9-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling south to Genoa, Florence, and Bologna

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Photo of Arch of Peace, or Arco della Pace, city gate in the centre of the Old Town of Milan in the sunny day, Lombardia, Italy.
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Explore the best of Italy on a remarkable 9-day road trip! Combine exploration with relaxation on a self-drive tour featuring Milan, Genoa, Pisa, Florence, and Bologna.

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. You will spend 3 nights in Milan, 2 nights in Genoa, 2 nights in Florence, and 1 night in Bologna. 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 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. Duomo Di Milano Museum and Ponte Vecchio are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Leaning Tower Of Pisa, learn more about the unique Piazza Del Duomo, Pisa, and immerse yourself in the vibrant atmosphere of Galleria Vittorio Emanuele Ii.

As you hit the open road and drive through Milan, Genoa, Pisa, Florence, and Bologna, 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, accommodations, 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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Driver’s age is 30 - 65
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Day 1

Day 1

  • Milan - Arrival day
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  • Piazza Gae Aulenti
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Welcome to Milan, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 2 nights discovering what to see in Milan before embarking on the next leg of your journey.

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 Piazza Gae Aulenti, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

Find your way to your hotel in Milan. We recommend choosing a hotel in a central location for easy exploring. Check-in typically starts between 2 and 4 PM at hotels in Italy. Settle in and make plans for the evening.

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.

Dine in style at Hotel Morfeo Milano, a top recommendation for dinner tonight. Or, for a change of pace, Contraste boasts a menu that's sure to impress. Also, be sure to check out UNAHOTELS Galles Milano. Known as a local hotspot, it’s a great choice for tonight in Milan.

To truly maximize your evening out, consider visiting Nottingham Forest after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Armani/bamboo Bar, another bar with an inviting ambiance. Similarly, Mag Cafe also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Raise a toast to the start of your 9-day road trip in Italy!

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Day 2

Day 2

  • Milan
  • More

Drive 1 km, 20 min

  • Royal Palace of Milan
  • Cathedral Square
  • Duomo di Milano
  • Galleria Vittorio Emanuele II
  • La Scala
  • More

Day 2 of your road trip will take you to the best attractions Milan has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Milan.

Royal Palace Of Milan is an ideal stop early in the day. This interesting palace is a must-visit in the city. When you’re ready for your next discovery, continue to Cathedral Square, which may be one of the most culturally significant places you will experience today.

One of the best things about exploring Milan 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 Duomo Di Milano Museum, an iconic church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Galleria Vittorio Emanuele Ii and La Scala.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

For an unforgettable shopping experience, visit Via della Moscova, the top shopping destination in Milan. Browse local boutique shops and stores, each offering delightful surprises. Find unique souvenirs or items to take home. After shopping, explore what Via della Moscova has to offer, including cafes, attractions, essential services, and vibrant community activities.

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.

Start your culinary exploration in Milan by securing a reservation at Enrico Bartolini al Mudec. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another dining delight, visit Seta by Antonio Guida, celebrated for its delectable international and contemporary menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Il Luogo Aimo e Nadia, a top local spot known for its tantalizing italian contemporary and modern menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

After savoring a delicious meal, step into the vibrant nightlife at Kilburn Cocktail Bar Milano, where the evening is just getting started. In the same way, Bar Frida offers a unique charm perfect for experiencing the local bar scene in Milan. The Friends Pub Milano 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 Milan and get some rest to prepare for another magical day of your road trip in Italy.

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Day 3

Day 3

  • Milan
  • Genoa
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Drive 150 km, 2 hours 44 min

  • Pinacoteca di Brera
  • Castello Sforzesco
  • Sempione Park
  • Arch of Peace
  • Leonardo da Vinci Museum of Science and Technology
  • More

Dive into day 3 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Milan. At the end of the day, you’ll unwind at one of the finest accommodations in Genoa, where you'll spend 2 nights.

Start your day at Pinacoteca Di Brera. This photogenic art gallery is an interesting place to see in Milan. Then, wander over to Sforzesco Castle Art Library. If historic sites excite you, this castle will be right up your alley. Nearby, you’ll also find Parco Sempione. This romantic park is a favorite among visitors.

Milan offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Arch Of Peace is an interesting spot in the city that will captivate you with its unique charm. When you’re done at the monument, don’t forget to check out the visually striking Museo Della Scienza E Della Tecnologia "leonardo Da Vinci". Take a moment to appreciate the fascinating details of this locally renowned museum.

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

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

Have a memorable dining experience in Genoa by booking a table at San Giorgio, a 1-star Michelin restaurant presenting an exceptional modern and ligurian menu. For a different culinary experience in Genoa, The Cook shines as one of the top destinations, known for its delicious modern cuisine. This 1-star Michelin-awardee consistently earns high praises, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Il Marin is known as a top local spot in Genoa for its delicious seafood and contemporary cuisine. This 1-star Michelin awardee is a highly recommended choice for an unforgettable meal.

After enjoying a fulfilling meal, continue your evening at Scurreria Beer & Bagel, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, La Lepre offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Pisacane Iii provides an excellent environment for a relaxed and enjoyable evening.

Head back to your accommodation in Genoa and get some rest to prepare for another magical day of your road trip in Italy.

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Day 4

Day 4

  • Genoa
  • More

Drive 2 km, 35 min

  • piazza De Ferrari
  • Genoa Cathedral
  • Aquarium of Genoa
  • porto antico
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Day 4 offers an itinerary packed with the best things to see in Genoa. You’ll stay in Genoa for 1 night more, offering you enough time to explore at a relaxed pace.

Enjoy all that Piazza De Ferrari has to offer. This is a locally renowned public square you should not miss. Another must-see is Genoa Cathedral, an increasingly popular church in Genoa.

When you’re ready for the next sight, head to Aquarium Of Genoa. From there, take a leisurely stroll to Porto Antico, another of the city’s captivating attractions.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

Indulge in a memorable dining experience at one of Genoa's most popular restaurants, and connect with friendly locals for a true cultural experience.

Enjoy a delicious meal at Zeffirino, a highly-rated dining destination in Genoa. If you're eager to try something different, consider Trattoria Vegia Zena, another top spot with a tantalizing menu. You might also want to secure a reservation at Trattoria delle Grazie. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Genoa this evening.

As the sun sets, rest up and recharge for the next leg of your road trip in Italy.

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Day 5

Day 5

  • Genoa
  • Florence
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Drive 293 km, 3 hours 57 min

  • Pisa Cathedral
  • Leaning Tower of Pisa
  • Piazza del Duomo, Pisa
  • Parco Regionale Migliarino, San Rossore, Massaciuccoli
  • More

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 places, which are Pisa and Cascine Vecchie. At the end of the day, you will retreat to the hotel of your choice in Florence, where will spend 2 nights.

Whatever your travel style is, Pisa Cathedral is an essential stop in Genoa. This up-and-coming church provides an insightful glimpse into the city's identity. Next, discover Leaning Tower Of Pisa, an UNESCO world heritage-listed monument, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Del Duomo, Pisa, an iconic public square. When you’re done, don’t forget to make a stop at the increasingly popular Parco Regionale Migliarino, San Rossore, Massaciuccoli.

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

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

Experience a symphony of flavors at Enoteca Pinchiorri in Florence by securing a reservation in advance. Renowned for its 3-star Michelin distinction, Enoteca Pinchiorri delights its guests with its exceptional variety of meals showcasing delicious italian contemporary cuisine. For a palate-pleasing alternative, make sure to dine at Santa Elisabetta, acclaimed for its delectable creative and mediterranean 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 Gucci Osteria da Massimo Bottura, 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 international cuisine in the city.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Manifattura stands out as an excellent choice for a post-dinner cocktail. Alternatively, Se·sto On Arno Rooftop Bar offers an ideal atmosphere to enjoy the pleasures of the night. Il Vinile is also a great option that provides a perfect setting for a relaxing evening.

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

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Day 6

Day 6

  • Florence
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Drive 3 km, 49 min

  • Galleria dell'Accademia
  • Cathedral of Santa Maria del Fiore
  • Central Market
  • Basilica of Santa Maria Novella
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Day 6 of your road trip across Italy promises a magnificent time exploring what to see in Florence. You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

Galleria Dell'accademia is must-visit art gallery and a great option for a daytime tour of the area. Continue your journey to Cathedral Of Santa Maria Del Fiore, an astonishing church, located just a leisurely stroll away. Next, head to Central Market, a photogenic food market, also available for your discovery today.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Florence. Enjoy a relaxing evening as you savor delicious local cuisine.

Have a fantastic dining experience at Ditta Artigianale, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Trattoria Da Burde offers an enticing alternative with its varied menu. Additionally, Casa Toscana is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

After your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

Raise your glass to another unforgettable day in Italy!

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Day 7

Day 7

  • Florence
  • Bologna
  • More

Drive 110 km, 2 hours 8 min

  • piazza della Signoria
  • Ponte Vecchio
  • Uffizi Gallery
  • Basilica of Santa Croce in Florence
  • piazzale Michelangelo
  • More

On day 7 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Florence are on today's agenda. In the evening, you’ll end up in Bologna, where you will stay for 1 night.

Check out the spectacular public square, Piazza Della Signoria. Afterward, continue to Ponte Vecchio, a historical landmark every traveler should visit. As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Uffizi Gallery. This extraordinary art gallery is an essential stop. Following that, head to Basilica Of Santa Croce In Florence, another must-visit site that will enhance your experience. Don’t forget to stop by Piazzale Michelangelo, an extraordinary observation deck in the city.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Bologna. Bologna offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

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 Bologna, it's often a good idea to reserve a table in advance.

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.

Continue the enjoyment post-dinner at Bar Al Bricco D'oro, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bar Freud E Squisito offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Osteria Del Sole. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Savor another day of unforgettable experiences in Italy!

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Day 8

Day 8

  • Bologna
  • Milan
  • More

Drive 223 km, 2 hours 49 min

  • Bologna Cathedral
  • Fountain of Neptune, Bologna
  • Piazza Maggiore
  • Two Towers
  • Piazza Santo Stefano
  • More

Your itinerary for day 8 of your road trip in Italy includes 1 stop and features some of the highlights of Bologna. At the end of the day, enjoy the comforts of a top-rated hotel in Milan, where you'll spend 1 night.

Catch Bologna Cathedral before the crowds roll in. This culturally significant church is sure to ignite your curiosity. Next, dive into the photogenic features of Fountain Of Neptune, Bologna, 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 Maggiore, an impressive public square. For a change of scene, check out Two Towers, known for its historic features. We also recommend visiting Piazza Santo Stefano. This public square is a must for anyone looking to experience the city to the fullest.

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.

Milan is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Milan.

Have a fantastic dining experience at Bice Restaurant, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Alto Ristorante offers an enticing alternative with its varied menu. Additionally, Nero 9 is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Milan.

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

Relax and recharge in preparation for another adventurous day in Italy!

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Day 9

Day 9

  • Milan - Departure day
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  • Garibaldi Gate
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Day 9 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.

If you're up for some more sightseeing, we recommend visiting Porta Garibaldi, a heritage-rich monument before you head out.

Take some time to indulge in shopping at Milan’s popular marketplace, Via della Moscova. Look for keepsakes or souvenirs to remind you of your trip. Browse boutiques to find unique and stylish fashion pieces. Wrap up your shopping with a drink and some pastries at a cozy cafe.

Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Milan.

Have a fantastic dining experience at Ristorante la Brisa, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Pasticceria San Carlo offers an enticing alternative with its varied menu.

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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Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.
Secure your spot
Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.
Get instant confirmation
Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

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