5-Day Italy Self-Drive Road Trip With Itinerary from Naples to Sorrento and Florence

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Explore the best of Italy on a 5-day road trip! Uncover hidden gems and experience the rich culture firsthand as you journey through Naples, Pompei, Positano, Alberi, Sorrento, Montepulciano, Siena, Florence, and Pisa. 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 Naples, 1 night in Sorrento, and 1 night 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 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. Ponte Vecchio and Leaning Tower Of Pisa are just a couple of the bucket-list attractions that await your discovery. Marvel at the remarkable Cathedral Of Santa Maria Del Fiore, learn more about the unique Piazza Del Campo, and immerse yourself in the vibrant atmosphere of Piazza Del Plebiscito.

As you hit the open road and drive through Naples, Pompei, Positano, Alberi, Sorrento, Montepulciano, Siena, Florence, 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
piazza del Plebiscito
Archaeological Park of PompeiiAmphitheatre of PompeiiSpiaggia di Positano Marina GrandeBelvedere SorrentoCathedral of Saints Philip and James
Porta al PratoPorta Camollia, SienaCathedral of Santa Maria del FiorePonte Vecchio
Leaning Tower of PisaFontebrandapiazza del Campo
Ovo Castle

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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 1 night 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.

Have a fantastic dining experience at L'Oca Nera Irish Pub, a highly recommended choice for tonight's dinner. If you're looking to mix things up, Mimì alla Ferrovia offers an enticing alternative with its varied menu. Additionally, Spuzzulè Winebar is worth considering. Renowned for satisfying diners, it’s an ideal option for tonight in Naples.

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
  • Sorrento
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Drive 86 km, 2 hours 48 min

  • Archaeological Park of Pompeii
  • Amphitheatre of Pompeii
  • Spiaggia di Positano Marina Grande
  • Belvedere Sorrento
  • Cathedral of Saints Philip and James
  • More

Experience an unparalleled adventure on day 2 of your road trip in Italy. This exciting part of your journey invites you to discover the renowned landmarks in 4 vibrant destinations - Pompei, Positano, Alberi, and Sorrento. After a day filled with exploration and new experiences, you will retreat to the hotel of your choice in Sorrento. You will spend 1 night here for some well-deserved relaxation.

Get ready for an exciting day in Naples. Today’s sightseeing agenda includes an archeological site, a beach, an observation deck, a church and much more! Begin your adventure at Archaeological Park Of Pompeii. This is a well-known archeological site you should not miss. Another must-see is Amphitheatre Of Pompeii, a well-known archeological site in Naples.

When you’re ready for the next sight, head to Spiaggia Di Positano Marina Grande. From there, take a leisurely stroll to Belvedere Sorrento, another of the town’s up-and-coming attractions. We recommend continuing your self-guided tour at Cathedral Of Saints Philip And James, an instagrammable place of interest in the town.

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

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

Enjoy a delicious meal at Frankie's Pizza Bar Sorrento Brunch & Vegan, a top-rated dining destination in Sorrento. If you're in the mood to try something new, consider Bougainvillea, another top spot with a mouthwatering menu. You might also want to secure a reservation at Banana Split. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Sorrento this evening.

Unwind after your meal by stepping into Leone Rosso Café. This venue is celebrated for its extensive drink selections and cozy vibes. Alternatively, Hotel Antiche Mura Sorrento offers a dynamic and energetic atmosphere for a glass or two.

Get a good night's sleep and look forward to another great day on the road in Italy!

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Day 3

Day 3

  • Sorrento
  • Florence
  • More

Drive 550 km, 7 hours 2 min

  • Porta al Prato
  • Porta Camollia, Siena
  • Cathedral of Santa Maria del Fiore
  • Ponte Vecchio
  • More

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 Montepulciano, Siena, and Florence. In the evening, you’ll end up in Florence, where you will stay for 1 night.

Get ready to discover some of the most iconic wonders in Sorrento, including a monument, a church, and a historical landmark. Start your day at Porta Al Prato. This history-steeped monument is an increasingly popular place to see in Sorrento. Then, wander over to Porta Camollia, Siena. If breathtaking sites excite you, this monument will be right up your alley. Nearby, you’ll also find Cathedral Of Santa Maria Del Fiore. This romantic church is a favorite among visitors.

Sorrento offers plenty to explore, ensuring every moment of your visit is filled with excitement and discovery. If you're up for more, Ponte Vecchio is a wondrous spot in the town that will captivate you with its unique charm.

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

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.

Treat yourself to a delightful dinner at Ristorante Oliviero 1962, highly recommended for tonight's dining. Or, if you're feeling adventurous, why not try Di Poneta Novoli? It's another excellent option with a diverse menu. Consider reserving a table at Caffe San Firenze as well. Known for its consistent customer satisfaction, it’s an ideal pick for tonight in Florence.

Keep the excitement of the evening going by visiting a bar or two. Manifattura is an excellent place to start. You could also check out Se·sto On Arno Rooftop Bar, offering a different kind of charm. A last recommendation for the day is Il Vinile. This bar promises an enjoyable experience with tasty drinks and a vibrant setting.

Savor another day of unforgettable experiences in Italy!

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Day 4

Day 4

  • Florence
  • Naples
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Drive 641 km, 7 hours 31 min

  • Leaning Tower of Pisa
  • Fontebranda
  • piazza del Campo
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On day 4 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 2 destinations, Pisa and Siena. When you’re not sightseeing, take time to relax at your selected hotel in Naples, where you’ll be staying for 1 night.

Bring your curiosity for today’s adventure around Florence. Some of the city’s most loved attractions await! Leaning Tower Of Pisa is the perfect place to start. This monument is one of the most iconic places to visit in Florence. Next, head to Fontebranda, an underrated historical landmark, known for its eye-catching features.

In between the sights, don’t hesitate to take small detours to explore local stores and eateries. When you’re ready to continue your adventure, head to Piazza Del Campo. This history-steeped public square is a highly recommended experience. Visit these for an interesting touch to your journey.

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.

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.

Don’t miss out on dining at Antica Pizzeria Di Matteo, a top-rated dining destination in Naples. If you're in the mood to try something new, consider Mercure Napoli Centro Angioino, another top spot with a mouthwatering menu. You might also want to secure a reservation at La Lazzara Trattoria e Pizzeria. With a reputation for consistently satisfying customers, it’s a perfect choice to enhance your stay in Naples this evening.

Continue your evening by exploring the vibrant nightlife scene at Archivio Storico - Cocktail Bar & Wonderfood, a prime destination for a thrilling night out. Also, don’t forget to check out Archeobar, a bar that offers unique local touches. Likewise, Babette Pub provides an excellent alternative for a fun evening.

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

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Day 5

Day 5

  • Naples - Departure day
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  • Ovo Castle
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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.

If you're up for some more sightseeing, begin at Ovo Castle. This captivating castle is a popular place to see in the city.

Make the most of your final day in Italy by visiting Naples’s iconic markets and shopping establishments in the buzzing Vomero. Secure the perfect souvenirs for your family and friends back home or buy yourself a remembrance of your amazing experience in Italy. You can also browse through boutiques for stylish fashion choices. Savor your final moments in Italy at a cozy cafe while relaxing with a cup of coffee or tea.

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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