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

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.

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.

Toast to another amazing day in Italy!

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 Bologna, where you’ll stay at a top-rated hotel of your choice for 3 nights.

In Bologna, 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.

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 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!

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 Bologna.

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.

Raise your glass to celebrate another day of your laid-back and relaxed road trip experience 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 Florence. There are so many fun and eye-opening activities to try out in Florence that will make your slow-paced self-drive tour in Italy more memorable.

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.

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

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

Day 6 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.

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

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

Raise your glass in celebration of your freedom and relaxed 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.

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 Venice, 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 Venice.

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

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 Venice, 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 Venice. There, you can look back on the highlights of today’s pleasant and invigorating travel experiences, have friendly conversations with locals, and unwind.

Grab yourself a drink and savor every moment of your 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.

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.

Experience the amazing nightlife in Venice and unwind at the coolest 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!

Day 10 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 Milan on this laid-back road trip through Italy. You'll stay here for 3 nights.

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.

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.

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

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 Florence. There are so many fun and eye-opening activities to try out in Florence 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.

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.

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

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 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.

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

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.

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.

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.

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.

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