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

Day 2 of your leisurely self-drive tour in Italy offers another chance for an in-depth travel experience. On this refreshing new day, you’ll travel from Ancona and continue your relaxed road trip adventure in Loreto and Senigallia. You’ll stay in Bologna for 4 nights.

Cathedral Basilica Of St. Cyriacus brings Ancona's character to life. This stunning church is a highlight of any visit in the city.

Continue your road trip and head to your next destination, Loreto. This car ride takes around 35 min.

For a more meaningful self-guided tour of the city's best attractions, visit Sanctuary Of The Holy House Of Loreto, a notable church that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey.

When you’ve had your share of Loreto, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Senigallia. Your travel time is around 41 min.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Rocca Roveresca, an underrated castle that everyone visiting Senigallia should see.

In Bologna, you’ll find plenty of places to unwind after a day on the road. Our top recommendations go perfectly with your laid-back road trip in Italy.

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.

Dive into a culinary adventure like no other in Bologna by booking a table at Ahimè. This popular restaurant holds a Bib Gourmand award and offers an exceptional menu of country cooking cuisine. For another dining option, venture to I Portici, celebrated for its delectable creative and contemporary menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Trattoria di Via Serra, a top local restaurant known for its tantalizing emilian menu. With a Bib Gourmand recognition, it promises an exceptional dining experience not to be missed.

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

Continue your lively evening at Bar Al Bricco D'oro, a perfect place for winding down or revving up the night, depending on which mood you’re in. Bar Freud E Squisito is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Osteria Del Sole ensures a night out tailored to your taste.

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

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

Bologna is brimming with adventures.

Make time for Palazzo Re Enzo, an intriguing palace that is worthwhile a visit in the city. Nearby, you’ll find Fountain Of Neptune, Bologna, enchanting visitors with its photogenic appeal. Continue your exploration at Bologna Cathedral. This church is one of the city’s most beloved spots.

Enjoy the freedom of exploring Bologna at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Piazza Maggiore. After exploring the public square, head to the often recommended Basilica Of San Domenico.

Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities. Bologna offers a wide selection of experiences for every traveler.

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

Make sure to reserve a table at 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.

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.

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.

Soak in the unique atmosphere of Bologna as you commemorate this day of your relaxed road trip 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.

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.

No visit to Bologna is complete without Devotional Portico Of St. Luke. This increasingly popular monument is one of the top attractions in the city. Proceed to Arco Del Meloncello, another must-visit attraction.

As you wander through the inviting streets of Bologna, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Two Towers. This notable monument is a traveler-favorite. Not far away, you’ll find International Museum And Library Of Music, another key site on your sightseeing itinerary. Piazza Santo Stefano is yet another highly recommended place to visit nearby, offering plenty to discover for curious travelers.

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

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 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, 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.

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

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

Enjoy all that Pinacoteca Nazionale Di Bologna has to offer. This is a frequently visited art gallery you should not miss. Another must-see is San Martino, an underrated church in Bologna.

When you’re ready for the next sight, head to La Piccola Venezia.

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 Bologna, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Treat yourself to a delicious dinner at Pappare' - Bologna, an excellent option for tonight's dining. Looking for something different? Mister Coffee Bistrò offers a tantalizing alternative with its diverse menu. And don’t miss All'Osteria Bottega. Known for great service, it’s a fantastic choice 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.

Explore the vibrant nightlife at Bar Piratello after your meal, a hub for lively evenings and memorable moments. Or, head to Bar Carlo for a great selection of flavorful drinks and a charming setting. Furthermore, Bar Maurizio is perfect for those looking to extend their night with a touch of local flavor.

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

Day 6 of your easy, relaxed road trip through Italy lets you travel at your own pace and visit multiple places in a single day. Begin by exploring the best sights in Arezzo. By evening, drive toward the Arezzo, where you’ll stay at a top-rated hotel of your choice for 2 nights.

As you explore Arezzo’s charming streets, take in the lively atmosphere and get to know the character of the city.

Set your GPS to Arezzo and hit the road. Expect a journey of approximately 2 hours 11 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Arezzo beckons with new experiences!

Arezzo Cathedral is an often recommended church we recommend visiting today. Discover its visually striking features before continuing your self-guided tour to Piazza Grande, a respected public square that’s well-regarded in the area.

Next, stop by Roman Amphitheatre Of Arezzo, a culturally significant archeological site.

You'll be staying in Arezzo on this laid-back road trip through 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.

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.

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

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

On day 7 of your relaxed road trip in Italy, you’ll start your self-paced adventure in Arezzo and visit amazing attractions in La Verna and Pratovecchio, just outside the city. You still have 1 night left in Arezzo, so today is another excellent opportunity to dine at some of the top-rated restaurants and bars in the area.

La Verna is brimming with adventures.

When you’re ready to jump back into the car and say goodbye to Arezzo, you’ll hit the road in the direction of La Verna. This drive usually takes around 1 hour 4 min.

Spend your afternoon discovering La Verna - Franciscan Sanctuary, an often recommended monastery known for its historic features.

Continue your road trip and head to your next destination, Pratovecchio. This car ride takes around 55 min.

Set out on a self-guided sightseeing tour at San Pietro A Romena and explore the enchanting features. Next, make your way to Romena Castle, another highlight in Pratovecchio.

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.

Enjoy a lovely meal at La Nuova Tagliatella, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, i 3 bicchieri is another top choice with a popular menu. You could also check for a table at Il Cantuccio. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Arezzo tonight.

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

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

Once you're ready to continue your road trip, it's time to buckle up and drive towards Vatican City, eagerly anticipating your arrival in Vatican City. This drive usually takes around 12 min, without any stops or traffic disruptions.

For a more meaningful self-guided tour of the city's best attractions, visit Vatican Museums, an iconic art museum that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey.

When you’re ready, continue to Sistine Chapel, an extraordinary chapel beloved by locals and tourists alike. Don't miss out on St. Peter's Basilica, another highlight of the area that promises a memorable visit.

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

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 delicious meal at RomAntica, a highly-rated dining destination in Rome. If you're eager to try something different, consider Coso Ristorante, another top spot with a tantalizing menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Rome this evening.

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

Following your dinner, dive into the local bar culture at 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.

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

On day 10 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!

Awaiting your discovery is the extraordinary Villa Borghese, a mesmerizing park in Rome. Next, go to Trevi Fountain.

After visiting Villa Borghese and Trevi Fountain, have a stroll along Rome's streets and take in the local charm. Continue your sightseeing by heading to Pantheon. This photogenic monument offers a unique experience. Piazza Navona is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Castel Sant'angelo, one of the most symbolic places to visit in Rome.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Ancona. There are so many fun and eye-opening activities to try out in Ancona 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.

Savor the flavors at Hotel de Russie, a top pick for dinner tonight. Alternatively, La Taverna Italiana beckons with its unique menu offerings. Also, consider The Parrot Bar. With its consistent customer satisfaction, it’s an excellent option for dining in Rome tonight.

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

After your delicious meal, get a taste of the vibrant nightlife with a visit to The Apartment Bar Roma, known for its inviting atmosphere. Hotel Hassler Roma is another great option if you’re looking for a place to get the night started.

Raise your glass and relax after another big day of your leisurely paced road trip 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.

Don’t miss Trastevere 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. While you’re in the area, consider visiting Monti, another neighborhood that adds to the charm of Rome.

Start your day at Altare Della Patria. This breathtaking monument is a well-known place to see in Rome. Then, wander over to Roman Forum. If breathtaking sites excite you, this archeological site will be right up your alley. Nearby, you’ll also find Colosseum. This UNESCO world heritage-listed archeological site is a favorite among visitors.

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 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.

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.

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.

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!

Set aside time today to explore Via del Corso, a standout street 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. You might also want to visit Via dei Condotti, a street offering another perspective on the city.

Spanish Steps makes a great addition to your morning plans. This widely recognized public square is an enchanting place to see in Rome. Continue your discovery at Piazza Di Spagna, a culturally significant public square 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 Piazza Del Popolo. This widely recognized public square offers an enchanting encounter with Rome. 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.

Italy makes the perfect setting for a calming but fun road trip experience. 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.

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

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.

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

Day 13 of your relaxed road trip in 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!

Fasten your seatbelt and make your way to your next stop — Teramo, home to many well-known sights in the region. Keep in mind that your travel time from Rome to Teramo may take around 2 hours 7 min without traffic disruptions. Upon arrival in Teramo, we highly recommend checking out some of the top attractions.

Savor the day by heading to Santuario Madonna Delle Grazie, an underrated church that draws visitors from near and far. When you're done, continue to Roman Theatre Of Teramo, where you can soak in the heritage-rich surroundings.

Next, explore Fontana Dei Due Leoni, yet another underrated place to see in the area.

Continue your laid-back road trip in Italy as you make your way to Ancona. Here, you’ll find top hotels and accommodations in the city, perfect for relaxing and recharging.

Exploring the food culture in Ancona 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 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.

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.

Let the evening flow smoothly from dinner to drinks at Alla Tazza D'oro, a top-rated bar in the area.

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