7-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling south to Venice, Florence, and Pisa

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Photo of Arch of Peace, or Arco della Pace, city gate in the centre of the Old Town of Milan in the sunny day, Lombardia, Italy.
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Escape the ordinary with this exciting 7-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 Milan, 1 night in Venice, 2 nights in Florence, and 1 night in Pisa. 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 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. 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 Milan, Venice, Florence, Siena, Pisa, and Genoa, 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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Day1

Day 1

  • Milan - Arrival day
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  • Piazza Gae Aulenti
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Welcome to Milan, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 1 night discovering what to see in Milan before embarking on the next leg of your journey.

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 Piazza Gae Aulenti. 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.

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.

Have a fantastic dining experience at Hotel Morfeo Milano, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Contraste offers an enticing alternative with its varied menu. Additionally, UNAHOTELS Galles Milano is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Milan.

Round off your dining experience by visiting Nottingham Forest, a prime location for a drink. Alternatively, explore the distinctive characteristics of Armani/bamboo Bar, a bar catering to every mood and preference. Mag Cafe likewise offers a unique atmosphere, perfect for a memorable night out.

Raise a toast to the start of your 7-day road trip in Italy!

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Day2

Day 2

  • Milan
  • Venice
  • More

Drive 267 km, 3 hours 26 min

  • Duomo di Milano
  • Galleria Vittorio Emanuele II
  • La Scala
  • Castello Sforzesco
  • Sempione Park
  • More

On day 2 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Milan. When you’re not sightseeing, take time to relax at your chosen hotel in Venice, where you’ll be staying for 1 night.

Awaiting your discovery is the wondrous Duomo Di Milano Museum, a history-steeped church in Milan. Next, go to Galleria Vittorio Emanuele Ii.

After visiting Duomo Di Milano Museum and Galleria Vittorio Emanuele Ii, have a stroll along Milan's streets and take in the local charm. Continue your sightseeing by heading to La Scala. This romantic opera house offers a unique experience. Sforzesco Castle Art Library is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Parco Sempione, one of the most eye-catching places to visit in Milan.

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.

Treat yourself to an extraordinary dining experience at Local, a 1-star Michelin restaurant offering an incredible contemporary menu. Alternatively, if your taste buds call for something different, Wistèria is one of the best restaurants for contemporary and venetian cuisine in Venice. This 1-star Michelin-awardee earns consistently high praises from guests. We also recommend checking out the menu at Quadri. As a top-rated establishment with 1 Michelin star, it is an ideal choice for modern cuisine in the city.

Round off your dining experience by visiting Al Parlamento, a prime location for a drink. Alternatively, explore the distinctive characteristics of The Caffe Rosso, a bar catering to every mood and preference. Adagio 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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Day3

Day 3

  • Venice
  • Florence
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Drive 260 km, 3 hours 15 min

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

On day 3 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Venice are on today's agenda. In the evening, you’ll end up in Florence, where you will stay for 2 nights.

Your adventure in Venice is only getting started when you visit Rialto Bridge, a timeless local hot spot. Another notable attraction to explore is Teatro La Fenice. This popular opera house 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 Piazza San Marco. This history-steeped public square offers a fascinating experience that many visitors find memorable. Doge's Palace is also worth visiting, along with Bridge Of Sighs. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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.

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

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.

If you’re not ready to end the night just yet, Manifattura offers a perfect venue to relax and savor a drink. Similarly, Se·sto On Arno Rooftop Bar is well-suited for those looking to unwind in a social setting. Il Vinile is another excellent spot to enjoy a nightcap after a delightful meal.

As the sun sets, rest up and recharge for the next leg of your road trip in Italy.

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Day4

Day 4

  • Florence
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Drive 160 km, 2 hours 56 min

  • piazza del Campo
  • Siena Cathedral
  • piazzale Michelangelo
  • Galleria dell'Accademia
  • Central Market
  • More

Greet day 4 of your road trip in Italy with a smile and start your day with a hearty breakfast. You have 1 night to stay in Florence, so get ready to make the most of your time in the region. On the agenda for this day, you’ll find only the best things to see and do in Siena and Florence.

Piazza Del Campo makes a great addition to your morning plans. This top-rated public square is a romantic place to see in Florence. Continue your discovery at Siena Cathedral, an inviting church with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Piazzale Michelangelo. This famous observation deck offers a romantic encounter with Florence. Next, make your way to Galleria Dell'accademia to add another highlight to your day. After that, visit Central Market, an interesting food market that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Florence.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Florence.

Florence is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Florence.

Enjoy a lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Florence tonight.

Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

Relax and look forward to more memorable moments to come!

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Day5

Day 5

  • Florence
  • Pisa
  • More

Drive 85 km, 1 hour 49 min

  • Cathedral of Santa Maria del Fiore
  • piazza della Signoria
  • Uffizi Gallery
  • Ponte Vecchio
  • The Boboli Gardens
  • More

Experience an unparalleled adventure on day 5 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 place, which are Florence. At the end of the day, you will retreat to the hotel of your choice in Pisa, where will spend 1 night.

Cathedral Of Santa Maria Del Fiore is an ideal stop early in the day. This widely recognized church is a must-visit in the city. When you’re ready for your next discovery, continue to Piazza Della Signoria, which may be one of the most noteworthy places you will experience today.

One of the best things about exploring Florence on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Uffizi Gallery, a famous art gallery in the city. If you’re up for more discoveries, don’t forget to reserve some time for Ponte Vecchio and The Boboli Gardens.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Pisa. Pisa offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

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

Savor the flavors at Anima di Grano Pizzeria Napoletana Pisa Italy, a top pick for dinner tonight. Alternatively, il Mercante beckons with its unique menu offerings. Also, consider La Ghiotteria. With its consistent customer satisfaction, it’s an excellent option for dining in Pisa tonight.

Continue the enjoyment post-dinner at Jeffer Cocktails & Friends, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Le Parisien Wine Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Las Volta Cocktailbar. 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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Day6

Day 6

  • Pisa
  • Milan
  • More

Drive 302 km, 3 hours 59 min

  • Leaning Tower of Pisa
  • Piazza del Duomo, Pisa
  • Pisa Cathedral
  • Priaruggia
  • More

Your itinerary for day 6 of your road trip in Italy includes 2 stops and features some of the highlights of Pisa and Genoa. At the end of the day, enjoy the comforts of a top-rated hotel in Milan, where you'll spend 1 night.

Start your day at Leaning Tower Of Pisa. This UNESCO world heritage-designated monument is a globally renowned place to see in Pisa. Then, wander over to Piazza Del Duomo, Pisa. If grand sites excite you, this public square will be right up your alley. Nearby, you’ll also find Pisa Cathedral. This grand church is a favorite among visitors.

Pisa offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Spiaggia Pubblica Di Priaruggia is a beloved spot in the city that will captivate you with its unique charm.

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.

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Milan. Enjoy a relaxing evening as you savor delicious local cuisine.

Have a memorable dining experience in Milan by booking a table at Enrico Bartolini al Mudec, a 3-star Michelin restaurant presenting an exceptional creative menu. For a different culinary experience in Milan, Seta by Antonio Guida shines as one of the top destinations, known for its delicious international and contemporary cuisine. This 2-star Michelin-awardee consistently earns high praises, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Il Luogo Aimo e Nadia is known as a top local spot in Milan for its delicious italian contemporary and modern cuisine. This 1-star Michelin awardee is a highly recommended choice for an unforgettable meal.

Explore the vibrant nightlife at Kilburn Cocktail Bar Milano after your meal, a hub for lively evenings and memorable moments. Or, head to Bar Frida for a great selection of flavorful drinks and a charming setting. Furthermore, The Friends Pub Milano is perfect for those looking to extend their night with a touch of local flavor.

Relax and recharge in preparation for another adventurous day in Italy!

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Day7

Day 7

  • Milan - Departure day
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  • Arch of Peace
  • More

Day 7 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 Arch Of Peace. This well-known monument is a hotspot among locals.

For a shopping spree in Milan, we recommend the lively Quadrilatero della Moda. Here, you'll find a range of shops you can browse for some souvenir shopping. Discover boutiques with stylish fashion choices to upgrade your wardrobe. You can also explore high-end shops for luxury items.

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 eager to try something different, consider Alto Ristorante, another top spot with a tantalizing 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!

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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.
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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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