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

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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
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.
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.
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.
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Sit back and enjoy a relaxed 15-day road trip in Italy with this laid-back self-drive vacation.

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, Milan, Monza, Verona, Bologna, and Florence. Make yourself at home at top-rated hotels and stay 2 nights in Pisa, 5 nights in Milan, 5 nights in Bologna, and 2 nights in Florence. 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 15-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 14 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 15 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 15-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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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, Massaciuccoli
Royal Palace of MilanCathedral SquareDuomo di MilanoGalleria Vittorio Emanuele IILa Scala
Arch of PeaceTriennale di MilanoSempione ParkCastello SforzescoPinacoteca di Brera
Basilica di Sant'AmbrogioLeonardo da Vinci Museum of Science and TechnologySanta Maria delle Grazie ChurchMUDEC - Museum of Cultures
Monumental CemeteryPiazza Gae AulentiMilan Natural History MuseumVilla Necchi Campiglio

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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.

Find your way to your hotel in Pisa. We recommend choosing a hotel in a central location for easy exploring. Check-in typically starts between 2 and 4 PM at hotels in Italy. Settle in and make plans for the evening.

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.

Make sure to reserve a table at Anima di Grano Pizzeria Napoletana Pisa Italy, an iconic dining spot in Pisa. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of il Mercante, a popular restaurant in Pisa. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of La Ghiotteria, a hidden gem nestled in Pisa. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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 enjoying a fulfilling meal, continue your evening at Jeffer Cocktails & Friends, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Le Parisien Wine Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Las Volta Cocktailbar provides an excellent environment for a relaxed and enjoyable 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
  • Milan
  • More

Drive 289 km, 3 hours 42 min

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

On day 2 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 to discover some of the most iconic wonders in Pisa, including a monument, a public square, a church, a nature reserve and much more! Start your day at Leaning Tower Of Pisa. This picture-perfect monument is a globally renowned place to see in Pisa. Then, wander over to Piazza Del Duomo, Pisa. If breathtaking sites excite you, this public square will be right up your alley. Nearby, you’ll also find Pisa Cathedral. This UNESCO world heritage-listed church is a favorite among visitors.

Pisa offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Parco Regionale Migliarino, San Rossore, Massaciuccoli is a frequently visited spot in the city that will captivate you with its unique charm.

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.

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.

Experience a harmony of flavors at Enrico Bartolini al Mudec in Milan by securing a reservation in advance. Known for its 3-star Michelin status, Enrico Bartolini al Mudec offers a delightful variety of dishes highlighting its delicious creative menu. If you're seeking an alternative culinary experience, be sure to explore Seta by Antonio Guida, a highly recommended restaurant known for its enticing international and contemporary cuisine. This popular 2-star Michelin-awarded venue consistently exceeds expectations, ensuring a memorable holiday experience. Ready for another culinary adventure? Indulge your senses at Il Luogo Aimo e Nadia, a highly acclaimed restaurant celebrated for its exceptional italian contemporary and modern menu.

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 enjoying a fulfilling meal, continue your evening at Nottingham Forest, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Armani/bamboo Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Mag Cafe provides an excellent environment for a relaxed and enjoyable evening.

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 3

Day 3

  • Milan
  • More

Drive 1 km, 20 min

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

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

Today's adventure in Milan promises more breathtaking discoveries and enriching experiences! Begin at Royal Palace Of Milan. This history-steeped palace is a highlight of any visit in the city. Then, enjoy Cathedral Square, another visually striking attraction that never fails to captivate visitors. Next, head over to Duomo Di Milano Museum, one of the city’s most wondrous attractions, known for its history-steeped features.

If you’re looking for more, spend time soaking in the atmosphere of Galleria Vittorio Emanuele Ii. This masterful shopping mall is frequented by locals and tourists alike. To complete your memorable day, make sure to visit La Scala, a notable opera house, and take a stroll around the area.

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.

Don’t miss out on dining at Dessert Bar Milano, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Radisson Blu Hotel Milan, another top spot with a mouthwatering menu. You might also want to secure a reservation at Ristorante Qui Si Mangia. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan 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 Kilburn Cocktail Bar Milano, where the evening is just getting started. In the same way, Bar Frida offers a unique charm perfect for experiencing the local bar scene in Milan. The Friends Pub Milano is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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 4

Day 4

  • Milan
  • More

Drive 7 km, 58 min

  • Arch of Peace
  • Triennale di Milano
  • Sempione Park
  • Castello Sforzesco
  • Pinacoteca di Brera
  • More

On day 4 of your leisurely self-drive tour across Italy, you’ll go deep into Milan, 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 Milan, and meet locals along the way!

Savor the day by visiting some of the best places to see in Milan, including a monument, a museum, a park, a castle, an art gallery and much more! Start your adventure at Arch Of Peace. This captivating monument is a must-visit for travelers looking for a unique holiday experience. Make your way to Triennale Di Milano located in Milan for another exciting encounter.

Next, immerse yourself in the setting of Parco Sempione. Its romantic features will captivate you. After the park, continue your tour of the city with a visit to Sforzesco Castle Art Library. Visitors usually appreciate the culturally significant features of this castle. Next up is Pinacoteca Di Brera, a highly recommended art gallery.

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.

Treat yourself to a delicious dinner at Bice Restaurant, an excellent option for tonight's dining. Looking for something different? Alto Ristorante offers a tantalizing alternative with its diverse menu. And don’t miss Nero 9. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Milan.

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

Cap off your dinner by heading to Bhangrabar, ideal for a leisurely evening with a drink in hand. Rufus Cocktail Bar is another bar that offers an enjoyable setting. Similarly, Ostello Bello Grande is also a popular place to go on a night out, perfect for relaxing and socializing.

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

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Day 5

Day 5

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

Immerse yourself in Milan’s rich culture with today's sightseeing itinerary. Start your journey at Basilica Di Sant'ambrogio. This instagrammable church is sure to ignite your curiosity. Next, dive into the eye-catching features of Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", a must-visit museum in the city.

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

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.

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 Ristorante la Brisa, a top pick for dinner tonight. Alternatively, Pasticceria San Carlo beckons with its unique menu offerings. Also, consider UNAHOTELS Cusani Milano. With its consistent customer satisfaction, it’s an excellent option for dining in Milan 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.

Continue your evening by exploring the vibrant nightlife scene at Qc Termemilano, a prime destination for a thrilling night out. Also, don’t forget to check out Yguana Cafè, a bar that offers unique local touches.

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 6

Day 6

  • Milan
  • More

Drive 8 km, 1 hour 4 min

  • Monumental Cemetery
  • Piazza Gae Aulenti
  • Milan Natural History Museum
  • Villa Necchi Campiglio
  • More

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

Enjoy the perfect balance of relaxation and exploration in Milan today. One of the most worthwhile attractions included on the itinerary is Monumental Cemetery. Then, take a leisurely stroll to Piazza Gae Aulenti and learn what makes this visually striking public square unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the worthwhile Milan Natural History Museum. After exploring the museum, head to Villa Necchi Campiglio. This often recommended museum is a highlight in Milan.

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

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.

Treat yourself to a wonderful meal at Vento di Sardegna, a top-rated dining spot in Milan. If you're in the mood for something new, try Palazzo Parigi Hotel & Grand Spa Milano, another premier location with a delectable menu. You might also want to book a table at Galleria Restaurant. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Milan.

After dinner, it’s time to fall in love with the amazing nightlife in Milan and unwind at some of the best bars in the city.

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

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Day 7

Day 7

  • Milan
  • Bologna
  • More

Drive 328 km, 4 hours 43 min

  • Monza Circuit
  • Parco di Monza
  • Castelvecchio Museum
  • Verona Arena
  • More

Day 7 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 Monza and continue your laid-back and relaxed road trip adventure in the city of Verona and the city of Bologna. You’ll stay in Bologna for 5 nights.

Today, you'll explore some of the most beautiful places in Milan, including a motor speedway, a park, a museum, a stadium and much more! Start your day with a visit to Monza Circuit. This locally renowned motor speedway is a must-visit in the city. When you’re ready for your next discovery, continue to Monza Park, which may be one of the most standout 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 Castelvecchio Museum, a well-known museum in the city. If you’re up for more discoveries, don’t forget to reserve some time for Verona Arena.

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

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.

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.

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 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.

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

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Day 8

Day 8

  • Bologna
  • More

Drive 9 km, 55 min

  • Eremo di Ronzano
  • Villa Ghigi
  • Porta Castiglione
  • Basilica of San Domenico
  • More

On day 8 of your leisurely self-drive tour across Italy, you’ll go deep into Bologna, 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 Bologna, and meet locals along the way!

Today, you'll explore some of the most beautiful places in Bologna, including a monastery, a park, a monument, a church and much more! Start your day with a visit to Eremo Di Ronzano. This underrated monastery is a must-visit in the city. When you’re ready for your next discovery, continue to Villa Ghigi, which may be one of the most instagrammable 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 Porta Castiglione, a locally appreciated monument in the city. If you’re up for more discoveries, don’t forget to reserve some time for Basilica Of San Domenico.

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 delicious meal 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.

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.

To truly maximize your evening out, consider visiting Lime Bar after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Macondo - Cocktail Bar, another bar with an inviting ambiance. Similarly, Bar Onda Marina By Night also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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

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Day 9

Day 9

  • Bologna
  • More

Drive 11 km, 1 hour 25 min

  • Devotional Portico of St. Luke
  • arco del Meloncello
  • Palazzo Pallavicini
  • Church of the Holy Savior
  • Porta Galliera
  • More

Day 9 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!

Start by visiting Devotional Portico Of St. Luke, a prime spot to begin your journey. This history-steeped monument is sure to impress. Next on your list is Arco Del Meloncello, another must-visit landmark and up-and-coming monument renowned for its culturally significant features.

While exploring and sightseeing, take time to savor the culture of Bologna by sampling some local delicacies. When you’re ready for more sightseeing, head to Palazzo Pallavicini. This picture-perfect palace is an essential place to visit for anyone looking for the full Bologna experience. We also recommend visiting Chiesa Del Santissimo Salvatore, a frequently visited church. Nearby, you'll also find Porta Galliera, ready to add charm to your journey.

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.

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 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 gains consistently high praises from customers, it’s an ideal choice in Bologna tonight.

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.

Let the evening flow smoothly from dinner to drinks at Aurum, a top-rated bar in the area. For other recommendations, Bar Senza Nome provides a perfect setting for rounding out your night with style and great drinks. Likewise, Caffè Ristretto offers a memorable night with diverse drink options and excellent service.

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

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Day 10

Day 10

  • Bologna
  • More

Drive 6 km, 1 hour 2 min

  • Pinacoteca Nazionale di Bologna
  • Two Towers
  • Piazza Santo Stefano
  • Porta Maggiore
  • Porta Santo Stefano
  • More

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

Set out on a day brimming with family-friendly attractions, picturesque spots, and history-rich sites. Start at the intriguing Pinacoteca Nazionale Di Bologna, a historic art gallery in Bologna. Next, go to Two Towers.

After visiting Pinacoteca Nazionale Di Bologna and Two Towers, have a stroll along Bologna's streets and take in the local charm. Continue your sightseeing by heading to Piazza Santo Stefano. This inviting public square offers a unique experience. Porta Maggiore is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Porta Santo Stefano, one of the most symbolic places to visit in Bologna.

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.

Treat yourself to a delightful dinner at Pappare' - Bologna, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Mister Coffee Bistrò? It's another excellent option with a diverse menu. Consider reserving a table at All'Osteria Bottega as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Bologna.

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.

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

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Day 11

Day 11

  • Bologna
  • More

Drive 0.6 km, 9 min

  • Palazzo d'Accursio
  • Bologna Cathedral
  • Piazza Maggiore
  • Fountain of Neptune, Bologna
  • Palazzo Re Enzo
  • More

On day 11 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!

Bring your curiosity for today’s adventure around Bologna. Some of the city’s most loved attractions await! Palazzo D'accursio is the perfect place to start. This palace is one of the most locally appreciated places to visit in Bologna. Next, head to Bologna Cathedral, a worthwhile church, known for its majestic features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Piazza Maggiore. This romantic public square is a highly recommended experience. Nearby, you'll also find Fountain Of Neptune, Bologna and Palazzo Re Enzo. Visit these for an interesting touch to your journey.

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!

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.

Make sure to reserve a table at Ristorante Rodrigo, 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 CDH Hotel Bologna, 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 Victoria Station, a hidden gem nestled in Bologna. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

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

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

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Day 12

Day 12

  • Bologna
  • Florence
  • More

Drive 127 km, 1 hour 58 min

  • Basilica di San Martino
  • La Piccola Venezia
  • Faizan-e-Madina Bologna
  • Ducati Museum
  • More

Day 12 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Florence for 2 nights. Along the route of your relaxed road trip, you can get a glimpse of the locals’ way of life and visit some of the most amazing locations in Italy.

Enjoy the perfect balance of relaxation and exploration in Bologna today. One of the most curiosity-inducing attractions included on the itinerary is San Martino. This culturally significant church will help you start your sightseeing on top. Then, take a leisurely stroll to La Piccola Venezia and learn what makes this romantic street unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the increasingly popular Faizan-e-madina Bologna. After exploring the mosque, head to Ducati Museum. This beloved museum is a highlight in Bologna.

You’ll be staying at the incredible city of Florence in this laid-back road trip in Italy. You'll stay here for 2 nights.

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 Florence.

Experience a symphony of flavors at Enoteca Pinchiorri in Florence by securing a reservation in advance. Renowned for its 3-star Michelin distinction, Enoteca Pinchiorri delights its guests with its exceptional variety of meals showcasing delicious italian contemporary cuisine. For a palate-pleasing alternative, make sure to dine at Santa Elisabetta, acclaimed for its delectable creative and mediterranean specialties. This local 2-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Gucci Osteria da Massimo Bottura, a top-rated restaurant known for its outstanding menu. Known as a top-rated 1-star Michelin establishment, it's a top choice for italian contemporary and international cuisine in the city.

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

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.

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

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Day 13

Day 13

  • Florence
  • More

Drive 4 km, 1 hour 5 min

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

Day 13 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!

Today’s itinerary in Florence covers several incredible sights, including an observation deck, a church, a public square, an art gallery, a historical landmark and much more! Start your adventure at Piazzale Michelangelo. This impressive observation deck is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the photogenic wonders of Basilica Of Santa Croce In Florence, a must-see church 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 Piazza Della Signoria. This astonishing public square offers an enriching experience. For a change of pace, head to Uffizi Gallery, where you can take in romantic features. Conclude your self-guided sightseeing tour with a visit to Ponte Vecchio. These sights offer a fulfilling end to a perfect day.

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 dining experience at Ditta Artigianale, a popular restaurant in Florence. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Florence at Trattoria Da Burde, 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 Casa Toscana. It’s yet another ideal choice to enhance your time in Florence tonight.

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

Continue the enjoyment post-dinner at Bar 50 Rosso, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Bitter Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Archea Brewery. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

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Day 14

Day 14

  • Florence
  • Pisa
  • More

Drive 83 km, 1 hour 38 min

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

Day 14 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 Pisa, where you’ll stay at a top-rated hotel of your choice for 1 night.

Get ready for a day filled with family-friendly attractions, romantic experiences, and scenic views in the charming city of Florence. Your adventure starts at Cathedral Of Santa Maria Del Fiore, a spectacular local hot spot. Another notable attraction to explore is Galleria Dell'accademia. This popular art gallery is known for its inviting appeal.

After soaking in the highlights of these sights, take some time to wander Florence's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Central Market. This instagrammable food market offers a fascinating experience that many visitors find memorable. Basilica Di Santa Maria Novella, Firenze (fi) is also worth visiting.

In the city of Pisa, 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.

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 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.

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

Keep the excitement of the evening going by visiting a bar or two. Bar Mocambo is an excellent place to start. You could also check out Tree, offering a different kind of charm. A last recommendation for the day is Chupiteria. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

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

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Day 15

Day 15

  • Pisa - Departure day
  • More
  • Palazzo Gambacorti
  • More

Day 15 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 Palazzo Gambacorti, a respected palace before you head out.

Unwind and look back at the past 15 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.

Enjoy a lovely meal at Restaurant -Pizzeria Il Mio Capriccio, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante alle Bandierine is another top choice with a popular menu.

Give yourself enough time to wave goodbye to Pisa and begin your journey home. The unforgettable experiences you’ve collected along your 15-day relaxed road trip in Italy is a story you will tell for the rest of your life.

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