Travel packages in Italy

Road trips in Italy

14-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling south to Venice, Padua, Siena, Rome, Florence, and Pisa

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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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Experience the freedom of the open road on an unforgettable 14-day road trip in Italy! Embark on a self-drive tour that caters to every traveler, featuring destinations like Milan, Sirmione, Verona, Venice, Padua, Bologna, Siena, Rome, Florence, Pisa, and Genoa.

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. You will spend 4 nights in Milan, 1 night in Venice, 1 night in Padua, 1 night in Siena, 3 nights in Rome, 2 nights in Florence, and 1 night in Pisa. 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. 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 Milan, Sirmione, Verona, Venice, Padua, Bologna, Siena, Rome, Florence, Pisa, 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, 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

Milan - Arrival day
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Arch of Peace
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Say hello to Milan! Your exciting road trip through Italy is just about to start. Navigating the top places to see in the region is a breeze with a car. The rental vehicle of your choice will be ready for pickup upon your arrival in the city. You will stay in Milan for 3 nights before you continue your adventure!

Milan is a beautiful city with plenty to discover. 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.

Raise a toast to the start of your 14-day road trip in Italy!

Day 2

Milan
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Drive 4 km, 41 min

Sempione Park
Castello Sforzesco
La Scala
Galleria Vittorio Emanuele II
Duomo di Milano
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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 Milan. Enjoy a satisfying meal that will recharge you for tonight's adventures.

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

Day 3

Milan
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Drive 280 km, 4 hours 23 min

Leonardo da Vinci Museum of Science and Technology
Beach brema Sirmione
Castello di Sirmione
Archaeological site of Grotte di Catullo
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On day 3 of your road trip, you’ll start and end your day in Milan, where you have 1 night left to stay.

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

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.

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

Day 4

Milan
Venice
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Drive 279 km, 3 hours 59 min

Castelvecchio Museum
Verona Arena
piazza delle Erbe
Museo Archeologico al Teatro Romano
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Experience an unparalleled adventure on day 4 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Verona. At the end of the day, you will retreat to the hotel of your choice in Venice, where will spend 1 night.

At the end of the day, you will drive to Venice, 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 Venice's most popular restaurants, and connect with friendly locals for a true cultural experience.

Celebrate another amazing day of your road trip adventure in Italy!

Day 5

Venice
Padua
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Drive 47 km, 56 min

Rialto Bridge
Piazza San Marco
St Mark's Basilica
Doge's Palace
Bridge of Sighs
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Your itinerary for day 5 of your road trip in Italy includes 1 stop and features some of the highlights of Venice. At the end of the day, enjoy the comforts of a top-rated hotel in Padua, where you'll spend 1 night.

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

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

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

Day 6

Padua
Siena
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Drive 290 km, 4 hours 10 min

Ragione Palace
The Basilica of St Anthony
Two Towers
Piazza Maggiore
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On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Padua and Bologna. When you’re not sightseeing, take time to relax at your chosen hotel in Siena, where you’ll be staying for 1 night.

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

Siena 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 Siena.

Raise your glass to another unforgettable day in Italy!

Day 7

Siena
Rome
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Drive 241 km, 3 hours 23 min

Sistine Chapel
St Peter's Basilica
Saint Peter's Square
Vatican Museums
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Dive into day 7 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Vatican City. At the end of the day, you’ll unwind at one of the finest accommodations in Rome, where you'll spend 3 nights.

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

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

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

Day 8

Rome
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Drive 9 km, 56 min

Altare della Patria
Trevi Fountain
Piazza di Spagna
Spanish Steps
piazza del Popolo
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Day 8 offers an itinerary packed with the best things to see in Milan. You’ll stay in Rome for 2 nights more, offering you enough time to explore at a relaxed pace.

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.

Rome 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 Rome.

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

Day 9

Rome
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Drive 9 km, 1 hour 20 min

Circus Maximus
largo di Torre Argentina
Pantheon
Campo de' Fiori
Castel Sant'Angelo
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You’ll stay in Rome for 1 night.

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

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

Day 10

Rome
Florence
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Drive 286 km, 3 hours 47 min

Roman Forum
Colosseum
Piazza Navona
Villa Borghese
Auditorium Parco della Musica
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On day 10 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Rome are on today's agenda. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Florence. Florence 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 Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

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

Day 11

Florence
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Drive 6 km, 45 min

piazza della Signoria
Palazzo Vecchio
Uffizi Gallery
Ponte Vecchio
piazzale Michelangelo
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You have 1 night left in Florence. Take the opportunity to experience more of the best attractions and activities in the city.

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

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

Day 12

Florence
Pisa
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Drive 85 km, 1 hour 50 min

Basilica of Santa Croce in Florence
Cathedral of Santa Maria del Fiore
Galleria dell'Accademia
Central Market
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Experience an unparalleled adventure on day 12 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Florence. At the end of the day, you will retreat to the hotel of your choice in Pisa, where will spend 1 night.

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

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

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

Day 13

Pisa
Milan
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Drive 302 km, 3 hours 59 min

Leaning Tower of Pisa
Piazza del Duomo, Pisa
Pisa Cathedral
Priaruggia
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Your itinerary for day 13 of your road trip in Italy includes 2 stops and features some of the highlights of Pisa and Genoa. At the end of the day, enjoy the comforts of a top-rated hotel in Milan, where you'll spend 1 night.

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 a true cultural experience.

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

Day 14

Milan - Departure day
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Piazza Gae Aulenti
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Day 14 of your road trip in Italy is your departure day. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing vacation. You can also browse through boutiques for stylish fashion choices. Elevate your style with pieces from high-end retail stores.

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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Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.

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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.

We guarantee

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

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