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
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Explore Italy and discover its unique charm on this 15-day relaxed road trip through Pisa, Milan, Monza, Verona, Bologna, and Florence. Delight in a stress-free journey that focuses on exploration through the country's most captivating landscapes.

This self-drive package allows you to travel through picture-perfect landscapes in Italy at a relaxed pace. Get a dose of comfort, fun, and recreation in Pisa, 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.

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

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

Enjoy a delicious meal at Anima di Grano Pizzeria Napoletana Pisa Italy, a highly-rated dining destination in Pisa. If you're eager to try something different, consider il Mercante, another top spot with a tantalizing menu. You might also want to secure a reservation at La Ghiotteria. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Pisa this evening.

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

After savoring a delicious meal, step into the vibrant nightlife at Jeffer Cocktails & Friends, where the evening is just getting started. In the same way, Le Parisien Wine Bar offers a unique charm perfect for experiencing the local bar scene in Pisa. Las Volta Cocktailbar is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

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 Italy promises an exciting agenda full of discovery. You’ll start your day in the city of Pisa and drive in the direction of the hamlet of Cascine Vecchie for some laid-back sightseeing. You’ll end your day in the city of Milan, where you’ll stay for 5 nights.

Set out on a day brimming with family-friendly attractions, scenic views, and picturesque spots. Start at the world-famous Leaning Tower Of Pisa, a breathtaking monument in Pisa. Next, go to Piazza Del Duomo, Pisa.

After visiting Leaning Tower Of Pisa and Piazza Del Duomo, Pisa, have a stroll along Pisa's streets and take in the local charm. Continue your sightseeing by heading to Pisa Cathedral. This historic church offers a unique experience. Parco Regionale Migliarino, San Rossore, Massaciuccoli is another noteworthy attraction worthwhile a visit.

After a day of exploration, relax at one of the top hotels or accommodations in Milan. Staying in the city enhances your laid-back road trip experience in Italy by offering a comfortable and welcoming environment to recharge in this charming destination.

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.

Discover the culinary delights of Milan by securing a reservation at Enrico Bartolini al Mudec. Esteemed for its 3-star Guide Michelin recognition, this restaurant offers a remarkable selection of creative cuisine. For an alternative dining experience, try Seta by Antonio Guida, renowned for its delicious international and contemporary dishes. This esteemed 2-star Michelin-recipient consistently impresses guests, making it a must-visit spot during your holiday. Craving more culinary excitement? Head to Il Luogo Aimo e Nadia, a highly recommended local eatery celebrated for its mouthwatering italian contemporary and modern menu. With its 1-star Michelin recognition, it offers an unforgettable dining adventure.

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.

Unwind after your meal by stepping into Nottingham Forest. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Armani/bamboo Bar offers a dynamic and energetic atmosphere for a glass or two. Don’t overlook Mag Cafe, another top-rated bar in the area.

Raise your glass and toast to another unforgettable, laid-back road trip adventure 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 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 Royal Palace Of Milan. This heritage-rich palace is sure to ignite your curiosity. Next, dive into the enchanting features of Cathedral Square, a must-visit public square 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 Duomo Di Milano Museum, an iconic church. For a change of scene, check out Galleria Vittorio Emanuele Ii, known for its romantic features. We also recommend visiting La Scala. This opera house is a must for anyone looking to experience the city to the fullest.

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 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.

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

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

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 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!

Start by visiting Arch Of Peace, a prime spot to begin your journey. This noteworthy monument is sure to impress. Next on your list is Triennale Di Milano, another must-visit landmark and curiosity-inducing museum renowned for its photogenic features.

While exploring and sightseeing, take time to savor the culture of Milan by sampling some local delicacies. When you’re ready for more sightseeing, head to Parco Sempione. This romantic park is an essential place to visit for anyone looking for the full Milan experience. We also recommend visiting Sforzesco Castle Art Library, a famous castle. Nearby, you'll also find Pinacoteca Di Brera, ready to add charm 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 Milan. There are so many fun and eye-opening activities to try out in Milan that will make your slow-paced self-drive tour in Italy more memorable. Check out all the most recommended and top-rated tour options in the city of Milan to find the best options for you!

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

Don’t miss out on dining at Bice Restaurant, a top-rated dining destination in Milan. If you're in the mood to try something new, consider Alto Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at Nero 9. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Milan this evening.

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

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

Toast to another unforgettable and relaxing road trip adventure 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 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 family-friendly attractions, photo-friendly spots, and history-rich sites. When you’re ready, kick off your sightseeing adventure at Basilica Di Sant'ambrogio. This popular church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", one of the city’s best highlights.

Next, check out Santa Maria Delle Grazie Church, one of the most well-known places to see in Milan. This church is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Mudec - Museum Of Cultures. Wander around and soak in the picture-perfect atmosphere this museum offers.

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 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.

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

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

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Qc Termemilano, a well-loved spot among locals and tourists. Or, head to Yguana Cafè. This bar boasts a welcoming environment that is perfect for winding down.

Raise your glass and relax after another big day of your leisurely paced road trip 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 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! Monumental Cemetery is the perfect place to start. This cemetery is one of the most worthwhile places to visit in Milan. Next, head to Piazza Gae Aulenti, a notable public square, known for its gorgeous 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 Milan Natural History Museum. This eye-catching museum is a highly recommended experience. Nearby, you'll also find Villa Necchi Campiglio. Visit these for an interesting touch to your journey.

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 Vento di Sardegna, a top pick for dinner tonight. Alternatively, Palazzo Parigi Hotel & Grand Spa Milano beckons with its unique menu offerings. Also, consider Galleria Restaurant. With its consistent customer satisfaction, it’s an excellent option for dining in Milan 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.

Raise your glass and toast to another unforgettable, laid-back 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

On day 7 of your laid-back and relaxed road trip adventure, you’ll have the chance to visit more than one remarkable area in Italy. Since this self-drive tour offers freedom and flexibility, you can decide how much time you want to spend in each place to enjoy the memorable travel destinations in Italy.

Today’s route brings fun adventures, scenic views, and photo-friendly spots. The first attraction of today is Monza Circuit. This interesting motor speedway is a respected place to see in Milan. Continue your discovery at Monza Park, an awe-inspiring park with stories to tell.

As you stroll around Milan, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Castelvecchio Museum. This notable museum offers an eye-catching encounter with Milan. Next, make your way to Verona Arena to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Milan.

You’ll be staying at the incredible city of Bologna in this laid-back road trip in Italy. You'll stay here for 5 nights.

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.

Enjoy an outstanding dining experience at Ahimè, a Bib Gourmand restaurant offering an exceptional country cooking menu. Alternatively, if you're in the mood for something different, consider the nearby 1-star Michelin-awardee, I Portici, known for its delicious creative and contemporary cuisine. Another highly-recommended place to eat in Bologna is Trattoria di Via Serra, a renowned Bib Gourmand restaurant and a delicious emilian menu.

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.

Following your dinner, dive into the local bar culture at Bar Al Bricco D'oro. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Bar Freud E Squisito, the perfect place for those looking to experience the best of the nightlife. Similarly, Osteria Del Sole provides excellent drinks and a great atmosphere, ensuring 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 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’s route brings fun adventures, romantic experiences, and scenic views. The first attraction of today is Eremo Di Ronzano. This increasingly popular monastery is a history-steeped place to see in Bologna. Continue your discovery at Villa Ghigi, a serene park with stories to tell.

As you stroll around Bologna, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Porta Castiglione. This increasingly popular monument offers a history-steeped encounter with Bologna. Next, make your way to Basilica Of San Domenico to add another highlight to your day. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day 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 it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Bologna, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

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

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.

Continue your evening by exploring the vibrant nightlife scene at Lime Bar, a prime destination for a thrilling night out. Also, don’t forget to check out Macondo - Cocktail Bar, a bar that offers unique local touches. Likewise, Bar Onda Marina By Night provides an excellent alternative for a fun 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 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 introduces you to many popular attractions and activities in Bologna, further proving that leisurely self-drive tours in Italy are extraordinary.

Savor the day by visiting some of the best places to see in Bologna, including a monument, a palace, and a church. Start your adventure at Devotional Portico Of St. Luke. This intriguing monument is a must-visit for travelers looking for a unique holiday experience. Make your way to Arco Del Meloncello located in Bologna for another exciting encounter.

Next, immerse yourself in the setting of Palazzo Pallavicini. Its historic features will captivate you. After the palace, continue your tour of the city with a visit to Chiesa Del Santissimo Salvatore. Visitors usually appreciate the culturally significant features of this church. Next up is Porta Galliera, a highly recommended monument.

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!

After a laid-back day of exploring top attractions in the area, it’s an excellent idea to sit down for a lovely and peaceful dinner. We’ve collected the most recommended restaurants in the city for you, so you can check out the menus and make your reservation in advance.

Treat yourself to a delightful dinner at Va Mo Là, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Trattoria dal Biassanot? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Enoteca da Lucia as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Bologna.

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.

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

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

A blend of fun adventures, photo-friendly spots, and historic treasures await you in Bologna on today’s itinerary. First up is the curiosity-inducing art gallery, Pinacoteca Nazionale Di Bologna. Afterward, continue to Two Towers, a monument every traveler should visit.

As you explore Bologna’s charming streets, take in the lively atmosphere and get to know the character of the city. Next, make your way to Piazza Santo Stefano. This often recommended public square is an essential stop. Following that, head to Porta Maggiore, another must-visit site that will enhance your experience. Don’t forget to stop by Porta Santo Stefano, a beloved monument in the city.

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

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

Enjoy a lovely dining experience at Pappare' - Bologna, 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 Mister Coffee Bistrò, 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 All'Osteria Bottega. It’s yet another ideal choice to enhance your time in Bologna tonight.

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

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

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

Bologna is brimming with adventures. Today’s wonderful stops include a palace, a church, a public square, a monument and much more! Begin your sightseeing adventure at the often recommended Palazzo D'accursio and allow yourself time to explore. Just a short distance away you'll find your next stop, Bologna Cathedral, a picture-perfect church that draws visitors from far and near.

Continue your journey to Piazza Maggiore, one of the city’s most astonishing spots that you shouldn’t miss. Another great site to visit is the worthwhile Fountain Of Neptune, Bologna. When you're finished at the monument, Palazzo Re Enzo awaits your visit. This palace is a historic highlight on today's itinerary.

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 delicious dinner at Ristorante Rodrigo, an excellent option for tonight's dining. Looking for something different? CDH Hotel Bologna offers a tantalizing alternative with its diverse menu. And don’t miss Victoria Station. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Bologna.

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

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

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 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 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!

Prepare for a day full of fun adventures, picturesque spots, and historic treasures. When you’re ready, kick off your sightseeing adventure at San Martino. This worthwhile church is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is La Piccola Venezia, one of the city’s best highlights.

Next, check out Faizan-e-madina Bologna, one of the most up-and-coming places to see in Bologna. This mosque is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Ducati Museum. Wander around and soak in the photogenic atmosphere this museum offers.

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

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

Get ready for an unforgettable culinary journey in Florence by reserving a table at Enoteca Pinchiorri. Renowned as a 3-star Michelin restaurant, it offers an exceptional italian contemporary menu. For a different taste experience, head to Santa Elisabetta, recognized for its delicious creative and mediterranean dishes. This 2-star Michelin restaurant consistently impresses guests, ensuring a memorable addition to your holiday. Looking for another option? Make sure to visit Gucci Osteria da Massimo Bottura, a local favorite known for its delightful italian contemporary and international cuisine in Florence. Nestled in the heart of the city, this restaurant with 1 Michelin star is an ideal choice for discerning italian contemporary and international foodies seeking culinary excellence.

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

Extend your evening after a delightful meal by visiting Manifattura, which offers the perfect atmosphere for a night out. Moreover, Se·sto On Arno Rooftop Bar is another popular option for a drink or two. Likewise, Il Vinile also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Cherish every minute of your relaxed road trip vacation across 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 introduces you to many popular attractions and activities in Florence, further proving that leisurely self-drive tours in Italy are extraordinary.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Piazzale Michelangelo. This symbolic observation deck is a highlight of any visit in the city. Then, enjoy Basilica Of Santa Croce In Florence, another culturally significant attraction that never fails to captivate visitors. Next, head over to Piazza Della Signoria, one of the city’s most astonishing attractions, known for its history-steeped features.

If you’re looking for more, spend time soaking in the atmosphere of Uffizi Gallery. This eye-catching art gallery is frequented by locals and tourists alike. To complete your memorable day, make sure to visit Ponte Vecchio, a wondrous historical landmark, and take a stroll around the area.

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 Florence offers you an exciting chance to connect with locals and experience diversity along your relaxed road trip. When you’re ready to eat, we recommend you visit one of the best dining spots in the city.

Make sure to reserve a table at Ditta Artigianale, an iconic dining spot in Florence. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Trattoria Da Burde, a popular restaurant in Florence. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Casa Toscana, a hidden gem nestled in Florence. 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 Florence. 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 50 Rosso, a top-rated bar in the area. For other recommendations, Bitter Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Archea Brewery 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 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.

Today's adventure in Florence promises more breathtaking discoveries and enriching experiences! Begin at Cathedral Of Santa Maria Del Fiore. This visually striking church is a highlight of any visit in the city. Then, enjoy Galleria Dell'accademia, another detailed attraction that never fails to captivate visitors. Next, head over to Central Market, one of the city’s most interesting attractions, known for its picture-perfect features.

If you’re looking for more, spend time soaking in the atmosphere of Basilica Di Santa Maria Novella, Firenze (fi). This visually striking church is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

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.

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

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

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

After enjoying a fulfilling meal, continue your evening at Bar Mocambo, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Tree offers a welcoming atmosphere for easing into the nightlife. Similarly, Chupiteria provides an excellent environment for a relaxed and enjoyable evening.

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, begin at Palazzo Gambacorti. This worthwhile 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.

Have a fantastic dining experience at Restaurant -Pizzeria Il Mio Capriccio, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Ristorante alle Bandierine offers an enticing alternative with its varied 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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