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

On day 2 of your leisurely self-drive tour across Italy, you’ll go deep into Bologna, where you'll stay for 2 nights, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Bologna, and meet locals along the way!

Set out on a day brimming with fun adventures, breathtaking views, and picturesque spots. Start at the frequently visited Palazzo Re Enzo, a picture-perfect palace in Bologna. Next, go to Fountain Of Neptune, Bologna.

After visiting Palazzo Re Enzo and Fountain Of Neptune, Bologna, have a stroll along Bologna's streets and take in the local charm. Continue your sightseeing by heading to Palazzo Del Podestà, Bologna. This instagrammable palace offers a unique experience. Bologna Cathedral is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazza Maggiore, one of the most majestic places to visit in Bologna.

Italy makes the perfect setting for a calming but fun exploration. Aside from amazing sights, Italy also offers plenty of tours to enhance your relaxed road trip experience.

When 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.

Experience a harmony of flavors at Ahimè in Bologna by securing a reservation in advance. Known for its Bib Gourmand status, Ahimè offers a delightful variety of dishes highlighting its delicious country cooking menu. If you're seeking an alternative culinary experience, be sure to explore I Portici, a highly recommended restaurant known for its enticing creative and contemporary cuisine. This popular 1-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Trattoria di Via Serra, a highly acclaimed restaurant celebrated for its exceptional emilian menu.

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 delicious meal, get a taste of the vibrant nightlife with a visit to Lime Bar, known for its inviting atmosphere. Macondo - Cocktail Bar is another great option if you’re looking for a place to get the night started. Similarly, Bar Onda Marina By Night provides a great setting to enjoy the night away.

Free your mind of worries as you enjoy the taste of freedom on your laid-back, relaxed road trip adventure across 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 route brings fun adventures, breathtaking views, and photo-friendly spots. The first attraction of today is Two Towers. This popular monument is a picture-perfect place to see in Bologna. Continue your discovery at International Museum And Library Of Music, a photogenic museum with stories to tell.

As you stroll around Bologna, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazza Santo Stefano. This frequently visited public square offers an enchanting encounter with Bologna. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Bologna.

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.

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.

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

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

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

Day 4 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!

A blend of family-friendly attractions, photo-friendly spots, and historic treasures await you in Bologna on today’s itinerary. First up is the curiosity-inducing palace, Palazzo Grassi, Bologna. Afterward, continue to San Martino, a church every traveler should visit.

As you explore Bologna’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to La Piccola Venezia. This increasingly popular street is an essential stop.

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.

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 delicious dinner at Enoteca I Terzi, an excellent option for tonight's dining. Looking for something different? Ristorante Tar-Tufo offers a tantalizing alternative with its diverse menu. And don’t miss Antica Trattoria Papei. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Siena.

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 lively evening at Meet Life Cafè, a perfect place for winding down or revving up the night, depending on which mood you’re in. Maudit Pub is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Bar Impero Siena ensures a night out tailored to your taste.

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

Brace yourself for today’s incredible lineup of attractions in Siena, featuring family-friendly attractions, breathtaking views, and picturesque spots. Start at Tower Of Mangia, an up-and-coming monument in the city. Then, head to Piazza Del Campo and soak in the ambiance of this enchanting public square.

There are many interesting places to see in Siena, and when you are ready for more, go to Opera Delle Metropolitana. This is one of the city’s most curiosity-inducing stunning spots of interest. After exploring the museum, visit the captivating Siena Cathedral.

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 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.

Dine in style at Osteria Quattro Venti, a top recommendation for dinner tonight. Or, for a change of pace, Fischi per Fiaschi boasts a menu that's sure to impress. Also, be sure to check out Osteria da Divo. Known as a local hotspot, it’s a great choice for tonight in Siena.

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

Continue 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.

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

Day 6 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Rome for 6 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 by visiting Santuario Di Santa Caterina, a prime spot to begin your journey. This culturally significant church is sure to impress. Next on your list is Basilica Of San Domenico, another must-visit landmark and increasingly popular church renowned for its stunning features.

While exploring and sightseeing, take time to savor the culture of Siena by sampling some local delicacies. When you’re ready for more sightseeing, head to Fortezza Medicea (siena). This breathtaking monument is an essential place to visit for anyone looking for the full Siena experience.

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.

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.

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

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.

Cap off your dinner by heading to La Botticella Of Poggi Giovanni, ideal for a leisurely evening with a drink in hand. Almalu Trastevere is another bar that offers an enjoyable setting. Similarly, Bar Viminale Di Pepi Maurilio is also a popular place to go on a night out, perfect for relaxing and socializing.

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

On day 7 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, where you'll stay for 5 nights, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Rome, and meet locals along the way!

Rome is brimming with adventures. Today’s wonderful stops include a monument, a public square, and an archeological site. Begin your sightseeing adventure at the world-famous Trevi Fountain and allow yourself time to explore. Just a short distance away you'll find your next stop, Altare Della Patria, a noteworthy monument that draws visitors from far and near.

Continue your journey to Capitoline Hill, one of the city’s most interesting spots that you shouldn’t miss. Another great site to visit is the wondrous Roman Forum. When you're finished at the archeological site, Colosseum awaits your visit. This archeological site is an awe-inspiring highlight on today's 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!

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 RomAntica, 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 Coso Ristorante, 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 DEROMA - Farine Romane, 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, it’s time to fall in love with the amazing nightlife in Rome and unwind at some of the best bars in the city.

Keep the evening going at Sant' Eustachio Caffè, a great choice for enjoying the after-dinner hours with a drink. You could also go to Yellowsquare Rome, which offers a similarly pleasant setting and great drinks. Another option is Caffè Portofino, 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!

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!

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

Get ready for an exciting day in Rome. Today’s sightseeing agenda includes an archeological site, a monument, and a public square. Begin your adventure at Largo Di Torre Argentina. This is a locally renowned archeological site you should not miss. Another must-see is Pantheon, a timeless monument in Rome.

When you’re ready for the next sight, head to Piazza Navona. From there, take a leisurely stroll to Campo De' Fiori, another of the city’s spectacular attractions.

Italy makes the perfect setting for a calming but fun exploration. Aside from amazing sights, Italy also offers plenty of tours to enhance your relaxed road trip experience.

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.

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.

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

If you’re not ready to end the night just yet, The Apartment Bar Roma offers a perfect venue to relax and savor a drink. Similarly, Hotel Hassler Roma is well-suited for those looking to unwind in a social setting.

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

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

Today, you'll explore some of the most beautiful places in Rome, including a museum, a park, a public square, a castle and much more! Start your day with a visit to Villa Borghese Pinciana. This interesting museum is a must-visit in the city. When you’re ready for your next discovery, continue to Villa Borghese, which may be one of the most remarkable 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 Piazza Del Popolo, an extraordinary public square in the city. If you’re up for more discoveries, don’t forget to reserve some time for Castel Sant'angelo.

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.

Don’t miss out on dining at Sofitel Roma Villa Borghese, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Centro, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Tema. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

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

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

On day 10 of your leisurely self-drive tour across Italy, you’ll go deep into Rome, where you'll stay for 2 nights, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Rome, and meet locals along the way!

A visit to Via dei Condotti in Rome is a must on the agenda today. This street is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights.

Savor the day by visiting some of the best places to see in Rome, including a park, an archeological site, and a public square. Start your adventure at Orange Garden. This well-known park is a must-visit for travelers looking for a unique holiday experience. Make your way to Circus Maximus located in Rome for another exciting encounter.

Next, immerse yourself in the setting of Spanish Steps. Its visually striking features will captivate you. After the public square, continue your tour of the city with a visit to Piazza Di Spagna. Visitors usually appreciate the romantic features of this public square.

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

When you’re not driving and exploring some of the best places in Italy, it’s time to make your relaxed road trip even more comforting. Sit down for a lovely meal at one of the best restaurants in Rome.

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

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!

Make sure to visit Monti, 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 well-planned self-sightseeing route offers several fun adventures, breathtaking views, and photo-friendly spots. 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. Archbasilica Of St. John Lateran is the first of them. Spend some time admiring this stunning church before continuing your journey. Basilica Di Santa Maria Maggiore is your next stop. This captivating church 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 Auditorium Parco Della Musica. This visually striking concert hall is a sight to behold. To round off your sightseeing experience, visit Foro Italico.

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

Exploring 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 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.

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.

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.

Get ready for a day filled with family-friendly attractions, romantic experiences, and breathtaking views in the charming city of Rome. Your adventure starts at The Medici Fortress Park, a frequently visited local hot spot. Another notable attraction to explore is Piazza Grande. This locally renowned public square is known for its enchanting appeal.

After soaking in the highlights of these sights, take some time to wander Rome's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to San Francesco, Arezzo. This photogenic church offers a fascinating experience that many visitors find memorable.

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

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

Begin your culinary exploration in Arezzo by securing a reservation at Octavin. This renowned restaurant holds 1 Michelin star and offers an exceptional menu of creative cuisine. Or, for a change of pace, La Clandestina boasts a menu that's sure to impress.

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.

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.

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

On day 13 of your relaxed road trip across Italy, you’ll explore the area around Arezzo, where you’ll be staying for another 1 night. With so many fun and inspiring experiences to offer, a tour of Arezzo will make you fall even more in love with the city and uniqueness of Italy.

Today’s route brings fun adventures, photo-friendly spots, and historic treasures. The first attraction of today is Aboca Museum. This increasingly popular museum is a history-steeped place to see in Arezzo. Continue your discovery at Museo Civico Di Sansepolcro, a photogenic museum with stories to tell.

As you stroll around Arezzo, take in the distinct atmosphere and learn what makes this town so unique. Maximize your sightseeing with a visit to La Verna - Franciscan Sanctuary. This curiosity-inducing monastery offers an instagrammable encounter with Arezzo. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Arezzo.

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

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.

Treat yourself to a delightful dinner at La Nuova Tagliatella, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try i 3 bicchieri? It's another excellent option with a diverse menu. Consider reserving a table at Il Cantuccio as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Arezzo.

Take a stroll around the area, head back to your accommodation for the night, or continue your evening at one of the best-rated bars in the city.

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