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

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Experience the freedom of the open road in Italy as you embark on an unforgettable 5-day road trip! This experience caters to every traveler, featuring destinations like Naples, Pompei, Ravello, Amalfi, Positano, Sorrento, and Alberi.

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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Driver’s age is 30 - 65
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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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Say hello to Naples! 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 Naples for 2 nights before you continue your adventure!

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.

Find your way to your hotel in Naples. 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 Naples, it's often a good idea to reserve a table in advance.

Enjoy a delicious meal at L'Oca Nera Irish Pub, a highly-rated dining destination in Naples. If you're eager to try something different, consider Mimì alla Ferrovia, another top spot with a tantalizing menu. You might also want to secure a reservation at Spuzzulè Winebar. With a reputation for consistently satisfying customers, it’s an excellent choice to enhance your stay in Naples this evening.

Round off your dining experience by visiting Happening Cocktail Bar, a prime location for a drink. Alternatively, explore the distinctive characteristics of Shanti Art Musik Bar, a bar catering to every mood and preference. Gran Caffè Gambrinus likewise offers a unique atmosphere, perfect for a memorable night out.

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

Chiaia is a fantastic place you can explore today in Naples. This neighborhood is a testament to the city’s character, and it's easy to spend hours just walking around and admiring the surroundings. Soak in the Naples-way-of-life and visit all the nearby sights.

Enjoy the perfect balance of relaxation and exploration in Naples today. One of the most popular attractions included on the itinerary is Castel Sant'elmo. This picture-perfect castle will help you start your sightseeing on top. Then, take a leisurely stroll to Ovo Castle and learn what makes this romantic castle unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the captivating Naples National Archaeological Museum. After exploring the museum, head to Chiesa Del Gesù Nuovo. This captivating church is a highlight in Naples. As your day continues, stop by Museo E Real Bosco Di Capodimonte, known for its eye-catching features.

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.

Visit Via dei Mille in Naples for an unforgettable shopping experience. Browse unique boutiques and luxurious stores, each offering delightful surprises. Find unique souvenirs or items to take home. After shopping, explore what Via dei Mille has to offer, including attractions, essential services, and vibrant community activities.

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

Enjoy a lovely dining experience at Antica Pizzeria Di Matteo, 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 Mercure Napoli Centro Angioino, 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 La Lazzara Trattoria e Pizzeria. It’s yet another ideal choice to enhance your time in Naples tonight.

Continue the enjoyment post-dinner at Archivio Storico - Cocktail Bar & Wonderfood, a cherished local gathering spot renowned for its welcoming atmosphere. Similarly, Archeobar offers a vibrant space for indulging in well-crafted drinks and engaging conversation. You may also want to check out Babette Pub. 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

  • 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 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 Pompei, Ravello, Castiglione, and Amalfi. In the evening, you’ll end up in Positano, where you will stay for 1 night.

Enjoy the perfect balance of relaxation and exploration in Naples today. One of the most captivating attractions included on the itinerary is Archaeological Park Of Pompeii. This instagrammable archeological site will help you start your sightseeing on top. Then, take a leisurely stroll to Amphitheatre Of Pompeii and learn what makes this breathtaking archeological site unique.

Throughout the day, make sure to take breaks to appreciate the surroundings. Next up, visit the notable Villa Rufolo. After exploring the historical landmark, head to Villa Cimbrone Gardens. This increasingly popular botanical garden is a highlight in Naples.

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

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

Enjoy a lovely meal at Terrazza Celè, a top-rated place to have dinner tonight. Alternatively, if your taste buds call for something different, Hotel Poseidon is another top choice with a popular menu. You could also check for a table at Hotel Villa Gabrisa. As an establishment that gains consistently high praises from customers, it’s an ideal choice in Positano tonight.

Raise your glass to another unforgettable day 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

Embark on another extraordinary experience on day 4 of your road trip in Italy. Today, you will make 3 stops and experience some of the highlights of Positano, Sorrento, and Alberi. At the end of the day, you will enjoy the comforts of a top-rated hotel in Naples, which will be your home away from home for 1 night.

Get ready for an exciting day in Positano. Today’s sightseeing agenda includes a beach, a church, a park, an observation deck and much more! Begin your adventure at Costiera Amalfitana Positano. This is an increasingly popular beach you should not miss. Another must-see is Basilica Sant'antonino, an often recommended church in Positano.

When you’re ready for the next sight, head to Villa Comunale Di Sorrento. From there, take a leisurely stroll to Cathedral Of Saints Philip And James, another of the village’s intriguing attractions. We recommend continuing your self-guided tour at Parco Di Villa Fiorentino, an eye-catching place of interest in the village. If time allows, add Belvedere Sorrento to your itinerary. This curiosity-inducing observation deck offers the perfect finishing touch to your day in Positano.

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.

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

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.

Cap off your dinner by heading to Gran Caffè Cimmino, ideal for a leisurely evening with a drink in hand. Flanagan's Bar is another bar that offers an enjoyable setting. Similarly, Bar Napoli is also a popular place to go on a night out, perfect for relaxing and socializing.

Relax and recharge in preparation for another adventurous day 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.

If you're eager to try something different, consider Osteria Il Gobbetto, another top spot with a tantalizing 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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