Cheap 5-Day Italy Road Trip from Milan traveling south to 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

Bring out the adventurer in you and embark on an exciting 5-day road trip through Italy! Travel to Milan and Florence with this cheap holiday package!

Explore Italy for less with this 5-day self-drive package. We'll introduce you to many famous and affordable vacation spots in the country. See the stunning Duomo di Milano Museum, the captivating Galleria Vittorio Emanuele II, and marvel at the uniqueness of each attraction. Dine with locals at popular restaurants and bars across Italy and get a taste of the people’s hospitality and authentic food. Lastly, this travel plan allows you to stay and feel comfortable at a top-rated budget hotel for 3 nights in Milan and 1 night in Florence.

This customizable and cheap Italy travel package promises non-stop adventure. We'll help you have an unforgettable road trip experience in Italy at the lowest price!

On arrival in Milan, you'll pick up your rental vehicle. From there, you'll begin your journey to the best and cheapest places to travel to in Italy. Explore the magnificent Ponte Vecchio to see its unique features. Visit the fascinating piazzale Michelangelo and take in its distinct atmosphere. Italy offers a wealth of world-class natural and scenic beauty you wouldn't want to miss!

During your journey, you'll have the pleasure of staying at top-rated budget accommodations, each selected for their exceptional value, comfort, and positive guest reviews. Each stop along your carefully planned route has been chosen to enhance your travel experience, offering you a blend of convenience, comfort, and a touch of local culture, ensuring a restful retreat after a day of adventures.

Choosing the handpicked recommendations gives you easy access to popular places of interest in Italy. With accommodation conveniently located in a downtown area, you can explore its surroundings at your leisure. Here, you can sample the country’s culinary delicacies and buy keepsakes of your travels in Italy.

This cheap holiday package will bring you close to many picture-perfect destinations in Italy, like the stunning Cathedral of Santa Maria del Fiore. You'll visit the incredible Leaning Tower of Pisa to make lasting memories. You'll also have the chance to admire the outstanding Piazza del Duomo, Pisa up close.

Your camera will be full of memories you can share with friends and family or on social media. By the end of your 5-day road trip, you'll leave Italy happy and inspired to go on another unique and budget-friendly adventure.

This affordable holiday package includes everything you need for a fantastic 5-day vacation in Italy. We'll offer you cheap flights and arrange your hotel reservations for 4 nights. We'll also provide you with the best budget rental car in Italy with CDW insurance.

You can customize your Italy travel plan for a more personalized holiday experience. Choose from popular and competitively-priced tours and tickets in Italy and add your picks to your itinerary. For example, get cheap tour tickets to uncover the stories behind Italy’s famous sights. Or, try out some of the most fantastic excursions There’s no better way to add more culture and inspiration to your trip!

Booking this cheap holiday package in Italy offers you many perks. You'll get 24/7 travel support. In addition, you'll have access to a step-by-step guide in our mobile app. Here you'll find all your travel documents organized in one place.

So what are you waiting for? Enjoy a hassle-free vacation in Italy with this cheap holiday deal! The best and most affordable tours to Italy fill up fast, so book your adventure 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 / 3 nights
Florence Aerial View of Ponte Vecchio Bridge during Beautiful Sunny Day, ItalyFlorence / 1 night
Pisa - city in ItalyPisa

Map

Attractions

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 medieval leaning tower of pisa (Torre di pisa) at piazza dei miracoli (Piazza del duomo), Tuscany, Italy.Leaning Tower of Pisa
photo of panorama of piazza dei miracoli with leaning tower of pisa, Italy.Piazza del Duomo, Pisa
photo of one of the world's oldest shopping malls galleria vittorio emanuele II at night in milan, lombardia, Italy.Galleria Vittorio Emanuele II
photo of View of statue of david on Piazzale Michelangelo at morning  in Florence, Italy.Piazzale Michelangelo
Cathedral of Santa Maria del Fiore, Quartiere 1, Florence, Metropolitan City of Florence, Tuscany, ItalyCathedral of Santa Maria del Fiore
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 New business district Milano Porta Nuova Garibaldi (Gae Aulenti) .Piazza Gae Aulenti
PHOTOPP OF Arco della Pace (Arch of Peace), Porta Sempione, Milan, Italy .Arch of Peace
photo of view of Teatro La Scala- famous opera house in Milan, Italy.La Scala
phopto of Church of Santo Stefano dei Cavalieri in Knights Square (Piazza dei Cavalieri), Pisa, Tuscany, ItalyKnights' Square
photo of Cittadella Nuova .Cittadella Nuova

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
  • Piazza Gae Aulenti
  • More

Your exciting road trip through Italy starts when you reach the incredible city of Milan, where you'll stay for 3 nights. You'll pick up your rental car in Milan and begin your adventure in Italy.

Milan is a popular cheap holiday destination in Italy with something to offer every traveler. When you're ready to explore the city, stop at some of the best places to visit in Milan and get this road trip adventure rolling.

A trip to the amazing Piazza Gae Aulenti will make your cheap holiday in Italy truly special. This attraction is a fascinating square that has an average rating of 4.6 out of 5 stars from 30,398 visitors.

When you're done sightseeing for the day, you'll check in at one of the best budget-friendly hotels or places to stay in the city.

When you're hungry and ready to take a break from your adventure, treat yourself to a delicious meal at one of the best restaurants in Milan. An excellent example is the popular L'immagine Bistrot Ristorante. Serving a menu of mouthwatering dishes, this restaurant is rated an average of 4.7 out of 5 stars by 2,020 customers.

Another restaurant you should check out during your cheap vacation in Italy is Contraste. Rated 4.7 out of 5 stars by 823 customers, this famous restaurant is one of the city's most recommended places to eat.

If you wish to dine at a restaurant locals love, go to the wonderful Ribot Restaurant. This restaurant has an average rating of 4.5 out of 5 stars from 3,991 customers, and is an awesome place to satisfy your craving for good food and service.

Mag Cafe is a great bar to relax after a busy day. About 3,270 customers have given this spot an average rating of 4.4 out of 5 stars, making it one of the most popular bars in the area.

Another bar in Milan we recommend is Nottingham Forest, an excellent place to meet new friends. This bar offers customers plenty of snack and drink options and is rated an average of 4.4 out of 5 stars by 2,686 customers.

The Friends Pub Milano is also one of the best places to go to unwind and chat with locals. Over 1,689 bar-goers have rated it an average of 4.3 out of 5 stars.

Enjoy toasting the start of a terrific road trip vacation and cheap holiday experience in Italy!

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Experiences

Day 2 – Milan

Day 2

Day 2 – Milan

  • Milan
  • More

Drive 3 km, 51 min

  • Duomo di Milano Museum
  • Sforzesco Castle Art Library
  • La Scala
  • Galleria Vittorio Emanuele II
  • Sempione Park
  • More

Day 2’s road trip itinerary introduces you to many popular attractions and activities in Milan, proving that cheap holidays in Italy can be extraordinary.

You'll begin sightseeing at the extraordinary Duomo di Milano Museum. This attraction is an art museum that has an average rating of 4.8 out of 5 stars from 138,554 travelers. Every year, the wonderful Duomo di Milano Museum gets around 341,609 visitors from across the globe.

Another of the best travel destinations you can explore in this fun and cheap holiday destination is the spectacular Galleria Vittorio Emanuele II. This popular place of interest is a stunning commercial gallery that boasts an average rating of 4.7 out of 5 stars from 91,394 visitors.

To make your trip to Milan more memorable, spend time at the fascinating La Scala. With an average rating of 4.7 out of 5 stars in 26,219 traveler reviews, it’s not surprising that the fantastic La Scala is often mentioned in Italy road trip itineraries.

The magnificent Sforzesco Castle Art Library is another stop you might want to add to your sightseeing plans. This library and popular travel destination is rated an average of 4.6 out of 5 stars in 68,714 reviews.

If you’re interested in seeing something else, make your way to the amazing Parco Sempione. More than 72,914 visitors have rated this park and tourist destination an average of 4.6 out of 5 stars.

Your discovery of Milan does not have to stop there. You can add a budget-friendly activity on your itinerary and get to know more about Milan on a personal level. Check out the fantastic selection of affordable tours and tickets offered on this leg of your journey across this top cheap holiday destination in Europe, Italy.

After exploring some of the most remarkable sights in Italy, you also have the chance to experience the country’s food culture. Eat at Galleria Restaurant, one of the best restaurants in Milan. This place is a local favorite and has an average rating of 4.4 out of 5 stars from 2,024 reviews.

You can also check out Palazzo Parigi Hotel & Grand Spa Milano. Offering appetizing foods and refreshing beverages at reasonable prices, this restaurant is an excellent choice for budget travelers in the city. This restaurant is rated an average of 4.7 out of 5 stars by 1,550 diners.

Another great restaurant we recommend you go to after your road trip activities is Vento di Sardegna. With an average rating of 4.5 out of 5 stars from 1,063 customers, this restaurant is sure to provide you a memorable dining experience in Milan.

When you’ve finished your meal, head to some of the most popular bars in Milan for an after-dinner drink. Cap off your night in this cheap holiday destination at Kilburn Cocktail Bar Milano and try some of its cocktails and snacks. This bar has an average rating of 4.5 out of 5 stars from 954 customers.

Rufus Cocktail Bar is another great place to hang out in and relax after a busy day in the city. This bar offers various drinks at affordable prices and is rated an average of 4.4 out of 5 stars by 643 customers.

If you want to have a drink or two with locals, you'll want to visit Ostello Bello Grande. Rated an average of 4.6 out of 5 stars by 3,635 customers, this bar is one of the best places to unwind and socialize in Milan.

Savor the rest of the night and celebrate another incredible road trip adventure in the magical Milan!

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Experiences

Day 3 – Florence

Day 3

Day 3 – Florence

  • Pisa
  • Florence
  • More

Drive 390 km, 5 hours 20 min

  • Cittadella Nuova
  • Knights' Square
  • Piazza del Duomo, Pisa
  • Leaning Tower of Pisa
  • More

On day 3 of your road trip through popular and cheap vacation spots across Italy, you’ll experience two places in one day. You’ll start your day in Pisa and end your day in the city of Florence, where you'll stay for 1 night. How much time you’ll spend in each location is up to you.

One of the best places to visit in Pisa is the amazing Cittadella Nuova. This travel destination is a fortress that has been rated an average of 4.4 out of 5 stars by 3,114 visitors.

This day is also your chance to stop at the incredible Knights' Square. Rated 4.5 out of 5 stars by 9,051 travelers, a visit to this well-known square and sightseeing spot in Pisa is likely to make your vacation in Italy even more memorable.

Another unforgettable sight in Pisa is the outstanding Piazza del Duomo, Pisa. This square has an average rating of 4.7 out of 5 stars from 104,550 visitors.

To make the most of your day in this cheap holiday destination in Italy, drop by the popular Leaning Tower of Pisa. This attraction, an amazing bell tower, has been rated 4.7 out of 5 stars by 116,882 travelers. As one of the top sights in Pisa, there’s no wonder that the spectacular Leaning Tower of Pisa attracts about 3,200,000 visitors annually.

Cheap, budget vacations are nothing but incredible, especially when you’re in Italy. To have the best affordable travel experience in Italy, make time for some unique, challenging, or inspiring activities. Adding a tour to your travel plan promises a one-of-a kind adventure that will make your cheap vacation in Italy unforgettable. Fortunately, you'll find plenty of budget-friendly tours and cheap holiday deals in Italy.

At the end of the day, you will drive to the city of Florence. Florence is another cheap travel destination in Italy where you have access to hotels, restaurants, bars, and other conveniences.

After a long day of driving and exploring some of the best attractions a budget vacation in Italy can afford, treat yourself to a hearty meal. You’ll find many great restaurants in Florence that offer delicious food to help keep you going.

One restaurant we recommend you try in Florence is Ristorante Paoli. This restaurant provides good food and service and has an average rating of 4.9 out of 5 stars from 6,031 customers.

When talking about the best restaurants in Florence, Osteria Vecchio Cancello is a name locals often mention. This local favorite offers a variety of options, helping it earn an average of 4.8 out of 5 stars from 1,589 diners.

Another restaurant worth trying is Ristorante Oliviero 1962. Many locals and cheap holiday goers in Florence enjoy dining at this restaurant. This restaurant has an average rating of 4.7 out of 5 stars from 1,046 customers.

As the day is coming to an end, stop at some of Florence’s best bars to celebrate this day of your road trip vacation in Italy. For example, you can visit Manifattura. Rated an average of 4.7 out of 5 stars by 509 customers, this bar is considered a favorite in the area.

Another great place to have a refreshing, celebratory drink is Caffe Concerto Paszkowski. This popular bar in Florence has an average rating of 4.3 out of 5 stars from 4,000 bar-goers.

You can also go to Ristorante Buca Mario as an alternative. More than a bar, the popular Ristorante Buca Mario is also a place for fun or relaxation. Around 1,879 customers have given this city bar an average rating of 4.4 out of 5 stars.

Raise your glass in celebration of your incredible road trip adventure and cheap holiday experience in Italy!

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Experiences

Day 4 – Milan

Day 4

Day 4 – Milan

  • Florence
  • Milan
  • More

Drive 309 km, 4 hours 7 min

  • Piazza della Signoria
  • Cathedral of Santa Maria del Fiore
  • Ponte Vecchio
  • Piazzale Michelangelo
  • More

On day 4 of your road trip through popular and cheap vacation spots across Italy, you’ll experience two places in one day. You’ll start your day in Florence and end your day in the city of Milan, where you'll stay for 1 night. How much time you’ll spend in each location is up to you.

One of the best places to visit in Florence is the amazing piazza della Signoria. This travel destination is a square that has been rated an average of 4.8 out of 5 stars by 66,956 visitors.

This day is also your chance to stop at the incredible Cathedral of Santa Maria del Fiore. Rated 4.8 out of 5 stars by 76,359 travelers, a visit to this well-known church and sightseeing spot in Florence is likely to make your vacation in Italy even more memorable.

Another unforgettable sight in Florence is the outstanding Ponte Vecchio. This deck arch bridge has an average rating of 4.7 out of 5 stars from 118,099 visitors.

To make the most of your day in this cheap holiday destination in Italy, drop by the popular piazzale Michelangelo. This attraction, an amazing square, has been rated 4.8 out of 5 stars by 77,744 travelers.

Cheap, budget vacations are nothing but incredible, especially when you’re in Italy. To have the best affordable travel experience in Italy, make time for some unique, challenging, or inspiring activities. Adding a tour to your travel plan promises a one-of-a kind adventure that will make your cheap vacation in Italy unforgettable. Fortunately, you'll find plenty of budget-friendly tours and cheap holiday deals in Italy.

At the end of the day, you will drive to the city of Milan. Milan is another cheap travel destination in Italy where you have access to hotels, restaurants, bars, and other conveniences.

After a long day of driving and exploring some of the best attractions a budget vacation in Italy can afford, treat yourself to a hearty meal. You’ll find many great restaurants in Milan that offer delicious food to help keep you going.

One restaurant we recommend you try in Milan is Primè. This restaurant provides good food and service and has an average rating of 4.3 out of 5 stars from 1,184 customers.

When talking about the best restaurants in Milan, da Vic is a name locals often mention. This local favorite offers a variety of options, helping it earn an average of 4.6 out of 5 stars from 557 diners.

Another restaurant worth trying is Nero 9. Many locals and cheap holiday goers in Milan enjoy dining at this restaurant. This restaurant has an average rating of 4.5 out of 5 stars from 573 customers.

As the day is coming to an end, stop at some of Milan’s best bars to celebrate this day of your road trip vacation in Italy. For example, you can visit Bar Frida. Rated an average of 4.1 out of 5 stars by 4,527 customers, this bar is considered a favorite in the area.

Another great place to have a refreshing, celebratory drink is BhangraBar. This popular bar in Milan has an average rating of 4 out of 5 stars from 4,036 bar-goers.

You can also go to Camparino in Galleria as an alternative. More than a bar, the popular Camparino in Galleria is also a place for fun or relaxation. Around 1,473 customers have given this city bar an average rating of 4.4 out of 5 stars.

Raise your glass in celebration of your incredible road trip adventure and cheap holiday experience in Italy!

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Experiences

Day 5 – Milan - departure day

Day 5

Day 5 – Milan - departure day

  • Milan - Departure day
  • More
  • Arch of Peace
  • More

It’s soon time to say goodbye to Italy as your road trip vacation is about to end. Day 5 is your departure day and your last chance to capture the beauty of Milan.

Depending on how much time you have before your flight back home, we recommend doing some last-minute shopping or sightseeing to make the most of your cheap holiday experience in Italy.

If you'd rather pass time visiting some attractions, this is your chance to go to places you may not have had the chance to explore yet.

One fantastic attraction you could visit on your last day in Milan is the remarkable Arch of Peace. This monument and popular place of interest has an average rating of 4.6 out of 5 stars from 27,502 visitors.

If you have an appetite for one last delicious meal in Milan, consider a top-rated restaurant like Bice Restaurant. This restaurant has a menu of appetizing and affordable meals and is rated at an average of 4.3 out of 5 stars by 579 customers.

Rosa Grand is an excellent alternative if you feel like eating something else. This restaurant serves a variety of savory and budget-friendly dishes and has an average rating of 4.4 out of 5 stars from 2,394 customers.

Another popular restaurant you could check out is Radisson Blu Hotel Milan. Rated an average of 4.3 out of 5 stars by 1,871 customers, this restaurant is a great place to enjoy meals that will remind you of Italy and your fun memories in Milan.

You’ll then say farewell to Milan and begin your journey home. You’ll leave filled with unforgettable memories from your terrific and affordable travel experiences in Italy!

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Experiences

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