Travel packages in Italy

Road trips in Italy

Two-Week Italy Self-Drive Road Trip With Itinerary from Milan traveling south to Venice, Bologna, Arezzo, 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 15-day road trip in Italy! Embark on a self-drive tour that caters to every traveler, featuring destinations like Milan, Sirmione, Verona, Venice, Bologna, Siena, Arezzo, 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 Bologna, 1 night in Arezzo, 4 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, Bologna, Siena, Arezzo, 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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Drop-off: 10:00

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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 3 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. 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.

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

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

Raise a toast to the start of your 15-day road trip in Italy!

Day 2

Milan
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Drive 4 km, 39 min

Duomo di Milano
Galleria Vittorio Emanuele II
La Scala
Castello Sforzesco
Sempione Park
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Day 2 offers an itinerary packed with the best things to see in Milan. You’ll stay in Milan 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.

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

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

Day 3

Milan
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Drive 274 km, 4 hours 9 min

Pinacoteca di Brera
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.

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

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

Day 4

Milan
Venice
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Drive 278 km, 3 hours 48 min

Castelvecchio Museum
Castelvecchio Bridge
Verona Arena
piazza delle Erbe
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Your itinerary for day 4 of your road trip in Italy includes 1 stop and features some of the highlights of Verona. At the end of the day, enjoy the comforts of a top-rated hotel in Venice, 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 Venice. Venice 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 Venice's best restaurants.

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

Day 5

Venice
Bologna
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Drive 155 km, 2 hours 2 min

Rialto Bridge
Piazza San Marco
St Mark's Basilica
Doge's Palace
Bridge of Sighs
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On day 5 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Venice are on today's agenda. In the evening, you’ll end up in Bologna, where you will stay for 1 night.

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

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

Relax and look forward to more memorable moments to come!

Day 6

Bologna
Arezzo
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Drive 243 km, 3 hours 31 min

Two Towers
Piazza Maggiore
Siena Cathedral
piazza del Campo
Tower of Mangia
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Dive into day 6 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Bologna and Siena. At the end of the day, you’ll unwind at one of the finest accommodations in Arezzo, where you'll spend 1 night.

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

When you’re done exploring for the day, you’ll drive to your hotel in Arezzo. 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 Arezzo. Enjoy a relaxing evening as you savor delicious local cuisine.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in Italy.

Day 7

Arezzo
Rome
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Drive 227 km, 2 hours 52 min

Vatican Museums
Sistine Chapel
Saint Peter's Square
St Peter's Basilica
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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 place, which are Vatican City. At the end of the day, you will retreat to the hotel of your choice in Rome, where will spend 4 nights.

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

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

Day 8

Rome
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Drive 20 km, 1 hour 12 min

Foro Italico
piazza del Popolo
Villa Borghese
Basilica di Santa Maria Maggiore
Archbasilica of St. John Lateran
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You’ll stay in Rome for 3 nights.

Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Rome.

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.

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

Day 9

Rome
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Drive 4 km, 58 min

Colosseum
Roman Forum
Capitoline Hill
Altare della Patria
largo di Torre Argentina
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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.

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

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

Day 10

Rome
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Drive 10 km, 1 hour 3 min

Orange Garden
Circus Maximus
Campo de' Fiori
Piazza Navona
Castel Sant'Angelo
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You have 1 night left in Rome. 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 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.

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

Day 11

Rome
Florence
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Drive 278 km, 3 hours 31 min

Pantheon
Trevi Fountain
Piazza di Spagna
Spanish Steps
Auditorium Parco della Musica
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On day 11 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Rome. When you’re not sightseeing, take time to relax at your chosen hotel in Florence, where you’ll be staying for 2 nights.

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.

Florence 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 Florence.

Savor another day of unforgettable experiences in Italy!

Day 12

Florence
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Drive 3 km, 49 min

Basilica of Santa Maria Novella
Central Market
Cathedral of Santa Maria del Fiore
Galleria dell'Accademia
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Day 12 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.

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

Raise your glass to another unforgettable day in Italy!

Day 13

Florence
Pisa
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Drive 88 km, 1 hour 53 min

piazza della Signoria
Ponte Vecchio
Uffizi Gallery
Basilica of Santa Croce in Florence
piazzale Michelangelo
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Your itinerary for day 13 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 Pisa, where you'll 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.

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

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

Day 14

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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On day 14 of your road trip in Italy, your travel plans include 2 stops at the most scenic, wondrous, and interesting places in the region. Pisa and Genoa are on today's agenda. In the evening, you’ll end up in Milan, where you will stay for 1 night.

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

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

Day 15

Milan - Departure day
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Arch of Peace
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Day 15 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.

If you’re in the mood for luxury shopping, high-end stores await you.

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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