10-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling west to Milan, Pisa, and Florence

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Explore the best of Italy on a 10-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Bologna, Milan, Sarzana, Pisa, and Florence. This road trip itinerary in Italy seamlessly combines exploration with relaxation.

This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. You will spend 2 nights in Bologna, 3 nights in Milan, 1 night in Pisa, and 3 nights in Florence. Anticipate well-spent days sightseeing, eating delicious food, and experiencing the highlights of each destination!

With this travel package, you can choose from an extensive selection of accommodations along your road trip route in Italy. We have handpicked the best hotels and places to stay across the country, including options for each budget. Whether you are in the mood for luxurious 5-star hotels or budget-friendly bed and breakfasts, we have got you covered.

Upon arriving in Bologna, the rental vehicle of your choice will be ready for collection. From there, the road trip can begin! Experience the ultimate freedom and uncover Italy on your own terms.

An expertly curated travel plan makes sure you don’t miss out on any of the best things to see and do on your road trip in Italy. Duomo Di Milano Museum and Ponte Vecchio are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Leaning Tower Of Pisa, learn more about the unique Piazza Del Duomo, Pisa, and immerse yourself in the vibrant atmosphere of Galleria Vittorio Emanuele Ii.

As you hit the open road and drive through Bologna, Milan, Sarzana, Pisa, and Florence, you will also enjoy plenty of opportunities to uncover hidden gems and experience the authentic charm of Italy. Whether you are exploring enchanting towns and villages, discovering scenic routes, or indulging in local cuisine, there is always something new and exciting to experience in Italy.

Throughout your road trip in Italy, take breaks from sightseeing to explore your favorite destinations' top shopping streets and markets. Discover unique souvenirs that will forever remind you of your self-drive adventure in Italy.

This package offers an all-in-one solution for your trip planning - choose flights, a rental car, accommodation, attractions, and tours that suit your needs and desires. You can customize each day of your road trip itinerary with flexible trip planning before and after booking.

The best services in Italy fill up quickly, so book your spot early. Select a date and start planning your road trip in Italy today!

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Itinerary summary

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Days
Destination
Attractions
Overnight
Day
City & Overnight
Attractions
arco del Meloncello
Bologna CathedralFountain of Neptune, BolognaPiazza MaggioreTwo TowersPiazza Santo Stefano
La ScalaGalleria Vittorio Emanuele IIDuomo di MilanoCathedral SquareRoyal Palace of Milan
Arch of PeaceSempione ParkCastello SforzescoPinacoteca di BreraPiazza Gae Aulenti
Basilica di Sant'AmbrogioLeonardo da Vinci Museum of Science and TechnologyFortezza Firmafede
Knights' SquareLeaning Tower of PisaPiazza del Duomo, PisaPisa CathedralParco Regionale Migliarino, San Rossore, Massaciuccoli

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Day 1

Day 1

  • Bologna - Arrival day
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  • arco del Meloncello
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Say hello to Bologna! Your exciting road trip through Italy is just about to start. Navigating the top places to see in the region is a breeze with a car. The rental vehicle of your choice will be ready for pickup upon your arrival in the city. You will stay in Bologna for 1 night before you continue your adventure!

Bologna 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 Arco Del Meloncello or taking a stroll in the city center. Soak in the lovely atmosphere and sit down for a bit to eat or drink.

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

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

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

Keep the excitement of the evening going by visiting a bar or two. Bar Al Bricco D'oro is an excellent place to start. You could also check out Bar Freud E Squisito, offering a different kind of charm. A last recommendation for the day is Osteria Del Sole. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Raise a toast to the start of your 10-day road trip in Italy!

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Day 2

Day 2

  • Bologna
  • Milan
  • More

Drive 223 km, 2 hours 49 min

  • Bologna Cathedral
  • Fountain of Neptune, Bologna
  • Piazza Maggiore
  • Two Towers
  • Piazza Santo Stefano
  • More

On day 2 of your road trip in Italy, you will get a true taste of the freedom a self-drive vacation in Europe entails. Today’s travel plans include stops at the most scenic, wondrous, and interesting places in Bologna. In the evening, you’ll end up in Milan, where you will stay for 3 nights.

Today’s agenda in Bologna includes a church, a monument, and a public square. Bologna Cathedral is must-visit church and a great starting point for the day. Next, continue your journey to Fountain Of Neptune, Bologna, an underrated monument, located just a leisurely stroll away. Next, head to Piazza Maggiore, a symbolic public square, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Bologna. If you’re looking for more, Two Towers is also a well-known attraction that is worthwhile a visit. Lastly, don’t miss Piazza Santo Stefano, an often recommended gem to see in the city.

When you’re done exploring for the day, you’ll drive to your hotel in Milan. Check in and spend some time relaxing before you head out to tour the city.

Indulge in a memorable dining experience at one of Milan's most popular restaurants, and connect with friendly locals for an authentic adventure.

Experience a symphony of flavors at Enrico Bartolini al Mudec in Milan by securing a reservation in advance. Renowned for its 3-star Michelin distinction, Enrico Bartolini al Mudec delights its guests with its exceptional variety of meals showcasing delicious creative cuisine. For a palate-pleasing alternative, make sure to dine at Seta by Antonio Guida, acclaimed for its delectable international and contemporary specialties. This local 2-star Michelin establishment consistently satisfies guests, ensuring an unforgettable holiday experience. Want to go on another culinary journey? Delight your senses at Il Luogo Aimo e Nadia, a top-rated restaurant known for its outstanding menu. Known as a top-rated 1-star Michelin establishment, it's a top choice for italian contemporary and modern cuisine in the city.

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 to another unforgettable day in Italy!

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Day 3

Day 3

  • Milan
  • More

Drive 1 km, 21 min

  • La Scala
  • Galleria Vittorio Emanuele II
  • Duomo di Milano
  • Cathedral Square
  • Royal Palace of Milan
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Day 3 of your road trip across Italy promises a magnificent time exploring Milan. You have 2 nights left in Milan. Take the opportunity to experience more of the best attractions and activities in the city.

Set out on a day brimming with family-friendly attractions, romantic experiences, and picturesque spots. Start at the locally renowned La Scala, a historic opera house in Milan. Next, go to Galleria Vittorio Emanuele Ii.

After visiting La Scala and Galleria Vittorio Emanuele Ii, take time to explore Milan's streets and absorb its charm. Continue your sightseeing by heading to Duomo Di Milano Museum. This romantic church offers a unique experience. Cathedral Square is another noteworthy stop. End your self-guided sightseeing tour on top with a visit to Royal Palace Of Milan, one of the most eye-catching places to visit in Milan.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

After a day of adventure, treat yourself to an exquisite dinner at one of Milan's best restaurants.

Treat yourself to a delicious dinner at Dessert Bar Milano, an excellent option for tonight's dining. Looking for something different? Radisson Blu Hotel Milan offers a tantalizing alternative with its diverse menu. And don’t miss Ristorante Qui Si Mangia. With its reputation for pleasing customers, it’s a fantastic choice for tonight in Milan.

Round off your dining experience by visiting Kilburn Cocktail Bar Milano, a prime location for a drink. Alternatively, explore the distinctive characteristics of Bar Frida, a bar catering to every mood and preference. The Friends Pub Milano likewise offers a unique atmosphere, perfect for a memorable night out.

Raise your glass to another unforgettable day in Italy!

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Day 4

Day 4

  • Milan
  • More

Drive 11 km, 1 hour 16 min

  • Arch of Peace
  • Sempione Park
  • Castello Sforzesco
  • Pinacoteca di Brera
  • Piazza Gae Aulenti
  • More

Day 4 of your road trip will take you to the best attractions Milan has to offer. Cherish the 1 night you have left in Milan by discovering the best things there are to see and do in the city.

Get ready for a day filled with fun adventures, scenic views, and photo-friendly spots in the charming city of Milan. Your adventure starts at Arch Of Peace, a notable local hot spot. Another notable attraction to explore is Parco Sempione. This impressive park is known for its culturally significant appeal.

After soaking in the highlights of these sights, take some time to wander Milan's streets and immerse yourself in the local atmosphere. When you're ready to continue your sightseeing adventure, head to Sforzesco Castle Art Library. This breathtaking castle offers a fascinating experience that many visitors find memorable. Pinacoteca Di Brera is also worth visiting, along with Piazza Gae Aulenti. These standout landmarks offer unique experiences that add to the day’s enjoyment.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Milan. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Treat yourself to a wonderful meal at Bice Restaurant, a top-rated dining spot in Milan. If you're in the mood for something new, try Alto Ristorante, another premier location with a delectable menu. You might also want to book a table at Nero 9. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Milan.

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

Raise your glass and celebrate another amazing day of your road trip in Italy!

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Day 5

Day 5

  • Milan
  • Sarzana
  • Pisa
  • More

Drive 295 km, 4 hours 1 min

  • Basilica di Sant'Ambrogio
  • Leonardo da Vinci Museum of Science and Technology
  • Fortezza Firmafede
  • More

Embark on another extraordinary experience on day 5 of your road trip in Italy. Today, you will make 2 stops and experience some of the highlights of Milan and Sarzana. At the end of the day, you will enjoy the comforts of a top-rated hotel in Pisa, which will be your home away from home for 1 night.

Today’s route brings family-friendly attractions, picturesque spots, and historic treasures. The first attraction of today is Basilica Di Sant'ambrogio. This interesting church is a culturally significant place to see in Milan. Continue your discovery at Museo Della Scienza E Della Tecnologia "leonardo Da Vinci", a standout museum with stories to tell.

After soaking in Milan’s unique atmosphere, jump into the car with a full heart and drive in the direction of your next destination: Sarzana. Expect your car journey to take a minimum of 2 hours 40 min. When you arrive in Sarzana, it's time to take a break from the road.

Head to Fortezza Di Firmafede, a curiosity-inducing castle in Sarzana. Explore its culturally significant features at your own pace before you continue your journey.

After soaking up all the sights of today's itinerary, you'll be ready to hit the road in the direction of your accommodation in Pisa. Pisa offers plenty of top-rated hotels and other places to stay on any travel budget. Take some time to relax before you head out to explore.

After a day of adventure, treat yourself to an exquisite dinner at one of Pisa's best restaurants.

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

Extend your evening after a delightful meal by visiting Jeffer Cocktails & Friends, which offers the perfect atmosphere for a night out. Moreover, Le Parisien Wine Bar is another popular option for a drink or two. Likewise, Las Volta Cocktailbar also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

Say good night to Pisa and look forward to another great day of your road trip in Italy!

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Day 6

Day 6

  • Pisa
  • Florence
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Drive 120 km, 1 hour 57 min

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

On day 6 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Pisa and Cascine Vecchie. When you’re not sightseeing, take time to relax at your selected hotel in Florence, where you’ll be staying for 3 nights.

Start by visiting Knights' Square, a prime spot to begin your journey. This picture-perfect public square is sure to impress. Next on your list is Leaning Tower Of Pisa, another must-visit landmark and wondrous monument renowned for its UNESCO world heritage-designated features.

While exploring and sightseeing, take time to savor the ambiance of Pisa by sampling some local delicacies or having a drink. When you’re ready for more sightseeing, head to Piazza Del Duomo, Pisa. This stunning public square is a remarkable attraction that offers a unique experience. Pisa Cathedral also adds charm to your journey.

As you’ve unraveled the marvels of Pisa, it’s time to gear up for the next part of your road trip adventure. Under favorable conditions, your drive to Cascine Vecchie may take around 9 min. Upon your arrival in Cascine Vecchie, you’ll be greeted with the opportunity to do some sightseeing and exploring.

Spend your afternoon discovering Parco Regionale Migliarino, San Rossore, Massaciuccoli, a curiosity-inducing nature reserve known for its eye-catching features.

At the end of the day, you will drive to Florence, where you'll have a room waiting for you at the perfect place to stay. Check in and enjoy some downtime.

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

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.

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.

As the day draws to a close, take a moment to unwind and prepare for the next exciting chapter of your road trip in in Italy.

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Day 7

Day 7

  • Florence
  • More

Drive 3 km, 56 min

  • The Boboli Gardens
  • Ponte Vecchio
  • Uffizi Gallery
  • Palazzo Vecchio
  • piazza della Signoria
  • More

Day 7 offers a multitude of experiences. You will stay in Florence for 2 nights more, offering you enough time to explore at a relaxed pace.

Today’s agenda in Florence includes a botanical garden, a historical landmark, an art gallery, a palace, a public square and much more! The Boboli Gardens is must-visit botanical garden and a great starting point for the day. Next, continue your journey to Ponte Vecchio, a globally renowned historical landmark, located just a leisurely stroll away. Next, head to Uffizi Gallery, an enchanting art gallery, also available for your discovery today.

Each stop on today’s itinerary promises to leave you with lasting memories and a deeper appreciation for Florence. If you’re looking for more, Palazzo Vecchio is also a notable attraction that is worthwhile a visit. Lastly, don’t miss Piazza Della Signoria, an extraordinary gem to see in the city.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

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

Enjoy a delicious meal 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.

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.

Savor another day of unforgettable experiences in Italy!

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Day 8

Day 8

  • Florence
  • More

Drive 16 km, 1 hour 19 min

  • Parco delle Cascine
  • Galleria dell'Accademia
  • David
  • Basilica of Santa Croce in Florence
  • piazzale Michelangelo
  • More

On day 8 of your road trip, you will have an entire day to explore Florence. You’ll stay in Florence for 1 night and discover all the best things to see and do in the area.

Today’s well-planned self-sightseeing route offers several family-friendly attractions, romantic experiences, and natural wonders. Whether you decide to explore Florence on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Parco Delle Cascine is the first of them. Spend some time admiring this serene park before continuing your journey. Galleria Dell'accademia is your next stop. This well-known art gallery is one of the best-rated sights in Florence.

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 David. To round off your sightseeing experience, visit Basilica Of Santa Croce In Florence and Piazzale Michelangelo.

Don’t forget to check out all the popular tours and activities you can add to your road trip itinerary. Italy is a beautiful travel destination that offers plenty of unique tours that will enhance your vacation experience. Explore and select your activities below.

As you explore more of Florence, you'll discover that its culinary landscape is as diverse as its attractions. Whether you're craving traditional dishes bursting with local flavors or innovative creations that push the boundaries of taste, you're sure to find a dining experience that satisfies your cravings.

Make sure to reserve a table at Ristorante Buca Mario, 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 Agricola Toscana, 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 Eataly Firenze, 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 enjoying a fulfilling meal, continue your evening at Gosh*, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Antico Caffè Del Moro - Art Bar Firenze offers a welcoming atmosphere for easing into the nightlife. Similarly, Quelo Bar provides an excellent environment for a relaxed and enjoyable evening.

As the sun sets on another day of adventure, rest up and recharge for the next leg of your road trip in Italy.

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Day 9

Day 9

  • Florence
  • Bologna
  • More

Drive 107 km, 2 hours 5 min

  • Cathedral of Santa Maria del Fiore
  • Central Market
  • Basilica of Santa Maria Novella
  • Palazzo Pitti
  • More

Dive into day 9 of your remarkable road trip in Italy. Today you will explore Florence, where you will have the opportunity to experience all the top things to see and do. At the end of the day, you’ll unwind at one of the finest accommodations in Bologna. You’ll stay here for 1 night.

Set out on a day brimming with fun adventures, romantic experiences, and breathtaking views. Start at the spectacular Cathedral Of Santa Maria Del Fiore, an inviting church in Florence. Next, go to Central Market.

After visiting Cathedral Of Santa Maria Del Fiore and Central Market, take time to explore Florence's streets and absorb its charm. Continue your sightseeing by heading to Basilica Di Santa Maria Novella, Firenze (fi). This history-steeped church offers a unique experience. Pitti Palace is another noteworthy stop.

When you’re done exploring for the day, you’ll drive to your hotel in Bologna. Check in and spend some time relaxing before you head out to tour the city.

After a long day of exploring, sit down for a delicious dinner at a top-rated restaurant in Bologna. Enjoy a satisfying meal that will recharge you for tonight's adventures.

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.

Round off your dining experience by visiting Lime Bar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Macondo - Cocktail Bar, a bar catering to every mood and preference. Bar Onda Marina By Night likewise offers a unique atmosphere, perfect for a memorable night out.

Take some time to reflect on your day and savor another beautiful night in Italy.

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Day 10

Day 10

  • Bologna - Departure day
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  • Porta Castiglione
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Day 10 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Bologna before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

Maximize your last day in Italy and go on a shopping spree in Bologna’s shopping center, the lively Galleria Cavour. Browse for souvenirs to remind you of your wonderful journey in Italy. You can also explore high-end shops for luxury items.

Get ready for a day filled with fun adventures, photo-friendly spots, and historic treasures in the charming city of Bologna. Your adventure starts at Porta Castiglione, an up-and-coming local hot spot.

Before you conclude your road trip in Italy, drop by another restaurant for a last chance at a memorable dining experience in Bologna.

You’ll then say farewell to Bologna. Drive to the airport, return your car, and take the opportunity to get some last-minute souvenirs before you board your flight home. We wish you a pleasant journey and hope you leave with many wonderful memories of your road trip in Italy!

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