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

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Discover Italy stress-free with this 15-day relaxed road trip, winding through Pisa, Milan, Monza, Verona, Bologna, and Florence. 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, 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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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.

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

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

Have a fantastic dining experience at Anima di Grano Pizzeria Napoletana Pisa Italy, a highly recommended choice for tonight's dinner. If you're looking to mix things up, il Mercante offers an enticing alternative with its varied menu. Additionally, La Ghiotteria is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Pisa.

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.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Jeffer Cocktails & Friends, a well-loved spot among locals and tourists. Or, head to Le Parisien Wine Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Las Volta Cocktailbar, another top-rated place in the area.

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

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!

Today’s agenda in Pisa includes a monument, a public square, a church, a nature reserve and much more! Leaning Tower Of Pisa is must-visit monument and a great starting point for the day. Next, continue your journey to Piazza Del Duomo, Pisa, a timeless public square, located just a leisurely stroll away. Next, head to Pisa Cathedral, a historic church, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Pisa. If you’re looking for more, Parco Regionale Migliarino, San Rossore, Massaciuccoli is also a beloved attraction that is worthwhile a visit.

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

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

Experience a symphony of flavors at Enrico Bartolini al Mudec in Milan by securing a reservation in advance. Renowned for its 3-star Michelin distinction, Enrico Bartolini al Mudec delights its guests with its exceptional variety of meals showcasing delicious creative cuisine. For a palate-pleasing alternative, make sure to dine at Seta by Antonio Guida, acclaimed for its delectable international and contemporary 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 Il Luogo Aimo e Nadia, 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 modern cuisine in the city.

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

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

Cherish every minute of your relaxed road trip vacation across 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.

Discover a day packed with family-friendly attractions, photo-friendly spots, and history-rich sites in Milan. Begin your sightseeing with Royal Palace Of Milan. This locally renowned palace is one of the top attractions in the city. Proceed to Cathedral Square, another must-visit attraction that enhances the city’s allure.

As you wander through the inviting streets of Milan, soak in the lively ambiance and take the opportunity to snap some photos. Next, head to Duomo Di Milano Museum. This wondrous church is a traveler-favorite. Not far away, you’ll find Galleria Vittorio Emanuele Ii, another key site on your sightseeing itinerary. Conclude your day at La Scala and uncover why it's recognized as one of the city's most popular attractions.

Make the most of your time in the country by joining activities that let you discover more about Italy. Check out all of the tours you can join this day of your leisurely self-drive holiday in Italy and ensure the experience of a lifetime.

When you’re not driving and exploring some of the best places in Italy, it’s time to make your relaxed road trip even more comforting. Sit down for a lovely meal at one of the best restaurants in Milan.

Enjoy a delicious meal at Dessert Bar Milano, a highly-rated dining destination in Milan. If you're eager to try something different, consider Radisson Blu Hotel Milan, another top spot with a tantalizing menu. You might also want to secure a reservation at Ristorante Qui Si Mangia. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Milan this evening.

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

Continue your evening by exploring the vibrant nightlife scene at Kilburn Cocktail Bar Milano, a prime destination for a thrilling night out. Also, don’t forget to check out Bar Frida, a bar that offers unique local touches. Likewise, The Friends Pub Milano provides an excellent alternative for a fun evening.

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

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Day 4

Day 4

  • 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!

A blend of family-friendly attractions, breathtaking views, and picturesque spots await you in Milan on today’s itinerary. First up is the notable monument, Arch Of Peace. Afterward, continue to Triennale Di Milano, a museum every traveler should visit.

As you explore Milan’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Parco Sempione. This famous park is an essential stop. Following that, head to Sforzesco Castle Art Library, another must-visit site that will enhance your experience. Don’t forget to stop by Pinacoteca Di Brera, a popular art gallery in the city.

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

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.

Have a fantastic dining experience at Bice Restaurant, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Alto Ristorante offers an enticing alternative with its varied menu. Additionally, Nero 9 is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Milan.

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.

Round off your dining experience by visiting Bhangrabar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Rufus Cocktail Bar, a bar catering to every mood and preference. Ostello Bello Grande likewise offers a unique atmosphere, perfect for a memorable night out.

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

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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!

Bring your curiosity for today’s adventure around Milan. Some of the city’s most loved attractions await. Basilica Di Sant'ambrogio is the perfect place to start. This church is one of the most notable places to visit in Milan. Next, head to Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", a popular museum, known for its heritage-rich 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 Santa Maria Delle Grazie Church. This UNESCO world heritage-listed church offers a unique experience that is highly recommended. Meanwhile, Mudec - Museum Of Cultures adds its own distinct 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.

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

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

Let the evening flow smoothly from dinner to drinks at Qc Termemilano, a top-rated bar in the area. For other recommendations, Yguana Cafè provides a perfect setting for rounding out your night with style and great drinks.

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

Prepare for a day full of fun adventures, breathtaking views, and picturesque spots. When you’re ready, kick off your sightseeing adventure at Monumental Cemetery. This locally appreciated cemetery is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Piazza Gae Aulenti, one of the city’s best highlights.

Next, check out Milan Natural History Museum, one of the most curiosity-inducing places to see in Milan. This museum is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Villa Necchi Campiglio. Wander around and soak in the romantic atmosphere this museum offers.

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.

Don’t miss out on dining at Vento di Sardegna, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Palazzo Parigi Hotel & Grand Spa Milano, another top spot with a mouthwatering menu. You might also want to secure a reservation at Galleria Restaurant. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

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.

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

  • Milan
  • Bologna
  • More

Drive 328 km, 4 hours 43 min

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

Day 7 of your self-drive tour in Italy is your opportunity to see and experience the diversity of the country. You’ll stay in Bologna for 5 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.

Savor the day by visiting some of the best places to see in Milan, including a motor speedway, a park, a museum, a stadium and much more! Start your adventure at Monza Circuit. This well-known motor speedway is a must-visit for travelers looking for a unique holiday experience. Make your way to Monza Park located in Milan for an enchanting atmosphere.

Next, immerse yourself in the setting of Castelvecchio Museum. Its historic features will captivate you. After the museum, continue your tour of the city with a visit to Verona Arena. This stadium has a visually striking appeal.

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

When 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.

Set out on a gastronomic journey in Bologna by reserving a table at Ahimè. Renowned for its Bib Gourmand award, this restaurant presents an outstanding menu of country cooking cuisine. For a different taste, head over to I Portici, renowned for its delectable creative and contemporary dishes. This distinguished 1-star Michelin-recipient is a favorite among guests, making it a worthy addition to your holiday plans. Craving more culinary excitement? Explore Trattoria di Via Serra, a highly rated local gem known for its exquisite emilian menu. With a Bib Gourmand acclaim, it promises a dining experience you won't want to miss. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Bologna.

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.

Let the evening flow smoothly from dinner to drinks at Bar Al Bricco D'oro, a top-rated bar in the area. For other recommendations, Bar Freud E Squisito provides a perfect setting for rounding out your night with style and great drinks. Likewise, Osteria Del Sole offers a memorable night with diverse drink options and excellent service.

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

Get ready for a day filled with fun adventures, romantic experiences, and breathtaking views in the charming city of Bologna. Your adventure starts at Eremo Di Ronzano, a frequently visited local hot spot. Another notable attraction to explore is Villa Ghigi. This intriguing park is known for its enchanting appeal.

After soaking in the highlights of these sights, take some time to wander Bologna's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Porta Castiglione. This culturally significant monument offers a fascinating experience that many visitors find memorable. Basilica Of San Domenico is also worth visiting.

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

Take a stroll around the area, head back to your accommodation for the night, or continue your evening at one of the best-rated bars in the city.

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

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

Bologna is brimming with adventures. Today’s wonderful stops include a monument, a palace, and a church. Begin your sightseeing adventure at the beloved Devotional Portico Of St. Luke. Just a short distance away is Arco Del Meloncello, a breathtaking monument that draws visitors from far and near.

Continue your journey to Palazzo Pallavicini, one of the city’s most locally appreciated spots that you shouldn’t miss. Another great site to visit is the worthwhile Chiesa Del Santissimo Salvatore. Last up on today’s itinerary is a monument. Make your way to Porta Galliera for some final sightseeing. Each attraction will leave you with lasting memories and a deeper appreciation for the rich heritage of Bologna.

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.

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.

Enjoy a lovely dining experience at Va Mo Là, a popular restaurant in Bologna. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Bologna at Trattoria dal Biassanot, 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 Ristorante Enoteca da Lucia. It’s yet another ideal choice to enhance your time 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.

Unwind after your meal by stepping into Aurum. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Bar Senza Nome offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Caffè Ristretto, another top-rated bar in the area.

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

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Day 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, photo-friendly spots, and history-rich sites. Start at the intriguing Pinacoteca Nazionale Di Bologna, a visually striking art gallery in Bologna. Next, go to Two Towers.

After visiting Pinacoteca Nazionale Di Bologna and Two Towers, take time to explore Bologna's streets and absorb its charm. Continue your sightseeing by heading to Piazza Santo Stefano. This enchanting public square offers a unique experience. Porta Maggiore is another noteworthy stop. End your self-guided sightseeing tour on top with a visit to Porta Santo Stefano, one of the most instagrammable places to visit in Bologna.

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 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.

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.

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

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

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

Savor the day by visiting some of the best places to see in Bologna, including a palace, a church, a public square, a monument and much more! Start your adventure at Palazzo D'accursio. This curiosity-inducing palace is a must-visit for travelers looking for a unique holiday experience. Make your way to Bologna Cathedral located in Bologna for an enchanting atmosphere.

Next, immerse yourself in the setting of Piazza Maggiore. Its romantic features will captivate you. After the public square, continue your tour of the city with a visit to Fountain Of Neptune, Bologna. This monument has a noteworthy appeal. For a change of pace, head to Palazzo Re Enzo. As one of the most underrated attractions in Bologna, this palace is an excellent place to end your self-guided tour.

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 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.

Savor the flavors at Ristorante Rodrigo, a top pick for dinner tonight. Alternatively, CDH Hotel Bologna beckons with its unique menu offerings. Also, consider Victoria Station. With its consistent customer satisfaction, it’s an excellent option for dining in Bologna tonight.

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

After your meal, keep the night alive at a bar like Brewdog Bar Bologna, known for its lively atmosphere. Kinotto Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Mio Bar 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 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

On day 12 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.

Set out on a day brimming with fun adventures, photo-friendly spots, and history-rich sites. Start at the underrated San Martino, a respected church in Bologna. Next, go to La Piccola Venezia.

After visiting San Martino and La Piccola Venezia, take time to explore Bologna's streets and absorb its charm. Continue your sightseeing by heading to Faizan-e-madina Bologna. This profound mosque offers a unique experience. Ducati Museum is another noteworthy stop.

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 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.

Begin your culinary exploration in Florence by securing a reservation at Enoteca Pinchiorri. This renowned restaurant holds 3 Michelin star and offers an exceptional menu of italian contemporary cuisine. For another dining delight, visit Santa Elisabetta, celebrated for its delectable creative and mediterranean menu. This acclaimed 2-star Michelin-recipient consistently leaves guests satisfied, making it a must-visit during your holiday. Looking for a different experience? Discover Gucci Osteria da Massimo Bottura, a top local spot known for its tantalizing italian contemporary and international menu. With a 1-star Michelin recognition, it guarantees an exceptional dining adventure.

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

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

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 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!

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Piazzale Michelangelo. This top-rated observation deck provides an insightful glimpse into the city's identity. Next, discover Basilica Of Santa Croce In Florence, a standout church, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Della Signoria, an impressive public square. When you’re done, don’t forget to make a stop at the famous Uffizi Gallery. Round off your day at Ponte Vecchio, another gem in Florence with visually striking features to discover.

Make the most of your time in the country by joining activities that let you discover more about Italy. Check out all of the tours you can join this day of your leisurely self-drive holiday in Italy and ensure the experience of a lifetime.

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.

Dine in style at Ditta Artigianale, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria Da Burde boasts a menu that's sure to impress. Also, be sure to check out Casa Toscana. Known as a local hotspot, it’s a great choice for tonight in Florence.

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

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

Cherish every minute of your relaxed road trip vacation across 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.

A blend of fun adventures, romantic experiences, and scenic views await you in Florence on today’s itinerary. First up is the top-rated church, Cathedral Of Santa Maria Del Fiore. Afterward, continue to Galleria Dell'accademia, an art gallery every traveler should visit.

As you explore Florence’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Central Market. This interesting food market is an essential stop. Following that, head to Basilica Di Santa Maria Novella, Firenze (fi), another must-visit site that will enhance your experience.

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.

Mealtimes are the perfect opportunities to immerse yourself in the local culture of Italy. When you're not appreciating the best places to visit in Pisa, explore the city like a local by trying out the best restaurants in the area.

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.

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

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

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 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.

Maximize your last day in Italy and go on a shopping spree in Pisa’s shopping center. Browse for souvenirs to remind you of your wonderful journey in Italy.

If you're up for some more sightseeing, begin at Palazzo Gambacorti. This locally appreciated palace is a popular place to see in the city.

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.

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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