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

Day 2 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 Ancona. By the end of the day, you’ll drive in the direction of the city of Bologna, where you’ll stay at a top-rated hotel of your choice for 4 nights.

Get ready to discover some of the most iconic wonders in Ancona, including a church and a castle. Start your day at Cathedral Basilica Of St. Cyriacus. This stunning church is an increasingly popular place to see in Ancona. Then, wander over to Sanctuary Of The Holy House Of Loreto. If historic sites excite you, this church will be right up your alley. Nearby, you’ll also find Rocca Roveresca. This culturally significant castle is a favorite among visitors.

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.

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.

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!

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!

Today, you'll explore some of the most beautiful places in Bologna, including a palace, a monument, a church, a public square and much more! Start your day with a visit to Palazzo Re Enzo. This beloved palace is a must-visit in the city. When you’re ready for your next discovery, continue to Fountain Of Neptune, Bologna, which may be one of the most noteworthy places you will experience today.

One of the best things about exploring Bologna 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 Bologna Cathedral, a curiosity-inducing church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Piazza Maggiore and Basilica Of San Domenico.

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

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

Dine in style at Bononia Cafè, a top recommendation for dinner tonight. Or, for a change of pace, Via Con Me boasts a menu that's sure to impress. Also, be sure to check out Trattoria Pizzeria La Mela. Known as a local hotspot, it’s a great choice for tonight 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.

Following your dinner, dive into the local bar culture at Lime Bar. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Macondo - Cocktail Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Onda Marina By Night provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Today's adventure in Bologna promises more breathtaking discoveries and enriching experiences! Begin at Devotional Portico Of St. Luke. This culturally significant monument is a highlight of any visit in the city. Then, enjoy Arco Del Meloncello, another respected attraction that never fails to captivate visitors. Next, head over to Two Towers, one of the city’s most notable attractions, known for its culturally significant features.

If you’re looking for more, spend time soaking in the atmosphere of International Museum And Library Of Music. This historic museum is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Piazza Santo Stefano, a frequently visited public square, and take a stroll around the area.

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 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.

Make sure to reserve a table at Va Mo Là, 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 Trattoria dal Biassanot, 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 Ristorante Enoteca da Lucia, 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 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.

Unwind after your meal by stepping into Aurum. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Senza Nome offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Caffè Ristretto, another top-rated bar in the area.

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 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!

Today’s well-planned self-sightseeing route offers several family-friendly attractions, picturesque spots, and history-rich sites. 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. Pinacoteca Nazionale Di Bologna is the first of them. Spend some time admiring this standout art gallery before continuing your journey. San Martino is your next stop. This locally appreciated church 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 La Piccola Venezia. This eye-catching street is a sight to behold.

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!

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.

Don’t miss out on dining at Pappare' - Bologna, a top-rated dining destination in Bologna. If you're in the mood to try something new, consider Mister Coffee Bistrò, another top spot with a mouthwatering menu. You might also want to secure a reservation at All'Osteria Bottega. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Bologna 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.

Cap off your dinner by heading to Bar Piratello, ideal for a leisurely evening with a drink in hand. Bar Carlo is another bar that offers an enjoyable setting. Similarly, Bar Maurizio is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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 itinerary in Bologna covers several incredible sights, including a church, a public square, and an archeological site. Start your adventure at Arezzo Cathedral. This curiosity-inducing church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the visually striking wonders of Piazza Grande, a must-see public square 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 Roman Amphitheatre Of Arezzo. This increasingly popular archeological site offers an enriching experience. These sights offer a fulfilling end to a perfect day.

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

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.

Get ready for an unforgettable culinary journey in Arezzo by reserving a table at Octavin. Renowned as a 1-star Michelin restaurant, it offers an exceptional creative menu. If you're in the mood to try something new, consider La Clandestina, another top spot with a mouthwatering 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.

Continue your evening by exploring the vibrant nightlife scene at Liquid Bar, a prime destination for a thrilling night out.

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

Enjoy the perfect balance of relaxation and exploration in Arezzo today. One of the most often recommended attractions included on the itinerary is La Verna - Franciscan Sanctuary. This historic monastery will help you start your sightseeing on top. Then, take a leisurely stroll to San Pietro A Romena and learn what makes this symbolic church unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the locally appreciated Romena Castle.

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

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

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.

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

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

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Rome allows for both. Start by heading to Vatican Museums. This timeless art museum provides an insightful glimpse into the city's identity.

Continue your sightseeing with a visit to Sistine Chapel, a famous chapel. When you’re done, don’t forget to make a stop at the globally renowned St. Peter's Basilica.

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

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.

Have a fantastic dining experience at RomAntica, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Coso Ristorante offers an enticing alternative with its varied menu. Additionally, DEROMA - Farine Romane is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Rome.

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

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

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 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!

Bring your curiosity for today’s adventure around Rome. Some of the city’s most loved attractions await! Villa Borghese is the perfect place to start. This park is one of the most impressive places to visit in Rome. Next, head to Trevi Fountain, a timeless monument, known for its visually striking 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 Pantheon. This photogenic monument is a highly recommended experience. Nearby, you'll also find Piazza Navona and Castel Sant'angelo. 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.

Treat yourself to a wonderful meal at Hotel de Russie, a top-rated dining spot in Rome. If you're in the mood for something new, try La Taverna Italiana, another premier location with a delectable menu. You might also want to book a table at The Parrot Bar. 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.

Keep the evening going at The Apartment Bar Roma, a great choice for enjoying the after-dinner hours with a drink. You could also go to Hotel Hassler Roma, which offers a similarly pleasant setting and great drinks.

Raise your glass to celebrate another day of your laid-back and relaxed road trip experience 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 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. While you’re in the area, consider visiting Monti, another neighborhood that adds to the charm of Rome.

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

Continue your journey to Colosseum, one of the city’s most wondrous spots that you shouldn’t miss.

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.

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 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.

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

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. For another highlight, head to Via dei Condotti, a street offering its own unique experiences.

Prepare for a day full of fun adventures, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Spanish Steps. This astonishing public square is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazza Di Spagna, one of the city’s best highlights.

Next, check out Piazza Del Popolo, one of the most extraordinary places to see in Rome. This public square is a favorite among locals and travelers alike.

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 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.

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

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

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

Today, you'll explore some of the most beautiful places in Rome, including a church, an archeological site, and a monument. Start your day with a visit to Santuario Madonna Delle Grazie. This beloved church is a must-visit in the city. When you’re ready for your next discovery, continue to Roman Theatre Of Teramo, which may be one of the most culturally significant 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 Fontana Dei Due Leoni, an intriguing monument in the city.

You’ll be staying at the incredible city of Ancona in this laid-back road trip in Italy. You'll stay here for 1 night.

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 Ancona, explore the city like a local by trying out the best restaurants in the area.

Discover the culinary delights of Ancona by securing a reservation at Sot'Ajarchi. Esteemed for its a Bib Gourmand award, this restaurant offers a remarkable selection of seafood and from the marches cuisine. Alternatively, Bontà delle Marche beckons with its unique menu offerings.

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 Alla Tazza D'oro, a well-loved spot among locals and tourists.

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