5-Day Italy Self-Drive Road Trip With Itinerary from Naples to Positano and surrounding area

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Escape the ordinary with this exciting 5-day road trip through Italy. Explore the diverse landscapes, lively cities, and beyond. Pack your bags, hit the road, and prepare for an unforgettable journey!

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 Naples and 1 night in Positano. 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 Naples, 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. Amalfi Coast and Piazza Del Plebiscito are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Archaeological Park Of Pompeii, learn more about the unique Ovo Castle, and immerse yourself in the vibrant atmosphere of Naples National Archaeological Museum.

As you hit the open road and drive through Naples, Pompei, Ravello, Amalfi, Positano, Sorrento, and Alberi, 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
piazza del Plebiscito
Castel Sant'ElmoOvo CastleNaples National Archaeological MuseumChiesa del Gesù NuovoMuseo e Real Bosco di CapodimonteChiaia
Archaeological Park of PompeiiAmphitheatre of PompeiiVilla RufoloVilla Cimbrone GardensAmalfi Coast
Costiera Amalfitana PositanoBasilica Sant'AntoninoVilla Comunale di SorrentoCathedral of Saints Philip and JamesParco di Villa FiorentinoBelvedere Sorrento
Via Toledo

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Day 1

Day 1

  • Naples - Arrival day
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  • piazza del Plebiscito
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Your road trip adventure in Italy begins as soon as you reach Naples and pick up your car. You’ll stay in Naples for 2 nights and explore the best things to see and do, sample the local cuisine, and choose from a curated selection of the best hotels and places to stay in the city.

Naples 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 Piazza Del Plebiscito, 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 Naples. Check-in typically starts around 2 to 4 PM at hotels in Italy. We recommend staying at a hotel in a central location for easy access to the best attractions, restaurants, and bars 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 Naples, it's often a good idea to reserve a table in advance.

Enjoy a lovely dining experience at L'Oca Nera Irish Pub, a popular restaurant in Naples. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Naples at Mimì alla Ferrovia, 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 Spuzzulè Winebar. It’s yet another ideal choice to enhance your time in Naples tonight.

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.

Raise a toast to the start of your 5-day road trip in Italy!

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Day 2

Day 2

  • Naples
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Drive 25 km, 1 hour 59 min

  • Castel Sant'Elmo
  • Ovo Castle
  • Naples National Archaeological Museum
  • Chiesa del Gesù Nuovo
  • Museo e Real Bosco di Capodimonte
  • Chiaia
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Day 2 of your road trip will take you to the best attractions Naples has to offer. Cherish the 1 night you have left in Naples by discovering the best things there are to see and do in the city.

One of the most iconic places you can visit today in Naples is Chiaia. Allow yourself some time to explore this neighborhood and discover its unique quirks. You'll also find many of the best sightseeing spots nearby.

Naples is home to plenty of attractions that offer family-friendly attractions, scenic views, and picturesque spots! Start at Castel Sant'elmo, a well-known castle that is worthwhile a visit in the city. Nearby, you’ll find Ovo Castle, enchanting visitors with its history-steeped appeal. Continue your exploration at Naples National Archaeological Museum. This museum is one of the city’s most locally renowned spots.

Enjoy the freedom of exploring Naples at your own pace and find hidden gems along the way. If you want to see more picture-perfect spots, make sure to visit Chiesa Del Gesù Nuovo. After exploring the church, head to the popular Museo E Real Bosco Di Capodimonte.

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 Naples's bustling shopping hub, Vomero. Enjoy a leisurely exploration of unique boutiques and stores where locals shop. Don’t forget to browse souvenirs, including artisan crafts and local specialties that make perfect gifts for your loved ones. Beyond shopping, Vomero offers plenty of options, including cafes, primary services, unique landmarks, and community events.

As you explore more of Naples, 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.

Enjoy a delicious meal at Antica Pizzeria Di Matteo, a highly-rated dining destination in Naples. If you're eager to try something different, consider Mercure Napoli Centro Angioino, another top spot with a tantalizing menu. You might also want to secure a reservation at La Lazzara Trattoria e Pizzeria. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Naples this evening.

Extend your evening after a delightful meal by visiting Archivio Storico - Cocktail Bar & Wonderfood, which offers the perfect atmosphere for a night out. Moreover, Archeobar is another popular option for a drink or two. Likewise, Babette Pub also provides a great ambiance for reminiscing about the day and raising a toast to your vacation.

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

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Day 3

Day 3

  • Naples
  • Positano
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Drive 82 km, 2 hours 49 min

  • Archaeological Park of Pompeii
  • Amphitheatre of Pompeii
  • Villa Rufolo
  • Villa Cimbrone Gardens
  • Amalfi Coast
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On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 4 destinations, Pompei, Ravello, Castiglione, and Amalfi. When you’re not sightseeing, take time to relax at your selected hotel in Positano, where you’ll be staying for 1 night.

Start your day at Archaeological Park Of Pompeii. This breathtaking archeological site is a well-known place to see in Naples. Then, wander over to Amphitheatre Of Pompeii. If breathtaking sites excite you, this archeological site will be right up your alley. Nearby, you’ll also find Villa Rufolo. This history-steeped historical landmark is a favorite among visitors.

Naples offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Villa Cimbrone Gardens is an up-and-coming spot in the town that will captivate you with its unique charm. Take a moment to appreciate the fascinating details of this spectacular coast.

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

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

Have a fantastic dining experience at Terrazza Celè, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Hotel Poseidon offers an enticing alternative with its varied menu. Additionally, Hotel Villa Gabrisa is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Positano.

Savor another day of unforgettable experiences in Italy!

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Day 4

Day 4

  • Positano
  • Naples
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Drive 70 km, 2 hours 15 min

  • Costiera Amalfitana Positano
  • Basilica Sant'Antonino
  • Villa Comunale di Sorrento
  • Cathedral of Saints Philip and James
  • Parco di Villa Fiorentino
  • Belvedere Sorrento
  • More

On day 4 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 Positano, Sorrento, and Alberi. In the evening, you’ll end up in Naples, where you will stay for 1 night.

Today’s well-planned self-sightseeing route offers several fun adventures, romantic experiences, and natural wonders. Whether you decide to explore Positano on foot, use public transport, or join a guided tour, there are a few attractions you don’t want to miss. Costiera Amalfitana Positano is the first of them. Spend some time admiring this mesmerizing beach before continuing your journey. Basilica Sant'antonino is your next stop. This worthwhile church is one of the best-rated sights in Positano.

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 Villa Comunale Di Sorrento. This enchanting park is a sight to behold. To round off your sightseeing experience, visit Cathedral Of Saints Philip And James and Parco Di Villa Fiorentino. If time allows, end your day with Belvedere Sorrento, an enchanting observation deck that offers a memorable conclusion to your exploration.

At the end of the day, you will drive to Naples, 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 Naples's most popular restaurants, and connect with friendly locals for an authentic adventure.

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

After enjoying a fulfilling meal, continue your evening at Gran Caffè Cimmino, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Flanagan's Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Bar Napoli provides an excellent environment for a relaxed and enjoyable evening.

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

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Day 5

Day 5

  • Naples - Departure day
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  • Via Toledo
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Day 5 of your road trip in Italy is your departure day. This is your chance to catch a last glimpse of Naples before saying goodbye to this wonderful destination. If you've still got time left, we recommend doing some last-minute shopping or sightseeing.

One of the best things to do on your last day is to explore Via Toledo, a street that captures the true essence of Naples. Take your time to uncover its best sides and enjoy its proximity to many of the area’s best attractions.

Maximize your last day in Italy and go on a shopping spree in Naples’s shopping center, the lively Via dei Mille. Browse for souvenirs to remind you of your wonderful journey in Italy. Discover boutiques with stylish fashion choices to upgrade your wardrobe. You can also explore high-end shops for luxury items.

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

Treat yourself to a delightful dinner at Piazza Sannazaro, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Osteria Il Gobbetto? It's another excellent option with a diverse menu.

You’ll then say farewell to Naples. 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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