4-Day Italy Self-Drive Road Trip With Itinerary from Milan to Florence

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Escape the ordinary with this exciting 4-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 2 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 Cathedral Of Santa Maria Del Fiore.

As you hit the open road and drive through Milan, Como, 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!

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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
La Scala
Duomo di MilanoPorta TorreUffizi GalleryPonte Vecchiopiazza della Signoria
Cathedral of Santa Maria del FiorePiazza del Duomo, PisaLeaning Tower of PisaSaint Regolo Bulwark
Castello Sforzesco

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Day 1

Day 1

  • Milan - Arrival day
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  • La Scala
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Your road trip adventure in Italy begins as soon as you reach Milan and pick up your car. You’ll stay in Milan for 1 night 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 La Scala, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

Find your way to your hotel in Milan. We recommend choosing a hotel in a central location for easy exploring. Check-in typically starts between 2 and 4 PM at hotels in Italy. Settle in and make plans for the evening.

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.

After your meal, keep the night alive at a bar like Nottingham Forest, known for its lively atmosphere. Armani/bamboo Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Mag Cafe offers an excellent atmosphere for those looking to amp up the evening.

Raise a toast to the start of your 4-day road trip in Italy!

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Day 2

Day 2

  • Milan
  • Florence
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Drive 408 km, 5 hours 3 min

  • Duomo di Milano
  • Porta Torre
  • Uffizi Gallery
  • Ponte Vecchio
  • piazza della Signoria
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On day 2 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Milan, Como, and Florence. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Bring your curiosity for today’s adventure around Milan. Some of the city’s most loved attractions await. Duomo Di Milano Museum is the perfect place to start. This church is one of the most wondrous places to visit in Milan. Next, head to Porta Torre, an increasingly popular monument, known for its culturally significant features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Uffizi Gallery. This picture-perfect art gallery offers a unique experience that is highly recommended. Meanwhile, Ponte Vecchio adds its own distinct charm to your journey. Finish your day with a visit to Piazza Della Signoria, a history-steeped public square in Milan.

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.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Enjoy a lovely dining experience at Ristorante Oliviero 1962, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Di Poneta Novoli, 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 Caffe San Firenze. It’s yet another ideal choice to enhance your time in Florence tonight.

Continue your lively evening at Manifattura, a perfect place for winding down or revving up the night, depending on which mood you’re in. Se·sto On Arno Rooftop Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Il Vinile ensures a night out tailored to your taste.

Take some time to reflect on your day and savor another beautiful night in Italy.

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Day 3

Day 3

  • Florence
  • Milan
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Drive 390 km, 5 hours 9 min

  • Cathedral of Santa Maria del Fiore
  • Piazza del Duomo, Pisa
  • Leaning Tower of Pisa
  • Saint Regolo Bulwark
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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 3 vibrant destinations - Florence, Pisa, and Lucca. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Milan. You will spend 1 night here for some well-deserved relaxation.

Immerse yourself in Florence’s rich culture with today's sightseeing itinerary. Start your journey at Cathedral Of Santa Maria Del Fiore. This UNESCO world heritage-designated church is sure to ignite your curiosity. Next, dive into the UNESCO world heritage-designated features of Piazza Del Duomo, Pisa, a must-visit public square in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Leaning Tower Of Pisa, a timeless monument. For a change of scene, check out Saint Regolo Bulwark, known for its culturally significant features.

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

Savor the flavors at Dessert Bar Milano, a top pick for dinner tonight. Alternatively, Radisson Blu Hotel Milan beckons with its unique menu offerings. Also, consider Ristorante Qui Si Mangia. With its consistent customer satisfaction, it’s an excellent option for dining in Milan tonight.

Continue the enjoyment post-dinner at Kilburn Cocktail Bar Milano, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bar Frida offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out The Friends Pub Milano. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Raise your glass to another unforgettable day in Italy!

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Day 4

Day 4

  • Milan - Departure day
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  • Castello Sforzesco
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Day 4 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 Sforzesco Castle Art Library. This famous castle 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 Galleria Vittorio Emanuele II. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy. Elevate your style with pieces from high-end retail stores.

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

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!

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