9-Day Italy Self-Drive Road Trip With Itinerary from Milan to Venice and Florence

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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 9-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 4 nights in Milan, 2 nights in Venice, and 2 nights 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 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, Lenno, Verona, Venice, Murano, Florence, Siena, San Gimignano, 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, 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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  • Brera
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Say hello to Milan! Your exciting road trip through Italy is just about to start. Navigating the top places to see in the region is a breeze with a car. The rental vehicle of your choice will be ready for pickup upon your arrival in the city. You will stay in Milan for 3 nights before you continue your adventure!

Milan is a beautiful city with plenty to discover. 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.

When you're ready for some downtime, make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Milan. Make yourself at home and unwind before heading out again.

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.

Make sure to reserve a table at Hotel Morfeo Milano, an iconic dining spot in Milan. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Contraste, a popular restaurant in Milan. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of UNAHOTELS Galles Milano, a hidden gem nestled in Milan. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Nottingham Forest, known for its inviting atmosphere. Armani/bamboo Bar is another great option if you’re looking for a place to get the night started. Similarly, Mag Cafe provides a great setting to enjoy the night away.

Raise a toast to the start of your 9-day road trip in Italy!

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Day2

Day 2

  • Milan
  • More

Drive 5 km, 50 min

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

Day 2 of your road trip will take you to the best attractions Milan has to offer. Cherish the 2 nights you have left in the city and use the provided itinerary to discover what to see in Milan.

Whether you decide to explore Milan on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Duomo Di Milano Museum is perfect for a self-paced visit during the day. This romantic church is sure to impress. Next on your list is Galleria Vittorio Emanuele Ii, another must-visit landmark and impressive shopping mall renowned for its visually striking features.

While exploring and sightseeing, take time to savor the culture of Milan by sampling some local delicacies. When you’re ready for more sightseeing, head to La Scala. This respected opera house is an essential place to visit for anyone looking for the full Milan experience. We also recommend visiting Sforzesco Castle Art Library, a spectacular castle. Nearby, you'll also find Parco Sempione, ready to add charm to your journey. End your self-guided sightseeing tour with a stop at Arch Of Peace and wrap up your day with its masterful appeal.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

After a day of adventure, treat yourself to an exquisite dinner at one of Milan's best restaurants.

Treat yourself to a delicious dinner at Dessert Bar Milano, an excellent option for tonight's dining. Looking for something different? Radisson Blu Hotel Milan offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Qui Si Mangia. Known for great service, it’s a fantastic choice for tonight in Milan.

Cap off your dinner by heading to Kilburn Cocktail Bar Milano, ideal for a leisurely evening with a drink in hand. Bar Frida is another bar that offers an enjoyable setting. Similarly, The Friends Pub Milano is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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Day3

Day 3

  • Milan
  • More

Drive 160 km, 2 hours 59 min

  • Villa del Balbianello
  • Villa Carlotta
  • Botanical Garden of Villa Carlotta
  • More

On day 3 of your road trip in Italy, you’ll start and end your day in Milan, but spend the day exploring what’s beyond the city. Since you still have 1 night to spend in Milan, there’s no need to rush. Experience Lenno and Rogaro to the fullest today with this curated day itinerary.

Make a stop at Villa Del Balbianello. This frequently visited villa is a must-visit for travelers looking for a unique holiday experience. Make your way to Villa Carlotta (lake Como) located in Milan for another exciting encounter.

Next, immerse yourself in the setting of Botanical Garden Of Villa Carlotta. Its noteworthy features will captivate you.

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

Milan 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 Milan.

Enjoy a delicious meal at Bice Restaurant, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Alto Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at Nero 9. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

Continue your evening by exploring the vibrant nightlife scene at Bhangrabar, a prime destination for a thrilling night out. Also, don’t forget to check out Rufus Cocktail Bar, a bar that offers unique local touches. Likewise, Ostello Bello Grande provides an excellent alternative for a fun evening.

Savor another day of unforgettable experiences in Italy!

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Day4

Day 4

  • Milan
  • Venice
  • More

Drive 278 km, 3 hours 56 min

  • Castelvecchio Museum
  • Castelvecchio Bridge
  • Verona Arena
  • piazza delle Erbe
  • Fontana Madonna Verona
  • piazza dei Signori
  • More

Your itinerary for day 4 of your road trip in Italy includes 1 stop and features some of the highlights of Verona. At the end of the day, enjoy the comforts of a top-rated hotel in Venice, where you'll spend 2 nights.

Start your day at Castelvecchio Museum. This standout museum is a captivating place to see in Milan. Then, wander over to Castelvecchio Bridge. If visually striking sites excite you, this monument will be right up your alley. Nearby, you’ll also find Verona Arena. This visually striking stadium is a favorite among visitors.

Milan offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Piazza Delle Erbe is a popular spot in the city that will captivate you with its unique charm. When you’re done at the public square, don’t forget to check out the history-steeped Fontana Madonna Verona. Take a moment to appreciate the fascinating details of this increasingly popular monument. Wrap up your self-guided tour of Milan's top attractions with a visit to Piazza Dei Signori.

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.

Have a fantastic dining experience at Bauer Hotel, a highly recommended choice for tonight's dinner. If you're looking to mix things up, L'Osteria Le Guglie offers an enticing alternative with its varied menu. Additionally, Corner Pub is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Venice.

Let the evening flow smoothly from dinner to drinks at Al Parlamento, a top-rated bar in the area. For other recommendations, The Caffe Rosso provides a perfect setting for rounding out your night with style and great drinks. Likewise, Adagio offers a memorable night with diverse drink options and excellent service.

Say good night to Venice and look forward to another great day of your road trip in Italy!

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Day5

Day 5

  • Venice
  • More

Drive 14 km, 31 min

  • Rialto Bridge
  • Piazza San Marco
  • St Mark's Basilica
  • Doge's Palace
  • Bridge of Sighs
  • Murano
  • More

On day 5 of your road trip, you’ll start and end your day in Venice, where you have 1 night left to stay.

Your adventure in Venice is only getting started when you visit Rialto Bridge, an iconic local hot spot. Another notable attraction to explore is Piazza San Marco. This globally renowned public square is known for its culturally significant 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 St Mark's Basilica. This majestic church 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. End your day at Murano. This frequently visited handicraft store provides a fitting finale to your sightseeing.

When you’re done exploring for the day, you’ll return to Venice and your accommodation.

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

Treat yourself to a delicious dinner at Generator Venice, an excellent option for tonight's dining. Looking for something different? Nevodi offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante La Piazza. Known for great service, it’s a fantastic choice for tonight in Venice.

Keep the evening going at Il Mercante, a great choice for enjoying the after-dinner hours with a drink. You could also go to The Irish Pub Venezia, which offers a similarly pleasant setting and great drinks. Another option is Ai Stagneri, which provides an inviting environment for unwinding after a busy day out.

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

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Day6

Day 6

  • Venice
  • Florence
  • More

Drive 262 km, 3 hours 25 min

  • Basilica of Santa Croce in Florence
  • Uffizi Gallery
  • Ponte Vecchio
  • Piazza della Repubblica
  • Cathedral of Santa Maria del Fiore
  • piazza della Signoria
  • More

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, including Florence. When you’re not sightseeing, take time to relax at your chosen hotel in Florence, where you’ll be staying for 2 nights.

Let Basilica Of Santa Croce In Florence set the tone for the day. Spend some time admiring this respected church before continuing your journey. Uffizi Gallery is your next stop. This top-rated art gallery is one of the best-rated sights in Venice.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Ponte Vecchio. This history-steeped historical landmark is a sight to behold. To round off your sightseeing experience, visit Piazza Della Repubblica and Cathedral Of Santa Maria Del Fiore. If time allows, end your day with Piazza Della Signoria, a romantic public square that offers a memorable conclusion to your exploration.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Florence. Florence 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 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.

Following your dinner, dive into the local bar culture at Manifattura. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Se·sto On Arno Rooftop Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Il Vinile provides excellent drinks and a great atmosphere, ensuring a memorable night out.

Raise your glass to another unforgettable day in Italy!

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Day7

Day 7

  • Florence
  • More

Drive 251 km, 4 hours 23 min

  • piazza del Campo
  • Siena Cathedral
  • Villa Calcinaia - Conti Capponi
  • SanGimignano1300
  • Piazza del Duomo, San Gimignano
  • More

Greet day 7 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, Greti, and San Gimignano.

Check out the top-rated public square, Piazza Del Campo. Afterward, continue to Siena Cathedral, a church every traveler should visit. As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Villa Calcinaia - Conti Capponi. This often recommended winery is an essential stop. Following that, head to Sangimignano1300, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Del Duomo, an up-and-coming public square in the city.

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

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 delicious meal at Ditta Artigianale, a highly-rated dining destination in Florence. If you're eager to try something different, consider Trattoria Da Burde, another top spot with a tantalizing menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence this evening.

Unwind after your meal by stepping into Bar 50 Rosso. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bitter Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Archea Brewery, another top-rated bar in the area.

Raise your glass to another unforgettable day in Italy!

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Day8

Day 8

  • Florence
  • Milan
  • More

Drive 383 km, 5 hours

  • Pisa Cathedral
  • Piazza del Duomo, Pisa
  • Leaning Tower of Pisa
  • Piazza dell'Anfiteatro
  • More

Experience an unparalleled adventure on day 8 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 2 places, which are Pisa and Lucca. At the end of the day, you will retreat to the hotel of your choice in Milan, where will spend 1 night.

One of the most up-and-coming attractions included on the itinerary is Pisa Cathedral. This picture-perfect church will help you start your sightseeing on top. Then, take a leisurely stroll to Piazza Del Duomo, Pisa and learn what makes this picture-perfect public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the world-famous Leaning Tower Of Pisa. After exploring the monument, head to Piazza Dell'anfiteatro. This well-known public square is a highlight in Florence.

When you’re done exploring for the day, you’ll drive to your hotel in Milan. Check in and relax before you head out to tour the city.

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.

Treat yourself to a wonderful meal at Ristorante la Brisa, a top-rated dining spot in Milan. If you're in the mood for something new, try Pasticceria San Carlo, another premier location with a delectable menu. You might also want to book a table at UNAHOTELS Cusani Milano. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Milan.

After savoring a delicious meal, step into the vibrant nightlife at Qc Termemilano, where the evening is just getting started. In the same way, Yguana Cafè offers a unique charm perfect for experiencing the local bar scene in Milan.

Savor another day of unforgettable experiences in Italy!

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Day9

Day 9

  • Milan - Departure day
  • More
  • Pinacoteca di Brera
  • More

Day 9 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, we recommend visiting Pinacoteca Di Brera, an eye-catching art gallery before you head out.

For a last-minute shopping spree in Milan, Via della Moscova is nearby. Enjoy a variety of retail stores, dining options, and essential services in one convenient location. Browse through boutiques to find unique and stylish fashion pieces to take home. When you need a break, visit a cafe and relax with a cup of coffee or tea.

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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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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