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

Day 2 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!

Start by visiting Cathedral Basilica Of St. Cyriacus, a prime spot to begin your journey. This historic church is sure to impress. Next on your list is Sanctuary Of The Holy House Of Loreto, another must-visit landmark and interesting church renowned for its symbolic features.

While exploring and sightseeing, take time to savor the culture of Ancona by sampling some local delicacies. When you’re ready for more sightseeing, head to Rocca Roveresca. This awe-inspiring castle is an essential place to visit for anyone looking for the full Ancona experience.

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.

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.

Set out on a gastronomic journey in Bologna by reserving a table at Ahimè. Renowned for its Bib Gourmand award, this restaurant presents an outstanding menu of country cooking cuisine. For a different taste, head over to I Portici, renowned for its delectable creative and contemporary dishes. This distinguished 1-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Trattoria di Via Serra, a highly rated local gem known for its exquisite emilian menu. With a Bib Gourmand acclaim, it promises a dining experience you won't want to miss. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Bologna.

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 Bologna. The bars in Bologna make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

If you’re not ready to end the night just yet, Bar Al Bricco D'oro offers a perfect venue to relax and savor a drink. Similarly, Bar Freud E Squisito is well-suited for those looking to unwind in a social setting. Osteria Del Sole is another excellent spot to enjoy a nightcap after a delightful meal.

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

Day 3 introduces you to many popular attractions and activities in Bologna, further proving that leisurely self-drive tours in Italy are extraordinary.

Savor the day by visiting some of the best places to see in Bologna, including a palace, a monument, a church, a public square and much more! Start your adventure at Palazzo Re Enzo. This underrated palace is a must-visit for travelers looking for a unique holiday experience. Make your way to Fountain Of Neptune, Bologna located in Bologna for another exciting encounter.

Next, immerse yourself in the setting of Bologna Cathedral. Its stunning features will captivate you. After the church, continue your tour of the city with a visit to Piazza Maggiore. Visitors usually appreciate the history-steeped features of this public square. Next up is Basilica Of San Domenico, a highly recommended church.

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 Bononia Cafè, 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 Via Con Me, 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 Trattoria Pizzeria La Mela, a hidden gem nestled in Bologna. 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.

Let the evening flow smoothly from dinner to drinks at Lime Bar, a top-rated bar in the area. For other recommendations, Macondo - Cocktail Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Bar Onda Marina By Night offers a memorable night with diverse drink options and excellent service.

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

On day 4 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!

Prepare for a day full of fun adventures, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Devotional Portico Of St. Luke. This worthwhile monument is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Arco Del Meloncello, one of the city’s best highlights.

Next, check out Two Towers, one of the most interesting places to see in Bologna. This monument is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, International Museum And Library Of Music. Wander around and soak in the eye-catching atmosphere this museum offers. Then, head to Piazza Santo Stefano, a top-rated public square that adds another dimension to your day.

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 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 Va Mo Là, a highly-rated dining destination in Bologna. If you're eager to try something different, consider Trattoria dal Biassanot, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante Enoteca da Lucia. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Bologna 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.

To truly maximize your evening out, consider visiting Aurum after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Senza Nome, another bar with an inviting ambiance. Similarly, Caffè Ristretto also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Day 5 of your relaxed road trip through Italy means 24 hours of making the best memories in Bologna. You’ll go sightseeing at famous attractions in Bologna. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Bologna!

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Bologna allows for both. Start by heading to Pinacoteca Nazionale Di Bologna. This intriguing 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, a locally appreciated street.

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.

Have a fantastic dining experience at Pappare' - Bologna, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Mister Coffee Bistrò offers an enticing alternative with its varied menu. Additionally, All'Osteria Bottega is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Bologna.

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

Continue the enjoyment post-dinner at Bar Piratello, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bar Carlo offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Maurizio. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

On day 6 of your laid-back and relaxed road trip adventure, you’ll have the chance to visit more than one remarkable area in Italy. Since this self-drive tour offers freedom and flexibility, you can decide how much time you want to spend in each place to enjoy the memorable travel destinations in Italy.

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and scenic views. Whether you decide to explore Bologna on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Arezzo Cathedral is the first of them. Spend some time admiring this romantic church before continuing your journey. Piazza Grande is your next stop. This popular public square is one of the best-rated sights in Bologna.

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 Roman Amphitheatre Of Arezzo. This culturally significant archeological site is a sight to behold.

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.

Have a memorable dining experience in Arezzo by booking a table at Octavin, renowned as a 1-star Michelin restaurant presenting an exceptional creative menu. Immerse yourself in the culinary delights of La Clandestina, a popular restaurant in Arezzo. With a menu designed to delight, it ensures a dining experience that transcends the ordinary.

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.

Extend your evening after a delightful meal by visiting Liquid Bar, which offers the perfect atmosphere for a night out.

Soak in the unique atmosphere of Arezzo 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 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.

Today, you'll explore some of the most beautiful places in Arezzo, including a monastery, a church, and a castle. Start your day with a visit to La Verna - Franciscan Sanctuary. This locally appreciated monastery is a must-visit in the hamlet. When you’re ready for your next discovery, continue to San Pietro A Romena, which may be one of the most culturally significant places you will experience today.

One of the best things about exploring Arezzo 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 Romena Castle, an often recommended castle in the hamlet.

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

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.

Savor the flavors at La Nuova Tagliatella, a top pick for dinner tonight. Alternatively, i 3 bicchieri beckons with its unique menu offerings. Also, consider Il Cantuccio. With its consistent customer satisfaction, it’s an excellent option for dining in Arezzo 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.

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

On day 9 of your relaxed road trip across Italy, you’ll explore the area around Rome, where you’ll be staying for another 4 nights. With so many fun and inspiring experiences to offer, a tour of Rome will make you fall even more in love with the city and uniqueness of Italy.

Saint Peter's Square is your next stop. This notable square 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 Sistine Chapel. To round off your sightseeing experience, visit St. Peter's Basilica.

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

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.

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

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Sant' Eustachio Caffè stands out as an excellent choice for a post-dinner cocktail. Alternatively, Yellowsquare Rome offers an ideal atmosphere to enjoy the pleasures of the night. Caffè Portofino is also a great option that provides a perfect setting for a relaxing evening.

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

Today’s itinerary in Rome covers several incredible sights, including a park, a monument, a public square, a castle and much more! Start your adventure at Villa Borghese. This famous park is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the history-steeped wonders of Trevi Fountain, 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 Pantheon. This wondrous monument offers an enriching experience. For a change of pace, head to Piazza Navona, where you can take in visually striking features. Conclude your self-guided sightseeing tour with a visit to Castel Sant'angelo. These sights offer a fulfilling end to a perfect day.

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.

Enjoy a lovely meal at Hotel de Russie, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Taverna Italiana is another top choice with a popular menu. You could also check for a table at The Parrot Bar. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Rome tonight.

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.

Round off your dining experience by visiting The Apartment Bar Roma, a prime location for a drink. Alternatively, explore the distinctive characteristics of Hotel Hassler Roma, a bar catering to every mood and preference.

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

On day 11 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!

Trastevere is a neighborhood 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. For another highlight, head to Monti, a neighborhood offering its own unique experiences.

Bring your curiosity for today’s adventure around Rome. Some of the city’s most loved attractions await! Altare Della Patria is the perfect place to start. This monument is one of the most well-known places to visit in Rome. Next, head to Roman Forum, a wondrous archeological site, known for its culturally significant 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 Colosseum. This breathtaking archeological site 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.

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 delightful dinner at Sofitel Roma Villa Borghese, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Centro? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Tema as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Rome.

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

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

Day 12 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!

A visit to Via del Corso 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. Don’t forget to check out Via dei Condotti as well, a street that adds another layer to your exploration.

Immerse yourself in Rome’s rich culture with today's sightseeing itinerary. Start your journey at Spanish Steps. This history-steeped public square is sure to ignite your curiosity. Next, dive into the visually striking features of Piazza Di Spagna, a must-visit public square 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 Del Popolo, a famous 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.

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.

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

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

Day 13 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Ancona for 1 night. 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.

Today’s agenda in Rome includes a church, an archeological site, and a monument. Santuario Madonna Delle Grazie is must-visit church and a great starting point for the day. Next, continue your journey to Roman Theatre Of Teramo, a worthwhile archeological site, located just a leisurely stroll away. Next, head to Fontana Dei Due Leoni, a symbolic monument, also available for your discovery today.

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.

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 Ancona.

Experience a taste of local culinary excellence while in Ancona by securing a table at Sot'Ajarchi. An esteemed Bib Gourmand restaurant, it features an exceptional seafood and from the marches menu. If you're in the mood for something new, try Bontà delle Marche, another premier location with a delectable menu.

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

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Alla Tazza D'oro stands out as an excellent choice for a post-dinner cocktail.

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