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

Escape the ordinary with this exciting 5-day road trip through Italy. Explore the diverse landscapes, lively cities, and beyond. Pack your bags, hit the road, and prepare for an unforgettable journey!

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

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.

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 hotel in a central location for easy access to the best attractions, restaurants, and bars 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.

Enjoy a delicious meal at Hotel Morfeo Milano, a highly-rated dining destination in Milan. If you're eager to try something different, consider Contraste, another top spot with a tantalizing menu. You might also want to secure a reservation at UNAHOTELS Galles Milano. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Milan this evening.

Keep the excitement of the evening going by visiting a bar or two. Nottingham Forest is an excellent place to start. You could also check out Armani/bamboo Bar, offering a different kind of charm. A last recommendation for the day is Mag Cafe. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

On day 2 of your road trip, you will have an entire day to explore Milan. You’ll stay in Milan for 1 night and discover all the best things to see and do in the area.

A visit to Navigli in Milan is a must on the agenda today. This neighborhood is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights.

Today’s well-planned self-sightseeing route offers several fun adventures, picturesque spots, and historic treasures. Whether you decide to explore Milan on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Santa Maria Delle Grazie Church is the first of them. Spend some time admiring this inviting church before continuing your journey. Parco Sempione is your next stop. This famous park is one of the best-rated sights in Milan.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Sforzesco Castle Art Library. This picture-perfect castle is a sight to behold. To round off your sightseeing experience, visit Galleria Vittorio Emanuele Ii and Duomo Di Milano Museum.

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 Quadrilatero della Moda in Milan for an unforgettable shopping experience. Browse unique boutiques and luxurious 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.

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

Enjoy a lovely dining experience at Dessert Bar Milano, a popular restaurant in Milan. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Milan at Radisson Blu Hotel Milan, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Ristorante Qui Si Mangia. It’s yet another ideal choice to enhance your time in Milan tonight.

After your meal, keep the night alive at a bar like Kilburn Cocktail Bar Milano, known for its lively atmosphere. Bar Frida is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, The Friends Pub Milano offers an excellent atmosphere for those looking to amp up the evening.

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

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

Experience an unparalleled adventure on day 3 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Florence. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Florence. You will spend 1 night here for some well-deserved relaxation.

Today’s well-planned self-sightseeing route offers several fun adventures, photo-friendly spots, and history-rich sites. Whether you decide to explore Milan on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Basilica Of Santa Croce In Florence is the first of them. Spend some time admiring this instagrammable church before continuing your journey. Uffizi Gallery is your next stop. This famous art gallery is one of the best-rated sights in Milan.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Ponte Vecchio. This visually striking historical landmark is a sight to behold. To round off your sightseeing experience, visit Cathedral Of Santa Maria Del Fiore and Piazza Della Signoria.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of 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.

As you explore more of Florence, 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.

Treat yourself to a wonderful meal at Ristorante Oliviero 1962, a top-rated dining spot in Florence. If you're in the mood for something new, try Di Poneta Novoli, another premier location with a delectable menu. You might also want to book a table at Caffe San Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

Explore the vibrant nightlife at Manifattura after your meal, a hub for lively evenings and memorable moments. Or, head to Se·sto On Arno Rooftop Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Il Vinile is perfect for those looking to extend their night with a touch of local flavor.

Raise your glass and celebrate another amazing day of your road trip 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

On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Pisa and Lucca. When you’re not sightseeing, take time to relax at your selected hotel in Milan, where you’ll be staying for 1 night.

Start by visiting Piazza Del Duomo, Pisa, a prime spot to begin your journey. This breathtaking public square is sure to impress. Next on your list is Leaning Tower Of Pisa, another must-visit landmark and world-famous monument renowned for its breathtaking features.

While exploring and sightseeing, take time to savor the culture of Florence by sampling some local delicacies. When you’re ready for more sightseeing, head to Mura Di Lucca. This visually striking historical landmark is an essential place to visit for anyone looking for the full Florence experience.

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.

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

Enjoy a delicious meal at Bice Restaurant, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Alto Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at Nero 9. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

Following your dinner, dive into the local bar culture at Bhangrabar. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Rufus Cocktail Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Ostello Bello Grande provides excellent drinks and a great atmosphere, ensuring a memorable night out.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in 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 notable public square is a popular place to see in the city.

Make the most of your final day in Italy by visiting Milan’s iconic markets and shopping establishments in the buzzing Via della Moscova. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy. You can also browse through boutiques for stylish fashion choices. Savor your final moments in Italy at a cozy cafe while relaxing with a cup of coffee or tea.

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

If you're in the mood to try something new, consider Pasticceria San Carlo, another top spot with a mouthwatering menu.

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.