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Road trips in Italy

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

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Panoramic view to Bridge Ponte Pietra in Verona on Adige river. Veneto region. Italy. Sunny summer day panorama and blue dramatic sky with clouds. Ancient european italian terracotta color houses

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Sit back and enjoy a relaxed 14-day self-drive holiday in Italy. Along the way, Verona, Peschiera del Garda, Valeggio sul Mincio, Florence, Orvieto, Rome, Siena, and Bologna invite you to discover their unique blend of culture, scenery, and memorable experiences.

Travel freely with this relaxed self-drive package in Italy, designed for comfort and exploration. Spend 4 nights in Verona, 4 nights in Florence, 4 nights in Rome, and 1 night in Siena, 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 Verona, 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 Trevi Fountain and soak in the atmosphere of the magnificent Colosseum.

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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Day 1

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

Verona 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.

When you're ready for some downtime, make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Verona. Make yourself at home and unwind before heading out again.

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

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.

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

Day 2

Verona
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Drive 4 km, 31 min

piazza delle Erbe
Torre dei Lamberti
piazza dei Signori
Ponte Pietra
Museo Archeologico al Teatro Romano
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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.

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

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

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

Day 3

Verona
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Drive 6 km, 53 min

Tomba di Giulietta
Castelvecchio Museum
Castelvecchio Bridge
Basilica di San Zeno Maggiore
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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.

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 Verona, 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, stop at some of Verona’s best bars to celebrate this day of your slow-paced adventure in Italy.

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

Day 4

Verona
Florence
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Drive 279 km, 3 hours 55 min

Porta Brescia
Fortifications
Parco Giardino Sigurtà
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Day 4 of your leisurely self-drive tour in Italy offers another chance for an in-depth travel experience. You’ll stay in Florence 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 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.

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

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

Day 5

Florence
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Drive 1.0 km, 12 min

piazza della Signoria
Palazzo Vecchio
Uffizi Gallery
Ponte Vecchio
Oltrarno
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Set aside time today to explore Oltrarno, 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.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Verona. There are so many fun and eye-opening activities to try out in Verona 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.

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.

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.

Day 6

Florence
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Drive 10 km, 1 hour

The Boboli Gardens
Giotto's Bell Tower
Florence Baptistery
Cathedral of Santa Maria del Fiore
Brunelleschi's dome
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Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities.

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.

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.

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

Day 7

Florence
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Drive 3 km, 45 min

David
Galleria dell'Accademia
Central Market
Basilica of Santa Maria Novella
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Throughout the day, make sure to take breaks to appreciate the surroundings.

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 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.

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.

Day 8

Florence
Rome
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Drive 299 km, 4 hours 10 min

Basilica of Santa Croce in Florence
Tower of San Niccolò
piazzale Michelangelo
Orvieto Cathedral
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Day 8 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 Rome, where you’ll stay at a top-rated hotel of your choice for 4 nights.

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

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.

Toast to another amazing day in Italy!

Day 9

Rome
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Drive 8 km, 1 hour 2 min

Trevi Fountain
Pantheon
Piazza Navona
Campo de' Fiori
Castel Sant'Angelo
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Exploring the food culture in Rome 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.

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

Day 10

Rome
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Drive 4 km, 54 min

Altare della Patria
Capitoline Hill
Roman Forum
Colosseum
Circus Maximus
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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 Rome, explore the city like a local by trying out the best restaurants in the area.

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

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

Day 11

Rome
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Drive 11 km, 52 min

Spanish Steps
Piazza di Spagna
piazza del Popolo
Passeggiata del Pincio
Villa Borghese
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Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities.

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

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

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

Day 12

Rome
Siena
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Drive 242 km, 2 hours 57 min

St Peter's Basilica
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Day 12 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!

Throughout the day, make sure to take breaks to appreciate the surroundings.

When you’re not exploring beautiful places, you can relax in Siena. 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 Siena, explore the city like a local by trying out the best restaurants in the area.

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

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

Day 13

Siena
Verona
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Drive 313 km, 4 hours

Tower of Mangia
piazza del Campo
Siena Cathedral
Piazza Maggiore
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On day 13 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.

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

Exploring the food culture in Verona 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.

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

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

Day 14

Verona - Departure day
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Porta Borsari
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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.

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.

How it works

Book your journey with Europe’s biggest travel platform—expert itineraries, instant confirmation, and full flexibility with 24/7 support.

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.

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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