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

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Explore Italy and discover its unique charm on this 14-day relaxed road trip through Pisa, Tirrenia, Florence, Bologna, Verona, Milan, and La Spezia. Delight in a stress-free journey that focuses on exploration through the country's most captivating landscapes.

This self-drive package allows you to travel through picture-perfect landscapes in Italy at a relaxed pace. Get a dose of comfort, fun, and recreation in Pisa, Tirrenia, Florence, Bologna, Verona, Milan, and La Spezia. Make yourself at home at top-rated hotels and stay 2 nights in Pisa, 2 nights in Florence, 4 nights in Bologna, and 5 nights in Milan. Finally, taste the local food and enjoy a refreshing drink at the most popular restaurants and bars along your road trip route in Italy.

Freedom of choice is key to a relaxing road trip in Italy. For your self-drive vacation, we’ll offer you a selection of the best rental vehicles with CDW insurance. Upon arrival in Pisa, you’ll collect your rental car of choice. From there, you’ll begin your 14-day journey across Italy and discover its unique culture, history, and diverse scenery.

Experience the essence of leisurely self-drive exploration across Italy with our handpicked selection of accommodations. From relaxed stays at renowned 5-star hotels offering magnificent views to comfortable 3-star options that cater to budget-conscious travelers, we ensure your journey is optimized for relaxation and comfort. Discover the perfect place to stay and unwind as you embark on a laid-back adventure in Italy.

We’ll introduce you to some of the best travel destinations in Italy. This relaxed road trip features the stunning Duomo Di Milano Museum. Another highlight of this self-drive tour is the captivating Verona Arena.

Traveling leisurely through Italy means you could spend as much time as you want at the magnificent Ponte Vecchio. With this travel plan, you could also soak in the atmosphere of the memorable Leaning Tower Of Pisa. Get close to the spectacular Piazza Del Duomo, Pisa and the wonderful Galleria Vittorio Emanuele Ii. You’ll have plenty of time to take in each attraction's unique features, learn its unique history, and appreciate it to the fullest.

Enjoy strolling through Italy's shopping hotspots near your accommodation. Visit shops, discover the locals’ way of life, or try various specialties. Don't forget to bring home a piece of the country that will remind you of your relaxing vacation in Italy.

Between sightseeing, you can make the most of your downtime and join a popular tour in Italy. This relaxed road trip also gives you plenty of time to stroll through Italy's shopping hotspots. Through these experiences, you'll have plenty of opportunities to discover the locals’ way of life and soak in the rich cultural heritage of the Italy.

This self-drive vacation package includes everything you need for a stress-free, easy road trip through Italy. You’ll have a cozy place to stay for 13 nights, with a selection of top-rated breakfast and restaurant options nearby. We'll also provide you with the best rental car you can use throughout the 14 days of your self-drive road trip in Italy. On top of all that, you also have the option to add flights to your travel plan and personalize each day of your itinerary by adding tours and tickets.

This self-drive package includes 24/7 travel support and a step-by-step guide. You can access the guide at any point of your journey through our mobile app, where you can also keep and organize your travel documents.

Spend an amazing 14-day vacation in Italy and get to know more about this fantastic destination. Choose your travel dates and plan a laid-back and relaxed road trip in Italy today!

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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
Knights' Square
Leaning Tower of PisaPiazza del Duomo, PisaPisa CathedralParco Regionale Migliarino, San Rossore, MassaciuccoliBagno degli Americani
piazzale MichelangeloBasilica of Santa Croce in Florencepiazza della SignoriaUffizi GalleryPonte Vecchio
Cathedral of Santa Maria del FioreGalleria dell'AccademiaCentral MarketBasilica of Santa Maria Novella
Palazzo PallaviciniBologna CathedralPiazza MaggioreFountain of Neptune, BolognaPalazzo Re Enzo
arco del MeloncelloBasilica of San DomenicoTwo TowersPiazza Santo StefanoPorta Santo Stefano

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Day 1

Day 1

  • Pisa - Arrival day
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  • Knights' Square
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Your relaxed road trip through Italy starts when you reach the incredible city of Pisa, where you'll stay for 1 night. You'll pick up your rental car in Pisa and begin your adventure in Italy.

Pisa is a beautiful city with plenty to discover. If you arrive before check-in time or prefer to get started on your sightseeing right away, we recommend checking out Knights' Square, or just taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

As afternoon approaches, head to your chosen hotel in Pisa. Check-in typically starts around 2 to 4 PM at hotels in Italy. We recommend staying at a hotel in a central location for easy access to the best attractions, restaurants, and bars in the city.

As dinnertime approaches, it's time to head out for a bite to eat. If you are looking to dine at a popular restaurant in Pisa, it's often a good idea to reserve a table in advance.

Enjoy a lovely dining experience at Anima di Grano Pizzeria Napoletana Pisa Italy, a popular restaurant in Pisa. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Pisa at il Mercante, 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 La Ghiotteria. It’s yet another ideal choice to enhance your time in Pisa tonight.

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.

Explore the vibrant nightlife at Jeffer Cocktails & Friends after your meal, a hub for lively evenings and memorable moments. Or, head to Le Parisien Wine Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Las Volta Cocktailbar is perfect for those looking to extend their night with a touch of local flavor.

Raise a toast as you look back into the highlights of today’s laid-back and relaxed road trip adventure in Italy. Enjoy your first taste of Pisa as you soak in the city’s unique vibe.

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Day 2

Day 2

  • Pisa
  • Florence
  • More

Drive 132 km, 2 hours 22 min

  • Leaning Tower of Pisa
  • Piazza del Duomo, Pisa
  • Pisa Cathedral
  • Parco Regionale Migliarino, San Rossore, Massaciuccoli
  • Bagno degli Americani
  • More

Day 2 of your leisurely self-drive tour in Italy is another opportunity for an in-depth travel experience in the country. On this refreshing new day, you’ll travel from Pisa and continue your laid-back and relaxed road trip adventure in the hamlet of Cascine Vecchie and the village of Tirrenia. You’ll stay in Florence for 2 nights.

A blend of fun adventures, breathtaking views, and picturesque spots await you in Pisa on today’s itinerary. First up is the globally renowned monument, Leaning Tower Of Pisa. Afterward, continue to Piazza Del Duomo, Pisa, a public square every traveler should visit.

As you explore Pisa’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Pisa Cathedral. This worthwhile church is an essential stop. Following that, head to Parco Regionale Migliarino, San Rossore, Massaciuccoli, another must-visit site that will enhance your experience. Don’t forget to stop by Bagno Degli Americani, a locally appreciated sightseeing destination in the city.

Continue your laid-back road trip exploration of the best attractions in Italy at Florence. Select from top hotels and accommodations in the city to recharge and rejuvenate.

Exploring the food culture in Florence 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.

Set out on a gastronomic journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned for its 3-star Michelin recognition, this restaurant presents an outstanding menu of italian contemporary cuisine. For a different taste, head over to Santa Elisabetta, renowned for its delectable creative and mediterranean dishes. This distinguished 2-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Gucci Osteria da Massimo Bottura, a highly rated local gem known for its exquisite italian contemporary and international menu. With a 1-star Michelin acclaim, it promises a dining experience you won't want to miss. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Florence.

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.

After your meal, keep the night alive at a bar like Manifattura, known for its lively atmosphere. Se·sto On Arno Rooftop Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Il Vinile offers an excellent atmosphere for those looking to amp up the evening.

Soak in the unique atmosphere of Florence 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!

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Day 3

Day 3

  • Florence
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Drive 4 km, 1 hour 5 min

  • piazzale Michelangelo
  • Basilica of Santa Croce in Florence
  • piazza della Signoria
  • Uffizi Gallery
  • Ponte Vecchio
  • More

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!

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes an observation deck, a church, a public square, an art gallery, a historical landmark and much more! Begin your adventure at Piazzale Michelangelo. This is a famous observation deck you should not miss. Another must-see is Basilica Of Santa Croce In Florence, a locally renowned church in Florence.

When you’re ready for the next sight, head to Piazza Della Signoria. From there, take a leisurely stroll to Uffizi Gallery, another of the city’s famous attractions. We recommend continuing your self-guided tour at Ponte Vecchio, a romantic 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. 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 gains consistently high praises from customers, it’s an ideal choice in Florence tonight.

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.

After your meal, keep the night alive at a bar like Bar 50 Rosso, known for its lively atmosphere. Bitter Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Archea Brewery offers an excellent atmosphere for those looking to amp up the evening.

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

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Day 4

Day 4

  • Florence
  • Bologna
  • More

Drive 105 km, 1 hour 54 min

  • Cathedral of Santa Maria del Fiore
  • Galleria dell'Accademia
  • Central Market
  • Basilica of Santa Maria Novella
  • More

Day 4 of your easy and relaxed road trip through Italy gives you the opportunity to travel leisurely and experience more than one place in one day. You will start your day by exploring some of the best sights in the city of Florence. By the end of the day, you’ll drive in the direction of the city of Bologna, where you’ll stay at a top-rated hotel of your choice for 4 nights.

Get ready for an exciting day in Florence. Today’s sightseeing agenda includes a church, an art gallery, and a food market. Begin your adventure at Cathedral Of Santa Maria Del Fiore. This is an astonishing church you should not miss. Another must-see is Galleria Dell'accademia, a popular art gallery in Florence.

When you’re ready for the next sight, head to Central Market. From there, take a leisurely stroll to Basilica Di Santa Maria Novella, Firenze (fi), another of the city’s interesting attractions.

After a day of exploration, relax at one of the top hotels or accommodations in Bologna. 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.

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

Experience a harmony of flavors at Ahimè in Bologna by securing a reservation in advance. Known for its Bib Gourmand status, Ahimè offers a delightful variety of dishes highlighting its delicious country cooking menu. If you're seeking an alternative culinary experience, be sure to explore I Portici, a highly recommended restaurant known for its enticing creative and contemporary cuisine. This popular 1-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Trattoria di Via Serra, a highly acclaimed restaurant celebrated for its exceptional emilian menu.

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

If you’re not ready to end the night just yet, Bar Al Bricco D'oro offers a perfect venue to relax and savor a drink. Similarly, Bar Freud E Squisito is well-suited for those looking to unwind in a social setting. Osteria Del Sole is another excellent spot to enjoy a nightcap after a delightful meal.

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

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Day 5

Day 5

  • Bologna
  • More

Drive 1 km, 26 min

  • Palazzo Pallavicini
  • Bologna Cathedral
  • Piazza Maggiore
  • Fountain of Neptune, Bologna
  • Palazzo Re Enzo
  • More

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!

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Bologna allows for both. Start by heading to Palazzo Pallavicini. This up-and-coming palace provides an insightful glimpse into the city's identity. Next, discover Bologna Cathedral, an awe-inspiring church, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Maggiore, a top-rated public square. When you’re done, don’t forget to make a stop at the beloved Fountain Of Neptune, Bologna. Round off your day at Palazzo Re Enzo, another gem in Bologna with history-steeped features to discover.

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

Make sure to reserve a table at Bononia Cafè, an iconic dining spot in Bologna. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Via Con Me, a popular restaurant in Bologna. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Trattoria Pizzeria La Mela, a hidden gem nestled in Bologna. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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

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

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

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Day 6

Day 6

  • Bologna
  • More

Drive 12 km, 1 hour 5 min

  • arco del Meloncello
  • Basilica of San Domenico
  • Two Towers
  • Piazza Santo Stefano
  • Porta Santo Stefano
  • More

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

Bologna is home to plenty of attractions that offer family-friendly attractions, scenic views, and photo-friendly spots! Start at Arco Del Meloncello, an up-and-coming monument that is worthwhile a visit in the city. Nearby, you’ll find Basilica Of San Domenico, enchanting visitors with its detailed appeal. Continue your exploration at Two Towers. This monument is one of the city’s most notable 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 Piazza Santo Stefano. After exploring the public square, head to the up-and-coming Porta Santo Stefano.

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 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 Va Mo Là, an excellent option for tonight's dining. Looking for something different? Trattoria dal Biassanot offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Enoteca da Lucia. With its reputation for pleasing customers, 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.

To truly maximize your evening out, consider visiting Aurum after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Senza Nome, another bar with an inviting ambiance. Similarly, Caffè Ristretto also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

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Day 7

Day 7

  • Bologna
  • More

Drive 19 km, 1 hour 11 min

  • Ducati Museum
  • Porta Galliera
  • Botanical Garden and Herbarium
  • Pinacoteca Nazionale di Bologna
  • More

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!

Get ready for a day filled with fun adventures, picturesque spots, and history-rich sites in the charming city of Bologna. Your adventure starts at Ducati Museum, an underrated local hot spot. Another notable attraction to explore is Porta Galliera. This locally appreciated monument is known for its instagrammable 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 Botanical Garden And Herbarium. This romantic botanical garden offers a fascinating experience that many visitors find memorable. Pinacoteca Nazionale Di Bologna is also worth visiting.

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

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.

Enjoy a delicious meal at Pappare' - Bologna, a highly-rated dining destination in Bologna. If you're eager to try something different, consider Mister Coffee Bistrò, another top spot with a tantalizing menu. You might also want to secure a reservation at All'Osteria Bottega. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Bologna 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.

After savoring a delicious meal, step into the vibrant nightlife at Bar Piratello, where the evening is just getting started. In the same way, Bar Carlo offers a unique charm perfect for experiencing the local bar scene in Bologna. Bar Maurizio is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Soak in the unique atmosphere of Bologna 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!

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Day 8

Day 8

  • Bologna
  • Milan
  • More

Drive 301 km, 4 hours 12 min

  • Castelvecchio Museum
  • Castelvecchio Bridge
  • Verona Arena
  • piazza delle Erbe
  • More

Day 8 of your relaxed road trip across Italy promises an exciting agenda full of discovery. You’ll start your day in the city of Verona and drive in the direction of the city of Milan for some laid-back sightseeing. You’ll end your day in the city of Milan, where you’ll stay for 5 nights.

Today’s agenda in Bologna includes a museum, a monument, a stadium, a public square and much more! Castelvecchio Museum is must-visit museum and a great starting point for the day. Next, continue your journey to Castelvecchio Bridge, a locally renowned monument, located just a leisurely stroll away. Next, head to Verona Arena, a visually striking stadium, also available for your discovery today.

In the city of Milan, you’ll find plenty of stay options that will accommodate your need for rest and relaxation after spending your day on the road. Our top recommendations perfectly complement your relaxed road trip vacation in Italy.

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.

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.

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.

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.

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

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Day 9

Day 9

  • Milan
  • More

Drive 1 km, 21 min

  • La Scala
  • Galleria Vittorio Emanuele II
  • Duomo di Milano
  • Cathedral Square
  • Royal Palace of Milan
  • More

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!

Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and picturesque spots. 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. La Scala is the first of them. Spend some time admiring this historic opera house before continuing your journey. Galleria Vittorio Emanuele Ii is your next stop. This top-rated shopping mall 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 Duomo Di Milano Museum. This enchanting church is a sight to behold. To round off your sightseeing experience, visit Cathedral Square and Royal Palace Of Milan.

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.

Treat yourself to a delightful dinner at Dessert Bar Milano, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Radisson Blu Hotel Milan? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Qui Si Mangia as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Milan.

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.

Let the evening flow smoothly from dinner to drinks at Kilburn Cocktail Bar Milano, a top-rated bar in the area. For other recommendations, Bar Frida provides a perfect setting for rounding out your night with style and great drinks. Likewise, The Friends Pub Milano offers a memorable night with diverse drink options and excellent service.

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

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Day 10

Day 10

  • Milan
  • More

Drive 6 km, 48 min

  • Arch of Peace
  • Triennale di Milano
  • Sempione Park
  • Castello Sforzesco
  • Piazza Castello Fountain
  • More

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

Today, you'll explore some of the most beautiful places in Milan, including a monument, a museum, a park, a castle, a public square and much more! Start your day with a visit to Arch Of Peace. This well-known monument is a must-visit in the city. When you’re ready for your next discovery, continue to Triennale Di Milano, which may be one of the most eye-catching places you will experience today.

One of the best things about exploring Milan 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 Parco Sempione, a spectacular park in the city. If you’re up for more discoveries, don’t forget to reserve some time for 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.

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.

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.

Continue your lively evening at Bhangrabar, a perfect place for winding down or revving up the night, depending on which mood you’re in. Rufus Cocktail Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Ostello Bello Grande ensures a night out tailored to your taste.

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.

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Day 11

Day 11

  • Milan
  • More

Drive 8 km, 1 hour 6 min

  • Piazza Gae Aulenti
  • Pinacoteca di Brera
  • Milan Natural History Museum
  • Villa Necchi Campiglio
  • More

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!

Discover a day packed with family-friendly attractions, scenic views, and picturesque spots in Milan. Begin your sightseeing with Piazza Gae Aulenti. This notable public square is one of the top attractions in the city. Proceed to Pinacoteca Di Brera, 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 Milan Natural History Museum. This frequently visited museum is a traveler-favorite. Not far away, you’ll find Villa Necchi Campiglio, another key site on your sightseeing itinerary.

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.

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 dining experience at Ristorante la Brisa, 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 Pasticceria San Carlo, 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 UNAHOTELS Cusani Milano. It’s yet another ideal choice to enhance your time in Milan tonight.

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.

Extend your evening after a delightful meal by visiting Qc Termemilano, which offers the perfect atmosphere for a night out. Moreover, Yguana Cafè is another popular option for a drink or two.

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

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Day 12

Day 12

  • Milan
  • More

Drive 9 km, 59 min

  • Basilica di Sant'Ambrogio
  • Leonardo da Vinci Museum of Science and Technology
  • Santa Maria delle Grazie Church
  • MUDEC - Museum of Cultures
  • More

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!

Immerse yourself in Milan’s rich culture with today's sightseeing itinerary. Start your journey at Basilica Di Sant'ambrogio. This culturally significant church is sure to ignite your curiosity. Next, dive into the history-steeped 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, an interesting church. For a change of scene, check out Mudec - Museum Of Cultures, known for its picture-perfect features.

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!

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.

Make sure to reserve a table at Vento di Sardegna, 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 Palazzo Parigi Hotel & Grand Spa Milano, 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 Galleria Restaurant, 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.

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

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Day 13

Day 13

  • Milan
  • Pisa
  • More

Drive 312 km, 4 hours 5 min

  • Castello San Giorgio
  • Giardini Pubblici
  • Technical Naval Museum of Spezia
  • More

On day 13 of your laid-back and relaxed road trip adventure, you’ll have the chance to visit more than one remarkable area in Italy. Since this self-drive tour offers freedom and flexibility, you can decide how much time you want to spend in each place to enjoy the memorable travel destinations in Italy.

Today’s well-planned self-sightseeing route offers several fun adventures, breathtaking views, and photo-friendly spots. 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. Castello San Giorgio is the first of them. Spend some time admiring this breathtaking castle before continuing your journey. Giardini Pubblici is your next stop. This locally appreciated park 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 Technical Naval Museum Of Spezia. This instagrammable museum is a sight to behold.

When you’re not exploring beautiful places, you’ll have a relaxed time at Pisa. Here, you can choose from the best selection of hotels and places to stay as you get to know more about this spectacular city.

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 Pisa, 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 Ristorante Capodimonte Pisa, a popular restaurant in Pisa. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Pisa at La Locanda Dei Pisani Doc Pisa, 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 Baribaldi Pisa. It’s yet another ideal choice to enhance your time in Pisa tonight.

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

After your delicious meal, get a taste of the vibrant nightlife with a visit to Bar Mocambo, known for its inviting atmosphere. Tree is another great option if you’re looking for a place to get the night started. Similarly, Chupiteria provides a great setting to enjoy the night away.

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

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Day 14

Day 14

  • Pisa - Departure day
  • More
  • Logge dei Banchi
  • More

Day 14 of your relaxed road trip in Italy is your departure day. If you have a flight to catch, you’ll drop off your rental car well in advance before your departure. Choose a late flight to enjoy a stress-free last day in Pisa.

Make the most of your final day in Italy by visiting Pisa’s iconic markets and shopping establishments. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy.

If you're up for some more sightseeing, begin at Logge Dei Banchi. This often recommended public square is a popular place to see in the city.

Unwind and look back at the past 14 days of your relaxed road trip over a bite to eat. This is your chance to enjoy one last traditional meal in Pisa or just grab something light to keep you going.

Give yourself enough time to wave goodbye to Pisa and begin your journey home. The unforgettable experiences you’ve collected along your 14-day relaxed road trip in Italy is a story you will tell for the rest of your life.

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