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

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Photo of piazza de spagna in Rome, Italy.
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Sit back and enjoy a relaxed 14-day self-drive holiday in Italy. Along the way, Rome, Arezzo, Bologna, Venice, and Florence 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 Rome, 1 night in Arezzo, 4 nights in Venice, 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 Rome, 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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Pick-up: 10:00
Drop-off: 10:00

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Day 1

Day 1

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

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

Experience the amazing nightlife in Rome and unwind at the coolest 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 Rome as you soak in the city’s unique vibe.

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Day 2

Day 2

  • Rome
  • More

Drive 5 km, 1 hour 7 min

  • Campo de' Fiori
  • Piazza Navona
  • Pantheon
  • Roman Forum
  • Colosseum
  • More

Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Rome.

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.

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

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Day 3

Day 3

  • Rome
  • More

Drive 13 km, 54 min

  • Villa Borghese
  • piazza del Popolo
  • Piazza di Spagna
  • Spanish Steps
  • Castel Sant'Angelo
  • More

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

For an unforgettable shopping experience, visit Galleria San Pietro, the top shopping destination in Rome. Browse local shops and stores, each offering delightful surprises. Find unique souvenirs or items to take home. After shopping, explore what Galleria San Pietro has to offer, including attractions, essential services, and vibrant community activities.

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.

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

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

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Day 4

Day 4

  • Rome
  • Arezzo
  • More

Drive 223 km, 2 hours 41 min

  • St Peter's Basilica
  • More

Day 4 of your relaxed road trip across Italy offers a day of exciting discoveries. You’ll end your day in Arezzo, where you’ll stay for 1 night.

When you’re not exploring beautiful places, you can relax in Arezzo. 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.

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

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

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Day 5

Day 5

  • Arezzo
  • Venice
  • More

Drive 331 km, 4 hours

  • Piazza Maggiore
  • Two Towers
  • Piazza Santo Stefano
  • More

Day 5 of your self-drive tour in Italy offers a chance to experience the country’s diversity. You’ll stay in Venice for 4 nights. Along the way, you’ll glimpse local life and explore some of the most remarkable places in Italy.

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

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 Venice.

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!

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Day 6

Day 6

  • Venice
  • More

Drive 2 km, 32 min

  • Piazza San Marco
  • St Mark's Campanile
  • St Mark's Basilica
  • Doge's Palace
  • Bridge of Sighs
  • 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 Venice 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, it’s time to fall in love with the amazing nightlife in Venice and unwind at some of the best bars in the city.

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

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Day 7

Day 7

  • Venice
  • More

Drive 2 km, 36 min

  • Ca' Pesaro International Gallery of Modern Art
  • Basilica S.Maria Gloriosa dei Frari
  • Santa Croce
  • 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.

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 Venice.

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.

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

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Day 8

Day 8

  • Venice
  • More

Drive 4 km, 37 min

  • Punta della Dogana - Pinault Collection
  • Santa Maria della Salute
  • Peggy Guggenheim Collection
  • 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, Venice 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 Venice. The bars in Venice make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

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 9

Day 9

  • Venice
  • Florence
  • More

Drive 273 km, 3 hours 28 min

  • Rialto Bridge
  • Teatro La Fenice
  • Gallerie dell'Accademia
  • More

Day 9 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!

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.

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.

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.

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

Read more
Day 10

Day 10

  • Florence
  • More

Drive 9 km, 49 min

  • Palazzo Pitti
  • The Boboli Gardens
  • Oltrarno
  • More

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

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

Raise your glass and toast to another unforgettable, laid-back road trip adventure in Italy!

Read more
Day 11

Day 11

  • Florence
  • More

Drive 2 km, 27 min

  • Florence Baptistery
  • Cathedral of Santa Maria del Fiore
  • Opera del Duomo Museum
  • Basilica of Santa Croce in Florence
  • 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 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, stop at some of Florence’s best bars to celebrate this day of your slow-paced adventure in Italy.

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

Read more
Day 12

Day 12

  • Florence
  • More

Drive 3 km, 45 min

  • David
  • Galleria dell'Accademia
  • Central Market
  • Basilica of Santa Maria Novella
  • 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 Florence, explore the city like a local by trying out the best restaurants in the area.

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

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

Read more
Day 13

Day 13

  • Florence
  • Rome
  • More

Drive 286 km, 3 hours 46 min

  • piazza della Signoria
  • Ponte Vecchio
  • Uffizi Gallery
  • piazzale Michelangelo
  • Tower of San Niccolò
  • More

Day 13 of your leisurely self-drive tour in Italy offers another chance for an in-depth travel experience. You’ll stay in Rome for 1 night.

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

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.

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

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

Read more
Day 14

Day 14

  • Rome - Departure day
  • More
  • Altare della Patria
  • 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.

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

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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