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

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Milan Cathedral, Duomo di Milano, and Piazza Duomo square in the Milan city center, Italy
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.
One-Week Relaxed Italy Self-Drive Road Trip With Itinerary from Milan to Florence
One-Week Relaxed Italy Self-Drive Road Trip With Itinerary from Milan to Florence
One-Week Relaxed Italy Self-Drive Road Trip With Itinerary from Milan to Florence
One-Week Relaxed Italy Self-Drive Road Trip With Itinerary from Milan to Florence
One-Week Relaxed Italy Self-Drive Road Trip With Itinerary from Milan to Florence
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Set out on this 8-day relaxed road trip in Italy, where Milan, Bologna, Florence, and Modena offer rich culture, beautiful views, and memorable experiences at every stop!

Travel freely with this relaxed self-drive package in Italy, designed for comfort and exploration. Spend 4 nights in Milan and 3 nights in Florence, staying at top-rated hotels near the heart of each city. Between drives, indulge in local cuisine, sip refreshing drinks, and enjoy the vibrant atmosphere at popular restaurants and bars along your road trip route in Italy.

Your journey starts in Milan, where your rental car with CDW insurance will be ready for pickup. Choose a vehicle that suits your style, then set off on your 8-day relaxed road trip in Italy to explore its rich culture, fascinating history, and stunning landscapes.

Every stop on this leisurely self-drive holiday comes with handpicked accommodations that make relaxation effortless. Choose from elegant 5-star hotels with breathtaking views or comfortable 3-star stays that offer excellent value, all providing a welcoming retreat after a day on the road.

With your self-drive itinerary in Italy already planned, you’ll enjoy the country’s most celebrated sights without the rush. Marvel at the stunning Duomo Di Milano Museum and soak in the atmosphere of the magnificent Ponte Vecchio.

Enjoy each stop as you explore the history, architecture, and character of each destination on this Italy road trip itinerary for 8 days.

As you travel between destinations, you’ll have plenty of time to explore local markets and boutique shops. These stops give you the chance to find unique souvenirs, taste regional specialties, and experience everyday life in Italy.

If you want to make your 8-day relaxed self-drive tour in Italy even more memorable, add optional tours or activities. Join a guided excursion, discover hidden neighborhoods, or spend an afternoon in your favorite market. Each choice deepens your connection to the places you visit.

Alongside these experiences, your laid-back self-drive package in Italy includes 7 nights in comfortable hotels, a rental car for 8 days, and convenient access to nearby dining options. You can also add flights and entry tickets to shape the trip exactly how you want it. With 24/7 travel support and a mobile app keeping your itinerary and documents organized, you can enjoy a relaxed drive and savor every mile of the road ahead.

Turn your travel plans into reality. Book your 8-day relaxed self-drive road trip in Italy today and enjoy a journey filled with discovery, freedom, and unforgettable moments!

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Driver’s age is 30 - 65
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Pick-up: 10:00
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Day1

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. 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.

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.

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.

Keep the evening going at Nottingham Forest, a great choice for enjoying the after-dinner hours with a drink. You could also go to Armani/bamboo Bar, which offers a similarly pleasant setting and great drinks. Another option is Mag Cafe, which provides an inviting environment for unwinding after a busy day out.

Raise a toast as you look back on the highlights of today’s relaxed road trip in Italy. Enjoy your first taste of Milan as you soak in the city’s unique vibe.

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Day2

Day 2

  • Milan
  • More

Drive 2 km, 33 min

  • Pinacoteca di Brera
  • La Scala
  • Galleria Vittorio Emanuele II
  • Duomo di Milano
  • Brera
  • More

Day 2 introduces you to many popular attractions and activities in Milan, further proving that leisurely self-drive tours in Italy are extraordinary.

A visit to Brera is a must on the agenda today. This neighborhood is full of hidden gems and character, perfect for a leisurely stroll. Plus, you’ll be close to some of the city’s most famous sights.

Check out the well-known art gallery, Pinacoteca Di Brera. Afterward, continue to La Scala, an opera house every traveler should visit. As you explore Milan’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Galleria Vittorio Emanuele Ii. This astonishing shopping mall is an essential stop. Following that, head to Duomo Di Milano Museum, another must-visit site that will enhance your experience.

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.

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 Milan, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Begin your culinary exploration in Milan by securing a reservation at Enrico Bartolini al Mudec. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another dining delight, visit Seta by Antonio Guida, celebrated for its delectable international and contemporary menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Il Luogo Aimo e Nadia, a top local spot known for its tantalizing italian contemporary and modern menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

Before calling it a day, visit one of the best bars in Milan. There, you can look back on the highlights of today’s pleasant and invigorating travel experiences, have friendly conversations with locals, and unwind.

Unwind after your meal by stepping into Kilburn Cocktail Bar Milano. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Frida offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook The Friends Pub Milano, another top-rated bar in the area.

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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Day3

Day 3

  • Milan
  • More

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!

Set aside time today to explore Navigli, a standout neighborhood that reflects the essence of the city. While you're there, you'll also be within reach of some of the city's top landmarks, making it easy to maximize your day.

Sforzesco Castle Art Library is must-visit castle and a great option for a daytime tour of the area. Continue your journey to Parco Sempione, a spectacular park, located just a leisurely stroll away. Next, head to Arch Of Peace, a historic monument, 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.

Exploring new places makes you hungry. Luckily, Milan 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 Bice Restaurant, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Alto Ristorante offers an enticing alternative with its varied menu. Additionally, Nero 9 is worth considering. Renowned for satisfying diners, it’s an ideal option 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.

Round off your dining experience by visiting Bhangrabar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Rufus Cocktail Bar, a bar catering to every mood and preference. Ostello Bello Grande likewise offers a unique atmosphere, perfect for a memorable night out.

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

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Day4

Day 4

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

  • Piazza Maggiore
  • Fountain of Neptune, Bologna
  • Palazzo Re Enzo
  • More

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

When you’ve had your share of Milan, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Bologna. Your travel time is around 2 hours 34 min.

Set out on a self-guided sightseeing tour at Piazza Maggiore and explore the enchanting features. Next, make your way to Fountain Of Neptune, Bologna, another highlight in Bologna. When you’re done exploring the monument, continue to Palazzo Re Enzo, a historic palace.

After a day of exploration, relax at one of the top hotels or accommodations in Florence. Staying in the city gives you a comfortable, welcoming place to recharge during your laid-back road trip 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.

Have a memorable dining experience in Florence by booking a table at Enoteca Pinchiorri, 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 consistently earns high praises, 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 in Florence for its delicious italian contemporary and international cuisine. This 1-star Michelin awardee is a highly recommended choice for an unforgettable meal.

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.

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

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

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Day5

Day 5

  • Florence
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Drive 1 km, 23 min

  • piazza della Signoria
  • Uffizi Gallery
  • Ponte Vecchio
  • Palazzo Pitti
  • Oltrarno
  • More

Day 5 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!

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

One of the most top-rated attractions included on the itinerary is Piazza Della Signoria. This culturally significant public square will help you start your sightseeing on top. Then, take a leisurely stroll to Uffizi Gallery and learn what makes this romantic art gallery unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the iconic Ponte Vecchio. After exploring the historical landmark, head to Pitti Palace. This locally renowned palace is a highlight in Florence.

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

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

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

After your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

Cherish every minute of your relaxed road trip vacation across Italy.

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Day6

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
  • More

Day 6 introduces you to many popular attractions and activities in Florence, further proving that leisurely self-drive tours in Italy are extraordinary.

David brings Florence's character to life. Then, enjoy Galleria Dell'accademia, another photogenic attraction that never fails to captivate visitors. Next, head over to Basilica Of Santa Croce In Florence, one of the city’s most notable attractions, known for its culturally significant features.

If you’re looking for more, spend time soaking in the atmosphere of Piazzale Michelangelo. This majestic observation deck is frequented by locals and tourists alike. To complete your memorable day, make sure to visit The Boboli Gardens, a captivating botanical garden, and 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 Milan. There are so many fun and eye-opening activities to try out in Milan 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!

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 Florence, explore the city like a local by trying out the best restaurants in the area.

Savor the flavors at Ristorante Buca Mario, a top pick for dinner tonight. Alternatively, Agricola Toscana beckons with its unique menu offerings. Also, consider Eataly Firenze. With its consistent customer satisfaction, it’s an excellent option for dining in Florence tonight.

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 enjoying a fulfilling meal, continue your evening at Gosh*, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers a welcoming atmosphere for easing into the nightlife. Similarly, Quelo Bar provides an excellent environment for a relaxed and enjoyable evening.

Free your mind of worries as you enjoy the taste of freedom on your laid-back road trip adventure across Italy.

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Day7

Day 7

  • Florence
  • Modena
  • 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
  • More

On day 7 of your laid-back road trip adventure in Italy, you can visit several remarkable places. With the freedom and flexibility of a self-drive tour, you decide how much time to spend in each, making the most of these memorable destinations.

Whatever your travel style is, Cathedral Of Santa Maria Del Fiore is an essential stop in Florence. This impressive church provides an insightful glimpse into the city's identity. Next, discover Central Market, a picture-perfect food market, promising a delightful encounter.

Continue your sightseeing with a visit to Basilica Di Santa Maria Novella, Firenze (fi), a notable church.

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Modena may take around 1 hour 39 min. Upon your arrival in Modena, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Set out on a self-guided sightseeing tour at Enzo Ferrari Park and explore the picture-perfect features.

When you’re not exploring beautiful places, you can relax in Milan. Here, you can choose from the best hotels and other accommodations as you get to know more about the culture in the city.

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.

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

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

Explore the vibrant nightlife at Qc Termemilano after your meal, a hub for lively evenings and memorable moments. Or, head to Yguana Cafè for a great selection of flavorful drinks and a charming setting.

Toast to another unforgettable and relaxing road trip adventure in Italy!

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Day8

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’re flying home, return your rental car with time to spare. For a stress-free farewell, book a later flight and enjoy a final, relaxed day in Milan.

For a last-minute shopping spree in Milan, Galleria Vittorio Emanuele II is nearby. Enjoy a variety of retail stores, dining options, and essential services in one convenient location. Explore high-end stores offering an exquisite selection of luxury items.

At the top of the list of places to visit today is 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.

Over a good meal, take a moment to unwind and reflect on the past 8 days of your relaxed road trip. Savor one last traditional dish in Milan, or keep it light with a quick bite before you go.

Savor the flavors at Vento di Sardegna, a top pick for dinner tonight. Alternatively, Palazzo Parigi Hotel & Grand Spa Milano beckons with its unique menu offerings.

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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Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
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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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