Two-Week Relaxed Italy Self-Drive Road Trip With Itinerary from Milan to Venice, Florence, and Rome

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, Milan has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of 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.

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.

On day 3 of your relaxed road trip across Italy, you’ll explore the area around Milan, where you’ll be staying for another 1 night. With so many fun and inspiring experiences to offer, a tour of Milan will make you fall even more in love with the city and uniqueness of Italy.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Milan.

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.

After dinner, it’s time to fall in love with the amazing nightlife in Milan and unwind at some of the best 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 4 of your relaxed road trip across Italy offers a day of exciting discoveries. You’ll end your day in Venice, where you’ll stay for 3 nights.

In Venice, 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 Venice, 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 Venice’s best bars to celebrate this day of your slow-paced adventure in Italy.

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

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

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.

Before calling it a day, visit one of the best bars in Venice. 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 to celebrate another day of your laid-back and relaxed road trip experience in Italy!

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.

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

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

Day 7 of your leisurely self-drive tour in Italy offers another chance for an in-depth travel experience. You’ll stay in Florence for 3 nights.

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.

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.

Before calling it a day, visit one of the best bars in Florence. 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 and relax after another big day of your leisurely paced road trip in Italy!

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.

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.

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

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

On day 9 of your relaxed road trip in Italy, you’ll start your self-paced adventure in Florence and visit amazing attractions in Pisa, just outside the city. You still have 1 night left in Florence, so today is another excellent opportunity to dine at some of the top-rated restaurants and bars in the area.

When you’re done exploring for the day, you’ll return to Florence and your accommodation.

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.

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

Day 10 of your self-drive tour in Italy offers a chance to experience the country’s diversity. You’ll stay in Rome for 4 nights. Along the way, you’ll glimpse local life and explore some of the most remarkable places in Italy.

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

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

Toast to another amazing day in Italy!

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

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

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

Your relaxed road trip in Italy continues on day 12 with more unforgettable memories to make. Today, you’ll get to know Italy better by exploring the top attractions of Rome and beyond. With 2 nights left in Rome, you’ll still have time to eat and unwind at popular restaurants and bars in the city.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Rome.

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.

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

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

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.

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

Toast to another amazing day in Italy!