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

Day 2 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!

Leaning Tower Of Pisa brings Pisa's character to life. This noteworthy monument is a highlight of any visit in the city. Then, enjoy Piazza Del Duomo, Pisa, another picture-perfect attraction that never fails to captivate visitors. Next, head over to Pisa Cathedral, one of the city’s most beloved attractions, known for its picture-perfect features.

When you’re ready to jump back into the car and say goodbye to Pisa, you’ll hit the road in the direction of Cascine Vecchie. This drive usually takes around 9 min.

For a more meaningful self-guided tour of the city's best attractions, visit Parco Regionale Migliarino, San Rossore, Massaciuccoli, a frequently visited nature reserve that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey.

When you’ve had your share of Cascine Vecchie, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Tirrenia. Your travel time is around 24 min.

For a more meaningful self-guided tour of the city's best attractions, visit Bagno Degli Americani, an intriguing point of interest that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey.

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 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 a taste of local culinary excellence while in Florence by securing a table at Enoteca Pinchiorri. An esteemed 3-star Michelin restaurant, it features an exceptional italian contemporary menu. For an alternative taste experience, visit Santa Elisabetta, famous for its scrumptious creative and mediterranean dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Gucci Osteria da Massimo Bottura, a local favorite celebrated for its exquisite italian contemporary and international cuisine in Florence. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary and international 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 Florence.

Round off your dining experience by visiting Manifattura, a prime location for a drink. Alternatively, explore the distinctive characteristics of Se·sto On Arno Rooftop Bar, a bar catering to every mood and preference. Il Vinile likewise offers a unique atmosphere, perfect for a memorable night out.

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

Day 3 of your relaxed road trip through Italy means 24 hours of making the best memories in Florence. You’ll go sightseeing at famous attractions in Florence. 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 Florence!

Florence is brimming with adventures.

One of the most famous attractions included on the itinerary is Piazzale Michelangelo. This romantic observation deck will help you start your sightseeing on top. Then, take a leisurely stroll to Basilica Of Santa Croce In Florence and learn what makes this heritage-rich church unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the top-rated Piazza Della Signoria. After exploring the public square, head to Uffizi Gallery. This famous art gallery is a highlight in Florence. As your day continues, stop by Ponte Vecchio, known for its enchanting features.

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

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.

Enjoy a lovely meal at Ditta Artigianale, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria Da Burde is another top choice with a popular menu. You could also check for a table at Casa Toscana. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Florence tonight.

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

Keep the evening going at Bar 50 Rosso, a great choice for enjoying the after-dinner hours with a drink. You could also go to Bitter Bar, which offers a similarly pleasant setting and great drinks. Another option is Archea Brewery, which provides an inviting environment for unwinding after a busy day out.

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

Day 4 of your relaxed road trip across Italy offers a day of exciting discoveries. You’ll start your day in Florence and drive in the direction of Bologna for some laid-back sightseeing. You’ll end your day in Bologna, where you’ll stay for 4 nights.

Experience Cathedral Of Santa Maria Del Fiore, a spectacular church in the city. Then, head to Galleria Dell'accademia and soak in the ambiance of this detailed art gallery.

There are many interesting places to see in Florence, and when you are ready for more, go to Central Market. This is one of the city’s most notable eye-catching spots of interest. After exploring the food market, visit the well-known Basilica Di Santa Maria Novella, Firenze (fi).

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.

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.

Dive into a culinary adventure like no other in Bologna by booking a table at Ahimè. This popular restaurant holds a Bib Gourmand award and offers an exceptional menu of country cooking cuisine. For another dining option, venture to I Portici, celebrated for its delectable creative and contemporary menu. This acclaimed 1-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Trattoria di Via Serra, a top local restaurant known for its tantalizing emilian menu. With a Bib Gourmand recognition, it promises an exceptional dining experience not to be missed.

As the day is coming to an end, stop at some of Bologna’s best bars to celebrate this day of your slow-paced adventure in Italy.

Unwind after your meal by stepping into Bar Al Bricco D'oro. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Freud E Squisito offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Osteria Del Sole, another top-rated bar in the area.

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

On day 5 of your leisurely self-drive tour across Italy, you’ll go deep into Bologna, where you'll stay for 3 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 Bologna, and meet locals along the way!

Palazzo Pallavicini is perfect for a self-paced visit during the day. This historic palace is sure to impress. Next on your list is Bologna Cathedral, another must-visit landmark and curiosity-inducing church renowned for its stunning features.

While exploring and sightseeing, take time to savor the culture of Bologna by sampling some local delicacies. When you’re ready for more sightseeing, head to Piazza Maggiore. This visually striking public square is an essential place to visit for anyone looking for the full Bologna experience. We also recommend visiting Fountain Of Neptune, Bologna, an underrated monument. Nearby, you'll also find Palazzo Re Enzo, ready to add charm to your journey.

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

Treat yourself to a delicious dinner at Bononia Cafè, an excellent option for tonight's dining. Looking for something different? Via Con Me offers a tantalizing alternative with its diverse menu. And don’t miss Trattoria Pizzeria La Mela. Known for great service, it’s a fantastic choice for tonight in Bologna.

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

Following your dinner, dive into the local bar culture at Lime Bar. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Macondo - Cocktail Bar, the perfect place for those looking to experience the best of the nightlife. Similarly, Bar Onda Marina By Night provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Day 6 introduces you to many popular attractions and activities in Bologna, further proving that leisurely self-drive tours in Italy are extraordinary.

Awaiting your discovery is the worthwhile Arco Del Meloncello, a culturally significant monument in Bologna. Next, go to Basilica Of San Domenico.

After visiting Arco Del Meloncello and Basilica Of San Domenico, have a stroll along Bologna's streets and take in the local charm. Continue your sightseeing by heading to Two Towers. This culturally significant monument offers a unique experience. Piazza Santo Stefano is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Porta Santo Stefano, one of the most photogenic places to visit in Bologna.

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 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.

Savor the flavors at Va Mo Là, a top pick for dinner tonight. Alternatively, Trattoria dal Biassanot beckons with its unique menu offerings. Also, consider Ristorante Enoteca da Lucia. With its consistent customer satisfaction, it’s an excellent option for dining in Bologna tonight.

As the day is coming to an end, stop at some of Bologna’s best bars to celebrate this day of your slow-paced adventure in Italy.

Explore the vibrant nightlife at Aurum after your meal, a hub for lively evenings and memorable moments. Or, head to Bar Senza Nome for a great selection of flavorful drinks and a charming setting. Furthermore, Caffè Ristretto is perfect for those looking to extend their night with a touch of local flavor.

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

Day 7 of your relaxed road trip through Italy means 24 hours of making the best memories in Bologna. You’ll go sightseeing at famous attractions in Bologna. 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 Bologna!

Whether you decide to explore Bologna on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Make time for Ducati Museum, an increasingly popular museum that is worthwhile a visit in the city. Nearby, you’ll find Porta Galliera, enchanting visitors with its heritage-rich appeal. Continue your exploration at Botanical Garden And Herbarium. This botanical garden is one of the city’s most intriguing spots.

Enjoy the freedom of exploring Bologna at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Pinacoteca Nazionale Di Bologna.

Gain a one-of-a-kind experience on your unhurried and relaxed road trip across Italy by joining a traveler-approved tour in Pisa. There are so many fun and eye-opening activities to try out in Pisa 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 Bologna to find the best options for you!

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

Dine in style at Pappare' - Bologna, a top recommendation for dinner tonight. Or, for a change of pace, Mister Coffee Bistrò boasts a menu that's sure to impress. Also, be sure to check out All'Osteria Bottega. Known as a local hotspot, it’s a great choice for tonight 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.

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

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

Day 8 of your self-drive tour in Italy offers a chance to experience the country’s diversity. You’ll start your day in Verona and end it in Milan. You’ll stay in Milan for 5 nights. Along the way, you’ll glimpse local life and explore some of the most remarkable places in Italy.

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

When you’re ready to jump back into the car and say goodbye to Bologna, you’ll hit the road in the direction of Verona. This drive usually takes around 1 hour 47 min.

Spend your afternoon discovering Castelvecchio Museum, an interesting museum known for its awe-inspiring features. Next, continue your sightseeing at Castelvecchio Bridge, a locally renowned monument.

If you're starting to feel hungry, this is a great time for a break at a nearby restaurant or cafe. When you're ready for more, stop by Verona Arena and uncover the details of this romantic stadium. Make sure to also explore Piazza Delle Erbe, a popular public square.

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

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.

Have a memorable dining experience in Milan by booking a table at Enrico Bartolini al Mudec, a 3-star Michelin restaurant presenting an exceptional creative menu. For a different culinary experience in Milan, Seta by Antonio Guida shines as one of the top destinations, known for its delicious international and contemporary cuisine. This 2-star Michelin-awardee consistently earns high praises, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Il Luogo Aimo e Nadia is known as a top local spot in Milan for its delicious italian contemporary and modern cuisine. This 1-star Michelin awardee is a highly recommended choice for an unforgettable meal.

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 Milan. The bars in Milan make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

Cap off your dinner by heading to Nottingham Forest, ideal for a leisurely evening with a drink in hand. Armani/bamboo Bar is another bar that offers an enjoyable setting. Similarly, Mag Cafe is also a popular place to go on a night out, perfect for relaxing and socializing.

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

On day 9 of your leisurely self-drive tour across Italy, you’ll go deep into Milan, where you'll stay for 4 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 all that La Scala has to offer. This is an interesting opera house you should not miss. Another must-see is Galleria Vittorio Emanuele Ii, a famous shopping mall in Milan.

When you’re ready for the next sight, head to Duomo Di Milano Museum. From there, take a leisurely stroll to Cathedral Square, another of the city’s intriguing attractions. We recommend continuing your self-guided tour at Royal Palace Of Milan, a photogenic place of interest in the city.

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

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.

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.

After savoring a delicious meal, step into the vibrant nightlife at Kilburn Cocktail Bar Milano, where the evening is just getting started. In the same way, Bar Frida offers a unique charm perfect for experiencing the local bar scene in Milan. The Friends Pub Milano is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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

Day 10 introduces you to many popular attractions and activities in Milan, further proving that leisurely self-drive tours in Italy are extraordinary.

Check out the interesting monument, Arch Of Peace. Afterward, continue to Triennale Di Milano, a museum every traveler should visit. As you explore Milan’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Parco Sempione. This impressive park is an essential stop. Following that, head to Sforzesco Castle Art Library, another must-visit site that will enhance your experience. Don’t forget to stop by Piazza Castello Fountain, an intriguing public square in the city.

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 Milan.

Don’t miss out on dining 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.

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

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

Day 11 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!

Let Piazza Gae Aulenti set the tone for the day. Spend some time admiring this awe-inspiring public square before continuing your journey. Pinacoteca Di Brera is your next stop. This popular art gallery is one of the best-rated sights in Milan.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Milan Natural History Museum. This visually striking museum is a sight to behold. To round off your sightseeing experience, visit Villa Necchi Campiglio.

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

Treat yourself to a wonderful meal at Ristorante la Brisa, a top-rated dining spot in Milan. If you're in the mood for something new, try Pasticceria San Carlo, another premier location with a delectable menu. You might also want to book a table at UNAHOTELS Cusani Milano. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Milan.

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.

Round off your dining experience by visiting Qc Termemilano, a prime location for a drink. Alternatively, explore the distinctive characteristics of Yguana Cafè, a bar catering to every mood and preference.

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 12 of your leisurely self-drive tour across Italy, you’ll go deep into Milan, where you'll stay for 1 night, 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!

Catch Basilica Di Sant'ambrogio before the crowds roll in. This photogenic church is sure to ignite your curiosity. Next, dive into the eye-catching features of Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", a must-visit museum in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Santa Maria Delle Grazie Church, a well-known church. For a change of scene, check out Mudec - Museum Of Cultures, known for its eye-catching features.

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

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.

Enjoy a delicious meal at Vento di Sardegna, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Palazzo Parigi Hotel & Grand Spa Milano, another top spot with a mouthwatering menu. You might also want to secure a reservation at Galleria Restaurant. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

Experience the amazing nightlife in Milan 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!

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.

Fasten your seatbelt and make your way to your next stop — La Spezia, home to many well-known sights in the region. Keep in mind that your travel time from Milan to La Spezia may take around 2 hours 47 min without traffic disruptions. Upon arrival in La Spezia, we highly recommend checking out some of the top attractions.

Savor the day by heading to Castello San Giorgio, a frequently visited castle that draws visitors from near and far. When you're done, continue to Giardini Pubblici, where you can soak in the romantic surroundings.

Next, explore Technical Naval Museum Of Spezia, yet another frequently visited place to see in the area.

You'll be staying in Pisa 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 Pisa, explore the city like a local by trying out the best restaurants in the area.

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. Known for great service, it’s a fantastic choice for tonight in Pisa.

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.

After your meal, keep the night alive at a bar like Bar Mocambo, known for its lively atmosphere. Tree is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Chupiteria offers an excellent atmosphere for those looking to amp up the evening.

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