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

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Explore the best of Italy on a 9-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Milan, Lenno, Ossuccio, Colonno, Como, Verona, Venice, Murano, Florence, Pisa, San Gimignano, Riomaggiore, and Manarola. This road trip itinerary in Italy seamlessly combines exploration with relaxation.

This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. 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 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. Piazza San Marco and Rialto Bridge are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Duomo Di Milano Museum, learn more about the unique Verona Arena, and immerse yourself in the vibrant atmosphere of Ponte Vecchio.

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, 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
Piazza Gae Aulenti
Sempione ParkCastello SforzescoGalleria Vittorio Emanuele IIDuomo di MilanoBreraNavigli
Orrido di BellanoVilla del BalbianelloSacro Monte della Beata Vergine del Soccorso - Ossuccio (co)Greenway del Lago di Como
Castelvecchio MuseumCastelvecchio BridgeVerona ArenaPorta Borsaripiazza delle ErbeScaliger Tombs
Rialto BridgePiazza San MarcoSt Mark's BasilicaDoge's PalaceBridge of SighsMurano
piazzale MichelangeloBasilica of Santa Croce in FlorenceUffizi GalleryPonte VecchioPiazza della Repubblicapiazza della Signoria

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Day 1

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 2 nights immersing yourself in Milan's charm 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, 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 delightful dinner at Hotel Morfeo Milano, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Contraste? It's another excellent option with a diverse menu. Consider reserving a table at UNAHOTELS Galles Milano as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Milan.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Nottingham Forest stands out as an excellent choice for a post-dinner cocktail. Alternatively, Armani/bamboo Bar offers an ideal atmosphere to enjoy the pleasures of the night. Mag Cafe is also a great option that provides a perfect setting for a relaxing evening.

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

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Day 2

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 of your road trip across Italy promises a magnificent time exploring Milan. You have 1 night left in Milan. Take the opportunity to experience more of the best attractions and activities in the city.

Don’t miss Brera in Milan 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.

Get ready for an exciting day in Milan. Today’s sightseeing agenda includes a park, a castle, a shopping mall, a church and much more! Begin your adventure at Parco Sempione. This is an extraordinary park you should not miss. Another must-see is Sforzesco Castle Art Library, a widely recognized castle in Milan.

When you’re ready for the next sight, head to Galleria Vittorio Emanuele Ii. From there, take a leisurely stroll to Duomo Di Milano Museum, another of the city’s timeless attractions.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As dinnertime approaches, it's time to head out for a bite to eat in Milan. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Have a fantastic dining experience at Dessert Bar Milano, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Radisson Blu Hotel Milan offers an enticing alternative with its varied menu. Additionally, Ristorante Qui Si Mangia is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Milan.

After your meal, keep the night alive at a bar like Kilburn Cocktail Bar Milano, known for its lively atmosphere. Bar Frida is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, The Friends Pub Milano offers an excellent atmosphere for those looking to amp up the evening.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

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Day 3

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

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 - Lenno, Ossuccio, and Colonno. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Como. You will spend 1 night here for some well-deserved relaxation.

Brace yourself for today’s incredible lineup of attractions in Milan, featuring family-friendly attractions, romantic experiences, and natural wonders. Start at Orrido Di Bellano, a captivating canyon in the village.

There are many interesting places to see in Milan, and when you are ready for more, go to Sacro Monte Della Beata Vergine Del Soccorso - Ossuccio (co). This is one of the village’s most underrated culturally significant spots of interest. After exploring the church, visit the often recommended Greenway Del Lago Di Como.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Como. Como 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 Como's most popular restaurants, and connect with friendly locals for an authentic adventure.

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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Fresco Cocktail Shop stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar Il Cortiletto offers an ideal atmosphere to enjoy the pleasures of the night. Bar Pinocchio is also a great option that provides a perfect setting for a relaxing evening.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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Day 4

Day 4

  • Como
  • Venice
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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, 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 Verona. In the evening, you’ll end up in Venice, where you will stay for 2 nights.

Today’s well-planned self-sightseeing route offers several fun adventures, scenic views, and picturesque spots. Whether you decide to explore Como on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Castelvecchio Museum is the first of them. Spend some time admiring this picture-perfect museum before continuing your journey. Castelvecchio Bridge is your next stop. This notable monument is one of the best-rated sights in Como.

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 Verona Arena. This enchanting stadium is a sight to behold. To round off your sightseeing experience, visit Porta Borsari and Piazza Delle Erbe. If time allows, end your day with Scaliger Tombs, a noteworthy monument that offers a memorable conclusion to your exploration.

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.

As dinnertime approaches, it's time to head out for a bite to eat in Venice. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

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

Explore the vibrant nightlife at Al Parlamento after your meal, a hub for lively evenings and memorable moments. Or, head to The Caffe Rosso for a great selection of flavorful drinks and a charming setting. Furthermore, Adagio is perfect for those looking to extend their night with a touch of local flavor.

Raise your glass to another unforgettable day in Italy!

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Day 5

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'll stay for 1 night more.

Today’s itinerary in Venice covers several incredible sights, including a historical landmark, a public square, a church, a palace, a monument, a handicraft store and much more! Start your adventure at Rialto Bridge. This world-famous historical landmark is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the culturally significant wonders of Piazza San Marco, a must-see public square 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 St Mark's Basilica. This well-known church offers an enriching experience. For a change of pace, head to Doge's Palace, where you can take in UNESCO world heritage-listed features. Conclude your self-guided sightseeing tour with a visit to Bridge Of Sighs and Murano. These sights offer a fulfilling end to a perfect day.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Venice. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

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. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Venice.

Let the evening flow smoothly from dinner to drinks at Il Mercante, a top-rated bar in the area. For other recommendations, The Irish Pub Venezia provides a perfect setting for rounding out your night with style and great drinks. Likewise, Ai Stagneri offers a memorable night with diverse drink options and excellent service.

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

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Day 6

Day 6

  • Venice
  • Florence
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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

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

Venice is brimming with adventures. Today’s wonderful stops include an observation deck, a church, an art gallery, a historical landmark, a public square and much more! Begin your sightseeing adventure at the spectacular Piazzale Michelangelo and allow yourself time to explore. Just a short distance away you'll find your next stop, Basilica Of Santa Croce In Florence, a respected church that draws visitors from far and near.

Continue your journey to Uffizi Gallery, one of the city’s most extraordinary spots that you shouldn’t miss. Another great site to visit is the timeless Ponte Vecchio. When you're finished at the historical landmark, Piazza Della Repubblica awaits your visit. This public square is a romantic highlight on today's itinerary. Last up is a public square - the top-rated Piazza Della Signoria.

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.

As you explore more of Florence, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Have a fantastic dining experience at Ristorante Oliviero 1962, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Di Poneta Novoli offers an enticing alternative with its varied menu. Additionally, Caffe San Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

After savoring a delicious meal, step into the vibrant nightlife at Manifattura, where the evening is just getting started. In the same way, Se·sto On Arno Rooftop Bar offers a unique charm perfect for experiencing the local bar scene in Florence. Il Vinile is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Head back to your accommodation in Florence and get some rest in preparation for another magical day of your road trip in Italy!

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Day 7

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

At the end of the day, you'll drive back to Florence, where you'll stay for 1 night more.

Today’s agenda in Florence includes a monument, a public square, a church, a museum and much more! Leaning Tower Of Pisa is must-visit monument and a great starting point for the day. Next, continue your journey to Piazza Del Duomo, Pisa, a wondrous public square, located just a leisurely stroll away. Next, head to Pisa Cathedral, an UNESCO world heritage-listed church, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Florence. When you're ready, let your sightseeing route take you to the curiosity-inducing Piazza Del Duomo. If you’re looking for more, Sangimignano1300 is also an underrated attraction that is worthwhile a visit.

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

As dinnertime approaches, it's time to head out for a bite to eat in Florence. If you are looking to dine at a popular restaurant in the city, it's often a good idea to reserve a table in advance.

Treat yourself to a delightful dinner at Ditta Artigianale, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria Da Burde? It's another excellent option with a diverse menu. Consider reserving a table at Casa Toscana as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

After enjoying a fulfilling meal, continue your evening at Bar 50 Rosso, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bitter Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Archea Brewery provides an excellent environment for a relaxed and enjoyable evening.

Raise your glass and celebrate another amazing day of your road trip in Italy!

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Day 8

Day 8

  • Florence
  • Milan
  • More

Drive 411 km, 6 hours 2 min

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

Embark on another extraordinary experience on day 8 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Riomaggiore and Manarola. At the end of the day, you will enjoy the comforts of a top-rated hotel in Milan, which will be your home away from home for 1 night.

Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most locally appreciated attractions included on the itinerary is Castle Of Riomaggiore. This romantic castle will help you start your sightseeing on top.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the underrated Manarola Overlook Viewpoint.

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.

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

Dine in style at Bice Restaurant, a top recommendation for dinner tonight. Or, for a change of pace, Alto Ristorante boasts a menu that's sure to impress. Also, be sure to check out Nero 9. Known as a local hotspot, it’s a great choice for tonight in Milan.

Following your dinner, dive into the local bar culture at Bhangrabar. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Rufus Cocktail Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Ostello Bello Grande provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

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Day 9

Day 9

  • Milan - Departure day
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  • Pinacoteca di Brera
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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 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 Quadrilatero della Moda. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy. You can also browse through boutiques for stylish fashion choices. 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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