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

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Uncover the beauty of Italy on this 15-day relaxed road trip, journeying through Pisa, Milan, Monza, Verona, Bologna, and Florence. Unwind at your leisure on this self-drive vacation, discovering hidden gems and immersing yourself in the serene exploration.

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

Personalize your itinerary

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Day 1

Day 1

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

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

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

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

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

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.

To truly maximize your evening out, consider visiting Jeffer Cocktails & Friends after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Le Parisien Wine Bar, another bar with an inviting ambiance. Similarly, Las Volta Cocktailbar also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

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!

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Pisa allows for both. Start by heading to Leaning Tower Of Pisa. This wondrous monument provides an insightful glimpse into the city's identity. Next, discover Piazza Del Duomo, Pisa, a breathtaking public square, promising a delightful encounter.

Continue your sightseeing with a visit to Pisa Cathedral, an underrated church. When you’re done, don’t forget to make a stop at the curiosity-inducing Parco Regionale Migliarino, San Rossore, Massaciuccoli.

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

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

Experience a taste of local culinary excellence while in Milan by securing a table at Enrico Bartolini al Mudec. An esteemed 3-star Michelin restaurant, it features an exceptional creative menu. For an alternative taste experience, visit Seta by Antonio Guida, famous for its scrumptious international and contemporary dishes. This 2-star Michelin venue consistently impresses guests, making it a standout addition to your holiday plans. Looking for another choice? Discover Il Luogo Aimo e Nadia, a local favorite celebrated for its exquisite italian contemporary and modern cuisine in Milan. Located in the heart of the city, this 1-star Michelin restaurant is an ideal pick for italian contemporary and modern cuisine lovers seeking top-notch culinary experiences.

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.

After savoring a delicious meal, step into the vibrant nightlife at Nottingham Forest, where the evening is just getting started. In the same way, Armani/bamboo Bar offers a unique charm perfect for experiencing the local bar scene in Milan. Mag Cafe is another top-recommended bar that is sure to get you into the mood for some dancing and celebrating.

Raise your glass and relax after another big day of your leisurely paced road trip 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.

Brace yourself for today’s incredible lineup of attractions in Milan, featuring fun adventures, picturesque spots, and historic treasures. Start at Royal Palace Of Milan, an interesting palace in the city. Then, head to Cathedral Square and soak in the ambiance of this enchanting public square.

There are many interesting places to see in Milan, and when you are ready for more, go to Duomo Di Milano Museum. This is one of the city’s most wondrous history-steeped spots of interest. After exploring the church, visit the impressive Galleria Vittorio Emanuele Ii. Not far away, you'll also find La Scala. This opera house is a romantic 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.

Dine in style at Dessert Bar Milano, a top recommendation for dinner tonight. Or, for a change of pace, Radisson Blu Hotel Milan boasts a menu that's sure to impress. Also, be sure to check out Ristorante Qui Si Mangia. Known as a local hotspot, it’s a great choice for tonight 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.

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.

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!

Get ready for an exciting day in Milan. Today’s sightseeing agenda includes a monument, a museum, a park, a castle, an art gallery and much more! Begin your adventure at Arch Of Peace. This is an interesting monument you should not miss. Another must-see is Triennale Di Milano, a curiosity-inducing museum in Milan.

When you’re ready for the next sight, head to Parco Sempione. From there, take a leisurely stroll to Sforzesco Castle Art Library, another of the city’s famous attractions. We recommend continuing your self-guided tour at Pinacoteca Di Brera, a photogenic place of interest in the city.

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

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 Bice Restaurant, a top pick for dinner tonight. Alternatively, Alto Ristorante beckons with its unique menu offerings. Also, consider Nero 9. With its consistent customer satisfaction, it’s an excellent option for dining in Milan tonight.

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 fulfilling meal, continue your evening at Bhangrabar, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Rufus Cocktail Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Ostello Bello Grande provides an excellent environment for a relaxed and enjoyable 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 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!

Set out on a day brimming with family-friendly attractions, picturesque spots, and historic treasures. Start at the well-known Basilica Di Sant'ambrogio, a photogenic church in Milan. Next, go to Museo Della Scienza E Della Tecnologia "leonardo Da Vinci".

After visiting Basilica Di Sant'ambrogio and Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", have a stroll along Milan's streets and take in the local charm. Continue your sightseeing by heading to Santa Maria Delle Grazie Church. This UNESCO world heritage-designated church offers a unique experience. Mudec - Museum Of Cultures is another noteworthy attraction worthwhile a visit.

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

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

Make sure to reserve a table at Ristorante la Brisa, an iconic dining spot in Milan. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Pasticceria San Carlo, a popular restaurant in Milan. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of UNAHOTELS Cusani Milano, a hidden gem nestled in Milan. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Milan. The bars in Milan make the perfect setting for a laid-back drink and chilled hangout with your travel companions.

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

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

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Day 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.

Milan is home to plenty of attractions that offer fun adventures, scenic views, and picturesque spots! Start at Monumental Cemetery, a locally appreciated cemetery that is worthwhile a visit in the city. Nearby, you’ll find Piazza Gae Aulenti, enchanting visitors with its stunning appeal. Continue your exploration at Milan Natural History Museum. This museum is one of the city’s most worthwhile spots.

Enjoy the freedom of exploring Milan at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Villa Necchi Campiglio.

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 Vento di Sardegna, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Palazzo Parigi Hotel & Grand Spa Milano is another top choice with a popular menu. You could also check for a table at Galleria Restaurant. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Milan tonight.

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

Raise your glass 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

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.

Get ready to discover some of the most iconic wonders in Milan, including a motor speedway, a park, a museum, a stadium and much more! Start your day at Monza Circuit. This stunning motor speedway is a captivating place to see in Milan. Then, wander over to Monza Park. If standout sites excite you, this park will be right up your alley. Nearby, you’ll also find Castelvecchio Museum. This eye-catching museum is a favorite among visitors.

Milan offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Verona Arena is a world-famous spot in the city that will captivate you with its unique charm.

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.

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.

Experience a symphony of flavors at Ahimè in Bologna by securing a reservation in advance. Renowned for its Bib Gourmand distinction, Ahimè delights its guests with its exceptional variety of meals showcasing delicious country cooking cuisine. For a palate-pleasing alternative, make sure to dine at I Portici, acclaimed for its delectable creative and contemporary specialties. This local 1-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Trattoria di Via Serra, a top-rated restaurant known for its outstanding menu. Known as a top-rated Bib Gourmand-establishment, it's a top choice for emilian cuisine in the city.

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.

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.

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 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!

Start by visiting Eremo Di Ronzano, a prime spot to begin your journey. This visually striking monastery is sure to impress. Next on your list is Villa Ghigi, another must-visit landmark and increasingly popular park renowned for its eye-catching 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 Porta Castiglione. This symbolic monument is an essential place to visit for anyone looking for the full Bologna experience. We also recommend visiting Basilica Of San Domenico, an intriguing church.

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.

Have a fantastic dining experience at Bononia Cafè, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Via Con Me offers an enticing alternative with its varied menu. Additionally, Trattoria Pizzeria La Mela is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Bologna.

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

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

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

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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!

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Bologna allows for both. Start by heading to Devotional Portico Of St. Luke. This curiosity-inducing monument provides an insightful glimpse into the city's identity. Next, discover Arco Del Meloncello, a standout monument, promising a delightful encounter.

Continue your sightseeing with a visit to Palazzo Pallavicini, an intriguing palace. When you’re done, don’t forget to make a stop at the often recommended Chiesa Del Santissimo Salvatore. Round off your day at Porta Galliera, another gem in Bologna with culturally significant features to discover.

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

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

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.

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.

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

Toast to another unforgettable and relaxing 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 introduces you to many popular attractions and activities in Bologna, 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 Pinacoteca Nazionale Di Bologna. This often recommended art gallery is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Two Towers, one of the city’s best highlights.

Next, check out Piazza Santo Stefano, one of the most underrated places to see in Bologna. This public square is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Porta Maggiore. Wander around and soak in the instagrammable atmosphere this monument offers. Then, head to Porta Santo Stefano, a top-rated monument that adds another dimension to your day.

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 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.

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.

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

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!

Enjoy the perfect balance of relaxation and exploration in Bologna today. One of the most frequently visited attractions included on the itinerary is Palazzo D'accursio. This picture-perfect palace will help you start your sightseeing on top. Then, take a leisurely stroll to Bologna Cathedral and learn what makes this culturally significant church unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the impressive Piazza Maggiore. After exploring the public square, head to Fountain Of Neptune, Bologna. This curiosity-inducing monument is a highlight in Bologna. As your day continues, stop by Palazzo Re Enzo, known for its history-steeped features.

Italy makes the perfect setting for a calming but fun exploration. Aside from amazing sights, Italy also offers plenty of tours to enhance your relaxed road trip experience.

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

Enjoy a delicious meal at Ristorante Rodrigo, a highly-rated dining destination in Bologna. If you're eager to try something different, consider CDH Hotel Bologna, another top spot with a tantalizing menu. You might also want to secure a reservation at Victoria Station. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Bologna this evening.

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

Round off your dining experience by visiting Brewdog Bar Bologna, a prime location for a drink. Alternatively, explore the distinctive characteristics of Kinotto Bar, a bar catering to every mood and preference. Mio Bar likewise offers a unique atmosphere, perfect for a memorable night out.

Raise your glass in celebration of your freedom and relaxed 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

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.

Get ready for an exciting day in Bologna. Today’s sightseeing agenda includes a church, a street, a mosque, a museum and much more! Begin your adventure at San Martino. This is an up-and-coming church you should not miss. Another must-see is La Piccola Venezia, a locally appreciated street in Bologna.

When you’re ready for the next sight, head to Faizan-e-madina Bologna. From there, take a leisurely stroll to Ducati Museum, another of the city’s increasingly popular attractions.

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

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

Start 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.

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

If you’re not ready to end the night just yet, Manifattura offers a perfect venue to relax and savor a drink. Similarly, Se·sto On Arno Rooftop Bar is well-suited for those looking to unwind in a social setting. Il Vinile is another excellent spot to enjoy a nightcap after a delightful meal.

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

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Day 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!

Get ready to discover some of the most iconic wonders in Florence, including an observation deck, a church, a public square, an art gallery, a historical landmark and much more! Start your day at Piazzale Michelangelo. This history-steeped observation deck is an astonishing place to see in Florence. Then, wander over to Basilica Of Santa Croce In Florence. If photogenic sites excite you, this church will be right up your alley. Nearby, you’ll also find Piazza Della Signoria. This detailed public square is a favorite among visitors.

Florence offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Uffizi Gallery is a famous spot in the city that will captivate you with its unique charm. When you’re done at the art gallery, don’t forget to check out the culturally significant Ponte Vecchio. Take a moment to appreciate the fascinating details of this iconic historical landmark.

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

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.

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.

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.

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.

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

On day 14 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.

Enjoy the perfect balance of relaxation and exploration in Florence today. One of the most spectacular attractions included on the itinerary is Cathedral Of Santa Maria Del Fiore. This inviting church will help you start your sightseeing on top. Then, take a leisurely stroll to Galleria Dell'accademia and learn what makes this history-steeped art gallery unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the notable Central Market. After exploring the food market, head to Basilica Di Santa Maria Novella, Firenze (fi). This popular church is a highlight in Florence.

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

When it’s time to eat, the city has a variety of restaurants and cuisines to suit your palate and complement your relaxed road trip experience. Take a leisurely walk around Pisa, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

Enjoy a lovely 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.

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

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.

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

As your final day in Italy unfolds, enjoy a last-minute shopping spree in Pisa's best shopping area. Enjoy finding the perfect gift or keepsake to remind you of your wonderful trip to Italy.

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.

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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