9-Day Italy Road Trip from Pisa to Siena, Rome, Florence, Venice, and Milan and surrounding area

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Experience the freedom of the open road in Italy as you embark on an unforgettable 9-day road trip! This experience caters to every traveler, featuring destinations like Pisa, Siena, Rome, Florence, Venice, Milan, and Genoa.

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 Pisa, 1 night in Siena, 2 nights in Rome, 1 night in Florence, 1 night in Venice, and 1 night in Milan. 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. Trevi Fountain and Colosseum are just a couple of the bucket-list attractions that await your discovery.

As you hit the open road and drive through Pisa, Siena, Rome, Florence, Venice, Milan, and Genoa, 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

Day 1 – Pisa - arrival day

  • Pisa - Arrival day
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  • Logge dei Banchi
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Your road trip adventure in Italy begins as soon as you reach Pisa and pick up your car. You’ll stay in Pisa for 1 night and explore the best things to see and do, sample the local cuisine, and choose from a curated selection of the best hotels and places to stay in the city.

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 Logge Dei Banchi or 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 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.

Have a fantastic dining experience at Ristorante Capodimonte Pisa, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Baribaldi Pisa offers an enticing alternative with its varied menu. Additionally, Restaurant -Pizzeria Il Mio Capriccio is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Pisa.

Let the evening flow smoothly from dinner to drinks at Jeffer Cocktails & Friends, a top-rated bar in the area. For other recommendations, Le Parisien Wine Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Las Volta Cocktailbar offers a memorable night with diverse drink options and excellent service.

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

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Day 2

Day 2 – Pisa, and Siena

  • Siena
  • Pisa
  • More

Drive 131 km, 2 hours 35 min

  • Leaning Tower of Pisa
  • Chiesa di Santa Maria della Spina
  • Cattedrale di Pisa
  • Piazza del Duomo
  • Camposanto
  • More

On day 2 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 Pisa. In the evening, you’ll end up in Siena, where you will stay for 1 night.

Make Leaning Tower Of Pisa your first stop of the day. Previous visitors have rated this bell tower an average of 4.7 out of 5 stars in 116,882 reviews. More than 3,200,000 people visit this place of interest every year.

Next up, make a stop at Santa Maria Della Spina. With an average rating of 4.5 out of 5 stars by 3,092 visitors, it's easy to understand why so many people visit this church building every year.

Pisa Cathedral is another attraction you can visit on this day of your vacation. This cathedral has an average rating of 4.8 out of 5 stars by 8,361 visitors.

When you’re finished at Pisa Cathedral, the perfect next stop is Piazza Del Duomo, Pisa. This square is rated an average of 4.7 out of 5 stars in 104,550 reviews.

If you’re keen to explore even more, then consider a visit to Campo Santo. This cemetery is a top place to visit, with a rating of 4.6 out of 5 stars from 586 reviews.

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

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

Enjoy a lovely meal at Antica Trattoria Papei, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Osteria Quattro Venti is another top choice with a popular menu. You could also check for a table at Osteria da Divo. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

Unwind after your meal by stepping into Meet Life Cafè. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Maudit Pub offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Bar Impero Siena, another top-rated bar in the area.

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

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Day 3

Day 3 – Siena, Vatican City, and Rome

  • Rome
  • More

Drive 241 km, 3 hours 23 min

  • Sistine Chapel
  • St Peter's Basilica
  • Saint Peter's Square
  • Vatican Museums
  • More

On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Vatican City. When you’re not sightseeing, take time to relax at your selected hotel in Rome, where you’ll be staying for 2 nights.

When you’re ready to jump back into the car and say goodbye to Siena, you’ll hit the road in the direction of Vatican City, Vatican City. Witness the landscapes transform as you cross the border to Vatican City. This drive usually takes around 2 hours 40 min. When you arrive, enjoy some sightseeing.

Make Sistine Chapel one of your first sightseeing stops in Vatican City. Rated an average of 4.7 out of 5 stars by 52,083 travelers, a visit to this local attraction makes for a great introduction to the area.

St. Peter's Basilica is a worthwhile attraction you can visit next. This major basilica is a valued place of interest in the area, with an average rating of 4.8 out of 5 stars from 131,043 reviews. Up to 11,000,000 travelers visit this site every year to make their time in Vatican City special.

Today is also the perfect opportunity to drop by Saint Peter's Square. This square has been rated an average of 4.8 out of 5 stars by 38,954 visitors.

If you’re keen to explore more, head to Vatican Museums and find out why 1,612,530 people visit this spot every year. A trip to this popular art museum is also your opportunity to see if it lives up to the reputable 4.6 out of 5-star rating as given by 133,310 previous visitors.

When you’re done exploring for the day, you’ll drive to Rome, where you'll have a hotel waiting for you. Check in and spend some time relaxing before you head out to explore the city.

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

Start your culinary exploration in Rome by securing a reservation at La Pergola. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of mediterranean, and contemporary cuisine. For another dining delight, visit Il Pagliaccio, celebrated for its delectable creative, and innovative 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 Enoteca La Torre, a top local spot known for its tantalizing mediterranean, and creative menu. With a 2-star Michelin recognition, it guarantees an exceptional dining adventure.

Keep the excitement of the evening going by visiting a bar or two. La Botticella Of Poggi Giovanni is an excellent place to start. You could also check out Sant' Eustachio Caffè, offering a different kind of charm. A last recommendation for the day is Caffè Portofino. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

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Day 4

Day 4 – Rome

  • Rome
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Drive 9 km, 1 hour 11 min

  • Colosseum
  • Roman Forum
  • Pantheon
  • Piazza Navona
  • Castel Sant'Angelo
  • More

Day 4 of your road trip across Italy promises a magnificent time exploring Rome. You have 1 night left in Rome. Take the opportunity to experience more of the best attractions and activities in the city.

A top pick for your self-guided sightseeing tour today is Colosseum. Over 7,400,000 travelers visit this attraction every year. Previous visitors have rated this roman amphitheatre an average of 4.7 out of 5 stars in 328,821 reviews.

Roman Forum is a local recommendation that you also can pay a visit today. This square is rated an average of 4.7 out of 5 stars in 114,450 reviews.

Another attraction you won't want to miss is Pantheon. This roman temple is rated an average of 4.8 out of 5 stars in 189,682 reviews. Every year, around 30,000,000 travelers visit this site to discover its unique features.

Piazza Navona is another outstanding experience in Rome. Around 158,771 travelers have rated this square an average of 4.7 out of 5 stars.

If you long for more, Castel Sant'angelo is not far away. This museum is a lovely addition to your itinerary. Previous visitors have rated it an average of 4.7 out of 5 stars in 72,431 reviews.

You can learn more about Rome today by going on a tour. Rome offers many top-rated tours and unique experiences that will inspire you. You can browse and select your favorites below.

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

Treat yourself to a wonderful meal at DEROMA - Farine Romane, a top-rated dining spot in Rome. If you're in the mood for something new, try La Taverna Italiana, another premier location with a delectable menu. You might also want to book a table at Centro. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.

After enjoying a fulfilling meal, continue your evening at The Apartment Bar Roma, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Hotel Hassler Roma offers a welcoming atmosphere for easing into the nightlife.

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

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Day 5

Day 5 – Rome, and Florence

  • Florence
  • Rome
  • More

Drive 280 km, 3 hours 54 min

  • Altar of the Fatherland
  • Trevi Fountain
  • Piazza di Spagna
  • Piazza del Popolo
  • Villa Borghese
  • More

Dive into day 5 of your remarkable road trip in Italy. Today you will explore Rome, 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 Florence. You’ll stay here for 1 night.

Drop by the renowned Altare Della Patria. This popular architectural structure has been rated an average of 4.8 out of 5 stars by 49,843 visitors. Based on recent data, this attraction is visited by more than 1,683,070 travelers every year.

Another unforgettable place to experience is Trevi Fountain. Rated 4.8 out of 5 stars by 343,494 visitors, this sculpture deserves a spot on today's sightseeing itinerary.

We also recommend a visit to Piazza Di Spagna. This square has been rated an average of 4.7 out of 5 stars in 113,658 reviews.

Another favorite attraction in the area is Piazza Del Popolo. This square and popular place of interest enjoys a rating of 4.6 out of 5 stars from 89,807 local and international travelers.

If you’re keen to explore even more, then consider a visit to Villa Borghese. With an average rating of 4.6 out of 5 stars from 69,749 travelers, this urban zone of rome is an attraction many avid travelers highly recommend visiting while in Rome.

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 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 and reflect on the day's adventures.

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 Il Palagio, 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 cuisine in the city.

After savoring a delicious meal, step into the vibrant nightlife at Manifattura, where the evening is just getting started. In the same way, Se·sto On Arno Rooftop Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Archea Brewery is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

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Day 6

Day 6 – Florence, and Venice

  • Venice
  • Florence
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Drive 261 km, 3 hours 35 min

  • Piazza della Signoria
  • Cathedral of Santa Maria del Fiore
  • Piazza della Repubblica
  • Ponte Vecchio
  • Piazzale Michelangelo
  • More

Embark on another extraordinary experience on day 6 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Venice, which will be your home away from home for 1 night.

Start your sightseeing with a visit to Piazza Della Signoria. This square is a popular stop on travelers’ itineraries in Florence, with an average rating of 4.8 out of 5 stars by 66,956 visitors.

Cathedral Of Santa Maria Del Fiore is another popular place of interest you can visit today. The average rating of 4.8 out of 5 stars from 76,359 reviews gives you an idea of other visitors’ experience at this attraction.

If it’s still bright and early, make your way to Piazza Della Repubblica. Visitors have rated this square an average of 4.6 out of 5 stars in 22,356 reviews.

Ponte Vecchio is another unique site you can experience today. This attraction is a deck arch bridge rated an average of 4.7 out of 5 stars in 118,099 reviews.

Make your way to the fantastic Piazzale Michelangelo, perhaps the most famous square in Florence. This attraction is rated 4.8 out of 5 stars by 77,744 travelers.

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

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

Experience a harmony of flavors at Local in Venice by securing a reservation in advance. Known for its 1-star Michelin status, Local offers a delightful variety of dishes highlighting its delicious contemporary menu. If you're seeking an alternative culinary experience, be sure to explore Wistèria, a highly recommended restaurant known for its enticing contemporary, and venetian cuisine. This popular 1-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Quadri, a highly acclaimed restaurant celebrated for its exceptional modern menu.

Continue your evening by exploring the vibrant nightlife scene at Al Parlamento, a prime destination for a thrilling night out. Also, don’t forget to check out Adagio, a bar that offers unique local touches. Likewise, Il Mercante provides an excellent alternative for a fun evening.

Raise your glass to another unforgettable day in Italy!

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Day 7

Day 7 – Venice, and Milan

  • Milan
  • Venice
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Drive 266 km, 3 hours 13 min

  • Rialto Bridge
  • St. Mark's Square
  • Saint Mark's Basilica
  • Doge's Palace
  • 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 - Venice. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Milan. You will spend 1 night here for some well-deserved relaxation.

Your sightseeing of the day begins at Rialto Bridge, a remarkable stone bridge where it’s easy to get lost in exploration. This top attraction is rated an average of 4.7 out of 5 stars in 141,666 reviews.

Next, satisfy your wanderlust at Piazza San Marco. This square has an average rating of 4.7 out of 5 stars from 152,982 travelers.

St Mark's Basilica is another must-visit attraction. This renowned cathedral offers a memorable experience, well worth a stop on your self-guided sightseeing tour. Rated 4.7 out of 5 stars by 18,439 travelers, it's one of the more popular places to see in the area.

Beyond the above-mentioned sites, you also have the opportunity to visit Doge's Palace. This well-loved palace boasts a 4.7 out of 5-star rating from 24,775 reviews. In a single year, approximately 318,104 visitors add this sightseeing spot to their travel itineraries.

When you’re done exploring for the day, you’ll drive to Milan, where you'll have a hotel waiting for you. Check in and spend some time relaxing before you head out to explore the city.

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 taste of local culinary excellence while in Milan by securing a table at Enrico Bartolini al Mudec. An esteemed 3-star Michelin restaurant, it features an exceptional creative menu. For an alternative taste experience, visit Seta by Antonio Guida, famous for its scrumptious international, and contemporary dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Il Luogo Aimo e Nadia, a local favorite celebrated for its exquisite italian contemporary, and modern cuisine in Milan. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary, and modern cuisine lovers seeking top-notch culinary experiences.

If you’re not ready to end the night just yet, Nottingham Forest offers a perfect venue to relax and savor a drink. Similarly, Armani/bamboo Bar is well-suited for those looking to unwind in a social setting. Mag Cafe is another excellent spot to enjoy a nightcap after a delightful meal.

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

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Day 8

Day 8 – Milan, Genoa, and Pisa

  • Pisa
  • Milan
  • Genoa
  • More

Drive 319 km, 4 hours 14 min

  • Cathedral Square
  • Galleria Vittorio Emanuele II
  • Duomo di Milano
  • Galata Museo del Mare
  • More

On day 8 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 Milan, and Genoa. In the evening, you’ll end up in Pisa, where you will stay for 1 night.

Be one of the day’s first visitors at Cathedral Square. This point of interest is rated an average of 4.8 out of 5 stars by 7,539 visitors.

When you’re finished at Cathedral Square, head to Galleria Vittorio Emanuele Ii. This one-of-a-kind commercial gallery is rated an average of 4.7 out of 5 stars in 91,394 reviews.

Beyond the above-mentioned attractions, you also have the opportunity to visit Duomo Di Milano Museum. This art museum is rated an average of 4.8 out of 5 stars by 138,554 visitors. Visiting Duomo Di Milano Museum means you'll be one of 341,609 people who do so every year.

When you’ve had your share of Milan, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Genoa. Your travel time is around 1 hour 56 min.

Start your sightseeing with a visit to Galata Museo Del Mare (complex). This building complex is rated an average of 4.5 out of 5 stars from 8,322 visitors.

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

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.

Savor the flavors at Ristorante alle Bandierine, a top pick for dinner tonight. Alternatively, Barrique Cocktail And Bistrot beckons with its unique menu offerings. Also, consider Filter Coffee Lab. With its consistent customer satisfaction, it’s an excellent option for dining in Pisa tonight.

Extend your evening after a delightful meal by visiting Bar Mocambo, which offers the perfect atmosphere for a night out. Moreover, Tree is another popular option for a drink or two. Likewise, Chupiteria also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

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Day 9

Day 9 – Pisa - departure day

  • Pisa - Departure day
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  • Piazza dei Cavalieri
  • More

Day 9 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.

Explore local shops for souvenirs to remember your trip or find unique gifts for loved ones.

A top pick for your self-guided sightseeing tour today is Knights' Square. Previous visitors have rated this square an average of 4.5 out of 5 stars in 9,051 reviews.

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

Have a fantastic dining experience at Sud, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Kiste' - La Pizza Artigianale. It's the second restaurant coming from the tower. Offers an enticing alternative with its varied 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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