5-Day Italy Self-Drive Road Trip With Itinerary from Florence traveling north to Venice and Milan

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Photo of Florence Aerial View of Ponte Vecchio Bridge during Beautiful Sunny Day, Italy.
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Escape the ordinary with this exciting 5-day road trip through Italy. Explore diverse landscapes, discover lively cities, and prepare for an unforgettable journey!

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. You will spend 2 nights in Florence, 1 night in Venice, and 1 night in Milan. 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 Florence, 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. Piazza San Marco and Rialto Bridge are just a couple of the bucket-list attractions that await your discovery.

As you hit the open road and drive through Florence, Venice, Milan, 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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Day1

Day 1

  • Florence - Arrival day
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  • piazzale Michelangelo
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Your road trip adventure in Italy begins as soon as you reach Florence and pick up your car. You’ll stay here for 1 night and explore what to see in Florence, sample the local cuisine, and choose from a curated selection of the best hotels and places to stay in the city.

Florence 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 Piazzale Michelangelo. 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.

As afternoon approaches, head to your chosen hotel in Florence. Check-in typically starts around 2 to 4 PM at hotels in Italy. We recommend staying at a central location for easy access to key areas 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 Florence, it's often a good idea to reserve a table in advance.

Enjoy a delicious meal at Ristorante Oliviero 1962, a highly-rated dining destination in Florence. If you're eager to try something different, consider Di Poneta Novoli, another top spot with a tantalizing menu. You might also want to secure a reservation at Caffe San Firenze. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

Cap off your dinner by heading to Manifattura, ideal for a leisurely evening with a drink in hand. Se·sto On Arno Rooftop Bar is another bar that offers an enjoyable setting. Similarly, Il Vinile is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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Day2

Day 2

  • Florence
  • Venice
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Drive 257 km, 3 hours 12 min

  • piazza della Signoria
  • Uffizi Gallery
  • Ponte Vecchio
  • Cathedral of Santa Maria del Fiore
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Your itinerary for day 2 of your road trip in Italy includes 1 stop and features some of the highlights of Florence. At the end of the day, enjoy the comforts of a top-rated hotel in Venice, where you'll spend 1 night.

Visiting Piazza Della Signoria is always a good idea. This spectacular public square is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the picture-perfect wonders of Uffizi Gallery, a must-see art gallery 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 Ponte Vecchio. This iconic historical landmark offers an enriching experience. For a change of pace, head to Cathedral Of Santa Maria Del Fiore, where you can take in UNESCO world heritage-designated features.

At the end of the day, you will drive to Venice, 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 Venice's best restaurants.

Dive into a culinary adventure like no other in Venice by booking a table at Local. This popular restaurant holds 1 Michelin star and offers an exceptional menu of contemporary cuisine. For another dining option, venture to Wistèria, celebrated for its delectable contemporary and venetian menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Quadri, a top local restaurant known for its tantalizing modern menu. With a 1-star Michelin recognition, it promises an exceptional dining experience not to be missed.

Following your dinner, dive into the local bar culture at Al Parlamento. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to The Caffe Rosso, the perfect place for those looking to experience the best of the nightlife. Similarly, Adagio 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 Italy.

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Day3

Day 3

  • Venice
  • Milan
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Drive 266 km, 3 hours 13 min

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

Dive into day 3 of your remarkable road trip in Italy. Today you'll explore 1 destination, including Venice. At the end of the day, you’ll unwind at one of the finest accommodations in Milan, where you'll spend 1 night.

Your adventure in Venice is only getting started when you visit Rialto Bridge, a timeless local hot spot. Another notable attraction to explore is Piazza San Marco. This world-famous public square is known for its visually striking appeal.

After soaking in the highlights of these sights, take some time to wander Venice's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Doge's Palace. This symbolic palace offers a fascinating experience that many visitors find memorable. Bridge Of Sighs is also worth visiting.

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.

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

Begin your culinary exploration in Milan by securing a reservation at Enrico Bartolini al Mudec. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another dining delight, visit Seta by Antonio Guida, celebrated for its delectable international and contemporary menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Il Luogo Aimo e Nadia, a top local spot known for its tantalizing italian contemporary and modern menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

Continue your lively evening at Nottingham Forest, a perfect place for winding down or revving up the night, depending on which mood you’re in. Armani/bamboo Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Mag Cafe ensures a night out tailored to your taste.

Raise your glass to another unforgettable day in Italy!

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Day4

Day 4

  • Milan
  • Bologna
  • Florence
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Drive 322 km, 3 hours 53 min

  • Duomo di Milano
  • Galleria Vittorio Emanuele II
  • Ducati Museum
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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 2 places, which are Milan and Bologna. At the end of the day, you will retreat to the hotel of your choice in Florence, where will spend 1 night.

Enjoy all that Duomo Di Milano Museum has to offer. This is a world-famous church you should not miss. Another must-see is Galleria Vittorio Emanuele Ii, an extraordinary shopping mall in Milan.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Bologna may take around 2 hours 17 min. Upon your arrival in Bologna, you’ll be greeted with the opportunity to do some sightseeing and exploring.

One of our top recommendations for your sightseeing is Ducati Museum. Spend some time admiring the historic features of the museum before you continue to your next stop.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. 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 Florence, it's often a good idea to reserve a table in advance.

Start your culinary exploration in Florence by securing a reservation at Enoteca Pinchiorri. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of italian contemporary cuisine. For another dining delight, visit Santa Elisabetta, celebrated for its delectable creative and mediterranean menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Gucci Osteria da Massimo Bottura, a top local spot known for its tantalizing italian contemporary and international menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

Round off your dining experience by visiting Bar 50 Rosso, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bitter Bar, a bar catering to every mood and preference. Archea Brewery likewise offers a unique atmosphere, perfect for a memorable night out.

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

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Day5

Day 5

  • Florence - Departure day
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  • Oltrarno
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Day 5 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Florence before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

One of the best things to do on your last day is to explore Oltrarno, a neighborhood that you shouldn't miss while in Florence. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.

Make the most of your final day in Italy by visiting Florence’s iconic markets and shopping establishments in the buzzing Mercato Centrale. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing vacation.

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

If you're eager to try something different, consider Agricola Toscana, another top spot with a tantalizing menu.

You’ll then say farewell to Florence. 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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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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