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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Escape the ordinary with this exciting 9-day road trip through Italy. Explore diverse landscapes, discover lively cities, and prepare for an unforgettable journey!

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.

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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Day1

Day 1

  • Milan - Arrival day
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  • Piazza Gae Aulenti
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Your road trip adventure in Italy begins as soon as you reach Milan and pick up your car. You’ll stay here for 2 nights and explore what to see in Milan, sample the local cuisine, and choose from a curated selection of the best hotels and places to stay in the city.

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. Taking a stroll in the city center is a great alternative. 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 central location for easy access to key areas 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.

Enjoy a delicious meal at Hotel Morfeo Milano, a highly-rated dining destination in Milan. If you're eager to try something different, consider Contraste, another top spot with a tantalizing menu. You might also want to secure a reservation at UNAHOTELS Galles Milano. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Milan this evening.

Continue your evening by exploring the vibrant nightlife scene at Nottingham Forest, a prime destination for a thrilling night out. Also, don’t forget to check out Armani/bamboo Bar, a bar that offers unique local touches. Likewise, Mag Cafe provides an excellent alternative for a fun evening.

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

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Day2

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 across Italy promises a magnificent time exploring what to see in Milan. You have 1 night left in Milan. Take the opportunity to experience more of the best attractions and activities in the city.

Catch Royal Palace Of Milan before the crowds roll in. This eye-catching palace is sure to ignite your curiosity. Next, dive into the history-steeped features of Cathedral Square, a must-visit public square 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 Duomo Di Milano Museum, a world-famous church. For a change of scene, check out Galleria Vittorio Emanuele Ii, known for its romantic features. We also recommend visiting La Scala. This opera house is a must for anyone looking to experience the city to the fullest.

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.

Bring home unique finds from Milan's bustling shopping hub, Galleria Vittorio Emanuele II. Enjoy a leisurely exploration of unique high-end stores where locals shop. Don’t forget to browse souvenirs and local specialties that make perfect gifts for your loved ones. Beyond shopping, Galleria Vittorio Emanuele II offers plenty of options, including primary services, unique landmarks, and community events.

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

Treat yourself to an extraordinary dining experience at Enrico Bartolini al Mudec, a 3-star Michelin restaurant offering an incredible creative menu. Alternatively, if your taste buds call for something different, Seta by Antonio Guida is one of the best restaurants for international and contemporary cuisine in Milan. This 2-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Il Luogo Aimo e Nadia. As a top-rated establishment with 1 Michelin star, it is an ideal choice for italian contemporary and modern cuisine in the city.

Round off your dining experience by visiting Kilburn Cocktail Bar Milano, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Frida, a bar catering to every mood and preference. The Friends Pub Milano likewise offers a unique atmosphere, perfect for a memorable night out.

Savor another day of unforgettable experiences in Italy!

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Day3

Day 3

  • Milan
  • Genoa
  • More

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

Experience an unparalleled adventure on day 3 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Milan. At the end of the day, you will retreat to the hotel of your choice in Genoa, where will spend 2 nights.

Experience Pinacoteca Di Brera, a well-known art gallery in the city. Then, head to Sforzesco Castle Art Library and soak in the ambiance of this historic castle.

There are many interesting places to see in Milan, and when you are ready for more, go to Parco Sempione. This is one of the city’s most top-rated romantic spots of interest. After exploring the park, visit the notable Arch Of Peace. Not far away, you'll also find Museo Della Scienza E Della Tecnologia "leonardo Da Vinci". This museum is a heritage-rich highlight in Milan.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Genoa. Genoa 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 Genoa, it's often a good idea to reserve a table in advance.

Experience a taste of local culinary excellence while in Genoa by securing a table at San Giorgio. An esteemed 1-star Michelin restaurant, it features an exceptional modern and ligurian menu. For an alternative taste experience, visit The Cook, famous for its scrumptious modern dishes. This 1-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Il Marin, a local favorite celebrated for its exquisite seafood and contemporary cuisine in Genoa. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for seafood and contemporary cuisine lovers seeking top-notch culinary experiences.

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.

Raise your glass to another unforgettable day in Italy!

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Day4

Day 4

  • Genoa
  • More

Drive 2 km, 35 min

  • piazza De Ferrari
  • Genoa Cathedral
  • Aquarium of Genoa
  • porto antico
  • More

Day 4 of your road trip will take you to the best attractions Genoa has to offer. Cherish the 1 night you have left in the city and use the provided itinerary to discover what to see in Genoa.

Enjoy all that Piazza De Ferrari has to offer. This is a well-known public square you should not miss. Another must-see is Genoa Cathedral, a frequently visited 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 popular 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.

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

Savor the flavors at Zeffirino, a top pick for dinner tonight. Alternatively, Trattoria Vegia Zena beckons with its unique menu offerings. Also, consider Trattoria delle Grazie. With its consistent customer satisfaction, it’s an excellent option for dining in Genoa tonight.

Say good night to Genoa and look forward to another great day of your road trip in Italy!

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Day5

Day 5

  • Genoa
  • Pisa
  • Florence
  • More

Drive 293 km, 3 hours 57 min

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

On day 5 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Pisa and Cascine Vecchie. When you’re not sightseeing, take time to relax at your chosen hotel in Florence, where you’ll be staying for 2 nights.

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

When you're ready for some sights, head to Pisa Cathedral, a beloved church in Pisa. Explore its UNESCO world heritage-designated features at your own pace before you continue your journey to your next attraction, Leaning Tower Of Pisa. This iconic monument is a top recommendation in the area.

When you’re ready to explore more, Piazza Del Duomo, Pisa is an excellent choice. Spend some time discovering what some claim to be the most UNESCO world heritage-listed public square in the region.

Fasten your seatbelt and make your way to your next stop — Cascine Vecchie, home to many well-known sights in the region. Keep in mind that your travel time from Pisa to Cascine Vecchie may take around 11 min without traffic disruptions. Upon arrival in Cascine Vecchie, we highly recommend checking out some of the top attractions.

Our first attraction recommendation in Cascine Vecchie is Parco Regionale Migliarino, San Rossore, Massaciuccoli, an intriguing nature reserve that draws attention for its mesmerizing features.

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.

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

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.

Explore the vibrant nightlife at Manifattura after your meal, a hub for lively evenings and memorable moments. Or, head to Se·sto On Arno Rooftop Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Il Vinile is perfect for those looking to extend their night with a touch of local flavor.

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

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Day6

Day 6

  • Florence
  • More

Drive 3 km, 49 min

  • Galleria dell'Accademia
  • Cathedral of Santa Maria del Fiore
  • Central Market
  • Basilica of Santa Maria Novella
  • More

Day 6 offers an itinerary packed with the best things to see in Milan. You’ll stay in Florence for 1 night more, offering you enough time to explore at a relaxed pace.

Florence is brimming with adventures.

Galleria Dell'accademia brings Florence's character to life. This photogenic art gallery is a highlight of any visit in the city. Then, enjoy Cathedral Of Santa Maria Del Fiore, another visually striking attraction that never fails to captivate visitors. Next, head over to Central Market, one of the city’s most notable attractions, known for its eye-catching features.

If you’re looking for more, spend time soaking in the atmosphere of Basilica Di Santa Maria Novella, Firenze (fi). This enchanting church is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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.

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.

Don’t miss out on dining at Ditta Artigianale, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Trattoria Da Burde, another top spot with a mouthwatering menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

Following your dinner, dive into the local bar culture at Bar 50 Rosso. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bitter Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Archea Brewery provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

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Day7

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

Your itinerary for day 7 of your road trip in Italy includes 1 stop and features some of the highlights of Florence. At the end of the day, enjoy the comforts of a top-rated hotel in Bologna, where you'll spend 1 night.

Piazza Della Signoria is must-visit public square and a great option for a daytime tour of the area. Continue your journey to Ponte Vecchio, an iconic historical landmark, located just a leisurely stroll away. Next, head to Uffizi Gallery, a romantic art gallery, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Florence. When you're ready, let your sightseeing route take you to the captivating Basilica Of Santa Croce In Florence. If you’re looking for more, Piazzale Michelangelo is also a spectacular attraction that is worthwhile a visit.

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

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

Get ready for an unforgettable culinary journey in Bologna by reserving a table at Ahimè. Renowned as a Bib Gourmand restaurant, it offers an exceptional country cooking menu. For a different taste experience, head to I Portici, recognized for its delicious creative and contemporary dishes. This 1-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Trattoria di Via Serra, a local favorite known for its delightful emilian cuisine in Bologna. Nestled in the heart of the city, this Bib Gourmand awardee is an ideal choice for emilian foodies seeking culinary excellence.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar Al Bricco D'oro stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar Freud E Squisito offers an ideal atmosphere to enjoy the pleasures of the night. Osteria Del Sole is also a great option that provides a perfect setting for a relaxing evening.

Say good night to Bologna and look forward to another great day of your road trip in Italy!

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Day8

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

On day 8 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Bologna are on today's agenda. In the evening, you’ll end up in Milan, where you will stay for 1 night.

Awaiting your discovery is the curiosity-inducing Bologna Cathedral, a majestic church in Bologna. Next, go to Fountain Of Neptune, Bologna.

After visiting Bologna Cathedral and Fountain Of Neptune, Bologna, have a stroll along Bologna's streets and take in the local charm. Continue your sightseeing by heading to Piazza Maggiore. This majestic public square offers a unique experience. Two Towers is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Piazza Santo Stefano, one of the most visually striking places to visit in Bologna.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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.

Enjoy a lovely meal at Bice Restaurant, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Alto Ristorante is another top choice with a popular menu. You could also check for a table at Nero 9. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Milan tonight.

Let the evening flow smoothly from dinner to drinks at Bhangrabar, a top-rated bar in the area. For other recommendations, Rufus Cocktail Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Ostello Bello Grande offers a memorable night with diverse drink options and excellent service.

Relax and look forward to more memorable moments to come!

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Day9

Day 9

  • Milan - Departure day
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  • Garibaldi Gate
  • More

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 photogenic monument before you head out.

For a shopping spree in Milan, we recommend the lively Galleria Vittorio Emanuele II. Here, you'll find a range of shops you can browse for some souvenir shopping. You can also explore high-end shops for luxury items.

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

Dine in style at Ristorante la Brisa, a top recommendation for dinner tonight. Or, for a change of pace, Pasticceria San Carlo boasts a menu that's sure to impress.

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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Your trip is protected, personalized, and priced right. No surprises, no stress.

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