Relaxed 14-Day Italy Self-Drive Road Trip With Itinerary from Bologna to Milan, Verona, and Florence

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Enjoy this 14-day relaxed road trip in Italy, with Bologna, Milan, Monza, Valeggio sul Mincio, Verona, and Florence showing you the beauty, culture, and peaceful moments that make this journey special!

Travel freely with this relaxed self-drive package in Italy, designed for comfort and exploration. Spend 3 nights in Bologna, 4 nights in Milan, 2 nights in Verona, and 4 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 Bologna, where your rental car with CDW insurance will be ready for pickup. Choose a vehicle that suits your style, then set off on your 14-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 Verona Arena.

Enjoy each stop as you explore the history, architecture, and character of each destination on this Italy road trip itinerary for 14 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 14-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 13 nights in comfortable hotels, a rental car for 14 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 14-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
Drop-off: 10:00

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Day 1

Day 1

  • Bologna - Arrival day
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  • Porta Galliera
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Your relaxed road trip through Italy starts when you reach the incredible city of Bologna, where you'll stay for 2 nights. You'll pick up your rental car in Bologna and begin your adventure in Italy.

Bologna 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 Bologna. 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 Bologna, it's often a good idea to reserve a table in advance.

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

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

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Day 2

Day 2

  • Bologna
  • More

Drive 2 km, 31 min

  • Palazzo Grassi, Bologna
  • Bologna Cathedral
  • Fountain of Neptune, Bologna
  • Piazza Maggiore
  • Basilica of San Domenico
  • More

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.

Exploring the food culture in Bologna 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 the amazing nightlife in Bologna and unwind at the coolest bars in the city.

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

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Day 3

Day 3

  • Bologna
  • Milan
  • More

Drive 215 km, 2 hours 52 min

  • Two Towers
  • Piazza Santo Stefano
  • International Museum and Library of Music
  • Porta Maggiore
  • arco del Meloncello
  • More

Day 3 of your easy, relaxed road trip through Italy lets you travel at your own pace and visit multiple places in a single day. By evening, drive toward the Milan, where you’ll stay at a top-rated hotel of your choice for 4 nights.

In Milan, you’ll find plenty of places to unwind after a day on the road. Our top recommendations go perfectly with your laid-back road trip in Italy.

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.

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

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

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Day 4

Day 4

  • Milan
  • More

Drive 1 km, 17 min

  • La Scala
  • Galleria Vittorio Emanuele II
  • Duomo di Milano
  • Royal Palace of Milan
  • Brera
  • More

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Bologna. There are so many fun and eye-opening activities to try out in Bologna that will make your slow-paced self-drive tour in Italy more memorable.

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.

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.

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

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Day 5

Day 5

  • Milan
  • More

Drive 9 km, 1 hour 3 min

  • Leonardo da Vinci Museum of Science and Technology
  • Basilica di Sant'Ambrogio
  • Castello Sforzesco
  • Sempione Park
  • Arch of Peace
  • More

Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities.

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.

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.

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

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Day 6

Day 6

  • Milan
  • More

Drive 6 km, 49 min

  • Pinacoteca di Brera
  • Piazza Gae Aulenti
  • Corso Vittorio Emanuele II
  • Via Monte Napoleone
  • Navigli
  • More

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.

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.

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

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Day 7

Day 7

  • Milan
  • Verona
  • More

Drive 197 km, 3 hours 25 min

  • Parco di Monza
  • Gardaland Resort
  • Parco Giardino Sigurtà
  • More

Day 7 of your leisurely self-drive tour in Italy offers another chance for an in-depth travel experience. You’ll stay in Verona for 2 nights.

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

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.

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

Toast to another amazing day in Italy!

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Day 8

Day 8

  • Verona
  • More

Drive 3 km, 52 min

  • Basilica di San Zeno Maggiore
  • Castelvecchio Bridge
  • Castelvecchio Museum
  • Porta Borsari
  • Verona Arena
  • More

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.

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 Verona.

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

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

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Day 9

Day 9

  • Verona
  • Florence
  • More

Drive 254 km, 3 hours 31 min

  • piazza delle Erbe
  • piazza dei Signori
  • Verona Cathedral
  • Ponte Pietra
  • Castel San Pietro
  • More

Day 9 of your relaxed road trip across Italy offers a day of exciting discoveries. You’ll end your day in Florence, where you’ll stay for 4 nights.

Continue your laid-back road trip in Italy as you make your way to Florence. Here, you’ll find top hotels and accommodations in the city, perfect for relaxing and recharging.

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.

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

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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Day 10

Day 10

  • Florence
  • More

Drive 2 km, 28 min

  • Cathedral of Santa Maria del Fiore
  • Brunelleschi's dome
  • Opera del Duomo Museum
  • Basilica of Santa Croce in Florence
  • More

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Bologna. There are so many fun and eye-opening activities to try out in Bologna that will make your slow-paced self-drive tour in Italy more memorable.

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.

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.

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

Read more
Day 11

Day 11

  • Florence
  • More

Drive 18 km, 1 hour 17 min

  • Parco delle Cascine
  • Strozzi Palace
  • Palazzo Pitti
  • The Boboli Gardens
  • Oltrarno
  • More

Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities.

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.

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

Grab yourself a drink and savor every moment of your relaxed road trip experience in Italy!

Read more
Day 12

Day 12

  • Florence
  • More

Drive 6 km, 45 min

  • piazza della Signoria
  • Palazzo Vecchio
  • Uffizi Gallery
  • Ponte Vecchio
  • piazzale Michelangelo
  • More

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.

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.

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.

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

Read more
Day 13

Day 13

  • Florence
  • Bologna
  • More

Drive 110 km, 2 hours 20 min

  • Basilica of Santa Maria Novella
  • Central Market
  • Galleria dell'Accademia
  • David
  • Piazza della Libertà
  • More

Day 13 of your relaxed road trip in Italy will take you on a self-paced journey to more than one incredible place in one day. See some of the best attractions in Italy, taste the most delectable foods and exquisite drinks, and make incredible memories as you go!

You'll be staying in Bologna on this laid-back road trip through Italy. You'll stay here for 1 night.

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

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 Bologna. The bars in Bologna make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

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

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Day 14

Day 14

  • Bologna - Departure day
  • More
  • Tombs of the glossators of Bologna
  • More

Day 14 of your relaxed road trip in Italy is your departure day. If you’re flying home, return your rental car with time to spare.

Discover boutiques offering an array of stylish fashion choices. For those seeking luxury items, check out the area’s high-end stores.

Over a good meal, take a moment to unwind and reflect on the past 14 days of your relaxed road trip.

The unforgettable experiences you’ve collected along your 14-day relaxed road trip in Italy is a story you will tell for the rest of your life.

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How it works

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Secure your spot
Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.
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Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.
Secure your spot
Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.
Get instant confirmation
Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

We guarantee

Your trip is protected, personalized, and priced right. No surprises, no stress.

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