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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Enjoy this 15-day relaxed road trip in Italy, with Pisa, Milan, Monza, Verona, Bologna, and Florence showing you the beauty, culture, and peaceful moments that make this journey special!

Travel freely with this relaxed self-drive package in Italy, designed for comfort and exploration. Spend 2 nights in Pisa, 5 nights in Milan, 5 nights in Bologna, and 2 nights in Florence, staying at top-rated hotels near the heart of each city. Between drives, indulge in local cuisine, sip refreshing drinks, and enjoy the vibrant atmosphere at popular restaurants and bars along your road trip route in Italy.

Your journey starts in Pisa, where your rental car with CDW insurance will be ready for pickup. Choose a vehicle that suits your style, then set off on your 15-day relaxed road trip in Italy to explore its rich culture, fascinating history, and stunning landscapes.

Every stop on this leisurely self-drive holiday comes with handpicked accommodations that make relaxation effortless. Choose from elegant 5-star hotels with breathtaking views or comfortable 3-star stays that offer excellent value, all providing a welcoming retreat after a day on the road.

With your self-drive itinerary in Italy already planned, you’ll enjoy the country’s most celebrated sights without the rush. Marvel at the stunning Duomo Di Milano Museum, wander through the remarkable Ponte Vecchio, and soak in the atmosphere of the magnificent Verona Arena.

Continue your journey with a visit to the iconic Leaning Tower Of Pisa, a highlight that captures the spirit of the destination. Visit the spectacular Piazza Del Duomo, Pisa and Galleria Vittorio Emanuele Ii. Enjoy each stop as you explore the history, architecture, and character of each destination on this Italy road trip itinerary for 15 days.

As you travel between destinations, you’ll have plenty of time to explore local markets and boutique shops. These stops give you the chance to find unique souvenirs, taste regional specialties, and experience everyday life in Italy.

If you want to make your 15-day relaxed self-drive tour in Italy even more memorable, add optional tours or activities. Join a guided excursion, discover hidden neighborhoods, or spend an afternoon in your favorite market. Each choice deepens your connection to the places you visit.

Alongside these experiences, your laid-back self-drive package in Italy includes 14 nights in comfortable hotels, a rental car for 15 days, and convenient access to nearby dining options. You can also add flights and entry tickets to shape the trip exactly how you want it. With 24/7 travel support and a mobile app keeping your itinerary and documents organized, you can enjoy a relaxed drive and savor every mile of the road ahead.

Turn your travel plans into reality. Book your 15-day relaxed self-drive road trip in Italy today and enjoy a journey filled with discovery, freedom, and unforgettable moments!

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Driver’s age is 30 - 65
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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 central location for easy access to key areas 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.

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.

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

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 on the highlights of today’s relaxed road trip in Italy. Enjoy your first taste of Pisa as you soak in the city’s unique vibe.

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Day 2

Day 2

  • Pisa
  • Milan
  • More

Drive 289 km, 3 hours 42 min

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

On day 2 of your laid-back road trip adventure in Italy, you can visit several remarkable places. With the freedom and flexibility of a self-drive tour, you decide how much time to spend in each, making the most of these memorable destinations.

Leaning Tower Of Pisa makes a great addition to your morning plans. This world-famous monument is a breathtaking place to see in Pisa. Continue your discovery at Piazza Del Duomo, Pisa, a symbolic public square with stories to tell.

As you stroll around Pisa, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Pisa Cathedral. This locally appreciated church offers a breathtaking encounter with Pisa. Next, make your way to Parco Regionale Migliarino, San Rossore, Massaciuccoli 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 Pisa.

You'll be staying in Milan on this laid-back road trip through 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.

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

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

After your meal, keep the night alive at a bar like Nottingham Forest, known for its lively atmosphere. Armani/bamboo Bar is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Mag Cafe offers an excellent atmosphere for those looking to amp up the evening.

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

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Day 3

Day 3

  • Milan
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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!

Whether you decide to explore Milan on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss.

Royal Palace Of Milan is an ideal stop early in the day. This locally renowned palace is a must-visit in the city. When you’re ready for your next discovery, continue to Cathedral Square, which may be one of the most visually striking places you will experience today.

One of the best things about exploring Milan on a self-guided tour is that you set the pace. There’s plenty of time for detours and discovering hidden gems. When you’re ready for your next stop, make your way to Duomo Di Milano Museum, a world-famous church in the city. If you’re up for more discoveries, don’t forget to reserve some time for Galleria Vittorio Emanuele Ii and La Scala.

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

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

Treat yourself to a delightful dinner at Dessert Bar Milano, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Radisson Blu Hotel Milan? It's another excellent option with a diverse menu. Consider reserving a table at Ristorante Qui Si Mangia as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Milan.

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.

To truly maximize your evening out, consider visiting Kilburn Cocktail Bar Milano after dinner. This bar is known for offering some of the best drinks and vibes in the city. Alternatively, head to Bar Frida, another bar with an inviting ambiance. Similarly, The Friends Pub Milano also offers a great atmosphere, ensuring a night filled with enjoyment and relaxation.

Cherish every minute of your relaxed road trip vacation across 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!

One of the most captivating attractions included on the itinerary is Arch Of Peace. This masterful monument will help you start your sightseeing on top. Then, take a leisurely stroll to Triennale Di Milano and learn what makes this picture-perfect museum unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the famous Parco Sempione. After exploring the park, head to Sforzesco Castle Art Library. This spectacular castle is a highlight in Milan. As your day continues, stop by Pinacoteca Di Brera, known for its historic features.

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.

Make sure to reserve a table at Bice Restaurant, an iconic dining spot in Milan. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Alto Ristorante, a popular restaurant in Milan. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of Nero 9, a hidden gem nestled in Milan. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

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.

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

Experience Basilica Di Sant'ambrogio, a locally renowned church in the city. Then, head to Museo Della Scienza E Della Tecnologia "leonardo Da Vinci" and soak in the ambiance of this standout museum.

There are many interesting places to see in Milan, and when you are ready for more, go to Santa Maria Delle Grazie Church. This is one of the city’s most notable UNESCO world heritage-listed spots of interest. After exploring the church, visit the captivating Mudec - Museum Of Cultures.

Italy makes the perfect setting for a calming but fun road trip experience. 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 Milan, while looking for a place to eat. Or, check out our top recommendations and treat yourself to a nice meal.

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

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

Round off your dining experience by visiting Qc Termemilano, a prime location for a drink. Alternatively, explore the distinctive characteristics of Yguana Cafè, a bar catering to every mood and preference.

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

Enjoy all that Monumental Cemetery has to offer. This is a curiosity-inducing cemetery you should not miss. Another must-see is Piazza Gae Aulenti, an interesting public square in Milan.

When you’re ready for the next sight, head to Milan Natural History Museum. From there, take a leisurely stroll to Villa Necchi Campiglio, another of the city’s locally appreciated 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.

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.

Dine in style at Vento di Sardegna, a top recommendation for dinner tonight. Or, for a change of pace, Palazzo Parigi Hotel & Grand Spa Milano boasts a menu that's sure to impress. Also, be sure to check out Galleria Restaurant. 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.

Free your mind of worries as you enjoy the taste of freedom on your laid-back road trip adventure across 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 easy, relaxed road trip through Italy lets you travel at your own pace and visit multiple places in a single day. Begin by exploring the best sights in Monza. By evening, drive toward the Bologna, where you’ll stay at a top-rated hotel of your choice for 5 nights.

Monza Circuit brings Milan's character to life. This historic motor speedway is a highlight of any visit in the city. Then, enjoy Monza Park, another standout attraction that never fails to captivate visitors. Next, head over to Castelvecchio Museum, one of the city’s most notable attractions, known for its history-steeped features.

If you’re looking for more, spend time soaking in the atmosphere of Verona Arena. This visually striking stadium is frequented by locals and tourists alike. To complete your memorable day, make sure to take a stroll around the area.

Continue your laid-back road trip in Italy as you make your way to Bologna. Here, you’ll find top hotels and accommodations in the city, perfect for relaxing and recharging.

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.

Prepare for an extraordinary culinary adventure in Bologna by booking a table at Ahimè, a Bib Gourmand restaurant that boasts an exceptional country cooking menu. For a different flavor experience, head to I Portici, renowned for its delectable creative and contemporary dishes. This 1-star Michelin restaurant consistently wows guests, making it a memorable stop during your holiday. Looking for another option? Visit Trattoria di Via Serra, a local gem known for its delightful emilian cuisine in Bologna. Nestled in the city's heart, this Bib Gourmand-awardee is a perfect choice for discerning restaurant-goers seeking a new experience.

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.

After enjoying a fulfilling meal, continue your evening at Bar Al Bricco D'oro, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Bar Freud E Squisito offers a welcoming atmosphere for easing into the nightlife. Similarly, Osteria Del Sole provides an excellent environment for a relaxed and enjoyable evening.

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

To truly experience Bologna, make sure to drop by Eremo Di Ronzano. This underrated monastery is a must-visit for anyone seeking a unique vacation experience. Another sight you shouldn’t miss is Villa Ghigi, one of the city’s best highlights.

Next, check out Porta Castiglione, one of the most underrated places to see in Bologna. This monument is a favorite among locals and travelers alike. Enjoy some downtime and refreshments before continuing to your next stop, Basilica Of San Domenico. Wander around and soak in the heritage-rich atmosphere this church offers.

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.

Enjoy a delicious meal at Bononia Cafè, a top-rated dining destination in Bologna. If you're in the mood to try something new, consider Via Con Me, another top spot with a mouthwatering menu. You might also want to secure a reservation at Trattoria Pizzeria La Mela. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Bologna this evening.

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

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

Toast to another unforgettable and relaxing road trip adventure 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 introduces you to many popular attractions and activities in Bologna, further proving that leisurely self-drive tours in Italy are extraordinary.

Let Devotional Portico Of St. Luke set the tone for the day. Spend some time admiring this enchanting monument before continuing your journey. Arco Del Meloncello is your next stop. This up-and-coming monument is one of the best-rated sights in Bologna.

Consider grabbing some lunch or a light snack to keep your energy going. Beyond the above-mentioned attractions, today is also the perfect time to visit Palazzo Pallavicini. This romantic palace is a sight to behold. To round off your sightseeing experience, visit Chiesa Del Santissimo Salvatore and Porta Galliera.

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 meal at Va Mo Là, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Trattoria dal Biassanot is another top choice with a popular menu. You could also check for a table at Ristorante Enoteca da Lucia. As an establishment that consistently gains high praises from customers, it’s an ideal choice 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.

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

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

Whatever your travel style is, Pinacoteca Nazionale Di Bologna is an essential stop in Bologna. This up-and-coming art gallery provides an insightful glimpse into the city's identity. Next, discover Two Towers, a stunning monument, promising a delightful encounter.

Continue your sightseeing with a visit to Piazza Santo Stefano, an underrated public square. When you’re done, don’t forget to make a stop at the underrated Porta Maggiore. Round off your day at Porta Santo Stefano, another gem in Bologna with heritage-rich features to discover.

Italy makes the perfect setting for a calming but fun road trip experience. 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 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.

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.

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

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

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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!

Palazzo D'accursio leaves a lasting impression. This palace is one of the most curiosity-inducing places to visit in Bologna. Next, head to Bologna Cathedral, a worthwhile church, known for its symbolic features.

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

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.

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.

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 Brewdog Bar Bologna, a top-rated bar in the area. For other recommendations, Kinotto Bar provides a perfect setting for rounding out your night with style and great drinks. Likewise, Mio Bar offers a memorable night with diverse drink options and excellent service.

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

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Day 12

Day 12

  • Bologna
  • Florence
  • More

Drive 127 km, 1 hour 58 min

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

Day 12 of your self-drive tour in Italy offers a chance to experience the country’s diversity. You’ll start your day in Bologna and end it in Florence. You’ll stay in Florence for 2 nights. Along the way, you’ll glimpse local life and explore some of the most remarkable places in Italy.

One of the most locally appreciated attractions included on the itinerary is San Martino. This photogenic church will help you start your sightseeing on top. Then, take a leisurely stroll to La Piccola Venezia and learn what makes this romantic street unique.

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

After a day of exploration, relax at one of the top hotels or accommodations in Florence. Staying in the city gives you a comfortable, welcoming place to recharge during your laid-back road trip 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 Florence, explore the city like a local by trying out the best restaurants in the area.

Have a memorable dining experience in Florence by booking a table at Enoteca Pinchiorri, a 3-star Michelin restaurant presenting an exceptional italian contemporary menu. For a different culinary experience in Florence, Santa Elisabetta shines as one of the top destinations, known for its delicious creative and mediterranean cuisine. This 2-star Michelin-awardee consistently earns high praises, making it a must-visit addition to your holiday experience. If you're looking for an alternative, Gucci Osteria da Massimo Bottura is known as a top local spot in Florence for its delicious italian contemporary and international cuisine. This 1-star Michelin awardee is a highly recommended choice for an unforgettable meal.

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.

Continue the enjoyment post-dinner at Manifattura, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Se·sto On Arno Rooftop Bar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Il Vinile. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

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

Florence is brimming with adventures.

Awaiting your discovery is the impressive Piazzale Michelangelo, a respected observation deck in Florence. Next, go to Basilica Of Santa Croce In Florence.

After visiting Piazzale Michelangelo and Basilica Of Santa Croce In Florence, have a stroll along Florence's streets and take in the local charm. Continue your sightseeing by heading to Piazza Della Signoria. This culturally significant public square offers a unique experience. Uffizi Gallery is another noteworthy attraction worthwhile a visit. End your self-guided sightseeing tour on top with a visit to Ponte Vecchio, one of the most symbolic places to visit in Florence.

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 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.

Don’t miss out on dining at Ditta Artigianale, a top-rated dining destination in Florence. If you're in the mood to try something new, consider Trattoria Da Burde, another top spot with a mouthwatering menu. You might also want to secure a reservation at Casa Toscana. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Florence this evening.

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

Explore the vibrant nightlife at Bar 50 Rosso after your meal, a hub for lively evenings and memorable moments. Or, head to Bitter Bar for a great selection of flavorful drinks and a charming setting. Furthermore, Archea Brewery is perfect for those looking to extend their night with a touch of local flavor.

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 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 relaxed road trip across Italy offers a day of exciting discoveries. You’ll start your day in Florence and drive in the direction of Pisa for some laid-back sightseeing. You’ll end your day in Pisa, where you’ll stay for 1 night.

Experience Cathedral Of Santa Maria Del Fiore, an extraordinary church in the city. Then, head to Galleria Dell'accademia and soak in the ambiance of this photogenic art gallery.

There are many interesting places to see in Florence, and when you are ready for more, go to Central Market. This is one of the city’s most interesting picture-perfect spots of interest. After exploring the food market, visit the interesting Basilica Di Santa Maria Novella, Firenze (fi).

In Pisa, you’ll find plenty of places to unwind after a day on the road. Our top recommendations go perfectly with your laid-back road trip 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.

Savor the flavors at Ristorante Capodimonte Pisa, a top pick for dinner tonight. Alternatively, La Locanda Dei Pisani Doc Pisa beckons with its unique menu offerings. Also, consider Baribaldi Pisa. With its consistent customer satisfaction, it’s an excellent option for dining in Pisa tonight.

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

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’re flying home, return your rental car with time to spare. For a stress-free farewell, book a later flight and enjoy a final, relaxed day in Pisa.

If you're up for some more sightseeing, we recommend visiting Palazzo Gambacorti, a historic palace before you head out.

Over a good meal, take a moment to unwind and reflect on the past 15 days of your relaxed road trip. Savor one last traditional dish in Pisa, or keep it light with a quick bite before you go.

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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Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.
Secure your spot
Confirm your package instantly and lock in the best rate with secure payment and guaranteed availability.
Get instant confirmation
Shortly after booking, you’ll receive your full itinerary, including schedules, locations, and everything you need for a stress-free trip.
Personalize your itinerary
Each package includes a professionally crafted itinerary you can tailor to your travel style. A dedicated travel expert will make sure every detail fits your needs perfectly.
Easily make changes
Need to update plans? No problem. Whether before your trip or mid-journey, we’re just seconds away to help with quick adjustments.
Enjoy seamless planning
With everything from accommodations to activities pre-arranged, our packages save you hours of research—so you can spend more time enjoying your trip, not planning it.
Explore with confidence
From scenic road trips to city-hopping adventures, we’re here 24/7 to support you across Europe—before, during, and after your trip.

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