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

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Photo of Morning view of Amalfi cityscape on coast line of mediterranean sea, Italy.
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Experience the freedom of the open road on an unforgettable 5-day road trip in Italy! Embark on a self-drive tour that caters to every traveler, featuring destinations like Naples, Pompei, Ravello, Amalfi, Positano, Sorrento, and Alberi.

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. 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 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, accommodations, 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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Pick-up: 10:00
Drop-off: 10:00

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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.

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

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 the city and use the provided itinerary to discover what to see in Naples.

At the top of the list of things to do today is to explore Chiaia, a neighborhood 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.

Experience Castel Sant'elmo, a well-known castle in the city. Then, head to Ovo Castle and soak in the ambiance of this enchanting castle.

There are many interesting places to see in Naples, and when you are ready for more, go to Naples National Archaeological Museum. This is one of the city’s most locally renowned detailed spots of interest. After exploring the museum, visit the interesting Chiesa Del Gesù Nuovo. Not far away, you'll also find Museo E Real Bosco Di Capodimonte. This museum is a historic highlight in Naples.

Don’t forget to check out all the popular tours and experiences you can add to your travel plans in Italy. You can explore and select activities under each day of your itinerary.

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.

Treat yourself to a delightful dinner at Antica Pizzeria Di Matteo, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Mercure Napoli Centro Angioino? It's another excellent option with a diverse menu. Consider reserving a table at La Lazzara Trattoria e Pizzeria as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Naples.

Round off your dining experience by visiting Archivio Storico - Cocktail Bar & Wonderfood, a prime location for a drink. Alternatively, explore the distinctive characteristics of Archeobar, a bar catering to every mood and preference. Babette Pub likewise offers a unique atmosphere, perfect for a memorable night out.

As the sun sets, rest up and recharge for the next leg 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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Your itinerary for day 3 of your road trip in Italy includes 4 stops and features some of the highlights of Pompei, Ravello, Castiglione, and Amalfi. At the end of the day, enjoy the comforts of a top-rated hotel in Positano, where you'll spend 1 night.

Archaeological Park Of Pompeii is perfect for a self-paced visit during the day. This UNESCO world heritage-listed archeological site is sure to impress. Next on your list is Amphitheatre Of Pompeii, another must-visit landmark and popular archeological site renowned for its picture-perfect features.

While exploring and sightseeing, take time to savor the culture of Naples by sampling some local delicacies. When you’re ready for more sightseeing, head to Villa Rufolo. This romantic historical landmark is an essential place to visit for anyone looking for the full Naples experience. We also recommend visiting Villa Cimbrone Gardens, an often recommended botanical garden. Nearby, you'll also find Amalfi Coast, ready to add charm to your journey.

After soaking up all the sights on today's itinerary, you'll be ready to head to 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 a true cultural experience.

Treat yourself to a wonderful meal at Terrazza Celè, a top-rated dining spot in Positano. If you're in the mood for something new, try Hotel Poseidon, another premier location with a delectable menu. You might also want to book a table at Hotel Villa Gabrisa. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Positano.

Raise your glass and celebrate another amazing day of your road trip 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, your travel plans include 3 stops at the most scenic, wondrous, and interesting places in the region. Positano, Sorrento, and Alberi are on today's agenda. In the evening, you’ll end up in Naples, where you will stay for 1 night.

Experience Costiera Amalfitana Positano, an increasingly popular beach in the village. Then, head to Basilica Sant'antonino and soak in the ambiance of this culturally significant church.

There are many interesting places to see in Positano, and when you are ready for more, go to Villa Comunale Di Sorrento. This is one of the village’s most locally appreciated romantic spots of interest. After exploring the park, visit the intriguing Cathedral Of Saints Philip And James. Not far away, you'll also find Parco Di Villa Fiorentino. This park is a visually striking highlight in Positano. Before wrapping up your self-guided sightseeing tour, head to Belvedere Sorrento, a frequently visited observation deck in the village.

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

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

Savor the flavors at Opera Restaurant, a top pick for dinner tonight. Alternatively, Trattoria San Ferdinando beckons with its unique menu offerings. Also, consider Anonymous Trattoria Gourmet. With its consistent customer satisfaction, it’s an excellent option for dining in Naples tonight.

Continue your evening by exploring the vibrant nightlife scene at Gran Caffè Cimmino, a prime destination for a thrilling night out. Also, don’t forget to check out Flanagan's Bar, a bar that offers unique local touches. Likewise, Bar Napoli provides an excellent alternative for a fun evening.

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.

At the top of the list of places to visit today is 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.

Take some time to indulge in shopping at Naples’s popular marketplace, Vomero. Look for keepsakes or souvenirs to remind you of your trip. Browse boutiques to find unique and stylish fashion pieces. Wrap up your shopping with a drink and some pastries at a cozy cafe.

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

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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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.
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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Your trip is protected, personalized, and priced right. No surprises, no stress.

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