10-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling south to Florence, Siena, Rome, Arezzo, 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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Description

Experience the freedom of the open road on an unforgettable 10-day road trip in Italy! Embark on a self-drive tour that caters to every traveler, featuring destinations like Milan, Parma, Florence, Siena, Rome, Arezzo, and Bologna.

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, 1 night in Florence, 1 night in Siena, 2 nights in Rome, 1 night in Arezzo, 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. 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, Parma, Florence, Siena, Rome, Arezzo, 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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Pick-up: 10:00
Drop-off: 10:00

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Customize tours under each day and destination

Day 1

Day 1

  • Milan - Arrival day
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  • Arch of Peace
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Welcome to Milan, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 2 nights discovering what to see in Milan before embarking on the next leg of your journey.

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 10-day road trip in Italy!

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Day 2

Day 2

  • Milan
  • More

Drive 9 km, 1 hour 18 min

  • Garibaldi Gate
  • Pinacoteca di Brera
  • Castello Sforzesco
  • Sempione Park
  • Leonardo da Vinci Museum of Science and Technology
  • More

Day 2 offers an itinerary packed with the best things to see in Milan. You’ll stay in Milan 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.

For an unforgettable shopping experience, visit Quadrilatero della Moda, the top shopping destination in Milan. Browse local boutique shops and luxury stores, each offering delightful surprises. Find unique souvenirs or items to take home. After shopping, explore what Quadrilatero della Moda has to offer, including attractions, essential services, and vibrant community activities.

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.

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

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Day 3

Day 3

  • Milan
  • Florence
  • More

Drive 324 km, 4 hours

  • La Scala
  • Galleria Vittorio Emanuele II
  • Duomo di Milano
  • Palazzo della Pilotta
  • More

On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Milan and Parma. When you’re not sightseeing, take time to relax at your chosen hotel in Florence, where you’ll be staying for 1 night.

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.

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

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Day 4

Day 4

  • Florence
  • Siena
  • More

Drive 71 km, 1 hour 46 min

  • piazza della Signoria
  • Cathedral of Santa Maria del Fiore
  • Ponte Vecchio
  • Uffizi Gallery
  • piazzale Michelangelo
  • More

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 Florence. At the end of the day, you will retreat to the hotel of your choice in Siena, where will spend 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.

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

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

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Day 5

Day 5

  • Siena
  • Rome
  • More

Drive 241 km, 3 hours 23 min

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

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. Vatican City are on today's agenda. In the evening, you’ll end up in Rome, 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 Rome. Rome offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

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

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

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Day 6

Day 6

  • Rome
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Drive 12 km, 1 hour 7 min

  • Castel Sant'Angelo
  • Trevi Fountain
  • Piazza di Spagna
  • piazza del Popolo
  • Villa Borghese
  • More

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.

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.

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Day 7

Day 7

  • Rome
  • Arezzo
  • More

Drive 224 km, 3 hours 22 min

  • Roman Forum
  • Colosseum
  • Altare della Patria
  • Pantheon
  • Piazza Navona
  • More

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

At the end of the day, you will drive to Arezzo, 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 Arezzo. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Relax and look forward to more memorable moments to come!

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Day 8

Day 8

  • Arezzo
  • Bologna
  • More

Drive 229 km, 3 hours 47 min

  • San Francesco, Arezzo
  • piazza Grande
  • La Verna - Franciscan Sanctuary
  • More

Dive into day 8 of your remarkable road trip in Italy. Today you'll explore 2 destinations, including Arezzo and La Verna. At the end of the day, you’ll unwind at one of the finest accommodations in Bologna, where you'll spend 1 night.

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.

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

Raise your glass to another unforgettable day in Italy!

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Day 9

Day 9

  • Bologna
  • Milan
  • More

Drive 223 km, 2 hours 49 min

  • Bologna Cathedral
  • Piazza Maggiore
  • Two Towers
  • Piazza Santo Stefano
  • More

On day 9 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Bologna. When you’re not sightseeing, take time to relax at your chosen hotel in Milan, where you’ll be staying 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.

Savor another day of unforgettable experiences in Italy!

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Day 10

Day 10

  • Milan - Departure day
  • More
  • Piazza Gae Aulenti
  • More

Day 10 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.

For those seeking luxury items, check out the area’s high-end 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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How it works

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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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