One-Week Relaxed Italy Self-Drive Road Trip With Itinerary from Milan to 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.
Photo of Milan, Italy. Bridge across the Naviglio Grande canal at the sunrise Milano, Lombardy.
Photo of Milano, Italy. Church Santa Maria delle Grazie in Milan, famous for hosting Leonardo da Vinci masterpiece "The Last Supper".
Photo of Sforza Castle or Castello Sforzesco aerial panoramic view. Sforza Castle is located in Milan city in northern Italy.
Photo of tourist girl holds hat in Sempione Square, Milan, Italy.
Photo of Milan Cathedral, Duomo di Milano, Italy, one of the largest churches in the world on sunrise.
Photo of Darsena artificial reservoir is located near Porta Ticinese in Milan in Lombardy region of northern Italy.
Photo of tourist woman with arms raised in Milan Cathedral Square, Italy.
Photo of the Basilica of San Lorenzo Maggiore is a roman catholic church in Milan city in Lombardy region of northern Italy.
Photo of town of Menaggio on lake Como, Milan, Italy.
Photo of Stazione Milano Centrale is the main railway station of the Milan city in Lombardy region of northern Italy.
photo of view of Duomo square and Milan Cathedral at sunrise, Italy.
photo of view of View of the Peace Arch with yellow tram in Milan, Italy
photo of  view of Milan Piazza Del Duomo at Sunrise, Italy.
Aerial view of the Cattedrale di Santa Maria del Fiore in Florence, Italy, overlooking the city
Photo of Florence Aerial View of Ponte Vecchio Bridge during Beautiful Sunny Day, Italy.
Photo of Woman enjoys beautiful view on famous Duomo cathedral in Florence, standing on empty cathedral square during morning time.
Photo of Summer street cafe on Piazza della Repubblica in Florence, Toscana province, Italy.
Photo of Giotto's Campanile - An aerial dusk view of Giotto's Campanile and the historical Old Town of Florence, as seen from the top of Brunelleschi's Dome of the Florence Cathedral. Florence, Tuscany, Italy.
Photo of Ponte Vecchio, old bridge over Arno River, Florence, Tuscany, Italy.
Photo of The Colossus of the Apennines, majestic stone sculpture by Giambologna located in the park of Villa Demidoff in Florence, Italy.
Photo of Fountain of Neptune in Florence in early morning.
Photo of Sunset view of Florence, Ponte Vecchio, Palazzo Vecchio and Florence Duomo, Italy. Architecture and landmark of Florence. Cityscape of Florence.
Vintage carousel and tourists in Piazza della Repubblica (Republic Square) and the arch in honor of the first king of united Italy on background in Florence, Italy.
Photo of Arches of the Vasari Corridor (Corridoio Vasariano) in Florence, Tuscany, Italy. View of the Lungarno degli Archibusieri.
cheerful senior woman cycling with her electric mountain bike above downtown of Florence with stunning view over the old city, Tuscany, Italy
Facade of Palazzo Pitti palace with Gallery of Modern Art large building on Piazza dei Pitti square in historical centre of Florence city, blue sky white clouds, Tuscany, Italy
photo of view of Florence,Italy.
photo of view of Florence,Italy.
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Experience Italy like never before on this 8-day relaxed road trip, traversing through Milan, Bologna, Florence, and Modena. This self-drive vacation offers a tranquil journey through the heart-stopping beauty found in Italy.

This self-drive package allows you to travel through picture-perfect landscapes in Italy at a relaxed pace. Get a dose of comfort, fun, and recreation in Milan, Bologna, Florence, and Modena. Make yourself at home at top-rated hotels and stay 4 nights in Milan and 3 nights in Florence. Finally, taste the local food and enjoy a refreshing drink at the most popular restaurants and bars along your road trip route in Italy.

Freedom of choice is key to a relaxing road trip in Italy. For your self-drive vacation, we’ll offer you a selection of the best rental vehicles with CDW insurance. Upon arrival in Milan, you’ll collect your rental car of choice. From there, you’ll begin your 8-day journey across Italy and discover its unique culture, history, and diverse scenery.

Experience the essence of leisurely self-drive exploration across Italy with our handpicked selection of accommodations. From relaxed stays at renowned 5-star hotels offering magnificent views to comfortable 3-star options that cater to budget-conscious travelers, we ensure your journey is optimized for relaxation and comfort. Discover the perfect place to stay and unwind as you embark on a laid-back adventure in Italy.

We’ll introduce you to some of the best travel destinations in Italy. This relaxed road trip features the stunning Duomo Di Milano Museum. Another highlight of this self-drive tour is the captivating Ponte Vecchio.

Traveling leisurely through Italy means you could spend as much time as you want at the magnificent Galleria Vittorio Emanuele Ii. With this travel plan, you could also soak in the atmosphere of the memorable Piazzale Michelangelo. Get close to the spectacular Cathedral Of Santa Maria Del Fiore and the wonderful Parco Sempione. You’ll have plenty of time to take in each attraction's unique features, learn its unique history, and appreciate it to the fullest.

Enjoy strolling through Italy's shopping hotspots near your accommodation. Visit shops, discover the locals’ way of life, or try various specialties. Don't forget to bring home a piece of the country that will remind you of your relaxing vacation in Italy.

Between sightseeing, you can make the most of your downtime and join a popular tour in Italy. This relaxed road trip also gives you plenty of time to stroll through Italy's shopping hotspots. Through these experiences, you'll have plenty of opportunities to discover the locals’ way of life and soak in the rich cultural heritage of the Italy.

This self-drive vacation package includes everything you need for a stress-free, easy road trip through Italy. You’ll have a cozy place to stay for 7 nights, with a selection of top-rated breakfast and restaurant options nearby. We'll also provide you with the best rental car you can use throughout the 8 days of your self-drive road trip in Italy. On top of all that, you also have the option to add flights to your travel plan and personalize each day of your itinerary by adding tours and tickets.

This self-drive package includes 24/7 travel support and a step-by-step guide. You can access the guide at any point of your journey through our mobile app, where you can also keep and organize your travel documents.

Spend an amazing 8-day vacation in Italy and get to know more about this fantastic destination. Choose your travel dates and plan a laid-back and relaxed road trip in Italy today!

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Driver’s age is 30 - 65
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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Via Monte Napoleone
Pinacoteca di BreraLa ScalaGalleria Vittorio Emanuele IIDuomo di MilanoBrera
Castello SforzescoSempione ParkArch of PeacePiazza Gae AulentiNavigli
Piazza MaggioreFountain of Neptune, BolognaPalazzo Re Enzo
piazza della SignoriaUffizi GalleryPonte VecchioPalazzo PittiOltrarno
DavidGalleria dell'AccademiaBasilica of Santa Croce in Florencepiazzale MichelangeloThe Boboli Gardens
Cathedral of Santa Maria del FioreCentral MarketBasilica of Santa Maria NovellaFerrari park
Corso Vittorio Emanuele II

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Day 1

Day 1

  • Milan - Arrival day
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  • Via Monte Napoleone
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Your relaxed road trip through Italy starts when you reach the incredible city of Milan, where you'll stay for 3 nights. You'll pick up your rental car in Milan and begin your adventure in Italy.

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 Via Monte Napoleone, a must-see street, and taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

As afternoon approaches, head to your chosen hotel in Milan. Check-in typically starts around 2 to 4 PM at hotels in Italy. We recommend staying at a hotel in a central location for easy access to the best attractions, restaurants, and bars in the city.

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.

If you’re not yet ready to call it a night, head back out to celebrate your vacation with a drink. This is a great time to slow down, look back at your day, and raise a toast to your wonderful holiday in Italy.

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 as you look back into the highlights of today’s laid-back and relaxed road trip adventure in Italy. Enjoy your first taste of Milan as you soak in the city’s unique vibe.

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Day 2

Day 2

  • Milan
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Drive 2 km, 33 min

  • Pinacoteca di Brera
  • La Scala
  • Galleria Vittorio Emanuele II
  • Duomo di Milano
  • Brera
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Day 2 of your relaxed road trip through Italy means 24 hours of making the best memories in Milan. You’ll go sightseeing at famous attractions in Milan. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Milan!

Brera is one of the highlights of today. Take your time exploring this iconic neighborhood in Milan, which offers a perfect blend of history and culture. Plus, it's close to many must-see landmarks in the city.

Today’s agenda in Milan includes an art gallery, an opera house, a shopping mall, a church and much more! Pinacoteca Di Brera is must-visit art gallery and a great starting point for the day. Next, continue your journey to La Scala, a notable opera house, located just a leisurely stroll away. Next, head to Galleria Vittorio Emanuele Ii, an enchanting shopping mall, also available for your discovery today.

Make the most of your time in the country by joining activities that let you discover more about Italy. Check out all of the tours you can join this day of your leisurely self-drive holiday in Italy and ensure the experience of a lifetime.

Mealtimes are the perfect opportunities to immerse yourself in the local culture of Italy. When you're not appreciating the best places to visit in Milan, explore the city like a local by trying out the best restaurants in the area.

Prepare for an extraordinary culinary adventure in Milan by booking a table at Enrico Bartolini al Mudec, a 3-star Michelin restaurant that boasts an exceptional creative menu. For a different flavor experience, head to Seta by Antonio Guida, renowned for its delectable international and contemporary dishes. This 2-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Il Luogo Aimo e Nadia, a local gem known for its delightful italian contemporary and modern cuisine in Milan. Nestled in the city's heart, this 1-star Michelin restaurant is a perfect choice for discerning restaurant-goers seeking a new experience.

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Milan. The bars in Milan make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

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.

Savor the rest of the night and celebrate another incredible relaxed road trip adventure in the magical Milan!

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Day 3

Day 3

  • Milan
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Drive 8 km, 53 min

  • Castello Sforzesco
  • Sempione Park
  • Arch of Peace
  • Piazza Gae Aulenti
  • Navigli
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On day 3 of your leisurely self-drive tour across Italy, you’ll go deep into Milan, where you'll stay for 1 night, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Milan, and meet locals along the way!

Navigli is a fantastic place you can explore today in Milan. This neighborhood is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Milan-way-of-life and visit all the nearby sights.

Today's adventure in Milan promises more breathtaking discoveries and enriching experiences! Begin at Sforzesco Castle Art Library. This picture-perfect castle is a highlight of any visit in the city. Then, enjoy Parco Sempione, another mesmerizing attraction that never fails to captivate visitors. Next, head over to Arch Of Peace, one of the city’s most locally renowned attractions, known for its historic features.

If you’re looking for more, spend time soaking in the atmosphere of Piazza Gae Aulenti. This eye-catching public square is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities. Milan offers a wide selection of experiences for every traveler.

After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Enjoy a lovely dining experience at Bice Restaurant, a popular restaurant in Milan. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Milan at Alto Ristorante, 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 Nero 9. It’s yet another ideal choice to enhance your time in Milan tonight.

Hang out and unwind at some of the top bars 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.

Raise your glass to celebrate another day of your laid-back and relaxed road trip experience in Italy!

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Day 4

Day 4

  • Milan
  • Florence
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Drive 335 km, 4 hours 14 min

  • Piazza Maggiore
  • Fountain of Neptune, Bologna
  • Palazzo Re Enzo
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On day 4 of your laid-back and relaxed road trip adventure, you’ll have the chance to visit more than one remarkable area in Italy. Since this self-drive tour offers freedom and flexibility, you can decide how much time you want to spend in each place to enjoy the memorable travel destinations in Italy.

Milan is home to plenty of attractions that offer fun adventures, romantic experiences, and breathtaking views! Start at Piazza Maggiore, a spectacular public square that is worthwhile a visit in the city. Nearby, you’ll find Fountain Of Neptune, Bologna, enchanting visitors with its photogenic appeal. Continue your exploration at Palazzo Re Enzo. This palace is one of the city’s most underrated spots.

After a day of exploration, relax at one of the top hotels or accommodations in Florence. Staying in the city enhances your laid-back road trip experience in Italy by offering a comfortable and welcoming environment to recharge in this charming destination.

Exploring new places makes you hungry. Luckily, Florence has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

Have a memorable dining experience in Florence by booking a table at Enoteca Pinchiorri, renowned as a 3-star Michelin restaurant presenting an exceptional italian contemporary menu. For a different culinary experience in Florence, Santa Elisabetta shines as one of the top destinations, known for its delicious creative and mediterranean cuisine. This 2-star Michelin-awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Gucci Osteria da Massimo Bottura is known as a top local spot for its delicious italian contemporary and international cuisine in Florence. This 1-star Michelin awardee is a highly recommended choice for an unforgettable meal.

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Florence. The bars in Florence make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

After your meal, keep the night alive at a bar like Manifattura, known for its lively atmosphere. Se·sto On Arno Rooftop Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Il Vinile offers an excellent atmosphere for those looking to amp up the evening.

Raise your glass and relax after another big day of your leisurely paced road trip in Italy!

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Day 5

Day 5

  • Florence
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Drive 1 km, 23 min

  • piazza della Signoria
  • Uffizi Gallery
  • Ponte Vecchio
  • Palazzo Pitti
  • Oltrarno
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Day 5 introduces you to many popular attractions and activities in Florence, further proving that leisurely self-drive tours in Italy are extraordinary.

Don’t miss Oltrarno in Florence 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.

Today, you'll explore some of the most beautiful places in Florence, including a public square, an art gallery, a historical landmark, a palace and much more! Start your day with a visit to Piazza Della Signoria. This famous public square is a must-visit in the city. When you’re ready for your next discovery, continue to Uffizi Gallery, which may be one of the most romantic 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 Ponte Vecchio, a wondrous historical landmark in the city. If you’re up for more discoveries, don’t forget to reserve some time for Pitti Palace.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Florence. There are so many fun and eye-opening activities to try out in Florence that will make your slow-paced self-drive tour in Italy more memorable. Check out all the most recommended and top-rated tour options in the city of Florence to find the best options for you!

Exploring the food culture in Florence offers you an exciting chance to connect with locals and experience diversity along your relaxed road trip. When you’re ready to eat, we recommend you visit one of the best dining spots in the city.

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 gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

After dinner, it’s time to fall in love with the amazing nightlife in Florence and unwind at some of the best bars in the city.

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 in celebration of your freedom and relaxed road trip adventure in Italy!

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Day 6

Day 6

  • Florence
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Drive 14 km, 1 hour 20 min

  • David
  • Galleria dell'Accademia
  • Basilica of Santa Croce in Florence
  • piazzale Michelangelo
  • The Boboli Gardens
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Day 6 of your relaxed road trip through Italy means 24 hours of making the best memories in Florence. You’ll go sightseeing at famous attractions in Florence. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Florence!

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to David. This notable statue provides an insightful glimpse into the city's identity. Next, discover Galleria Dell'accademia, a photogenic art gallery, promising a delightful encounter.

Continue your sightseeing with a visit to Basilica Of Santa Croce In Florence, a popular church. When you’re done, don’t forget to make a stop at the impressive Piazzale Michelangelo. Round off your day at The Boboli Gardens, another gem in Florence with history-steeped features to discover.

Italy makes the perfect setting for a calming but fun exploration. Aside from amazing sights, Italy also offers plenty of tours to enhance your relaxed road trip experience.

Exploring new places makes you hungry. Luckily, Florence has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

Have a fantastic dining experience at Ristorante Buca Mario, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Agricola Toscana offers an enticing alternative with its varied menu. Additionally, Eataly Firenze is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Florence.

A visit to a top-rated local bar is one of the most refreshing ways to cap off a beautiful night in Florence.

Let the evening flow smoothly from dinner to drinks at Gosh*, a top-rated bar in the area. For other recommendations, Antico Caffè Del Moro - Art Bar Firenze provides a perfect setting for rounding out your night with style and great drinks. Likewise, Quelo Bar offers a memorable night with diverse drink options and excellent service.

Grab a drink and enjoy every passing minute of this night of your relaxed road trip experience in Italy!

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Day 7

Day 7

  • Florence
  • Milan
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Drive 314 km, 3 hours 59 min

  • Cathedral of Santa Maria del Fiore
  • Central Market
  • Basilica of Santa Maria Novella
  • Ferrari park
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Day 7 of your relaxed road trip across Italy promises an exciting agenda full of discovery. You’ll start your day in the city of Florence and drive in the direction of the city of Modena for some laid-back sightseeing. You’ll end your day in the city of Milan, where you’ll stay for 1 night.

Florence is brimming with adventures. Today’s wonderful stops include a church, a food market, and a park. Begin your sightseeing adventure at the impressive Cathedral Of Santa Maria Del Fiore and allow yourself time to explore. Just a short distance away you'll find your next stop, Central Market, a visually striking food market that draws visitors from far and near.

Continue your journey to Basilica Di Santa Maria Novella, Firenze (fi), one of the city’s most popular spots that you shouldn’t miss. Another great site to visit is the increasingly popular Enzo Ferrari Park.

In the city of Milan, you’ll find plenty of stay options that will accommodate your need for rest and relaxation after spending your day on the road. Our top recommendations perfectly complement your relaxed road trip vacation in Italy.

After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Dine in style at Ristorante la Brisa, a top recommendation for dinner tonight. Or, for a change of pace, Pasticceria San Carlo boasts a menu that's sure to impress. Also, be sure to check out UNAHOTELS Cusani Milano. Known as a local hotspot, it’s a great choice for tonight in Milan.

If you feel like it, head out to a bar to celebrate another fantastic day in Milan and take the pulse of the city’s nightlife. Enjoy the night without rushing to fully appreciate it.

Continue your evening by exploring the vibrant nightlife scene at Qc Termemilano, a prime destination for a thrilling night out. Also, don’t forget to check out Yguana Cafè, a bar that offers unique local touches.

A leisurely self-drive holiday in Florence can’t get any better than this! Toast to another amazing day in Italy!

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Day 8

Day 8

  • Milan - Departure day
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  • Corso Vittorio Emanuele II
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Day 8 of your relaxed road trip in Italy is your departure day. If you have a flight to catch, you’ll drop off your rental car well in advance before your departure. Choose a late flight to enjoy a stress-free last day in Milan.

Explore local shops for souvenirs to remember your trip or find unique gifts for loved ones. Discover boutiques offering an array of stylish fashion choices. Take a break with a cup of coffee or tea while savoring the local vibe in a coffee shop.

At the top of the list of things to do today is to explore Corso Vittorio Emanuele II, a street that captures the true essence of Milan. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.

Unwind and look back at the past 8 days of your relaxed road trip over a bite to eat. This is your chance to enjoy one last traditional meal in Milan or just grab something light to keep you going.

Give yourself enough time to wave goodbye to Milan and begin your journey home. The unforgettable experiences you’ve collected along your 8-day relaxed road trip in Italy is a story you will tell for the rest of your life.

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