Relaxed 14-Day Italy Self-Drive Road Trip With Itinerary from Ancona to Bologna, Arezzo, and Rome

Day 2 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll start your day in the city of Ancona and end it in the city of Bologna. You’ll stay in Bologna for 4 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.

Discover a day packed with family-friendly attractions, scenic views, and photo-friendly spots in Ancona. Begin your sightseeing with Cathedral Basilica Of St. Cyriacus. This curiosity-inducing church is one of the top attractions in the city. Proceed to Sanctuary Of The Holy House Of Loreto, another must-visit attraction.

As you wander through the inviting streets of Ancona, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Rocca Roveresca. This beloved castle is a traveler-favorite.

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

Treat yourself to an extraordinary dining experience at Ahimè, a Bib Gourmand restaurant offering an incredible country cooking menu. Alternatively, if your taste buds call for something different, I Portici is one of the best restaurants for creative and contemporary cuisine in Bologna. This 1-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Trattoria di Via Serra. As a top-rated establishment with a Bib Gourmand status, it is an ideal choice for emilian cuisine in the city.

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

Explore the vibrant nightlife at Bar Al Bricco D'oro after your meal, a hub for lively evenings and memorable moments. Or, head to Bar Freud E Squisito for a great selection of flavorful drinks and a charming setting. Furthermore, Osteria Del Sole is perfect for those looking to extend their night with a touch of local flavor.

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

Day 3 of your relaxed road trip through Italy means 24 hours of making the best memories in Bologna. You’ll go sightseeing at famous attractions in Bologna. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Bologna!

A blend of family-friendly attractions, scenic views, and picturesque spots await you in Bologna on today’s itinerary. First up is the often recommended palace, Palazzo Re Enzo. Afterward, continue to Fountain Of Neptune, Bologna, a monument 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 Bologna Cathedral. This up-and-coming church is an essential stop. Following that, head to Piazza Maggiore, another must-visit site that will enhance your experience. Don’t forget to stop by Basilica Of San Domenico, an intriguing church in the city.

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.

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 Bologna, 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 Bononia Cafè, a highly-rated dining destination in Bologna. If you're eager to try something different, consider Via Con Me, another top spot with a tantalizing menu. You might also want to secure a reservation at Trattoria Pizzeria La Mela. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Bologna this evening.

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 savoring a delicious meal, step into the vibrant nightlife at Lime Bar, where the evening is just getting started. In the same way, Macondo - Cocktail Bar offers a unique charm perfect for experiencing the local bar scene in Bologna. Bar Onda Marina By Night is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Soak in the unique atmosphere of Bologna 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 4 introduces you to many popular attractions and activities in Bologna, further proving that leisurely self-drive tours in Italy are extraordinary.

Start by visiting Devotional Portico Of St. Luke, a prime spot to begin your journey. This history-steeped monument is sure to impress. Next on your list is Arco Del Meloncello, another must-visit landmark and beloved monument renowned for its historic features.

While exploring and sightseeing, take time to savor the culture of Bologna by sampling some local delicacies. When you’re ready for more sightseeing, head to Two Towers. This picture-perfect monument is an essential place to visit for anyone looking for the full Bologna experience. We also recommend visiting International Museum And Library Of Music, an often recommended museum. Nearby, you'll also find Piazza Santo Stefano, ready to add charm to your journey.

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

Exploring 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.

Treat yourself to a wonderful meal at Va Mo Là, a top-rated dining spot in Bologna. If you're in the mood for something new, try Trattoria dal Biassanot, another premier location with a delectable menu. You might also want to book a table at Ristorante Enoteca da Lucia. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Bologna.

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.

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.

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 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!

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Bologna allows for both. Start by heading to Pinacoteca Nazionale Di Bologna. This locally appreciated art gallery provides an insightful glimpse into the city's identity. Next, discover San Martino, a culturally significant church, promising a delightful encounter.

Continue your sightseeing with a visit to La Piccola Venezia, an often recommended street.

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.

Treat yourself to a delightful dinner at Pappare' - Bologna, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Mister Coffee Bistrò? It's another excellent option with a diverse menu. Consider reserving a table at All'Osteria Bottega as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Bologna.

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.

After enjoying a fulfilling meal, continue your evening at Bar Piratello, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bar Carlo offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Maurizio provides an excellent environment for a relaxed and enjoyable evening.

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

Day 6 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 an exciting day in Bologna. Today’s sightseeing agenda includes a church, a public square, and an archeological site. Begin your adventure at Arezzo Cathedral. This is a beloved church you should not miss. Another must-see is Piazza Grande, an interesting public square in Bologna.

When you’re ready for the next sight, head to Roman Amphitheatre Of Arezzo.

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

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.

Prepare for an extraordinary culinary adventure in Arezzo by booking a table at Octavin, a 1-star Michelin restaurant that boasts an exceptional creative menu. If you're eager to try something different, consider La Clandestina, another top spot with a tantalizing menu.

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

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.

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

On day 7 of your relaxed road trip, you’ll start your self-paced adventure in Arezzo and visit amazing attractions in La Verna and Pratovecchio 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.

Immerse yourself in Arezzo’s rich culture with today's sightseeing itinerary. Start your journey at La Verna - Franciscan Sanctuary. This picture-perfect monastery is sure to ignite your curiosity. Next, dive into the inviting features of San Pietro A Romena, a must-visit church in the hamlet.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Romena Castle, a locally appreciated castle.

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

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 a delicious meal at La Nuova Tagliatella, a top-rated dining destination in Arezzo. If you're in the mood to try something new, consider i 3 bicchieri, another top spot with a mouthwatering menu. You might also want to secure a reservation at Il Cantuccio. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Arezzo this evening.

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.

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

Your laid-back and relaxed road trip in Italy continues on day 9, 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 Rome and beyond. With 4 nights left in Rome, you’ll have enough time to eat and unwind at popular restaurants and bars in the city.

Continue your journey to Sistine Chapel, one of the city’s most astonishing spots that you shouldn’t miss. Another great site to visit is the timeless St. Peter's Basilica.

When you’re done exploring for the day, you’ll return to Rome 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 Rome, explore the city like a local by trying out the best restaurants in the area.

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

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.

Continue your evening by exploring the vibrant nightlife scene at Sant' Eustachio Caffè, a prime destination for a thrilling night out. Also, don’t forget to check out Yellowsquare Rome, a bar that offers unique local touches. Likewise, Caffè Portofino provides an excellent alternative for a fun evening.

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

Today’s agenda in Rome includes a park, a monument, a public square, a castle and much more! Villa Borghese is must-visit park and a great starting point for the day. Next, continue your journey to Trevi Fountain, a world-famous monument, located just a leisurely stroll away. Next, head to Pantheon, a photogenic monument, 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 iconic Piazza Navona. If you’re looking for more, Castel Sant'angelo is also an extraordinary attraction that is worthwhile a visit.

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 Rome.

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.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at The Apartment Bar Roma, a well-loved spot among locals and tourists. Or, head to Hotel Hassler Roma. This bar boasts a welcoming environment that is perfect for winding down.

Toast to another unforgettable and relaxing road trip adventure 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.

Trastevere is a fantastic place you can explore today in Rome. This neighborhood 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. You should also check out Monti, a neighborhood offering more opportunities to enjoy the city’s vibrant atmosphere and landmarks.

Savor the day by visiting some of the best places to see in Rome, including a monument and an archeological site. Start your adventure at Altare Della Patria. This popular monument is a must-visit for travelers looking for a unique holiday experience. Make your way to Roman Forum located in Rome for another exciting encounter.

Next, immerse yourself in the setting of Colosseum. Its UNESCO world heritage-listed features will captivate you.

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.

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.

Enjoy a lovely dining experience at Sofitel Roma Villa Borghese, 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 Centro, 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 Ristorante Tema. It’s yet another ideal choice to enhance your time in Rome tonight.

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

On day 12 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!

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. You can also visit Via dei Condotti, an ideal street for continued sightseeing.

Bring your curiosity for today’s adventure around Rome. Some of the city’s most loved attractions await! Spanish Steps is the perfect place to start. This public square is one of the most astonishing places to visit in Rome. Next, head to Piazza Di Spagna, a wondrous public square, known for its history-steeped 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 grand public square is a highly recommended experience. Visit these for an interesting touch to your journey.

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

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.

Savor the flavors at Ristorante Va. Do. , a top pick for dinner tonight. Alternatively, Giulia Restaurant beckons with its unique menu offerings. Also, consider L'Archeologia. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

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.

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

Day 13 of your relaxed road trip across Italy promises an exciting agenda full of discovery. You’ll start your day in the city of Teramo and drive in the direction of the city of Ancona for some laid-back sightseeing. You’ll end your day in the city of Ancona, where you’ll stay for 1 night.

Set out on a day brimming with fun adventures, photo-friendly spots, and historic treasures. Start at the intriguing Santuario Madonna Delle Grazie, an inviting church in Rome. Next, go to Roman Theatre Of Teramo.

After visiting Santuario Madonna Delle Grazie and Roman Theatre Of Teramo, have a stroll along Rome's streets and take in the local charm. Continue your sightseeing by heading to Fontana Dei Due Leoni. This symbolic monument offers a unique experience.

In the city of Ancona, you’ll find plenty of stay options that will accommodate your need for rest and relaxation after spending your day on the road. Our top recommendations perfectly complement your relaxed road trip vacation in Italy.

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

Experience a harmony of flavors at Sot'Ajarchi in Ancona by securing a reservation in advance. Known for its Bib Gourmand status, Sot'Ajarchi offers a delightful variety of dishes highlighting its delicious seafood and from the marches menu. If you're looking to mix things up, Bontà delle Marche offers an enticing alternative with its varied 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 enjoying a fulfilling meal, continue your evening at Alla Tazza D'oro, ideal for those looking to unwind with a drink in a comfortable setting.

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