5-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling east to Florence

Perfect travel plans
Everything included
Fully customizable

Description

Included

Flights
Select dates
Hotel
Select dates
Car rental
Select dates
Tours & tickets
Select dates
Travel plan
All inclusive app
Travel agent
24/7 fast service

Description

Experience the freedom of the open road in Italy as you embark on an unforgettable 5-day road trip! This experience caters to every traveler, featuring destinations like Milan, Florence, Pisa, and Lucca.

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 Milan and 1 night 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 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. 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 Milan, Florence, Pisa, and Lucca, 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!

Read more

Travel details

Set your travel details to find the best price

Flights

Round trip
Round trip
Travel dates

Travelers

Rooms

Flights

Compare and choose from the best flights to Milan

Car

Choose from the best car rental deals or see all options

Driver’s age is 30 - 65
I live in

Itinerary summary

See a summary of the itinerary that you can fully customize

Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Brera
Santa Maria delle Grazie ChurchSempione ParkCastello SforzescoGalleria Vittorio Emanuele IIDuomo di MilanoNavigli
Basilica of Santa Croce in FlorenceUffizi GalleryPonte VecchioCathedral of Santa Maria del Fiorepiazza della Signoria
Piazza del Duomo, PisaLeaning Tower of PisaWalls of Lucca
Piazza Gae Aulenti

Personalize your itinerary

Customize tours under each day and destination

Day 1

Day 1

  • Milan - Arrival day
  • More
  • Brera
  • More

Your road trip adventure in Italy begins as soon as you reach Milan and pick up your car. You’ll stay in Milan for 2 nights 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.

Milan 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 Brera, a must-see neighborhood, and 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 Milan. 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 Milan, it's often a good idea to reserve a table in advance.

Treat yourself to a delicious dinner at Hotel Morfeo Milano, an excellent option for tonight's dining. Looking for something different? Contraste offers a tantalizing alternative with its diverse menu. And don’t miss UNAHOTELS Galles Milano. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Milan.

To truly maximize your evening out, consider visiting Nottingham Forest after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Armani/bamboo Bar, another bar with an inviting ambiance. Similarly, Mag Cafe also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Raise a toast to the start of your 5-day road trip in Italy!

Read more
Day 2

Day 2

  • Milan
  • More

Drive 5 km, 1 hour 7 min

  • Santa Maria delle Grazie Church
  • Sempione Park
  • Castello Sforzesco
  • Galleria Vittorio Emanuele II
  • Duomo di Milano
  • Navigli
  • More

Day 2 offers a multitude of experiences. You will stay in Milan for 1 night more, offering you enough time to explore at a relaxed pace.

Navigli is one of the highlights of today. Take your time exploring this iconic neighborhood in Milan, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks 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 Santa Maria Delle Grazie Church. This interesting church provides an insightful glimpse into the city's identity. Next, discover Parco Sempione, a romantic park, promising a delightful encounter.

Continue your sightseeing with a visit to Sforzesco Castle Art Library, an astonishing castle. When you’re done, don’t forget to make a stop at the widely recognized Galleria Vittorio Emanuele Ii. Round off your day at Duomo Di Milano Museum, another gem in Milan with culturally significant 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.

Visit Via della Moscova in Milan for an unforgettable shopping experience. Browse unique boutiques and stores, each offering delightful surprises. Find unique souvenirs or items to take home. After shopping, explore what Via della Moscova has to offer, including cafes, attractions, essential services, and vibrant community activities.

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.

Treat yourself to a delightful dinner at Dessert Bar Milano, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Radisson Blu Hotel Milan? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Qui Si Mangia as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Milan.

After enjoying a fulfilling meal, continue your evening at Kilburn Cocktail Bar Milano, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bar Frida offers a welcoming atmosphere for easing into the nightlife. Similarly, The Friends Pub Milano provides an excellent environment for a relaxed and enjoyable evening.

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

Read more
Day 3

Day 3

  • Milan
  • Florence
  • More

Drive 309 km, 3 hours 59 min

  • Basilica of Santa Croce in Florence
  • Uffizi Gallery
  • Ponte Vecchio
  • Cathedral of Santa Maria del Fiore
  • piazza della Signoria
  • More

Embark on another extraordinary experience on day 3 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 Florence, which will be your home away from home for 1 night.

Milan is home to plenty of attractions that offer family-friendly attractions, photo-friendly spots, and history-rich sites! Start at Basilica Of Santa Croce In Florence, a popular church that is worthwhile a visit in the city. Nearby, you’ll find Uffizi Gallery, enchanting visitors with its romantic appeal. Continue your exploration at Ponte Vecchio. This historical landmark is one of the city’s most globally renowned spots.

Enjoy the freedom of exploring Milan at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Cathedral Of Santa Maria Del Fiore. After exploring the church, head to the widely recognized Piazza Della Signoria.

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 dinnertime approaches, it's time to head out for a bite to eat in Florence. 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.

Treat yourself to a delicious dinner at Ristorante Oliviero 1962, an excellent option for tonight's dining. Looking for something different? Di Poneta Novoli offers a tantalizing alternative with its diverse menu. And don’t miss Caffe San Firenze. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

Continue your evening by exploring the vibrant nightlife scene at Manifattura, a prime destination for a thrilling night out. Also, don’t forget to check out Se·sto On Arno Rooftop Bar, a bar that offers unique local touches. Likewise, Il Vinile provides an excellent alternative for a fun evening.

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

Read more
Day 4

Day 4

  • Florence
  • Milan
  • More

Drive 381 km, 4 hours 55 min

  • Piazza del Duomo, Pisa
  • Leaning Tower of Pisa
  • Walls of Lucca
  • More

Dive into day 4 of your remarkable road trip in Italy. Today you will explore Pisa and Lucca, 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 1 night.

Today’s itinerary in Florence covers several incredible sights, including a public square, a monument, and a historical landmark. Start your adventure at Piazza Del Duomo, Pisa. This globally renowned public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the masterful wonders of Leaning Tower Of Pisa, a must-see monument in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Mura Di Lucca. This worthwhile historical landmark offers an enriching experience. These sights offer a fulfilling end to a perfect day.

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.

As you explore more of Milan, 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.

Make sure to reserve a table at Bice Restaurant, an iconic dining spot in Milan. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Alto Ristorante, a popular restaurant in Milan. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Nero 9, a hidden gem nestled in Milan. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bhangrabar, a well-loved spot among locals and tourists. Or, head to Rufus Cocktail Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Ostello Bello Grande, another top-rated place in the area.

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

Read more
Day 5

Day 5

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

Day 5 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Milan 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, begin at Piazza Gae Aulenti. This well-known public square is a popular place to see in the city.

As your final day in Italy unfolds, enjoy a last-minute shopping spree in Milan's best shopping area, Galleria Vittorio Emanuele II. Enjoy finding the perfect gift or keepsake to remind you of your wonderful trip to Italy. Explore high-end stores offering an exquisite selection of luxury items.

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

Dine in style at Ristorante la Brisa, a top recommendation for dinner tonight. Or, for a change of pace, Pasticceria San Carlo boasts a menu that's sure to impress.

You’ll then say farewell to Milan. 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!

Read more

Similar travel packages

Discover other popular vacations in Italy

Link to appstore phone
Install Europe’s biggest travel app

Download Europe’s biggest travel marketplace to your phone to manage your entire trip in one place

Scan this QR code with your phone camera and press the link that appears to add Europe’s biggest travel marketplace into your pocket. Enter your phone number or email address to receive an SMS or email with the download link.