5-Day Italy road trip from Milan to Venice and Florence

Milan Cathedral, Duomo di Milano, and Piazza Duomo square in the Milan city center, Italy
Perfect travel plans
Everything included
Fully customizable

Description

Summary

Duration
5 days & 4 nights
Available
Jan. - Dec.
Hotel
4 nights included
Car rental
5 days included
Flights
Optional
Travel app
All vouchers, itinerary, & map

Description

Have the adventure of a lifetime with this 5-day road trip through Italy.

This incredible self-drive vacation package will take you through the best destinations in Italy. With this perfectly planned travel package, you will stay 2 nights in Milan, 1 night in Venice, and 1 night in Florence, experiencing the ultimate road trip in Italy. Your road trip will enable you to discover the country's most popular attractions and restaurants in Milan, Venice, Florence, and Bologna. We'll help you experience the best 5 days in Italy you can imagine so you can leave happy and inspired.

Upon arriving in Milan, you'll collect the rental vehicle of your choice. From there, you'll be off to discover some of the most popular attractions in Italy, including the stunning Duomo di Milano Museum and Galleria Vittorio Emanuele II.

You'll have an extensive selection of accommodations to choose from throughout your road trip. We have handpicked the best hotels and places to stay across the country, catering to all budgets. Whether you're in the mood for luxurious five-star hotels or cozy, budget-friendly accommodations, we've got you covered.

Your road trip will bring you close to the best attractions and most incredible sights in Italy. From the magnificent Parco Sempione to the breathtaking Rialto Bridge and Piazza San Marco, your journey will take you on a thrilling adventure through some of the most iconic travel destinations in the country. Your discovery doesn't end there. Make sure to marvel at the remarkable piazza della Signoria and learn more about the unique Ponte Vecchio to truly immerse yourself in the local culture. As you hit the open road and drive through Milan, Venice, Florence, and Bologna, you'll also have plenty of opportunities to uncover hidden gems and experience the authentic charm of Italy. Whether you're exploring enchanting small towns, discovering scenic routes, or indulging in local cuisine, there's always something new and exciting to experience in Italy.

Add tours and tickets to each day of your trip to make the most of your time in Italy. You'll have the opportunity to choose from the best tours and activities that your travel destinations have to offer, meaning you'll never have a boring moment on your road trip through Italy.

Your travel plan itinerary also gives you multiple opportunities to look for souvenirs to memorialize your road trip in Italy.

You'll return home having experienced the very best of everything Italy has to offer. Each twist and turn of the journey adds a unique charm to your travel tales.

You can customize each day of your road trip vacation itinerary with flexible trip planning before and after booking. Enjoy the benefits of exploring all these great attractions at your own speed.

Your travel plan includes everything you need to experience the best of Italy. You'll be booked at the best hotels for 4 nights, with plenty of top-rated breakfast and restaurant options nearby. We'll provide you with the best car rental for 4 days during your self-drive road trip, including CDW insurance.

You'll have access to 24/7 travel support, a personal travel agent, and a step-by-step guide via our flexible mobile app. You can choose and add your flight preferences as needed. Make your vacation in Italy extra special by adding tours and tickets to each day of your itinerary.

The best services in Italy fill up quickly, so book your spot early. Select a date and start planning your self-drive road trip in Italy today!

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Included

Hotel, 4 nights
Rental car, 5 days
CDW Insurance
Step-by-step guide
Personal travel agent
24/7 travel support

Destinations

High dynamic range (HDR) Aerial view of the city of Milan, Italy.Milan / 2 nights
Florence Aerial View of Ponte Vecchio Bridge during Beautiful Sunny Day, ItalyFlorence / 1 night
Famous buildings, gondolas and monuments by the Rialto Bridge of Venice on the Grand Canal, Italy.Venice / 1 night
Photo of Italy Piazza Maggiore in Bologna old town tower of town hall with big clock and blue sky on background, antique buildings terracotta galleries.Bologna

Map

Attractions

photo of sunrise in san marco square with campanile and san marco's basilica. Panorama of the main square of the old town. Venice, Italy.Piazza San Marco
photo of beautiful view from the canal grande to the famous rialto bridge in Venice, Italy, without people and clear, emerald water.Rialto Bridge
photo of night panoramic view of Duomo square in Milano,Italy.Duomo di Milano Museum
photo of golden sunset over ponte vecchio bridge with traditional boat on the arno river, Florence, Italy.Ponte Vecchio
photo of one of the world's oldest shopping malls galleria vittorio emanuele II at night in milan, lombardia, Italy.Galleria Vittorio Emanuele II
Sempione Park, Municipio 1, Milan, Lombardy, ItalySempione Park
photo of square of signoria in florence at sunrise, Italy.Piazza della Signoria
photo of Sunset view of Sforza Castle (Castello Sforzesco) in Milan, Italy. Architecture and landmarks of Milan. Night cityscape of MilanSforzesco Castle Art Library
photo of bologna, Italy. Piazza maggiore with torre dell'orologio and torre dell’arengo, landmark in emilia-romagna historical province.Piazza Maggiore
photo of uffizi gallery in piazzale degli uffizi at night in florence Italy.Uffizi Gallery
PHOTO OF New business district Milano Porta Nuova Garibaldi (Gae Aulenti) .Piazza Gae Aulenti
photo of Night view of piazza San Marco and Doge's Palace (Palazzo Ducale) in Venice, Italy. Architecture and landmark of Venice. Night cityscape of Venice .Doge's Palace
photo of The traditional bridge of the sighs of Barranco in Lima-PERU .Bridge of Sighs
Teatro La Fenice, Italy.Teatro La Fenice
Aerial view of the Rotunda della Besana. Blue sky. Historical buildings in the city. A cruciform church surrounded by a wall. Rotonda della Besana
Quadrilatero del Silenzio

Flights
Yes
No

Round trip
Economy
Round trip
Economy

Travel details

Flights

Round trip
Economy
Round trip
Economy
Travel dates

Include flights?

Yes
No

Travelers

Rooms

Flights

Car
Yes
No

Car

Small car

Small car

Category
small car
Transmission
People
Large bags
Medium car

Medium car

Category
Medium
Transmission
People
Large bags
Premium car

Premium car

Category
premium car
Transmission
People
Large bags

Hotels

Personalize your itinerary

Day 1 – Milan - arrival day

Day 1

Day 1 – Milan - arrival day

  • Milan - Arrival day
  • More
  • Rotonda della Besana
  • More

Your road trip adventure in Italy begins as soon as you reach the incredible city of Milan. You’ll stay in Milan for 2 nights, experiencing all the best things to do and see in the city.

Milan has many popular destinations you can explore. You could visit attractions like the incredible Rotonda della Besana. This attraction is a must-see tourist destination and has an average rating of 4.4 out of 5 stars by 2,614 visitors.

When you're done sightseeing for the day, you'll check in at one of the best hotels or places to stay in the city. Your stay promises to be a delightful continuation of your exploration, providing comfort and tranquility to recharge for the adventures that lie ahead.

When you’re ready for dinner, we recommend you try one of the best restaurants in the city of Milan, Galleria Restaurant. The restaurant is rated an average of 4.4 out of 5 stars by 2,024 customers.

Another of the best restaurants in the city of Milan is Vento di Sardegna. This restaurant is rated an average of 4.5 out of 5 stars by 1,063 customers.

Locals recommend Nero 9 as one of the best restaurants in the city of Milan. This restaurant has an average rating of 4.5 out of 5 stars by 573 customers.

Milan also has several great bars that will fit all travel budgets. One of the best bars in the city of Milan is The Friends Pub Milano. This bar has an average rating of 4.3 out of 5 stars by 1,689 customers.

Another of the best bars in the city of Milan is Camparino in Galleria. This bar is rated an average of 4.4 out of 5 stars by 1,473 customers.

Locals also enjoy G. B. Bar. This bar has an average rating of 4.6 out of 5 stars by 820 customers.

Enjoy toasting the start of your 5-day vacation in Italy!

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Experiences

Day 2 – Milan and Venice

Day 2

Day 2 – Milan and Venice

  • Milan
  • Venice
  • More

Drive 268 km, 3 hours 30 min

  • Duomo di Milano Museum
  • Galleria Vittorio Emanuele II
  • Sforzesco Castle Art Library
  • Sempione Park
  • Piazza Gae Aulenti
  • More

Day 2 of your road trip through Italy gives you the opportunity to experience two places in one day. You'll start your day with some exploring in the city of Milan and end it at a top-rated hotel in the city of Venice. You will stay in Venice for 1 night. Have a hearty breakfast and get excited for a wonderful day ahead!

One of the best places to visit today in Milan is the amazing Duomo di Milano Museum. As such, over 341,609 people visit Duomo di Milano Museum yearly. This attraction is an art museum that is rated an average of 4.8 out of 5 stars by 138,554 visitors.

You could also stop at the incredible commercial gallery, Galleria Vittorio Emanuele II. With an average rating of 4.7 out of 5 stars by 91,394 visitors, this attraction is one of the top sights in the area.

Another unforgettable travel destination in the Milan is the outstanding Sforzesco Castle Art Library. This popular library and travel destination has an average rating of 4.6 out of 5 stars by 68,714 visitors. Approximately 341,609 travelers come to Milan every year to see the stunning Duomo di Milano Museum with their own eyes.

The spectacular Parco Sempione is another popular attraction you can visit today. This fascinating park and attraction has an average rating of 4.6 out of 5 stars from 72,914 visitors.

If you’re keen to explore even more, then consider a visit to the fantastic Piazza Gae Aulenti. This attraction is a popular square that has an average rating of 4.6 out of 5 stars from 30,398 visitors.

You can make the most of your new day in Milan by joining activities and tours that let you discover what else the city has in store for you. There are many top-rated experiences you can include in your travel plan to add flavor to your road trip in Italy. Browse all of your options and reserve your slot before it's too late.

At the end of the day, you will drive to the city of Venice, where you will access the best hotels and places to stay.

After a long day of driving and exploring, we recommend you try Trattoria Al Gazzettino, one of the best restaurants in the city of Venice. This restaurant has an average rating of 4.3 out of 5 stars by 3,378 customers.

Locals also recommend Nevodi as one of the best restaurants in the city of Venice. Nevodi is rated an average of 4.6 out of 5 stars by 2,127 customers.

Another of the best restaurants in the city of Venice is Osteria Alla Staffa. This restaurant has been rated an average of 4.5 out of 5 stars by 869 customers.

After dinner, visit Adagio, which is considered one of the best bars in the city of Venice. This bar is rated an average of 4.9 out of 5 stars by 621 customers.

You can also enjoy drinks at a popular bar like Il Mercante. This bar has an average rating of 4.8 out of 5 stars by 666 customers.

Alternatively, The Irish Pub Venezia is one of the best bars that locals recommend in the city of Venice. This bar is rated an average of 4.4 out of 5 stars by 1,420 customers.

Raise your glass in celebration of your incredible road trip adventure through Italy!

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Experiences

Day 3 – Venice and Florence

Day 3

Day 3 – Venice and Florence

  • Venice
  • Florence
  • More

Drive 260 km, 3 hours 15 min

  • Rialto Bridge
  • Teatro La Fenice
  • Piazza San Marco
  • Doge's Palace
  • Bridge of Sighs
  • More

As you rise to greet the dawn on day 3 of your epic road trip in Italy, you'll awaken to the bustling city of Venice. Today, you'll hit the road once again, setting off on a journey towards the stunning city of Florence. You’ll stay in Florence for 1 night. But before you begin your drive, we recommend taking the time to explore some of Venice’s must-see attractions and local hotspots.

If you’re curious to see more of Venice, start your day with a visit to the amazing Rialto Bridge. This much-appreciated stone bridge and attraction is rated 4.7 out of 5 stars by 141,666 visitors.

You could also stop at another of the best local travel destinations in the area, the fascinating Teatro La Fenice. This opera house and spectacular attraction has an average rating of 4.7 out of 5 stars from 10,677 visitors.

We also recommend you spend some time at the popular Piazza San Marco to make the most of your road trip across Italy. The spectacular Piazza San Marco is a square that has been rated an average of 4.7 out of 5 stars by 152,982 visitors.

The lovely Doge's Palace is yet another attraction you could pay a visit. Around 24,775 visitors have left this palace average ratings of 4.7 out of 5 stars. This popular attraction gets around 318,104 visits every year.

If you feel like visiting another type of sight or don’t want to jump into the car quite yet, spend some time at the spectacular Bridge of Sighs. This attraction is a footbridge rated an average of 4.6 out of 5 stars in 18,223 reviews.

After soaking up all the sights and sounds that Venice has to offer, you'll be ready to hit the open road and continue your unforgettable road trip towards the city of Florence. Florence offers plenty of options for top-rated hotels and other places to stay that fit all travel budgets.

After you’ve settled into your accommodation, we recommend a dinner at the popular Ristorante Paoli. This popular restaurant is one of the locals’ most recommended restaurants in the city, with ratings of 4.9 out of 5 stars in 6,031 reviews.

The remarkable Ristorante Oliviero 1962 is another top restaurant in Florence we recommend. This restaurant offers an unforgettable dining experience and is rated an average of 4.7 out of 5 stars by 1,046 customers.

If you would rather go somewhere else, the famous Il Vezzo is also an excellent choice. This well-loved restaurant is rated an average of 4.8 out of 5 stars by 862 customers.

After your meal, we recommend you drink at one of the best bars in Florence, the fantastic Manifattura. This bar has an average rating of 4.7 out of 5 stars by 509 customers.

To end your night the best way possible, we recommend going to the wonderful Ditta Artigianale. This bar offers a great variety of drinks and has been rated an average of 4.3 out of 5 stars by 1,877 customers.

Another bar with a great atmosphere is Archea Brewery. This bar is rated an average of 4.7 out of 5 stars by 723 customers, so don’t forget to check this one out as well!

Celebrate another amazing vacation day filled with adventure in Italy!

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Experiences

Day 4 – Florence, Bologna, and Milan

Day 4

Day 4 – Florence, Bologna, and Milan

  • Florence
  • Bologna
  • Milan
  • More

Drive 331 km, 4 hours 14 min

  • Piazza della Signoria
  • Ponte Vecchio
  • Uffizi Gallery
  • Piazza Maggiore
  • More

Rise and shine on day 4 of your road trip in Italy. Today, you'll wake up in Florence and embark on a scenic drive to Milan, where you'll stay at one of the best hotels for 1 night. Seize the opportunity to explore spectacular attractions in Florence before you reach your end destination for the day.

It’s hard not to feel excited about visiting attractions in a destination as lovely as Florence. When you’re eager to explore the city and nearby areas, we recommend visiting some local favorites, such as the wonderful piazza della Signoria. This attraction is a square that has an average rating of 4.8 out of 5 stars from 66,956 visitors.

You could also stop at the incredible Ponte Vecchio. This attraction, a beloved deck arch bridge, has an average rating of 4.7 out of 5 stars from 118,099 visitors.

If you have time, another site you could explore in Florence is the stunning Uffizi Gallery. This national museum and travel destination has an average rating of 4.7 out of 5 stars by 61,794 visitors. Approximately 2,011,219 travelers come to Florence every year to see this fascinating attraction.

One of the most popular attractions you can visit is the remarkable Piazza Maggiore. This attraction is a square that has an average rating of 4.7 out of 5 stars from 64,523 visitors.

We recommend you end the day with a dinner at a popular restaurant near your accommodation, like Bice Restaurant. This restaurant offers various delicious and comforting meals and has an average rating of 4.3 out of 5 stars from 579 customers.

Locals also recommend DeRos Restaurant, another of the best restaurants in Milan. DeRos Restaurant is rated an average of 4.7 out of 5 stars by 285 customers.

If you feel like having something else, check out the menu at Alto Ristorante. This restaurant has been rated an average of 4.8 out of 5 stars by 137 customers and is a great place to enjoy a lovely meal.

After dinner, visit Armani/Bamboo Bar to enjoy a couple of drinks and relax. This bar is one of the best in Milan, with an average rating of 4.3 out of 5 stars by 272 customers.

You can also enjoy drinks at a popular bar like Dessert Bar Milano. This bar is a great spot to meet new friends and celebrate your vacation. Dessert Bar Milano has an average rating of 5 out of 5 stars by 144 customers.

Carico is another bar locals often recommend. This bar offers a great variety of snacks and drinks and is rated an average of 4.4 out of 5 stars by 125 customers.

End your day by raising your glass in celebration of your incredible road trip adventure in Italy, and look forward to more great days to come!

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Experiences

Day 5 – Milan - departure day

Day 5

Day 5 – Milan - departure day

  • Milan - Departure day
  • More
  • Quadrilatero del Silenzio
  • More

Day 5 of your road trip in Italy is your departure day. This is your chance to catch one last glimpse of Milan before saying goodbye to this wonderful destination. When you have time to explore the area before you make your way home, we recommend visiting some of the following attractions.

Take a stroll along the main shopping streets of Milan and find some souvenirs to remind you of your road trip in Italy.

You’ll then say farewell to Milan. We wish you a pleasant journey home, with many wonderful memories of your unforgettable vacation in Italy!

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Experiences

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