Monti in Rome is a must on the agenda today. This neighborhood 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.

Prepare for a day full of fun adventures, scenic views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Archbasilica Of St. John Lateran. This popular church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Basilica Di Santa Maria Maggiore, one of the city’s best highlights.

Next, check out Auditorium Parco Della Musica, one of the most interesting places to see in Rome. This concert hall is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Foro Italico. Wander around and soak in the heritage-rich atmosphere this sports complex offers.

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.

Savor the flavors at Caffè Antica Roma, a top pick for dinner tonight. Alternatively, Maccheroni beckons with its unique menu offerings. Also, consider In Roma - since 1917. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

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

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

Set out on a day brimming with fun adventures, romantic experiences, and scenic views. Start at the up-and-coming The Medici Fortress Park, a romantic park in Rome. Next, go to Piazza Grande.

After visiting The Medici Fortress Park and Piazza Grande, take time to explore Rome's streets and absorb its charm. Continue your sightseeing by heading to San Francesco, Arezzo. This culturally significant church offers a unique 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.

Exploring the food culture in Arezzo offers you an exciting chance to connect with locals and experience diversity along your relaxed road trip. When you’re ready to eat, we recommend you visit one of the best dining spots in the city.

Experience a taste of local culinary excellence while in Arezzo by securing a table at Octavin. An esteemed 1-star Michelin restaurant, it features an exceptional creative menu. If you're in the mood for something new, try La Clandestina, another premier location with a delectable menu.

If you feel like it, head out to a bar to celebrate another fantastic day in Arezzo and take the pulse of the city’s nightlife. Enjoy the night without rushing to fully appreciate it.

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

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

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

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

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

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.

Enjoy a lovely dining experience at La Nuova Tagliatella, a popular restaurant in Arezzo. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Arezzo at i 3 bicchieri, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Il Cantuccio. It’s yet another ideal choice to enhance your time in Arezzo tonight.

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

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