10-Day Italy Self-Drive Road Trip With Itinerary from Pisa traveling north to Milan and Florence

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Escape the ordinary with this exciting 10-day road trip through Italy. Explore the diverse landscapes, lively cities, and beyond. Pack your bags, hit the road, and prepare for an unforgettable journey!

This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. You will spend 3 nights in Pisa, 4 nights in Milan, and 2 nights 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 Pisa, 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 Pisa, Noceto, Priorato, Milan, Bologna, and Florence, 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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Driver’s age is 30 - 65
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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Knights' Square
Cittadella NuovaPiazza del Duomo, PisaPisa CathedralLeaning Tower of PisaParco Regionale Migliarino, San Rossore, Massaciuccoli
Castello della MusicaLabirinto della MasoneRocca Sanvitale
La ScalaGalleria Vittorio Emanuele IIDuomo di MilanoRoyal Palace of MilanBrera
Leonardo da Vinci Museum of Science and TechnologySanta Maria delle Grazie ChurchCastello SforzescoSempione ParkArch of Peace
Pinacoteca di BreraPiazza Gae AulentiCorso Vittorio Emanuele IIVia Monte NapoleoneNavigli

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Day 1

Day 1

  • Pisa - Arrival day
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  • Knights' Square
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Say hello to Pisa! 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 Pisa for 2 nights before you continue your adventure!

Pisa 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 Knights' Square, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

Make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Pisa. Make yourself at home and enjoy some downtime before heading 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 Pisa, it's often a good idea to reserve a table in advance.

Enjoy a lovely dining experience at Anima di Grano Pizzeria Napoletana Pisa Italy, a popular restaurant in Pisa. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Pisa at il Mercante, 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 La Ghiotteria. It’s yet another ideal choice to enhance your time in Pisa tonight.

Continue your lively evening at Jeffer Cocktails & Friends, a perfect place for winding down or revving up the night, depending on which mood you’re in. Le Parisien Wine Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Las Volta Cocktailbar ensures a night out tailored to your taste.

Raise a toast to the start of your 10-day road trip in Italy!

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Day 2

Day 2

  • Pisa
  • More

Drive 17 km, 47 min

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

Greet day 2 of your road trip in Italy with a smile and start your day with a hearty breakfast. You will return to Pisa for your remaining 1 night in the city later today, but first, it’s time for some exploring! On the agenda for this day, you’ll find only the best things to see and do in Pisa and Cascine Vecchie.

Today’s agenda in Pisa includes a park, a public square, a church, a monument, a nature reserve and much more! Cittadella Nuova is must-visit park and a great starting point for the day. Next, continue your journey to Piazza Del Duomo, Pisa, an iconic public square, located just a leisurely stroll away. Next, head to Pisa Cathedral, an UNESCO world heritage-listed church, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Pisa. When you're ready, let your sightseeing route take you to the timeless Leaning Tower Of Pisa. If you’re looking for more, Parco Regionale Migliarino, San Rossore, Massaciuccoli is also a worthwhile attraction that is worthwhile a visit.

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

As you explore more of Pisa, 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 a delicious dinner at Ristorante Capodimonte Pisa, an excellent option for tonight's dining. Looking for something different? La Locanda Dei Pisani Doc Pisa offers a tantalizing alternative with its diverse menu. And don’t miss Baribaldi Pisa. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Pisa.

Round off your dining experience by visiting Bar Mocambo, a prime location for a drink. Alternatively, explore the distinctive characteristics of Tree, a bar catering to every mood and preference. Chupiteria likewise offers a unique atmosphere, perfect for a memorable night out.

Raise your glass to another unforgettable day in Italy!

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Day 3

Day 3

  • Pisa
  • Milan
  • More

Drive 295 km, 3 hours 40 min

  • Castello della Musica
  • Labirinto della Masone
  • Rocca Sanvitale
  • More

Dive into day 3 of your remarkable road trip in Italy. Today you will explore Noceto, Priorato II, and Priorato, 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 Milan. You’ll stay here for 4 nights.

Today’s agenda in Pisa includes a castle and a maze. Castello Della Musica is must-visit castle and a great starting point for the day. Next, continue your journey to Labirinto Della Masone, an underrated maze, located just a leisurely stroll away. Next, head to Rocca Sanvitale, a romantic castle, also available for your discovery today.

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.

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

Prepare for an extraordinary culinary adventure in Milan by booking a table at Enrico Bartolini al Mudec, a 3-star Michelin restaurant that boasts an exceptional creative menu. For a different flavor experience, head to Seta by Antonio Guida, renowned for its delectable international and contemporary dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Il Luogo Aimo e Nadia, a local gem known for its delightful italian contemporary and modern cuisine in Milan. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

Round off your dining experience by visiting Nottingham Forest, a prime location for a drink. Alternatively, explore the distinctive characteristics of Armani/bamboo Bar, a bar catering to every mood and preference. Mag Cafe likewise offers a unique atmosphere, perfect for a memorable night out.

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

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Day 4

Day 4

  • Milan
  • More

Drive 1 km, 17 min

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

Day 4 offers a multitude of experiences. You will stay in Milan for 3 nights more, offering you enough time to explore at a relaxed pace.

Don’t miss Brera in Milan today, a must-see neighborhood that offers a glimpse into the city’s vibrant character. Take your time to explore its best features, and enjoy the convenience of nearby top-rated landmarks.

Discover a day packed with fun adventures, romantic experiences, and photo-friendly spots in Milan. Begin your sightseeing with La Scala. This locally renowned opera house 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 Duomo Di Milano Museum. This wondrous church is a traveler-favorite. Not far away, you’ll find Royal Palace Of Milan, another key site on your sightseeing itinerary.

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 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.

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

Following your dinner, dive into the local bar culture at Kilburn Cocktail Bar Milano. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar Frida, the perfect place for those looking to experience the best of the nightlife. Similarly, The Friends Pub Milano provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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Day 5

Day 5

  • Milan
  • More

Drive 9 km, 1 hour

  • Leonardo da Vinci Museum of Science and Technology
  • Santa Maria delle Grazie Church
  • Castello Sforzesco
  • Sempione Park
  • Arch of Peace
  • More

Day 5 of your road trip across Italy promises a magnificent time exploring Milan. You have 2 nights left in Milan. 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 Milan allows for both. Start by heading to Museo Della Scienza E Della Tecnologia "leonardo Da Vinci". This notable museum provides an insightful glimpse into the city's identity. Next, discover Santa Maria Delle Grazie Church, an UNESCO world heritage-designated church, promising a delightful encounter.

Continue your sightseeing with a visit to Sforzesco Castle Art Library, a spectacular castle. When you’re done, don’t forget to make a stop at the top-rated Parco Sempione. Round off your day at Arch Of Peace, another gem in Milan with awe-inspiring features to discover.

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 Milan's most popular restaurants, and connect with friendly locals for an authentic adventure.

Savor the flavors at Bice Restaurant, a top pick for dinner tonight. Alternatively, Alto Ristorante beckons with its unique menu offerings. Also, consider Nero 9. With its consistent customer satisfaction, it’s an excellent option for dining 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.

Savor another day of unforgettable experiences in Italy!

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Day 6

Day 6

  • Milan
  • More

Drive 6 km, 49 min

  • Pinacoteca di Brera
  • Piazza Gae Aulenti
  • Corso Vittorio Emanuele II
  • Via Monte Napoleone
  • Navigli
  • More

Day 6 of your road trip will take you to the best attractions Milan has to offer. Cherish the 1 night you have left in Milan by discovering the best things there are to see and do in the city.

Set aside time today to explore Corso Vittorio Emanuele II, a standout street that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day. You might also want to visit Via Monte Napoleone, a street offering another perspective on the city.

Enjoy the perfect balance of relaxation and exploration in Milan today. One of the most locally renowned attractions included on the itinerary is Pinacoteca Di Brera. This historic art gallery will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Gae Aulenti and learn what makes this picture-perfect public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings.

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

Don’t miss out on dining at Ristorante la Brisa, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Pasticceria San Carlo, another top spot with a mouthwatering menu. You might also want to secure a reservation at UNAHOTELS Cusani Milano. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

Continue your lively evening at Qc Termemilano, a perfect place for winding down or revving up the night, depending on which mood you’re in. Yguana Cafè is another excellent bar that offers a great selection of drinks to suit any mood.

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.

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Day 7

Day 7

  • Milan
  • Florence
  • More

Drive 335 km, 4 hours 14 min

  • Piazza Maggiore
  • Fountain of Neptune, Bologna
  • Palazzo Re Enzo
  • More

Experience an unparalleled adventure on day 7 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Bologna. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 2 nights here for some well-deserved relaxation.

Enjoy the perfect balance of relaxation and exploration in Milan today. One of the most impressive attractions included on the itinerary is Piazza Maggiore. This respected public square will help you start your sightseeing on top. Then, take a leisurely stroll to Fountain Of Neptune, Bologna and learn what makes this heritage-rich monument unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the beloved Palazzo Re Enzo.

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.

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.

Experience a taste of local culinary excellence while in Florence by securing a table at Enoteca Pinchiorri. An esteemed 3-star Michelin restaurant, it features an exceptional italian contemporary menu. For an alternative taste experience, visit Santa Elisabetta, famous for its scrumptious creative and mediterranean dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Gucci Osteria da Massimo Bottura, a local favorite celebrated for its exquisite italian contemporary and international cuisine in Florence. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary and international cuisine lovers seeking top-notch culinary experiences.

Continue the enjoyment post-dinner at Manifattura, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Se·sto On Arno Rooftop Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Il Vinile. 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

  • Florence
  • More

Drive 17 km, 1 hour 6 min

  • Central Market
  • Cathedral of Santa Maria del Fiore
  • Galleria dell'Accademia
  • piazzale Michelangelo
  • The Boboli Gardens
  • More

On day 8 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 1 night and discover all the best things to see and do in the area.

Today’s route brings family-friendly attractions, picturesque spots, and budget-friendly activities. The first attraction of today is Central Market. This locally renowned food market is a visually striking place to see in Florence. Continue your discovery at Cathedral Of Santa Maria Del Fiore, an UNESCO world heritage-listed church with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Galleria Dell'accademia. This notable art gallery offers a noteworthy encounter with Florence. Next, make your way to Piazzale Michelangelo to add another highlight to your day. After that, visit The Boboli Gardens, an interesting botanical garden that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Florence.

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 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.

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

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Day 9

Day 9

  • Florence
  • Pisa
  • More

Drive 82 km, 1 hour 23 min

  • piazza della Signoria
  • Uffizi Gallery
  • Ponte Vecchio
  • Palazzo Pitti
  • More

On day 9 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 Florence. In the evening, you’ll end up in Pisa, where you will stay for 1 night.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Piazza Della Signoria. This top-rated public square provides an insightful glimpse into the city's identity. Next, discover Uffizi Gallery, a romantic art gallery, promising a delightful encounter.

Continue your sightseeing with a visit to Ponte Vecchio, a wondrous historical landmark. When you’re done, don’t forget to make a stop at the captivating Pitti Palace.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Pisa. Pisa 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 in Pisa. 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.

Enjoy a lovely dining experience at Restaurant -Pizzeria Il Mio Capriccio, a popular restaurant in Pisa. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Pisa at Ristorante alle Bandierine, 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 Barrique Cocktail And Bistrot. It’s yet another ideal choice to enhance your time in Pisa tonight.

Following your dinner, dive into the local bar culture at Bar Livorno. Enjoy this evening's relaxed ambiance with delightful drinks.

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

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Day 10

Day 10

  • Pisa - Departure day
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  • Logge dei Banchi
  • More

Day 10 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Pisa 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 Logge Dei Banchi, a historic public square before you head out.

Make the most of your final day in Italy by visiting Pisa’s iconic markets and shopping establishments. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy.

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

Enjoy a lovely meal at Anita Osteria, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La corte di San Leonardo is another top choice with a popular menu.

You’ll then say farewell to Pisa. 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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