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

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Tourist female in Pisa, Arno river, lamp and buildings reflection. Lungarno view.santa maria della spina
Blue hour twilight with Duomo and world famous Leaning Tower travel background in Tuscany.
Landscape with Pisa old town and Arno river, Tuscany, Italy.
 Tourists and locals enjoy a sunny day on the Corso Italia, the main shopping and dining street through the Tuscan city of Pisa, Italy.
Gothic church of Santa Maria della Spina, built around 1230 in the Pisan Gothic style.
Building in botanical garden of Pisa (Orto botanico di Pisa) in Italy
Photo of Tourists at the Primatial Metropolitan Cathedral of the Assumption of Mary in Pisa.
Carriage with horse in front of the leaning tower of Pisa
San Miniato, Pisa, Tuscany, Italy: the ancient catholic theological seminary in the picturesque old town.
Piazza Vittorio Emanuele square in the centre of Pisa city in Tuscany, Italy
Beautiful building of University on Piazza dei Cavalieri (Palazzo della Carovana) decorated with sgraffiti and sculptures of Grand Dukes of Tuscany. The statue depicts Cosimo I de' Medici. Pisa, Italy
The Cittadella Nuova now called the Giardino di Scotto or Giardino Scotto is an old fortress in Pisa, Italy
Piazza dei Cavalieri, Palazzo della Carovana, Palazzo dell'Orologio in Pisa, Italy. Architecture and landmark of Pisa. Cityscape of Pisa
Pisa, Italy. Leaning Tower of Pisa. Panoramic view in the evening. Aerial view
Aerial view of the Cattedrale di Santa Maria del Fiore in Florence, Italy, overlooking the city
Photo of Florence Aerial View of Ponte Vecchio Bridge during Beautiful Sunny Day, Italy.
Photo of Woman enjoys beautiful view on famous Duomo cathedral in Florence, standing on empty cathedral square during morning time.
Photo of Summer street cafe on Piazza della Repubblica in Florence, Toscana province, Italy.
Photo of Giotto's Campanile - An aerial dusk view of Giotto's Campanile and the historical Old Town of Florence, as seen from the top of Brunelleschi's Dome of the Florence Cathedral. Florence, Tuscany, Italy.
Photo of Ponte Vecchio, old bridge over Arno River, Florence, Tuscany, Italy.
Photo of The Colossus of the Apennines, majestic stone sculpture by Giambologna located in the park of Villa Demidoff in Florence, Italy.
Photo of Fountain of Neptune in Florence in early morning.
Photo of Sunset view of Florence, Ponte Vecchio, Palazzo Vecchio and Florence Duomo, Italy. Architecture and landmark of Florence. Cityscape of Florence.
Vintage carousel and tourists in Piazza della Repubblica (Republic Square) and the arch in honor of the first king of united Italy on background in Florence, Italy.
Photo of Arches of the Vasari Corridor (Corridoio Vasariano) in Florence, Tuscany, Italy. View of the Lungarno degli Archibusieri.
cheerful senior woman cycling with her electric mountain bike above downtown of Florence with stunning view over the old city, Tuscany, Italy
Facade of Palazzo Pitti palace with Gallery of Modern Art large building on Piazza dei Pitti square in historical centre of Florence city, blue sky white clouds, Tuscany, Italy
photo of view of Florence,Italy.
photo of view of Florence,Italy.
Medieval and Renaissance buildings and structures feature in Bologna, Italy
Photo of panoramic view of Bologna,Italy.
Photo of Channel river in Bologna Italy.
Photo of Fontana di Nettuno or Neptune fountain on Piazza Maggiore square at the morning dusk designed by Tommaso Laureti (1565).
Photo of Bologna main square aerial view from Asinelli tower.
Photo of ancient sanctuary of the Madonna di San Luca, old church on the hill.
Photo of quirky castle in the Emilian Apennines, Bologna, Italy.
Photo of Basilica of SantApolinare in Classe.
Photo of View of Basilica di San Petronio on sunrise.
Photo of Sunset view of a small lake located in a park in the center of Bologna, Italy.
Bologna, Italy. View of Basilica di San Petronio on sunrise
Palazzo Re Enzo. Splendid cityscape of Bologna, Italy.
photo of view of Bologna, Italy.
Milan Cathedral, Duomo di Milano, and Piazza Duomo square in the Milan city center, Italy
Photo of Arch of Peace, or Arco della Pace, city gate in the centre of the Old Town of Milan in the sunny day, Lombardia, Italy.
Photo of Milan, Italy. Bridge across the Naviglio Grande canal at the sunrise Milano, Lombardy.
Photo of Milano, Italy. Church Santa Maria delle Grazie in Milan, famous for hosting Leonardo da Vinci masterpiece "The Last Supper".
Photo of Sforza Castle or Castello Sforzesco aerial panoramic view. Sforza Castle is located in Milan city in northern Italy.
Photo of tourist girl holds hat in Sempione Square, Milan, Italy.
Photo of Milan Cathedral, Duomo di Milano, Italy, one of the largest churches in the world on sunrise.
Photo of Darsena artificial reservoir is located near Porta Ticinese in Milan in Lombardy region of northern Italy.
Photo of tourist woman with arms raised in Milan Cathedral Square, Italy.
Photo of the Basilica of San Lorenzo Maggiore is a roman catholic church in Milan city in Lombardy region of northern Italy.
Photo of town of Menaggio on lake Como, Milan, Italy.
Photo of Stazione Milano Centrale is the main railway station of the Milan city in Lombardy region of northern Italy.
photo of view of Duomo square and Milan Cathedral at sunrise, Italy.
photo of view of View of the Peace Arch with yellow tram in Milan, Italy
photo of  view of Milan Piazza Del Duomo at Sunrise, Italy.
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Discover Italy stress-free with this 14-day relaxed road trip, winding through Pisa, Tirrenia, Florence, Bologna, Verona, Milan, and La Spezia. Enjoy a relaxing self-drive holiday through stunning landscapes and calm adventures.

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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Driver’s age is 30 - 65
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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.

Make your way to your chosen hotel. Check-in typically starts between 2 and 4 PM in Pisa. Make yourself at home and enjoy some downtime before heading out again.

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.

Savor the flavors at Anima di Grano Pizzeria Napoletana Pisa Italy, a top pick for dinner tonight. Alternatively, il Mercante beckons with its unique menu offerings. Also, consider La Ghiotteria. With its consistent customer satisfaction, it’s an excellent option for dining in Pisa tonight.

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

Continue your evening by exploring the vibrant nightlife scene at Jeffer Cocktails & Friends, a prime destination for a thrilling night out. Also, don’t forget to check out Le Parisien Wine Bar, a bar that offers unique local touches. Likewise, Las Volta Cocktailbar provides an excellent alternative for a fun evening.

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 relaxed road trip across the beautiful country of Italy will take you on a self-paced journey to more than one incredible place in one day. See some of the best attractions in Italy, taste the most delectable foods and exquisite drinks, and make incredible memories as you go!

Brace yourself for today’s incredible lineup of attractions in Pisa, featuring family-friendly attractions, scenic views, and picturesque spots. Start at Leaning Tower Of Pisa, a world-famous monument in the city. Then, head to Piazza Del Duomo, Pisa and soak in the ambiance of this historic public square.

There are many interesting places to see in Pisa, and when you are ready for more, go to Pisa Cathedral. This is one of the city’s most up-and-coming breathtaking spots of interest. After exploring the church, visit the curiosity-inducing Parco Regionale Migliarino, San Rossore, Massaciuccoli. Not far away, you'll also find Bagno Degli Americani.

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.

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.

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.

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.

Keep the excitement of the evening going by visiting a bar or two. Manifattura is an excellent place to start. You could also check out Se·sto On Arno Rooftop Bar, offering a different kind of charm. A last recommendation for the day is Il Vinile. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

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 home to plenty of attractions that offer fun adventures, romantic experiences, and scenic views! Start at Piazzale Michelangelo, an impressive observation deck that is worthwhile a visit in the city. Nearby, you’ll find Basilica Of Santa Croce In Florence, enchanting visitors with its respected appeal. Continue your exploration at Piazza Della Signoria. This public square is one of the city’s most spectacular spots.

Enjoy the freedom of exploring Florence at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Uffizi Gallery. After exploring the art gallery, head to the wondrous Ponte Vecchio.

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.

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 Florence, 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 Ditta Artigianale, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Trattoria Da Burde, another top spot with a mouthwatering menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

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

To truly maximize your evening out, consider visiting Bar 50 Rosso after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bitter Bar, another bar with an inviting ambiance. Similarly, Archea Brewery also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

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Day 4

Day 4

  • Florence
  • Bologna
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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 relaxed road trip across Italy promises an exciting agenda full of discovery. You’ll start your day in the city of Florence and drive in the direction of the city of Bologna for some laid-back sightseeing. You’ll end your day in the city of Bologna, where you’ll stay for 4 nights.

Set out on a day brimming with family-friendly attractions, romantic experiences, and breathtaking views. Start at the famous Cathedral Of Santa Maria Del Fiore, a romantic church in Florence. Next, go to Galleria Dell'accademia.

After visiting Cathedral Of Santa Maria Del Fiore and Galleria Dell'accademia, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Central Market. This photogenic food market offers a unique experience. Basilica Di Santa Maria Novella, Firenze (fi) is another noteworthy attraction worthwhile a visit.

In the city of Bologna, 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.

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.

Have a memorable dining experience in Bologna by booking a table at Ahimè, renowned as a Bib Gourmand restaurant presenting an exceptional country cooking menu. For a different culinary experience in Bologna, I Portici shines as one of the top destinations, known for its delicious creative and contemporary cuisine. This 1-star Michelin-awardee earns consistently high praises from previous guests, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Trattoria di Via Serra is known as a top local spot for its delicious emilian cuisine in Bologna. This Bib Gourmand awardee is a highly recommended choice for an unforgettable meal.

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

To truly maximize your evening out, consider visiting Bar Al Bricco D'oro after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Freud E Squisito, another bar with an inviting ambiance. Similarly, Osteria Del Sole 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 5

Day 5

  • Bologna
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Drive 1 km, 26 min

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

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!

A blend of fun adventures, romantic experiences, and picturesque spots await you in Bologna on today’s itinerary. First up is the beloved palace, Palazzo Pallavicini. Afterward, continue to Bologna Cathedral, a church every traveler should visit.

As you explore Bologna’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Piazza Maggiore. This astonishing public square is an essential stop. Following that, head to Fountain Of Neptune, Bologna, another must-visit site that will enhance your experience. Don’t forget to stop by Palazzo Re Enzo, a frequently visited palace 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.

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 lovely meal at Bononia Cafè, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Via Con Me is another top choice with a popular menu. You could also check for a table at Trattoria Pizzeria La Mela. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Bologna 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.

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

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

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Day 6

Day 6

  • Bologna
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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 brimming with adventures. Today’s wonderful stops include a monument, a church, and a public square. Begin your sightseeing adventure at the beloved Arco Del Meloncello and allow yourself time to explore. Just a short distance away you'll find your next stop, Basilica Of San Domenico, a photogenic church that draws visitors from far and near.

Continue your journey to Two Towers, one of the city’s most locally renowned spots that you shouldn’t miss. Another great site to visit is the intriguing Piazza Santo Stefano. When you're finished at the public square, Porta Santo Stefano awaits your visit. This monument is a heritage-rich highlight on today's itinerary.

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.

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 Va Mo Là, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria dal Biassanot boasts a menu that's sure to impress. Also, be sure to check out Ristorante Enoteca da Lucia. Known as a local hotspot, it’s a great choice for tonight in Bologna.

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

Extend your evening after a delightful meal by visiting Aurum, which offers the perfect atmosphere for a night out. Moreover, Bar Senza Nome is another popular option for a drink or two. Likewise, Caffè Ristretto also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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 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

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!

Immerse yourself in Bologna’s rich culture with today's sightseeing itinerary. Start your journey at Ducati Museum. This respected museum is sure to ignite your curiosity. Next, dive into the heritage-rich features of Porta Galliera, a must-visit monument 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 Botanical Garden And Herbarium, an increasingly popular botanical garden. For a change of scene, check out Pinacoteca Nazionale Di Bologna, 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 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!

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.

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. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Bologna.

Experience the amazing nightlife in Bologna 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 Piratello, known for its inviting atmosphere. Bar Carlo is another great option if you’re looking for a place to get the night started. Similarly, Bar Maurizio provides a great setting to enjoy the night away.

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

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Day 8

Day 8

  • Bologna
  • Milan
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Drive 301 km, 4 hours 12 min

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

Day 8 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 Verona. By the end of the day, you’ll drive in the direction of the city of Milan, where you’ll stay at a top-rated hotel of your choice for 5 nights.

Bring your curiosity for today’s adventure around Bologna. Some of the city’s most loved attractions await! Castelvecchio Museum is the perfect place to start. This museum is one of the most notable places to visit in Bologna. Next, head to Castelvecchio Bridge, a locally renowned monument, known for its visually striking features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Verona Arena. This grand stadium is a highly recommended experience. Nearby, you'll also find Piazza Delle Erbe. Visit these for an interesting touch to your journey.

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

Exploring the food culture in Milan 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.

Get ready for an unforgettable culinary journey in Milan by reserving a table at Enrico Bartolini al Mudec. Renowned as a 3-star Michelin restaurant, it offers an exceptional creative menu. For a different taste experience, head to Seta by Antonio Guida, recognized for its delicious international and contemporary dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Il Luogo Aimo e Nadia, a local favorite known for its delightful italian contemporary and modern cuisine in Milan. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for discerning italian contemporary and modern foodies seeking culinary excellence.

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.

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.

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

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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

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!

Today’s itinerary in Milan covers several incredible sights, including an opera house, a shopping mall, a church, a public square, a palace and much more! Start your adventure at La Scala. This interesting opera house is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the romantic wonders of Galleria Vittorio Emanuele Ii, a must-see shopping mall in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Duomo Di Milano Museum. This globally renowned church offers an enriching experience. For a change of pace, head to Cathedral Square, where you can take in history-steeped features. Conclude your self-guided sightseeing tour with a visit to Royal Palace Of Milan. These sights offer a fulfilling end to a perfect day.

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 Milan 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.

Have a fantastic dining experience at Dessert Bar Milano, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Radisson Blu Hotel Milan offers an enticing alternative with its varied menu. Additionally, Ristorante Qui Si Mangia is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Milan.

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

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

Raise your glass in celebration of your freedom and relaxed road trip adventure 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’s agenda in Milan includes a monument, a museum, a park, a castle, a public square and much more! Arch Of Peace is must-visit monument and a great starting point for the day. Next, continue your journey to Triennale Di Milano, a frequently visited museum, located just a leisurely stroll away. Next, head to Parco Sempione, a serene park, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Milan. When you're ready, let your sightseeing route take you to the impressive Sforzesco Castle Art Library. If you’re looking for more, Piazza Castello Fountain is also an intriguing 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 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.

Make sure to reserve a table at Bice Restaurant, 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 Alto Ristorante, 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 Nero 9, a hidden gem nestled in Milan. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

Explore the vibrant nightlife at Bhangrabar after your meal, a hub for lively evenings and memorable moments. Or, head to Rufus Cocktail Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Ostello Bello Grande is perfect for those looking to extend their night with a touch of local flavor.

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 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

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!

Get ready for a day filled with fun adventures, scenic views, and picturesque spots in the charming city of Milan. Your adventure starts at Piazza Gae Aulenti, a locally renowned local hot spot. Another notable attraction to explore is Pinacoteca Di Brera. This notable art gallery is known for its mesmerizing appeal.

After soaking in the highlights of these sights, take some time to wander Milan's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Milan Natural History Museum. This visually striking museum offers a fascinating experience that many visitors find memorable. Villa Necchi Campiglio is also worth visiting.

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.

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 Ristorante la Brisa, a highly-rated dining destination in Milan. If you're eager to try something different, consider Pasticceria San Carlo, another top spot with a tantalizing menu. You might also want to secure a reservation at UNAHOTELS Cusani Milano. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Milan this evening.

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 enjoying a fulfilling meal, continue your evening at Qc Termemilano, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Yguana Cafè offers a welcoming atmosphere for easing into the nightlife.

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

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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

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!

Today’s well-planned self-sightseeing route offers several fun adventures, photo-friendly spots, and history-rich sites. 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. Basilica Di Sant'ambrogio is the first of them. Spend some time admiring this standout church before continuing your journey. Museo Della Scienza E Della Tecnologia "leonardo Da Vinci" is your next stop. This popular 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 Santa Maria Delle Grazie Church. This culturally significant church is a sight to behold. To round off your sightseeing experience, visit Mudec - Museum Of Cultures.

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!

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 Vento di Sardegna, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Palazzo Parigi Hotel & Grand Spa Milano? It's another excellent option with a diverse menu. Consider reserving a table at Galleria Restaurant as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Milan.

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

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

Get ready for a day filled with fun adventures, breathtaking views, and photo-friendly spots in the charming city of Milan. Your adventure starts at Castello San Giorgio, a frequently visited local hot spot. Another notable attraction to explore is Giardini Pubblici. This locally appreciated park is known for its picture-perfect appeal.

After soaking in the highlights of these sights, take some time to wander Milan's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Technical Naval Museum Of Spezia. This photogenic museum offers a fascinating experience that many visitors find memorable.

You’ll be staying at the incredible city of Pisa in this laid-back road trip in Italy. You'll stay here for 1 night.

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

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 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.

Raise your glass and toast to another unforgettable, laid-back road trip adventure 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.

On your last day in Italy, take time to indulge in shopping at Pisa’s popular marketplace. Look for keepsakes or souvenirs to remind you of your trip.

If you're up for some more sightseeing, we recommend visiting Logge Dei Banchi, a historic public square before you head out.

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.

Dine in style at Restaurant -Pizzeria Il Mio Capriccio, a top recommendation for dinner tonight. Or, for a change of pace, Ristorante alle Bandierine boasts a menu that's sure to impress.

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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