One-Week Italy Self-Drive Road Trip With Itinerary from Milan traveling south to Bologna, Arezzo, Rome, and Florence
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Experience the freedom of the open road in Italy as you embark on an unforgettable 8-day road trip! This experience caters to every traveler, featuring destinations like Milan, Bologna, Siena, Arezzo, Rome, Florence, and Parma.
This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. You will spend 2 nights in Milan, 1 night in Bologna, 1 night in Arezzo, 2 nights in Rome, and 1 night in Florence. Anticipate well-spent days sightseeing, eating delicious food, and experiencing the highlights of each destination!
With this travel package, you can choose from an extensive selection of accommodations along your road trip route in Italy. We have handpicked the best hotels and places to stay across the country, including options for each budget. Whether you are in the mood for luxurious 5-star hotels or budget-friendly bed and breakfasts, we have got you covered.
Upon arriving in Milan, the rental vehicle of your choice will be ready for collection. From there, the road trip can begin! Experience the ultimate freedom and uncover Italy on your own terms.
An expertly curated travel plan makes sure you don’t miss out on any of the best things to see and do on your road trip in Italy. Trevi Fountain and Colosseum are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Pantheon, learn more about the unique Piazza Navona, and immerse yourself in the vibrant atmosphere of Duomo Di Milano Museum.
As you hit the open road and drive through Milan, Bologna, Siena, Arezzo, Rome, Florence, and Parma, you will also enjoy plenty of opportunities to uncover hidden gems and experience the authentic charm of Italy. Whether you are exploring enchanting towns and villages, discovering scenic routes, or indulging in local cuisine, there is always something new and exciting to experience in Italy.
Throughout your road trip in Italy, take breaks from sightseeing to explore your favorite destinations' top shopping streets and markets. Discover unique souvenirs that will forever remind you of your self-drive adventure in Italy.
This package offers an all-in-one solution for your trip planning - choose flights, a rental car, accommodation, attractions, and tours that suit your needs and desires. You can customize each day of your road trip itinerary with flexible trip planning before and after booking.
The best services in Italy fill up quickly, so book your spot early. Select a date and start planning your road trip in Italy today!
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Day 1
- Milan - Arrival day
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- Brera
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Say hello to Milan! Your exciting road trip through Italy is just about to start. Navigating the top places to see in the region is a breeze with a car. The rental vehicle of your choice will be ready for pickup upon your arrival in the city. You will stay in Milan for 1 night before you continue your adventure!
Milan is a beautiful city with plenty to discover. If you arrive before check-in time or prefer to get started on your sightseeing right away, we recommend checking out Brera, a must-see neighborhood, and taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.
As afternoon approaches, head to your chosen hotel in Milan. Check-in typically starts around 2 to 4 PM at hotels in Italy. We recommend staying at a hotel in a central location for easy access to the best attractions, restaurants, and bars in the city.
As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Milan, it's often a good idea to reserve a table in advance.
Make sure to reserve a table at Hotel Morfeo Milano, an iconic dining spot in Milan. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Contraste, a popular restaurant in Milan. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of UNAHOTELS Galles Milano, a hidden gem nestled in Milan. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.
Continue your lively evening at Nottingham Forest, a perfect place for winding down or revving up the night, depending on which mood you’re in. Armani/bamboo Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Mag Cafe ensures a night out tailored to your taste.
Raise a toast to the start of your 8-day road trip in Italy!
Day 2
- Milan
- Bologna
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Drive 218 km, 3 hours 3 min
- Duomo di Milano
- Galleria Vittorio Emanuele II
- Castello Sforzesco
- Sempione Park
- More
Dive into day 2 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 Bologna. You’ll stay here for 1 night.
Discover a day packed with fun adventures, romantic experiences, and scenic views in Milan. Begin your sightseeing with Duomo Di Milano Museum. This wondrous church is one of the top attractions in the city. Proceed to Galleria Vittorio Emanuele Ii, another must-visit attraction.
As you wander through the inviting streets of Milan, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Sforzesco Castle Art Library. This widely recognized castle is a traveler-favorite. Not far away, you’ll find Parco Sempione, another key site on your sightseeing itinerary.
At the end of the day, you will drive to Bologna, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.
As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Bologna. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.
Experience a taste of local culinary excellence while in Bologna by securing a table at Ahimè. An esteemed Bib Gourmand restaurant, it features an exceptional country cooking menu. For an alternative taste experience, visit I Portici, famous for its scrumptious creative and contemporary dishes. This 1-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Trattoria di Via Serra, a local favorite celebrated for its exquisite emilian cuisine in Bologna. Located in the heart of the city, this Bib Gourmand-awardee is an ideal pick for emilian cuisine lovers seeking top-notch culinary experiences.
After enjoying a fulfilling meal, continue your evening at Bar Al Bricco D'oro, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bar Freud E Squisito offers a welcoming atmosphere for easing into the nightlife. Similarly, Osteria Del Sole provides an excellent environment for a relaxed and enjoyable evening.
Take some time to reflect on your day and savor another beautiful night in Italy.
Day 3
- Bologna
- Arezzo
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Drive 257 km, 3 hours 41 min
- Piazza Maggiore
- Two Towers
- Siena Cathedral
- piazza del Campo
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On day 3 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 Bologna and Siena. In the evening, you’ll end up in Arezzo, where you will stay for 1 night.
Today's adventure in Bologna promises more breathtaking discoveries and enriching experiences! Begin at Piazza Maggiore. This romantic public square is a highlight of any visit in the city. Then, enjoy Two Towers, another stunning attraction that never fails to captivate visitors. Next, head over to Siena Cathedral, one of the city’s most interesting attractions, known for its culturally significant features.
If you’re looking for more, spend time soaking in the atmosphere of Piazza Del Campo. This history-steeped public square is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.
After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Arezzo. Arezzo offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.
Indulge in a memorable dining experience at one of Arezzo's most popular restaurants, and connect with friendly locals for an authentic adventure.
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.
Cap off your dinner by heading to Liquid Bar, ideal for a leisurely evening with a drink in hand.
Celebrate another amazing day of your road trip adventure in Italy!
Day 4
- Arezzo
- Rome
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Drive 228 km, 3 hours 15 min
- Vatican Museums
- Saint Peter's Square
- Sistine Chapel
- St Peter's Basilica
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Experience an unparalleled adventure on day 4 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Vatican City. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rome. You will spend 2 nights here for some well-deserved relaxation.
Saint Peter's Square is your next stop. This popular square is one of the best-rated sights in Arezzo.
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 for the day, you’ll drive to your hotel in Rome. Check in and spend some time relaxing before you head out to tour the city.
As you explore more of Rome, 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 harmony of flavors at La Pergola in Rome by securing a reservation in advance. Known for its 3-star Michelin status, La Pergola offers a delightful variety of dishes highlighting its delicious mediterranean and contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Il Pagliaccio, a highly recommended restaurant known for its enticing creative and innovative 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 Enoteca La Torre, a highly acclaimed restaurant celebrated for its exceptional mediterranean and creative menu.
Extend your evening after a delightful meal by visiting La Botticella Of Poggi Giovanni, which offers the perfect atmosphere for a night out. Moreover, Almalu Trastevere is another popular option for a drink or two. Likewise, Bar Viminale Di Pepi Maurilio also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.
Raise your glass to another unforgettable day in Italy!
Day 5
- Rome
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Drive 5 km, 48 min
- Piazza Navona
- Roman Forum
- Colosseum
- Trastevere
- Monti
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Day 5 of your road trip will take you to the best attractions Rome has to offer. Cherish the 1 night you have left in Rome by discovering the best things there are to see and do in the city.
A top thing to do today is to explore Trastevere, a must-see neighborhood in Rome. It's the perfect starting point for touring the top attractions in the area. You can also visit Monti, an ideal neighborhood for continued sightseeing.
Today, you'll explore some of the most beautiful places in Rome, including a public square and an archeological site. Start your day with a visit to Piazza Navona. This wondrous public square is a must-visit in the city. When you’re ready for your next discovery, continue to Roman Forum, which may be one of the most picture-perfect 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 Colosseum, a world-famous archeological site 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 delicious dinner at RomAntica, an excellent option for tonight's dining. Looking for something different? Coso Ristorante offers a tantalizing alternative with its diverse menu. And don’t miss DEROMA - Farine Romane. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Rome.
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.
Savor another day of unforgettable experiences in Italy!
Day 6
- Rome
- Florence
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Drive 278 km, 3 hours 34 min
- Pantheon
- Trevi Fountain
- Piazza di Spagna
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On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Rome. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 1 night.
Immerse yourself in Rome’s rich culture with today's sightseeing itinerary. Start your journey at Pantheon. This heritage-rich monument is sure to ignite your curiosity. Next, dive into the visually striking features of Trevi Fountain, a must-visit monument 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 Di Spagna, a timeless public square.
At the end of the day, you will drive to Florence, 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 Florence. 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.
Treat yourself to an extraordinary dining experience at Enoteca Pinchiorri, a 3-star Michelin restaurant offering an incredible italian contemporary menu. Alternatively, if your taste buds call for something different, Santa Elisabetta is one of the best restaurants for creative and mediterranean cuisine in Florence. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Gucci Osteria da Massimo Bottura. As a top-rated establishment with 1 Michelin star, it is an ideal choice for italian contemporary and international cuisine in the city.
Continue your lively evening at Manifattura, a perfect place for winding down or revving up the night, depending on which mood you’re in. Se·sto On Arno Rooftop Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Il Vinile ensures a night out tailored to your taste.
Relax and reminisce about your day in Italy and look forward to more memorable moments to come!
Day 7
- Florence
- Milan
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Drive 318 km, 4 hours 12 min
- piazza della Signoria
- Ponte Vecchio
- Cathedral of Santa Maria del Fiore
- Parma Cathedral
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Embark on another extraordinary experience on day 7 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Florence and Parma. 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.
Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most top-rated attractions included on the itinerary is Piazza Della Signoria. This romantic public square will help you start your sightseeing on top. Then, take a leisurely stroll to Ponte Vecchio and learn what makes this enchanting historical landmark unique.
Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the widely recognized Cathedral Of Santa Maria Del Fiore. After exploring the church, head to Parma Cathedral. This up-and-coming church is a highlight in Florence.
After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Milan. Milan offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.
After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Milan. Enjoy a satisfying meal that will recharge you for tonight's adventures.
Experience a symphony of flavors at Enrico Bartolini al Mudec in Milan by securing a reservation in advance. Renowned for its 3-star Michelin distinction, Enrico Bartolini al Mudec delights its guests with its exceptional variety of meals showcasing delicious creative cuisine. For a palate-pleasing alternative, make sure to dine at Seta by Antonio Guida, acclaimed for its delectable international and contemporary specialties. This local 2-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Il Luogo Aimo e Nadia, a top-rated restaurant known for its outstanding menu. Known as a top-rated 1-star Michelin establishment, it's a top choice for italian contemporary and modern cuisine in the city.
To truly maximize your evening out, consider visiting Kilburn Cocktail Bar Milano after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Frida, another bar with an inviting ambiance. Similarly, The Friends Pub Milano also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.
As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.
Day 8
- Milan - Departure day
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- Corso Vittorio Emanuele II
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Day 8 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Milan before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.
At the top of the list of things to do today is to explore Corso Vittorio Emanuele II, a street that captures the true essence of Milan. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.
Explore local shops for souvenirs to remember your trip or find unique gifts for loved ones. Discover boutiques offering an array of stylish fashion choices. Take a break with a cup of coffee or tea while savoring the local vibe in a coffee shop.
Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Milan.
You’ll then say farewell to Milan. Drive to the airport, return your car, and take the opportunity to get some last-minute souvenirs before you board your flight home. We wish you a pleasant journey and hope you leave with many wonderful memories of your road trip in Italy!
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