One-Week Relaxed Italy Self-Drive Road Trip With Itinerary from Milan to Florence

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Explore Italy and discover its unique charm on this 8-day relaxed road trip through Milan, Bologna, Florence, and Modena. Delight in a stress-free journey that focuses on exploration through the country's most captivating landscapes.

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.

Find your way to your hotel in Milan. We recommend choosing a hotel in a central location for easy exploring. Check-in typically starts between 2 and 4 PM at hotels in Italy. Settle in and make plans for the evening.

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

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

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.

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 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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On day 2 of your leisurely self-drive tour across Italy, you’ll go deep into Milan, where you'll stay for 2 nights, 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!

Brera is a neighborhood that stands out as one of the must-see places in Milan. Take a moment to explore its distinct atmosphere, and don’t miss the popular sightseeing spots just a short walk away.

Get ready to discover some of the most iconic wonders in Milan, including an art gallery, an opera house, a shopping mall, a church and much more! Start your day at Pinacoteca Di Brera. This eye-catching art gallery is a notable place to see in Milan. Then, wander over to La Scala. If picture-perfect sites excite you, this opera house will be right up your alley. Nearby, you’ll also find Galleria Vittorio Emanuele Ii. This visually striking shopping mall 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, Duomo Di Milano Museum is a timeless spot in the city that will captivate you with its unique charm.

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.

Exploring the food culture in Milan 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.

Experience a symphony of flavors at Enrico Bartolini al Mudec in Milan by securing a reservation in advance. Renowned for its 3-star Michelin distinction, Enrico Bartolini al Mudec delights its guests with its exceptional variety of meals showcasing delicious creative cuisine. For a palate-pleasing alternative, make sure to dine at Seta by Antonio Guida, acclaimed for its delectable international and contemporary specialties. This local 2-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Il Luogo Aimo e Nadia, a top-rated restaurant known for its outstanding menu. Known as a top-rated 1-star Michelin establishment, it's a top choice for italian contemporary and modern cuisine in the city.

As the day is coming to an end, stop at some of Milan’s best bars to celebrate this day of your slow-paced adventure in Italy.

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

Soak in the unique atmosphere of Milan as you commemorate this day of your relaxed road trip through Italy with a toast. Cheers to a memorable leisurely self-drive holiday in Italy!

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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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Day 3 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!

One of the most iconic places you can visit today in Milan is Navigli. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Savor the day by visiting some of the best places to see in Milan, including a castle, a park, a monument, a public square and much more! Start your adventure at Sforzesco Castle Art Library. This spectacular castle is a must-visit for travelers looking for a unique holiday experience. Make your way to Parco Sempione located in Milan for another exciting encounter.

Next, immerse yourself in the setting of Arch Of Peace. Its awe-inspiring features will captivate you. After the monument, continue your tour of the city with a visit to Piazza Gae Aulenti. Visitors usually appreciate the visually striking features of this public square.

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.

Experience shopping bliss at Milan as you explore Via della Moscova. Take a leisurely stroll through unique boutiques and shops, where local treasures are waiting to be found. Beyond shopping, Via della Moscova offers more options, including cafes, unique attractions, key services, and vibrant events.

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.

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.

Hang out and unwind at some of the top bars in Milan.

After enjoying a fulfilling meal, continue your evening at Bhangrabar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Rufus Cocktail Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Ostello Bello Grande provides an excellent environment for a relaxed and enjoyable evening.

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

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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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Day 4 of your relaxed road trip across Italy promises an exciting agenda full of discovery. You’ll start your day in the city of Bologna and drive in the direction of the city of Florence for some laid-back sightseeing. You’ll end your day in the city of Florence, where you’ll stay for 3 nights.

Start by visiting Piazza Maggiore, a prime spot to begin your journey. This culturally significant public square is sure to impress. Next on your list is Fountain Of Neptune, Bologna, another must-visit landmark and curiosity-inducing monument renowned for its respected 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 Palazzo Re Enzo. This history-steeped palace is an essential place to visit for anyone looking for the full Milan experience.

You’ll be staying at the incredible city of Florence in this laid-back road trip in Italy. You'll stay here for 3 nights.

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.

Set out on a gastronomic journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of italian contemporary cuisine. For a different taste, head over to Santa Elisabetta, renowned for its delectable creative and mediterranean dishes. This distinguished 2-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Gucci Osteria da Massimo Bottura, a highly rated local gem known for its exquisite italian contemporary and international menu. With a 1-star Michelin acclaim, it promises a dining experience you won't want to miss. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

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.

Let the evening flow smoothly from dinner to drinks at Manifattura, a top-rated bar in the area. For other recommendations, Se·sto On Arno Rooftop Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Il Vinile 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 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.

Oltrarno is a fantastic place you can explore today in Florence. 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 Florence-way-of-life and visit all the nearby sights.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Piazza Della Signoria. This visually striking public square is a highlight of any visit in the city. Then, enjoy Uffizi Gallery, another respected attraction that never fails to captivate visitors. Next, head over to Ponte Vecchio, one of the city’s most timeless attractions, known for its visually striking features.

If you’re looking for more, spend time soaking in the atmosphere of Pitti Palace. This romantic palace is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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!

When you’re not driving and exploring some of the best places in Italy, it’s time to make your relaxed road trip even more comforting. Sit down for a lovely meal at one of the best restaurants in Florence.

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

Experience the amazing nightlife in Florence and unwind at the coolest bars in the city.

To truly maximize your evening out, consider visiting Bar 50 Rosso after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bitter Bar, another bar with an inviting ambiance. Similarly, Archea Brewery also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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 6

Day 6

  • Florence
  • More

Drive 14 km, 1 hour 20 min

  • David
  • Galleria dell'Accademia
  • Basilica of Santa Croce in Florence
  • piazzale Michelangelo
  • The Boboli Gardens
  • More

On day 6 of your leisurely self-drive tour across Italy, you’ll go deep into Florence, 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 Florence, and meet locals along the way!

Florence is home to plenty of attractions that offer family-friendly attractions, photo-friendly spots, and historic treasures! Start at David, a captivating statue that is worthwhile a visit in the city. Nearby, you’ll find Galleria Dell'accademia, enchanting visitors with its instagrammable appeal. Continue your exploration at Basilica Of Santa Croce In Florence. This church is one of the city’s most captivating spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Piazzale Michelangelo. After exploring the observation deck, head to the interesting The Boboli Gardens.

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.

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Florence, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Dine in style at Ristorante Buca Mario, a top recommendation for dinner tonight. Or, for a change of pace, Agricola Toscana boasts a menu that's sure to impress. Also, be sure to check out Eataly Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.

After dinner, you can choose between heading back to your hotel to recharge, taking a leisurely stroll, or going out to a bar for a relaxed drink in great company.

After savoring a delicious meal, step into the vibrant nightlife at Gosh*, where the evening is just getting started. In the same way, Antico Caffè Del Moro - Art Bar Firenze offers a unique charm perfect for experiencing the local bar scene in Florence. Quelo Bar is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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 leisurely self-drive tour in Italy is another opportunity for an in-depth travel experience in the country. On this refreshing new day, you’ll travel from Florence and continue your laid-back and relaxed road trip adventure in the city of Modena and the city of Milan. You’ll stay in Milan for 1 night.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Cathedral Of Santa Maria Del Fiore. This famous church provides an insightful glimpse into the city's identity. Next, discover Central Market, a visually striking food market, promising a delightful encounter.

Continue your sightseeing with a visit to Basilica Di Santa Maria Novella, Firenze (fi), a popular church. When you’re done, don’t forget to make a stop at the underrated 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.

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.

Make sure to reserve a table at Ristorante la Brisa, 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 Pasticceria San Carlo, 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 Cusani 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.

Take a stroll around the area, head back to your accommodation for the night, or continue your evening at one of the best-rated bars in the city.

After your meal, keep the night alive at a bar like Qc Termemilano, known for its lively atmosphere. Yguana Cafè is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance.

Look back at an amazing day filled with adventure in Italy. And don’t forget to get some rest so you can continue your relaxed holiday in Italy tomorrow with new energy.

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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.

On your last day in Italy, take time to indulge in shopping at Milan’s popular marketplace, Galleria Vittorio Emanuele II. Look for keepsakes or souvenirs to remind you of your trip. If you’re in the mood for luxury shopping, high-end stores await you.

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.

Treat yourself to a delicious dinner at Vento di Sardegna, an excellent option for tonight's dining. Looking for something different? Palazzo Parigi Hotel & Grand Spa Milano offers a tantalizing alternative with its diverse menu. And don’t miss Galleria Restaurant.

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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