11-Day Italy Self-Drive Road Trip With Itinerary from Bologna traveling south to Florence, Siena, Rome, and Naples

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Experience the freedom of the open road in Italy as you embark on an unforgettable 11-day road trip! This experience caters to every traveler, featuring destinations like Bologna, Florence, Siena, Rome, Naples, Pompei, and Pisa.

This perfectly planned road trip itinerary in Italy takes you through some of the best places to see in the country. You will spend 3 nights in Bologna, 2 nights in Florence, 1 night in Siena, 2 nights in Rome, and 2 nights in Naples. 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. Trevi Fountain and Colosseum are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Pantheon, learn more about the unique Piazza Navona, and immerse yourself in the vibrant atmosphere of St. Peter's Basilica.

As you hit the open road and drive through Bologna, Florence, Siena, Rome, Naples, Pompei, and Pisa, 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
Church of the Holy Savior
Bologna CathedralPiazza MaggioreBiblioteca comunale dell'ArchiginnasioBasilica of San Domenicoarco del Meloncello
Basilica of Santa Croce in FlorenceBargello National MuseumPalazzo VecchioUffizi GalleryPonte Vecchiopiazza della Signoria
piazzale MichelangeloThe Boboli GardensCathedral of Santa Maria del FioreGalleria dell'AccademiaCentral MarketOltrarno
Fortezza MediceaBasilica of San DomenicoSiena CathedralPorta TufiPubblico Palacepiazza del Campo
ColosseumRoman ForumTrevi FountainPantheonCampo de' Fiori

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Day 1

Day 1

  • Bologna - Arrival day
  • More
  • Church of the Holy Savior
  • More

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 2 nights 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 Chiesa Del Santissimo Salvatore, 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 Bologna. 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 Bologna, it's often a good idea to reserve a table in advance.

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

After your meal, keep the night alive at a bar like Bar Al Bricco D'oro, known for its lively atmosphere. Bar Freud E Squisito is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Osteria Del Sole offers an excellent atmosphere for those looking to amp up the evening.

Raise a toast to the start of your 11-day road trip in Italy!

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Day 2

Day 2

  • Bologna
  • More

Drive 7 km, 37 min

  • Bologna Cathedral
  • Piazza Maggiore
  • Biblioteca comunale dell'Archiginnasio
  • Basilica of San Domenico
  • arco del Meloncello
  • More

On day 2 of your road trip, you will have an entire day to explore Bologna. You’ll stay in Bologna for 1 night and discover all the best things to see and do in the area.

Today, you'll explore some of the most beautiful places in Bologna, including a church, a public square, a library, a monument and much more! Start your day with a visit to Bologna Cathedral. This worthwhile church is a must-visit in the city. When you’re ready for your next discovery, continue to Piazza Maggiore, which may be one of the most majestic places you will experience today.

One of the best things about exploring Bologna 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 Biblioteca Comunale Dell'archiginnasio, an up-and-coming library in the city. If you’re up for more discoveries, don’t forget to reserve some time for Basilica Of San Domenico and Arco Del Meloncello.

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.

Bring home unique finds from Bologna's bustling shopping hub, Galleria Cavour. Enjoy a leisurely exploration of unique high-end stores where locals shop. Don’t forget to browse souvenirs and local specialties that make perfect gifts for your loved ones. Beyond shopping, Galleria Cavour offers plenty of options, including primary services, unique landmarks, and community events.

As dinnertime approaches, it's time to head out for a bite to eat in Bologna. 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 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.

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

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

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Day 3

Day 3

  • Bologna
  • Florence
  • More

Drive 111 km, 1 hour 59 min

  • Basilica of Santa Croce in Florence
  • Bargello National Museum
  • Palazzo Vecchio
  • Uffizi Gallery
  • Ponte Vecchio
  • piazza della Signoria
  • More

Embark on another extraordinary experience on day 3 of your road trip in Italy. Today, you will make 1 stop and experience some of the highlights of Florence. At the end of the day, you will enjoy the comforts of a top-rated hotel in Florence, which will be your home away from home for 2 nights.

Today’s itinerary in Bologna covers several incredible sights, including a church, a museum, a palace, an art gallery, a historical landmark, a public square and much more! Start your adventure at Basilica Of Santa Croce In Florence. This captivating church is a place that is appreciated by travelers and locals alike. Next, immerse yourself in the standout wonders of Bargello National Museum, a must-see museum in the city.

Consider stopping for a small bite to eat or a drink at a local eatery to keep your energy going. When you’re ready, continue your discovery with a visit to Palazzo Vecchio. This interesting palace offers an enriching experience. For a change of pace, head to Uffizi Gallery, where you can take in romantic features. Conclude your self-guided sightseeing tour with a visit to Ponte Vecchio and Ponte Vecchio. These sights offer a fulfilling end to a perfect day.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. 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 Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

Dine in style at Ristorante Oliviero 1962, a top recommendation for dinner tonight. Or, for a change of pace, Di Poneta Novoli boasts a menu that's sure to impress. Also, be sure to check out Caffe San Firenze. Known as a local hotspot, it’s a great choice for tonight in Florence.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Manifattura, known for its inviting atmosphere. Se·sto On Arno Rooftop Bar is another great option if you’re looking for a place to get the night started. Similarly, Il Vinile provides a great setting to enjoy the night away.

Savor another day of unforgettable experiences in Italy!

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Day 4

Day 4

  • Florence
  • More

Drive 9 km, 1 hour 34 min

  • piazzale Michelangelo
  • The Boboli Gardens
  • Cathedral of Santa Maria del Fiore
  • Galleria dell'Accademia
  • Central Market
  • Oltrarno
  • More

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

At the top of the list of things to do today is to explore Oltrarno, a neighborhood that captures the true essence of Florence. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.

Today’s route brings fun adventures, romantic experiences, and scenic views. The first attraction of today is Piazzale Michelangelo. This famous observation deck is a romantic place to see in Florence. Continue your discovery at The Boboli Gardens, a history-steeped botanical garden with stories to tell.

As you stroll around Florence, take in the distinct atmosphere and learn what makes this city so unique. Maximize your sightseeing with a visit to Cathedral Of Santa Maria Del Fiore. This extraordinary church offers a visually striking encounter with Florence. Next, make your way to Galleria Dell'accademia to add another highlight to your day. After that, visit Central Market, a popular food market that’s sure to impress. Whether you decide to get entrance tickets for all attractions or you prefer admiring from a distance, amazing experiences await on this day in Florence.

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 Florence. Enjoy a satisfying meal that will recharge you for tonight's adventures.

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.

Cap off your culinary experience with a visit to some of the most celebrated bars in the area. For instance, Bar 50 Rosso stands out as an excellent choice for a post-dinner cocktail. Alternatively, Bitter Bar offers an ideal atmosphere to enjoy the pleasures of the night. Archea Brewery is also a great option that provides a perfect setting for a relaxing evening.

Head back to your accommodation in Florence and get some rest in preparation for another magical day of your road trip in Italy!

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Day 5

Day 5

  • Florence
  • Siena
  • More

Drive 78 km, 2 hours 1 min

  • Fortezza Medicea
  • Basilica of San Domenico
  • Siena Cathedral
  • Porta Tufi
  • Pubblico Palace
  • piazza del Campo
  • More

On day 5 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 Siena. In the evening, you’ll end up in Siena, where you will stay for 1 night.

Whether you prefer a leisurely exploration or a more fast-paced adventure, this itinerary in Florence allows for both. Start by heading to Fortezza Medicea (siena). This worthwhile monument provides an insightful glimpse into the city's identity. Next, discover Basilica Of San Domenico, a respected church, promising a delightful encounter.

Continue your sightseeing with a visit to Siena Cathedral, a notable church. When you’re done, don’t forget to make a stop at the increasingly popular Porta Tufi. Round off your day at Pubblico Palace, another gem in Florence with picture-perfect features to discover.

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

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

Enjoy a lovely meal at Enoteca I Terzi, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Ristorante Tar-Tufo is another top choice with a popular menu. You could also check for a table at Antica Trattoria Papei. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Siena tonight.

Extend your evening after a delightful meal by visiting Meet Life Cafè, which offers the perfect atmosphere for a night out. Moreover, Maudit Pub is another popular option for a drink or two. Likewise, Bar Impero Siena also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

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Day 6

Day 6

  • Siena
  • Rome
  • More

Drive 243 km, 3 hours 41 min

  • Colosseum
  • Roman Forum
  • Trevi Fountain
  • Pantheon
  • Campo de' Fiori
  • More

Experience an unparalleled adventure on day 6 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 1 vibrant destinations - Rome. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Rome. You will spend 2 nights here for some well-deserved relaxation.

Immerse yourself in Siena’s rich culture with today's sightseeing itinerary. Start your journey at Colosseum. This picture-perfect archeological site is sure to ignite your curiosity. Next, dive into the breathtaking features of Roman Forum, a must-visit archeological site in the city.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Trevi Fountain, a globally renowned monument. For a change of scene, check out Pantheon, known for its heritage-rich features.

After soaking up all the sights of today's itinerary, you'll be ready to head in the direction of your accommodation in Rome. Rome offers plenty of top-rated hotels for every travel budget. Take some time to relax before you go out again.

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

Treat yourself to a wonderful meal at La Bottega Roma, a top-rated dining spot in Rome. If you're in the mood for something new, try Pasta In Corso, another premier location with a delectable menu. You might also want to book a table at Trattoria Vecchia Roma. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Rome.

Continue the enjoyment post-dinner at La Botticella Of Poggi Giovanni, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Almalu Trastevere offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Bar Viminale Di Pepi Maurilio. This bar is a favorite among both locals and visitors looking for a delightful evening out filled with laughter and fun.

Relax and reminisce about your day in Italy and look forward to more memorable moments to come!

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Day 7

Day 7

  • Rome
  • More

Drive 17 km, 1 hour 54 min

  • Vatican Museums
  • St Peter's Basilica
  • Sistine Chapel
  • Castel Sant'Angelo
  • Piazza Navona
  • Spanish Steps
  • More

At the end of the day, you'll drive back to Rome, where you'll stay for 1 night more.

Immerse yourself in Rome’s rich culture with today's sightseeing itinerary. Start your journey at Vatican Museums.

In between sights, stop by local stores, picturesque photo spots, and small eateries. When you’re ready for your next attraction, proceed to Sistine Chapel, a top-rated chapel. For a change of scene, check out Castel Sant'angelo, known for its culturally significant features.

When you’re done exploring the area’s best attractions, you’ll drive back to your accommodation in Rome.

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

Enjoy a delicious meal at RomAntica, a top-rated dining destination in Rome. If you're in the mood to try something new, consider Coso Ristorante, another top spot with a mouthwatering menu. You might also want to secure a reservation at DEROMA - Farine Romane. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Rome this evening.

Explore the vibrant nightlife at Sant' Eustachio Caffè after your meal, a hub for lively evenings and memorable moments. Or, head to Yellowsquare Rome for a great selection of flavorful drinks and a charming setting. Furthermore, Caffè Portofino is perfect for those looking to extend their night with a touch of local flavor.

Raise your glass to another unforgettable day in Italy!

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Day 8

Day 8

  • Rome
  • Naples
  • More

Drive 243 km, 3 hours 38 min

  • Castel Sant'Elmo
  • Naples National Archaeological Museum
  • Cappella Sansevero
  • Ovo Castle
  • piazza del Plebiscito
  • More

On day 8 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 1 destination, Naples. When you’re not sightseeing, take time to relax at your selected hotel in Naples, where you’ll be staying for 2 nights.

Rome is brimming with adventures. Today’s wonderful stops include a castle, a museum, and a public square. Begin your sightseeing adventure at the interesting Castel Sant'elmo. Just a short distance away is Naples National Archaeological Museum, an instagrammable museum that draws visitors from far and near.

Continue your journey to Cappella Sansevero, one of the city’s most interesting spots that you shouldn’t miss. Another great site to visit is the interesting Ovo Castle. Last up on today’s itinerary is a public square. Make your way to Piazza Del Plebiscito for some final sightseeing. Each attraction will leave you with lasting memories and a deeper appreciation for the rich heritage of Rome.

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

As you are wrapping up for the day, treat yourself to a satisfying dinner at a nice restaurant in Naples. Enjoy a relaxing evening as you savor delicious local cuisine and reflect on the day's adventures.

Treat yourself to a delightful dinner at L'Oca Nera Irish Pub, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Mimì alla Ferrovia? It's another excellent option with a diverse menu. Consider reserving a table at Spuzzulè Winebar as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Naples.

Continue your lively evening at Happening Cocktail Bar, a perfect place for winding down or revving up the night, depending on which mood you’re in. Shanti Art Musik Bar is another excellent bar that offers a great selection of drinks to suit any mood. If you prefer to go somewhere else, Gran Caffè Gambrinus ensures a night out tailored to your taste.

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 9

Day 9

  • Naples
  • More

Drive 53 km, 1 hour 20 min

  • Archaeological Park of Pompeii
  • Amphitheatre of Pompeii
  • More

On day 9 of your road trip, you’ll start and end your day in Naples, but spend part of the day exploring places of interest outside the immediate city. On today's itinerary, you'll find attractions in Pompei. You still have 1 night left in Naples.

Just a short distance away is Amphitheatre Of Pompeii, a historic archeological site that draws visitors from far and near.

When you’re done exploring for the day, you’ll return to Naples and your accommodation.

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

Make sure to reserve a table at Antica Pizzeria Di Matteo, an iconic dining spot in Naples. This culinary treasure and its outstanding menu have enchanted food enthusiasts from around the world. Immerse yourself in the culinary delights of Mercure Napoli Centro Angioino, a popular restaurant in Naples. With a menu designed to delight, it ensures a dining experience that transcends the ordinary. Experience the culinary magic of La Lazzara Trattoria e Pizzeria, a hidden gem nestled in Naples. 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. Archivio Storico - Cocktail Bar & Wonderfood is an excellent place to start. You could also check out Archeobar, offering a different kind of charm. A last recommendation for the day is Babette Pub. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Relax and recharge in preparation for another adventurous day in Italy!

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Day 10

Day 10

  • Naples
  • Bologna
  • More

Drive 733 km, 7 hours 40 min

  • Leaning Tower of Pisa
  • Angelo Caduto
  • More

Dive into day 10 of your remarkable road trip in Italy. Today you will explore Pisa, 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.

Today's adventure in Naples promises more breathtaking discoveries and enriching experiences! Begin at Leaning Tower Of Pisa. This breathtaking monument is a highlight of any visit in the city.

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

As you explore more of Bologna, 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 Va Mo Là, 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 Trattoria dal Biassanot, 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 Ristorante Enoteca da Lucia, a hidden gem nestled in Bologna. Known for its exquisite cuisine and inviting atmosphere, it's a dining experience you won't soon forget.

After your meal, keep the night alive at a bar like Aurum, known for its lively atmosphere. Bar Senza Nome is another top recommendation that provides the perfect setting with well-crafted drinks and a welcoming ambiance. Similarly, Caffè Ristretto offers an excellent atmosphere for those looking to amp up the evening.

Celebrate another amazing day of your road trip adventure in Italy!

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Day 11

Day 11

  • Bologna - Departure day
  • More
  • Two Towers
  • More

Day 11 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.

If you're up for some more sightseeing, begin at Two Towers. This interesting monument is a popular place to see in the city.

On your last day in Italy, take time to indulge in shopping at Bologna’s popular marketplace, Galleria Cavour. Look for keepsakes or souvenirs to remind you of your trip. If you’re in the mood for luxury shopping, high-end stores await you.

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

Dine in style at Pappare' - Bologna, a top recommendation for dinner tonight. Or, for a change of pace, Mister Coffee Bistrò boasts a menu that's sure to impress.

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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