9-Day Italy Self-Drive Road Trip With Itinerary from Milan traveling east to Como, 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 3 nights in Milan, 1 night in Como, 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, Ossuccio, Colonno, Como, Verona, Venice, Murano, Florence, Pisa, San Gimignano, Riomaggiore, and Manarola, 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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Your road trip adventure in Italy begins as soon as you reach Milan and pick up your car. You’ll stay here for 2 nights and explore what to see in Milan, 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 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.

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.

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.

Unwind after your meal by stepping into Nottingham Forest. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Armani/bamboo Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Mag Cafe, another top-rated bar in the area.

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

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Day2

Day 2

  • Milan
  • More

Drive 4 km, 38 min

  • Sempione Park
  • Castello Sforzesco
  • Galleria Vittorio Emanuele II
  • Duomo di Milano
  • Brera
  • Navigli
  • More

Day 2 offers an itinerary packed with the best things to see in Milan. You’ll stay in Milan for 1 night more, offering you enough time to explore at a relaxed pace.

Don’t miss Brera today, a must-see neighborhood that offers a glimpse into the city’s vibrant character. Take your time to explore its best features, and enjoy the convenience of nearby top-rated landmarks. While you’re in the area, consider visiting Navigli, another neighborhood that adds to the charm of Milan.

Catch Parco Sempione before the crowds roll in. This instagrammable park is sure to ignite your curiosity. Next, dive into the culturally significant features of Sforzesco Castle Art Library, a must-visit castle 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 Galleria Vittorio Emanuele Ii, an impressive shopping mall. For a change of scene, check out Duomo Di Milano Museum, known for its majestic features.

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.

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 Dessert Bar Milano, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Radisson Blu Hotel Milan, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Qui Si Mangia. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

Extend your evening after a delightful meal by visiting Kilburn Cocktail Bar Milano, which offers the perfect atmosphere for a night out. Moreover, Bar Frida is another popular option for a drink or two. Likewise, The Friends Pub Milano also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Savor another day of unforgettable experiences in Italy!

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Day3

Day 3

  • Milan
  • Como
  • More

Drive 174 km, 3 hours 45 min

  • Orrido di Bellano
  • Villa del Balbianello
  • Sacro Monte della Beata Vergine del Soccorso - Ossuccio (co)
  • Greenway del Lago di Como
  • More

Dive into day 3 of your remarkable road trip in Italy. Today you'll explore 3 destinations, including Lenno, Ossuccio, and Colonno. At the end of the day, you’ll unwind at one of the finest accommodations in Como, where you'll spend 1 night.

Awaiting your discovery is the captivating Orrido Di Bellano, a romantic canyon in Milan. Next, go to Villa Del Balbianello.

After visiting Orrido Di Bellano and Villa Del Balbianello, have a stroll along Milan's streets and take in the local charm. Continue your sightseeing by heading to Sacro Monte Della Beata Vergine Del Soccorso - Ossuccio (co). This visually striking church offers a unique experience. Greenway Del Lago Di Como is another noteworthy attraction worthwhile a visit.

At the end of the day, you will drive to Como, 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 Como. Enjoy a relaxing evening as you savor delicious local cuisine.

Make sure to reserve a table at La Vita è Bella Ristorante - Insalateria, an iconic dining spot in Como. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world.

If you’re not ready to end the night just yet, Fresco Cocktail Shop offers a perfect venue to relax and savor a drink. Similarly, Bar Il Cortiletto is well-suited for those looking to unwind in a social setting. Bar Pinocchio is another excellent spot to enjoy a nightcap after a delightful meal.

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

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Day4

Day 4

  • Como
  • Venice
  • More

Drive 319 km, 4 hours 12 min

  • Castelvecchio Museum
  • Castelvecchio Bridge
  • Verona Arena
  • Porta Borsari
  • piazza delle Erbe
  • Scaliger Tombs
  • More

On day 4 of your road trip in Italy, your travel plans include 1 stop at the most scenic, wondrous, and interesting places in the region. Verona are on today's agenda. In the evening, you’ll end up in Venice, where you will stay for 2 nights.

To truly experience Como, make sure to drop by Castelvecchio Museum. This well-known museum is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Castelvecchio Bridge, one of the city’s best highlights.

Next, check out Verona Arena, one of the most world-famous places to see in Como. This stadium is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Porta Borsari. Wander around and soak in the symbolic atmosphere this historical landmark offers. Then, head to Piazza Delle Erbe, a top-rated public square that adds another dimension to your day. Finally, visit the worthwhile Scaliger Tombs, the last of our attraction recommendations for today.

After soaking up all the sights on today's itinerary, you'll be ready to head to your accommodation in Venice. Venice offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go 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 Venice, it's often a good idea to reserve a table in advance.

Enjoy a delicious meal at Bauer Hotel, a highly-rated dining destination in Venice. If you're eager to try something different, consider L'Osteria Le Guglie, another top spot with a tantalizing menu. You might also want to secure a reservation at Corner Pub. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Venice this evening.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Al Parlamento, known for its inviting atmosphere. The Caffe Rosso is another great option if you’re looking for a place to get the night started. Similarly, Adagio provides a great setting to enjoy the night away.

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

Wake up to day 5 of your road trip in Italy. On this day, you’ll embark on an exciting expedition discovering the enchanting sights and activities of Venice and Murano. With 1 night to stay in Venice, we encourage you to seize the day and discover the unexplored beauty of the city’s surroundings!

Venice is brimming with adventures.

Look forward to a unique sightseeing adventure at the timeless Rialto Bridge and allow yourself time to explore. Just a short distance away you'll find your next stop, Piazza San Marco, an UNESCO world heritage-listed public square that draws visitors from far and near.

Continue your journey to St Mark's Basilica, one of the city’s most well-known spots that you shouldn’t miss. Another great site to visit is the well-known Doge's Palace. When you're finished at the palace, Bridge Of Sighs awaits your visit. This monument is an enchanting highlight on today's itinerary. Last up is a handicraft store - the curiosity-inducing Murano.

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

Venice 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 Venice.

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

Continue your evening by exploring the vibrant nightlife scene at Il Mercante, a prime destination for a thrilling night out. Also, don’t forget to check out The Irish Pub Venezia, a bar that offers unique local touches. Likewise, Ai Stagneri provides an excellent alternative for a fun evening.

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

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Day6

Day 6

  • Venice
  • Florence
  • More

Drive 263 km, 3 hours 39 min

  • piazzale Michelangelo
  • Basilica of Santa Croce in Florence
  • Uffizi Gallery
  • Ponte Vecchio
  • Piazza della Repubblica
  • piazza della Signoria
  • More

Your itinerary for day 6 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 Florence, where you'll spend 2 nights.

Check out the famous observation deck, Piazzale Michelangelo. Afterward, continue to Basilica Of Santa Croce In Florence, a church every traveler should visit. As you explore Venice’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Uffizi Gallery. This spectacular art gallery is an essential stop. Following that, head to Ponte Vecchio, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Della Repubblica, a well-known public square in the city. Finally, end your day with a visit to Piazza Della Signoria, a history-steeped public square that offers the perfect conclusion to your sightseeing of the day.

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.

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.

Make sure to reserve a table at Ristorante Oliviero 1962, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Di Poneta Novoli, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Caffe San Firenze, a hidden gem nestled in Florence. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

Explore the vibrant nightlife at Manifattura after your meal, a hub for lively evenings and memorable moments. Or, head to Se·sto On Arno Rooftop Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Il Vinile 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

  • Florence
  • More

Drive 223 km, 3 hours 51 min

  • Leaning Tower of Pisa
  • Piazza del Duomo, Pisa
  • Pisa Cathedral
  • Piazza del Duomo, San Gimignano
  • SanGimignano1300
  • 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 Pisa and San Gimignano.

Your adventure in Florence is only getting started when you visit Leaning Tower Of Pisa, a wondrous local hot spot. Another notable attraction to explore is Piazza Del Duomo, Pisa. This world-famous public square is known for its culturally significant appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Pisa Cathedral. This breathtaking church offers a fascinating experience that many visitors find memorable. Piazza Del Duomo is also worth visiting, along with Sangimignano1300. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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

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

Treat yourself to a delicious dinner at Ditta Artigianale, an excellent option for tonight's dining. Looking for something different? Trattoria Da Burde offers a tantalizing alternative with its diverse menu. And don’t miss Casa Toscana. Known for great service, it’s a fantastic choice for tonight in Florence.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar 50 Rosso, known for its inviting atmosphere. Bitter Bar is another great option if you’re looking for a place to get the night started. Similarly, Archea Brewery provides a great setting to enjoy the night away.

Relax and look forward to more memorable moments to come!

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Day8

Day 8

  • Florence
  • Milan
  • More

Drive 411 km, 6 hours 2 min

  • Castle of Riomaggiore
  • Riomaggiore
  • Manarola Overlook Viewpoint
  • More

On day 8 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, including Riomaggiore and Manarola. When you’re not sightseeing, take time to relax at your chosen hotel in Milan, where you’ll be staying for 1 night.

Make a stop at Castle Of Riomaggiore. This locally appreciated castle is a must-visit for travelers looking for a unique holiday experience. Make your way to Riomaggiore located in Florence for another exciting encounter.

Next, immerse yourself in the setting of Manarola Overlook Viewpoint. Its serene features will captivate you.

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.

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

Treat yourself to a wonderful meal at Bice Restaurant, a top-rated dining spot in Milan. If you're in the mood for something new, try Alto Ristorante, another premier location with a delectable menu. You might also want to book a table at Nero 9. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Milan.

Extend your evening after a delightful meal by visiting Bhangrabar, which offers the perfect atmosphere for a night out. Moreover, Rufus Cocktail Bar is another popular option for a drink or two. Likewise, Ostello Bello Grande also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise your glass to another unforgettable day 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, begin at Pinacoteca Di Brera. This captivating art gallery is a hotspot among locals.

Take some time to indulge in shopping at Milan’s popular marketplace, Via della Moscova. Look for keepsakes or souvenirs to remind you of your trip. Browse boutiques to find unique and stylish fashion pieces. Wrap up your shopping with a drink and some pastries at a cozy cafe.

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 in the mood to try something new, consider Pasticceria San Carlo, another top spot with a mouthwatering 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.
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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