Relaxed 9-Day Italy Self-Drive Road Trip With Itinerary from Pisa to Milan

On day 2 of your leisurely self-drive tour across Italy, you’ll go deep into Tirrenia, where you'll stay for 2 nights, and see some of the village’s unforgettable attractions. To learn more of the village's culture, you'll also dine at the most popular restaurants in Tirrenia, and meet locals along the way!

Discover a day packed with fun adventures, scenic views, and picturesque spots in Pisa. Begin your sightseeing with Bagno Degli Americani. This frequently visited sightseeing destination is one of the top attractions in the village. Proceed to Leaning Tower Of Pisa, another must-visit attraction that enhances the village’s allure.

As you wander through the inviting streets of Pisa, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Piazza Del Duomo, Pisa. This world-famous public square is a traveler-favorite. Not far away, you’ll find Pisa Cathedral, another key site on your sightseeing itinerary. Conclude your day at Parco Regionale Migliarino, San Rossore, Massaciuccoli and uncover why it's recognized as one of the village's most worthwhile attractions.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Tirrenia. There are so many fun and eye-opening activities to try out in Tirrenia that will make your slow-paced self-drive tour in Italy more memorable. Check out all the most recommended and top-rated tour options in the village of Tirrenia to find the best options for you!

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 Pisa.

Treat yourself to a delicious dinner at Ristorante Capodimonte Pisa, an excellent option for tonight's dining. Looking for something different? La Locanda Dei Pisani Doc Pisa offers a tantalizing alternative with its diverse menu. And don’t miss Baribaldi Pisa. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Pisa.

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.

Continue the enjoyment post-dinner at Bar Mocambo, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Tree offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Chupiteria. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Raise your glass to celebrate another day of your laid-back and relaxed road trip experience in Italy!

Day 3 introduces you to many popular attractions and activities in Pisa, further proving that leisurely self-drive tours in Italy are extraordinary.

Prepare for a day full of fun adventures, romantic experiences, and scenic views. When you’re ready, kick off your sightseeing adventure at Cittadella Nuova. This underrated park is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Logge Dei Banchi, one of the city’s best highlights.

Next, check out Palazzo Blu, one of the most locally appreciated places to see in Pisa. This art gallery is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Santa Maria Della Spina. Wander around and soak in the enchanting atmosphere this church offers. Then, head to “tuttomondo” (keith Haring), a top-rated art installation that adds another dimension to your day.

Another way to make your easygoing and relaxed road trip in Italy more special is by joining unique tours and activities. Pisa offers a wide selection of experiences for every traveler.

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.

Treat yourself to a delightful dinner at Restaurant -Pizzeria Il Mio Capriccio, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Ristorante alle Bandierine? It's another excellent option with a diverse menu. Consider reserving a table at Barrique Cocktail And Bistrot as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Pisa.

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

Extend your evening after a delightful meal by visiting Bar Livorno, which offers the perfect atmosphere for a night out.

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

Day 4 of your relaxed road trip across Italy promises an exciting agenda full of discovery. You’ll start your day in the town of Collecchio and drive in the direction of the hamlet of Priorato II for some laid-back sightseeing. You’ll end your day in the city of Milan, where you’ll stay for 4 nights.

Today, you'll explore some of the most beautiful places in Pisa, including a park, a maze, and a castle. Start your day with a visit to Parco Nevicati. This underrated park is a must-visit in the town. When you’re ready for your next discovery, continue to Labirinto Della Masone, which may be one of the most picture-perfect places you will experience today.

One of the best things about exploring Pisa on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Rocca Sanvitale, a frequently visited castle in the town.

You’ll be staying at the incredible city of Milan in this laid-back road trip in Italy. You'll stay here for 4 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.

Experience a taste of local culinary excellence while in Milan by securing a table at Enrico Bartolini al Mudec. An esteemed 3-star Michelin restaurant, it features an exceptional creative menu. For an alternative taste experience, visit Seta by Antonio Guida, famous for its scrumptious international and contemporary dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Il Luogo Aimo e Nadia, a local favorite celebrated for its exquisite italian contemporary and modern cuisine in Milan. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary and modern cuisine lovers seeking top-notch culinary experiences.

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

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Nottingham Forest stands out as an excellent choice for a post-dinner cocktail. Alternatively, Armani/bamboo Bar offers an ideal atmosphere to enjoy the pleasures of the night. Mag Cafe is also a great option that provides a perfect setting for a relaxing evening.

A leisurely self-drive holiday in Collecchio can’t get any better than this! Toast to another amazing day in Italy!

Day 5 of your relaxed road trip through Italy means 24 hours of making the best memories in Milan. You’ll go sightseeing at famous attractions in Milan. In the evening, you will experience one of the most popular dining spots in the city. So buckle up and prepare to be blown away by Milan!

Bring your curiosity for today’s adventure around Milan. Some of the city’s most loved attractions await. Royal Palace Of Milan is the perfect place to start. This palace is one of the most locally renowned places to visit in Milan. Next, head to Cathedral Square, an intriguing public square, known for its majestic features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Duomo Di Milano Museum. This visually striking church offers a unique experience that is highly recommended. Meanwhile, Galleria Vittorio Emanuele Ii adds its own distinct charm to your journey. Finish your day with a visit to La Scala, a respected opera house in Milan.

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

Make sure to reserve a table at Dessert Bar Milano, an iconic dining spot in Milan. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Radisson Blu Hotel Milan, a popular restaurant in Milan. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Ristorante Qui Si Mangia, a hidden gem nestled in Milan. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Kilburn Cocktail Bar Milano stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bar Frida offers an ideal atmosphere to enjoy the pleasures of the night. The Friends Pub Milano is also a great option that provides a perfect setting for a relaxing evening.

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

On day 6 of your leisurely self-drive tour across Italy, you’ll go deep into Milan, where you'll stay for 2 nights, and see some of the city’s unforgettable attractions. To learn more of the city's culture, you'll also dine at the most popular restaurants in Milan, and meet locals along the way!

Enjoy the perfect balance of relaxation and exploration in Milan today. One of the most captivating attractions included on the itinerary is Arch Of Peace. This detailed monument will help you start your sightseeing on top. Then, take a leisurely stroll to Parco Sempione and learn what makes this instagrammable park unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the spectacular Sforzesco Castle Art Library. After exploring the castle, head to Pinacoteca Di Brera. This captivating art gallery is a highlight in Milan. Lastly, don’t forget to check out the captivating Piazza Gae Aulenti. Enjoy exploring this incredible public square at your own pace.

Italy makes the perfect setting for a calming but fun exploration. 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.

Enjoy a delicious meal at Bice Restaurant, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Alto Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at Nero 9. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

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.

If you’re not ready to end the night just yet, Bhangrabar offers a perfect venue to relax and savor a drink. Similarly, Rufus Cocktail Bar is well-suited for those looking to unwind in a social setting. Ostello Bello Grande is another excellent spot to enjoy a nightcap after a delightful meal.

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

Day 7 introduces you to many popular attractions and activities in Milan, further proving that leisurely self-drive tours in Italy are extraordinary.

Today’s route brings family-friendly attractions, picturesque spots, and history-rich sites. The first attraction of today is Basilica Di Sant'ambrogio. This locally renowned church is a culturally significant place to see in Milan. Continue your discovery at Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", a heritage-rich museum with stories to tell.

As you stroll around Milan, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Santa Maria Delle Grazie Church. This popular church offers a heritage-rich encounter with Milan. Next, make your way to Mudec - Museum Of Cultures to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Milan.

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. Check out all the most recommended and top-rated tour options in the city of Milan to find the best options for you!

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.

Enjoy a lovely meal at Ristorante la Brisa, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Pasticceria San Carlo is another top choice with a popular menu. You could also check for a table at UNAHOTELS Cusani Milano. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Milan tonight.

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.

To truly maximize your evening out, consider visiting Qc Termemilano after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Yguana Cafè, another bar with an inviting ambiance.

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

Day 8 of your relaxed road trip across the beautiful country of 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!

Enjoy the perfect balance of relaxation and exploration in Milan today. One of the most often recommended attractions included on the itinerary is Parco Giochi La Maggiolina. Then, take a leisurely stroll to Castello San Giorgio and learn what makes this historic castle unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the increasingly popular Giardini Pubblici. After exploring the park, head to Technical Naval Museum Of Spezia. This worthwhile museum is a highlight in Milan.

After a day of exploration, relax at one of the top hotels or accommodations in Pisa. Staying in the city enhances your laid-back road trip experience in Italy by offering a comfortable and welcoming environment to recharge in this charming destination.

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

Enjoy a delicious meal at Anita Osteria, a top-rated dining destination in Pisa. If you're in the mood to try something new, consider La corte di San Leonardo, another top spot with a mouthwatering menu. You might also want to secure a reservation at Filter Coffee Lab. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Pisa this evening.

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.

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