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

On day 2 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Loreto and Senigallia. When you’re not sightseeing, take time to relax at your selected hotel in Bologna, where you’ll be staying for 1 night.

After soaking in Ancona’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Loreto. Expect your car journey to take a minimum of 31 min. When you arrive in Loreto, it's time to take a break from the road.

Head to Sanctuary Of The Holy House Of Loreto, a notable church in Loreto. Explore its stunning features at your own pace before you continue your journey.

Embrace the thrill of the open road as you wave goodbye to Loreto and set your GPS to Senigallia. While on the road, immerse yourself in your favorite road trip tunes or sample the sounds from a local radio station. This car ride usually takes around 41 min. Upon reaching Senigallia, unwind, observe, and explore. The best things to do, see, and eat are waiting for you.

Take your self-guided tour to Rocca Roveresca, an intriguing castle that everyone visiting Senigallia should see. Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Next, head to Piazza Garibaldi. This eye-catching public square is one of the most beloved attractions in the region.

When you’re done exploring for the day, you’ll drive to your hotel in Bologna. Check in and spend some time relaxing before you head out to tour the city.

As you explore more of Bologna, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

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.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar Al Bricco D'oro, known for its inviting atmosphere. Bar Freud E Squisito is another great option if you’re looking for a place to get the night started. Similarly, Osteria Del Sole provides a great setting to enjoy the night away.

Raise your glass to another unforgettable day in Italy!

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Bologna. At the end of the day, you will enjoy the comforts of a top-rated hotel in Milan, which will be your home away from home for 1 night.

Start by visiting Bologna Cathedral, a prime spot to begin your journey. This picture-perfect church is sure to impress. Next on your list is Fountain Of Neptune, Bologna, another must-visit landmark and increasingly popular monument renowned for its noteworthy features.

While exploring and sightseeing, take time to savor the ambiance of Bologna by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to Piazza Maggiore. This symbolic public square is a remarkable attraction that offers a unique experience. Two Towers also adds charm to your journey, and Piazza Santo Stefano wraps up your day with its symbolic appeal.

At the end of the day, you will drive to Milan, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

As dinnertime approaches, it's time to head out for a bite to eat in Milan. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Get ready for an unforgettable culinary journey in Milan by reserving a table at Enrico Bartolini al Mudec. Renowned as a 3-star Michelin restaurant, it offers an exceptional creative menu. For a different taste experience, head to Seta by Antonio Guida, recognized for its delicious international and contemporary dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Il Luogo Aimo e Nadia, a local favorite known for its delightful italian contemporary and modern cuisine in Milan. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for discerning italian contemporary and modern foodies seeking culinary excellence.

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

Take some time to reflect on your day and savor another beautiful night in Italy.

Dive into day 4 of your remarkable road trip in Italy. Today you will explore Milan, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Genoa. You’ll stay here for 1 night.

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and scenic views. Whether you decide to explore Milan on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Duomo Di Milano Museum is the first of them. Spend some time admiring this inviting church before continuing your journey. Galleria Vittorio Emanuele Ii is your next stop. This extraordinary shopping mall is one of the best-rated sights in Milan.

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 Pinacoteca Di Brera. This photogenic art gallery is a sight to behold. To round off your sightseeing experience, visit Sforzesco Castle Art Library and Parco Sempione.

After soaking up all the sights of today's itinerary, you'll be ready to hit the road in the direction of your accommodation in Genoa. Genoa offers plenty of top-rated hotels and other places to stay on any travel budget. Take some time to relax before you head out to explore.

After a day of adventure, treat yourself to an exquisite dinner at one of Genoa's best restaurants.

Start your culinary exploration in Genoa by securing a reservation at San Giorgio. This renowned restaurant holds 1 Michelin star and offers an exceptional menu of modern and ligurian cuisine. For another dining delight, visit The Cook, celebrated for its delectable modern menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Il Marin, a top local spot known for its tantalizing seafood and contemporary menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

Keep the excitement of the evening going by visiting a bar or two. Scurreria Beer & Bagel is an excellent place to start. You could also check out La Lepre, offering a different kind of charm. A last recommendation for the day is Bar Pisacane Iii. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Get a good night's sleep and look forward to another great day on the road in Italy!

On day 5 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Genoa and Pisa. In the evening, you’ll end up in Florence, where you will stay for 3 nights.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Genoa allows for both. Start by heading to Piazza De Ferrari. This notable public square provides an insightful glimpse into the city's identity. Next, discover Aquarium Of Genoa, an eye-catching aquarium, promising a delightful encounter.

As you’ve unraveled the marvels of Genoa, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Pisa may take around 2 hours 3 min. Upon your arrival in Pisa, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Spend your afternoon discovering Piazza Del Duomo, Pisa, a timeless public square known for its historic features. After taking in the atmosphere, continue to Leaning Tower Of Pisa, a globally renowned monument that is a must-see for anyone visiting the region.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and spend some time relaxing before you head out to tour the city.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

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

Unwind after your meal by stepping into Manifattura. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Se·sto On Arno Rooftop Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Il Vinile, another top-rated bar in the area.

Raise your glass and celebrate another amazing day of your road trip in Italy!

On day 6 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 2 nights and discover all the best things to see and do in the area.

Brace yourself for today’s incredible lineup of attractions in Florence, featuring fun adventures, romantic experiences, and scenic views. Start at The Boboli Gardens, a well-known botanical garden in the city. Then, head to Ponte Vecchio and soak in the ambiance of this visually striking historical landmark.

There are many interesting places to see in Florence and when you are ready for more, go to Uffizi Gallery. This is one of the city’s most impressive spots. After exploring the art gallery, visit the captivating Palazzo Vecchio. Before wrapping up your self-guided sightseeing tour, head to the top-rated Piazza Della Signoria, a top-rated public square in the city.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

Indulge in a memorable dining experience at one of Florence's most popular restaurants, and connect with friendly locals for an authentic adventure.

Enjoy a lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

Raise your glass and celebrate another amazing day of your road trip in Italy!

Day 7 of your road trip across Italy promises a magnificent time exploring Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Pitti Palace. This captivating palace provides an insightful glimpse into the city's identity. Next, discover Strozzi Palace Mantua, a historic palace, promising a delightful encounter.

Continue your sightseeing with a visit to Basilica Di Santa Maria Novella, Firenze (fi), a well-known church. When you’re done, don’t forget to make a stop at the top-rated Cathedral Of Santa Maria Del Fiore.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As you explore more of Florence, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Enjoy a lovely dining experience at Ristorante Buca Mario, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Agricola Toscana, 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 Eataly Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

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

Head back to your accommodation in Florence and get some rest in preparation for another magical day of your road trip in Italy!

Experience an unparalleled adventure on day 8 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Arezzo. You will spend 1 night here for some well-deserved relaxation.

Start your adventure at Central Market. This popular food market is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the heritage-rich wonders of Galleria Dell'accademia, a must-see art gallery 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 David. This popular statue offers an enriching experience. For a change of pace, head to Basilica Of Santa Croce In Florence, where you can take in its culturally significant features. Conclude your self-guided sightseeing tour with a visit to Piazzale Michelangelo. This history-steeped observation deck offers a fulfilling end to a perfect day.

At the end of the day, you will drive to Arezzo, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

Indulge in a memorable dining experience at one of Arezzo's most popular restaurants, and connect with friendly locals for an authentic adventure.

Discover the culinary delights of Arezzo by securing a reservation at Octavin. Esteemed for its 1-star Guide Michelin recognition, this restaurant offers a remarkable selection of creative cuisine. Alternatively, La Clandestina beckons with its unique menu offerings.

Continue the enjoyment post-dinner at Liquid Bar, a cherished local gathering spot renowned for its welcoming atmosphere.

Celebrate another amazing day of your road trip adventure in Italy!

On day 9 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Vatican City. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 4 nights.

When you’re ready to jump back into the car and say goodbye to Arezzo, you’ll hit the road in the direction of Vatican City, Vatican City. Witness the landscapes transform as you cross the border to Vatican City. This drive usually takes around 2 hours 32 min. When you arrive, enjoy some sightseeing.

After taking in the atmosphere, continue to Sistine Chapel, an extraordinary chapel that is a must-see for anyone visiting the region. Make sure to also explore St. Peter's Basilica, a wondrous major basilica that offers a unique experience.

After soaking up all the sights of today's itinerary, you'll be ready to hit the road in the direction of your accommodation in Rome. Rome offers plenty of top-rated hotels and other places to stay on any travel budget. Take some time to relax before you head out to explore.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Rome. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Enjoy an outstanding dining experience at La Pergola, a 3-star Michelin restaurant offering an exceptional mediterranean and contemporary menu. Alternatively, if you're in the mood for something different, consider the nearby 2-star Michelin-awardee, Il Pagliaccio, known for its delicious creative and innovative cuisine. Another highly-recommended place to eat in Rome is Enoteca La Torre, a renowned restaurant with a 2-star Guide Michelin recognition and a delicious mediterranean and creative menu.

After savoring a delicious meal, step into the vibrant nightlife at La Botticella Of Poggi Giovanni, where the evening is just getting started. In the same way, Almalu Trastevere offers a unique charm perfect for experiencing the local bar scene in Rome. Bar Viminale Di Pepi Maurilio is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Head back to your accommodation in Rome and get some rest in preparation for another magical day of your road trip in Italy!

Day 10 offers a multitude of experiences. You will stay in Rome for 3 nights more, offering you enough time to explore at a relaxed pace.

Get ready for an exciting day in Rome. Today’s sightseeing agenda includes a monument, a public square, and a castle. Begin your adventure at Trevi Fountain. This is a wondrous monument you should not miss. Another must-see is Pantheon, a wondrous monument in Rome.

When you’re ready for the next sight, head to Piazza Navona. From there, take a leisurely stroll to Campo De' Fiori, another of the city’s astonishing attractions. We recommend ending your self-guided tour of the city with a history-steeped castle. Castel Sant'angelo is a truly remarkable place to visit in Rome.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Rome. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Make sure to reserve a table at RomAntica, an iconic dining spot in Rome. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Coso Ristorante, a popular restaurant in Rome. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of DEROMA - Farine Romane, a hidden gem nestled in Rome. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

Raise your glass to another unforgettable day in Italy!

Day 11 of your road trip will take you to the best attractions Rome has to offer. Cherish the 2 nights you have left in Rome by discovering the best things there are to see and do in the city.

Today's adventure in Rome promises more breathtaking discoveries and enriching experiences! Begin at Villa Borghese. This mesmerizing park is a highlight of any visit in the city. Then, enjoy Altare Della Patria, another culturally significant attraction that never fails to captivate visitors. Next, head over to Roman Forum, one of the city’s most globally renowned attractions, known for its picture-perfect features.

If you’re looking for more, spend time soaking in the atmosphere of Colosseum. This UNESCO world heritage-designated archeological site is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Circus Maximus, a notable archeological site, and take a stroll around the area.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As dinnertime approaches, it's time to head out for a bite to eat in Rome. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

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.

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.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

On day 12 of your road trip, you will have an entire day to explore Rome. You’ll stay in Rome for 1 night and discover all the best things to see and do in the area.

Today’s agenda in Rome includes a public square and a church. Piazza Del Popolo is must-visit public square and a great starting point for the day. Next, continue your journey to Spanish Steps, an impressive public square, located just a leisurely stroll away. Next, head to Piazza Di Spagna, a visually striking public square, 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. If you’re looking for more, Basilica Di Santa Maria Maggiore is also a well-known attraction that is worthwhile a visit. Lastly, don’t miss Archbasilica Of St. John Lateran, a popular gem to see in the city.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

After a day of adventure, treat yourself to an exquisite dinner at one of Rome's best restaurants.

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.

Get a good night's sleep and look forward to another great day on the road in Italy!

Embark on another extraordinary experience on day 13 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Teramo and Giulianova. At the end of the day, you will enjoy the comforts of a top-rated hotel in Ancona, which will be your home away from home for 1 night.

When you’ve had your share of Rome, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Teramo. Your travel time is around 2 hours 7 min.

One of our top recommendations for your sightseeing is Castello Della Monica. Spend some time admiring the respected features of the castle before you continue to your next stop.

When you’re ready to jump back into the car and say goodbye to Teramo, you’ll hit the road in the direction of Giulianova. This drive usually takes around 27 min. When you arrive, enjoy some sightseeing.

Belvedere is an underrated public square we recommend making time to visit today. Discover its romantic features before continuing your self-guided tour to Duomo Of Saint Flavian, a culturally significant church that’s well-regarded in the area.

When you’re done exploring for the day, you’ll drive to your hotel in Ancona. Check in and spend some time relaxing before you head out to tour the city.

As you explore more of Ancona, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Experience a symphony of flavors at Sot'Ajarchi in Ancona by securing a reservation in advance. Renowned for its Bib Gourmand distinction, Sot'Ajarchi delights its guests with its exceptional variety of meals showcasing delicious seafood and from the marches cuisine. Or, if you're feeling adventurous, why not try Bontà delle Marche? It's another excellent option with a diverse menu.

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.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.