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

Day 2 of your self-drive tour in Italy offers a chance to experience the country’s diversity. You’ll start your day in Pisa and end it in Florence. You’ll stay in Florence for 2 nights. Along the way, you’ll glimpse local life and explore some of the most remarkable places in Italy.

Awaiting your discovery is the iconic Leaning Tower Of Pisa, an UNESCO world heritage-listed monument in Pisa. Next, go to Piazza Del Duomo, Pisa.

After visiting Leaning Tower Of Pisa and Piazza Del Duomo, Pisa, have a stroll along Pisa's streets and take in the local charm. Continue your sightseeing by heading to Pisa Cathedral. This picture-perfect church offers a unique experience.

Set your GPS to Cascine Vecchie and hit the road. Expect a journey of approximately 9 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Cascine Vecchie beckons with new experiences!

Savor the day by heading to Parco Regionale Migliarino, San Rossore, Massaciuccoli, an often recommended nature reserve that draws visitors from near and far.

Tirrenia’s wonders await as you prepare for another journey on the road, leaving the breathtaking surroundings of Cascine Vecchie behind. This drive usually takes around 24 min. Tirrenia welcomes you with a multitude of unique vacation experiences.

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

You'll be staying in Florence on this laid-back road trip through Italy. You'll stay here for 2 nights.

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.

Dive into a culinary adventure like no other in Florence by booking a table at Enoteca Pinchiorri. This popular restaurant holds 3 Michelin star and offers an exceptional menu of italian contemporary cuisine. For another dining option, venture to Santa Elisabetta, celebrated for its delectable creative and mediterranean menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, ensuring an essential addition to your holiday itinerary. Seeking an alternative? Discover Gucci Osteria da Massimo Bottura, a top local restaurant known for its tantalizing italian contemporary and international menu. With a 1-star Michelin recognition, it promises an exceptional dining experience not to be missed.

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, Manifattura stands out as an excellent choice for a post-dinner cocktail. Alternatively, Se·sto On Arno Rooftop Bar offers an ideal atmosphere to enjoy the pleasures of the night. Il Vinile is also a great option that provides a perfect setting for a relaxing evening.

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

On day 3 of your leisurely self-drive tour across Italy, you’ll go deep into Florence, 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 Florence, and meet locals along the way!

Florence is brimming with adventures.

Awaiting your discovery is the astonishing Piazzale Michelangelo, a history-steeped observation deck in Florence. Next, go to Basilica Of Santa Croce In Florence.

After visiting Piazzale Michelangelo and Basilica Of Santa Croce In Florence, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Piazza Della Signoria. This culturally significant public square offers a unique experience. Uffizi Gallery is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Ponte Vecchio, one of the most culturally significant places to visit in Florence.

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 Florence to find the best options for you!

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.

Enjoy a delicious meal at Ditta Artigianale, a highly-rated dining destination in Florence. If you're eager to try something different, consider Trattoria Da Burde, another top spot with a tantalizing menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Florence 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.

If you’re not ready to end the night just yet, Bar 50 Rosso offers a perfect venue to relax and savor a drink. Similarly, Bitter Bar is well-suited for those looking to unwind in a social setting. Archea Brewery is another excellent spot to enjoy a nightcap after a delightful meal.

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

Day 4 of your leisurely self-drive tour in Italy offers another chance for an in-depth travel experience. You’ll stay in Bologna for 4 nights.

Check out the top-rated church, Cathedral Of Santa Maria Del Fiore. Afterward, continue to Galleria Dell'accademia, an art gallery every traveler should visit. As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city.

Next, make your way to Central Market. This interesting food market is an essential stop. Following that, head to Basilica Di Santa Maria Novella, Firenze (fi), another must-visit site that will enhance your experience.

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

Experience a taste of local culinary excellence while in Bologna by securing a table at Ahimè. An esteemed Bib Gourmand restaurant, it features an exceptional country cooking menu. For an alternative taste experience, visit I Portici, famous for its scrumptious creative and contemporary dishes. This 1-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Trattoria di Via Serra, a local favorite celebrated for its exquisite emilian cuisine in Bologna. Located in the heart of the city, this Bib Gourmand-awardee is an ideal pick for emilian cuisine lovers seeking top-notch culinary experiences.

Before calling it a day, visit one of the best bars in Bologna. There, you can look back on the highlights of today’s pleasant and invigorating travel experiences, have friendly conversations with locals, and unwind.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar Al Bricco D'oro, known for its inviting atmosphere. Bar Freud E Squisito is another great option if you’re looking for a place to get the night started. Similarly, Osteria Del Sole provides a great setting to enjoy the night away.

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

Day 5 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!

Palazzo Pallavicini is must-visit palace and a great option for a daytime tour of the area. Continue your journey to Bologna Cathedral, a curiosity-inducing church, located just a leisurely stroll away. Next, head to Piazza Maggiore, a history-steeped public square, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Bologna. When you're ready, let your sightseeing route take you to the curiosity-inducing Fountain Of Neptune, Bologna. If you’re looking for more, Palazzo Re Enzo is also a locally appreciated attraction that is worthwhile a visit.

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.

Don’t miss out on dining at Bononia Cafè, a top-rated dining destination in Bologna. If you're in the mood to try something new, consider Via Con Me, another top spot with a mouthwatering menu. You might also want to secure a reservation at Trattoria Pizzeria La Mela. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Bologna this evening.

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 delicious meal, get a taste of the vibrant nightlife with a visit to Lime Bar, known for its inviting atmosphere. Macondo - Cocktail Bar is another great option if you’re looking for a place to get the night started. Similarly, Bar Onda Marina By Night provides a great setting to enjoy the night away.

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

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

Your adventure in Bologna is only getting started when you visit Arco Del Meloncello, an intriguing local hot spot. Another notable attraction to explore is Basilica Of San Domenico. This frequently visited church is known for its respected appeal.

After soaking in the highlights of these sights, take some time to wander Bologna's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Two Towers. This culturally significant monument offers a fascinating experience that many visitors find memorable. Piazza Santo Stefano is also worth visiting, along with Porta Santo Stefano. These standout landmarks offer unique experiences that add to the day’s enjoyment.

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

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.

Enjoy a lovely meal at Va Mo Là, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria dal Biassanot is another top choice with a popular menu. You could also check for a table at Ristorante Enoteca da Lucia. As an establishment that consistently gains high praises from customers, it’s an ideal choice 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.

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

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

On day 7 of your leisurely self-drive tour across Italy, you’ll go deep into Bologna, 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 Bologna, and meet locals along the way!

Ducati Museum is an ideal stop early in the day. This intriguing museum is a must-visit in the city. When you’re ready for your next discovery, continue to Porta Galliera, which may be one of the most heritage-rich places you will experience today.

One of the best things about exploring Bologna 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 Botanical Garden And Herbarium, a worthwhile botanical garden in the city. If you’re up for more discoveries, don’t forget to reserve some time for Pinacoteca Nazionale Di 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.

Treat yourself to a delicious dinner at Pappare' - Bologna, an excellent option for tonight's dining. Looking for something different? Mister Coffee Bistrò offers a tantalizing alternative with its diverse menu. And don’t miss All'Osteria Bottega. Known for great service, it’s a fantastic choice for tonight in Bologna.

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

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

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

On day 8 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.

When you’ve had your share of Bologna, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Verona. Your travel time is around 1 hour 47 min.

When you're ready for some sights, head to Castelvecchio Museum, a well-known museum in Verona. Explore its breathtaking features at your own pace before you continue your journey to your next attraction, Castelvecchio Bridge. This popular monument is a top recommendation in the area.

When you’re ready to explore more, Verona Arena is an excellent choice. Spend some time discovering what some claim to be the most history-steeped stadium in the region. Next, continue your sightseeing at the popular Piazza Delle Erbe and discover what makes this public square unique.

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 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.

Begin your culinary exploration in Milan by securing a reservation at Enrico Bartolini al Mudec. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of creative cuisine. For another dining delight, visit Seta by Antonio Guida, celebrated for its delectable international and contemporary menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Il Luogo Aimo e Nadia, a top local spot known for its tantalizing italian contemporary and modern menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

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

To truly maximize your evening out, consider visiting Nottingham Forest after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Armani/bamboo Bar, another bar with an inviting ambiance. Similarly, Mag Cafe also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

Day 9 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!

Check out the captivating opera house, La Scala. Afterward, continue to Galleria Vittorio Emanuele Ii, a shopping mall 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 Duomo Di Milano Museum. This world-famous church is an essential stop. Following that, head to Cathedral Square, another must-visit site that will enhance your experience. Don’t forget to stop by Royal Palace Of Milan, a well-known palace in the city.

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!

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.

Savor the flavors at Dessert Bar Milano, a top pick for dinner tonight. Alternatively, Radisson Blu Hotel Milan beckons with its unique menu offerings. Also, consider Ristorante Qui Si Mangia. With its consistent customer satisfaction, it’s an excellent option for dining in Milan tonight.

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

Extend your evening after a delightful meal by visiting Kilburn Cocktail Bar Milano, which offers the perfect atmosphere for a night out. Moreover, Bar Frida is another popular option for a drink or two. Likewise, The Friends Pub Milano also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Raise your glass to celebrate another day of your laid-back and 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.

Let Arch Of Peace set the tone for the day. Spend some time admiring this remarkable monument before continuing your journey. Triennale Di Milano is your next stop. This up-and-coming museum 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 Parco Sempione. This serene park is a sight to behold. To round off your sightseeing experience, visit Sforzesco Castle Art Library and Piazza Castello Fountain.

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.

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.

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.

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

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Bhangrabar, a well-loved spot among locals and tourists. Or, head to Rufus Cocktail Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Ostello Bello Grande, another top-rated place in the area.

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

On day 11 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!

Make time for Piazza Gae Aulenti, a locally renowned public square that is worthwhile a visit in the city. Nearby, you’ll find Pinacoteca Di Brera, enchanting visitors with its photogenic appeal. Continue your exploration at Milan Natural History Museum. This museum is one of the city’s most beloved spots.

Enjoy the freedom of exploring Milan at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Villa Necchi Campiglio.

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.

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.

Dine in style at Ristorante la Brisa, a top recommendation for dinner tonight. Or, for a change of pace, Pasticceria San Carlo boasts a menu that's sure to impress. Also, be sure to check out UNAHOTELS Cusani Milano. Known as a local hotspot, it’s a great choice for tonight 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.

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.

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

Day 12 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!

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

No visit to Milan is complete without Basilica Di Sant'ambrogio. This captivating church is one of the top attractions in the city. Proceed to Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", another must-visit attraction.

As you wander through the inviting streets of Milan, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Santa Maria Delle Grazie Church. This locally renowned church is a traveler-favorite. Not far away, you’ll find Mudec - Museum Of Cultures, another key site on your sightseeing itinerary.

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

Enjoy a lovely dining experience at Vento di Sardegna, a popular restaurant in Milan. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Milan at Palazzo Parigi Hotel & Grand Spa Milano, another great place to eat. With a menu designed to impress, it promises a journey of flavors that will leave you captivated. A third option to check out is the top-rated Galleria Restaurant. It’s yet another ideal choice to enhance your time in Milan tonight.

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.

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

Day 13 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!

It’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to La Spezia may take around 2 hours 47 min. Upon your arrival in La Spezia, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Castello San Giorgio, an underrated castle that everyone visiting La Spezia should see. Next, head to Giardini Pubblici. This serene park is one of the most frequently visited attractions in the region.

If you're keen to see more, don’t miss out on Technical Naval Museum Of Spezia, a photogenic museum popular among locals as well as travelers.

After a day of exploration, relax at one of the top hotels or accommodations in Pisa. 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, Pisa has multiple restaurants that offer fantastic dining experiences to continue your laid-back and stress-free discovery of the city.

Enjoy a lovely meal at Ristorante Capodimonte Pisa, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, La Locanda Dei Pisani Doc Pisa is another top choice with a popular menu. You could also check for a table at Baribaldi Pisa. As an establishment that consistently gains high praises from customers, it’s an ideal choice in Pisa tonight.

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.

Round off your dining experience by visiting Bar Mocambo, a prime location for a drink. Alternatively, explore the distinctive characteristics of Tree, a bar catering to every mood and preference. Chupiteria 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!