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

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Photo of Morning view of Amalfi cityscape on coast line of mediterranean sea, Italy.

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

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

This perfectly planned road trip itinerary takes you through some of the best places to see in Italy. 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 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.

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, 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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Day1

Day 1

Naples - Arrival day
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piazza del Plebiscito
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Welcome to Naples, the perfect starting point for your road trip in Italy! Pick up your rental car and let the adventure begin. You will spend 1 night discovering what to see in Naples before embarking on the next leg of your journey.

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. Taking a stroll in the city center is a great alternative. 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.

Dine in style at L'Oca Nera Irish Pub, a top recommendation for dinner tonight. Or, for a change of pace, Mimì alla Ferrovia boasts a menu that's sure to impress. Also, be sure to check out Spuzzulè Winebar. Known as a local hotspot, it’s a great choice for tonight in Naples.

After enjoying a delightful dinner, why not delve into the vibrant local bar scene? You might want to spend the evening at Happening Cocktail Bar, a well-loved spot among locals and tourists. Or, head to Shanti Art Musik Bar. This bar boasts a welcoming environment that is perfect for winding down. You could also continue your night at Gran Caffè Gambrinus, another top-rated place in the area.

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

Day2

Day 2

Naples
Pompei
Positano
Alberi
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
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On day 2 of your road trip in Italy, your travel plans include 4 stops at the most scenic, wondrous, and interesting places in the region. Pompei, Positano, Alberi, and Sorrento are on today's agenda. In the evening, you’ll end up in Sorrento, where you will stay for 1 night.

When you’re ready to jump back into the car and say goodbye to Naples, you’ll hit the road in the direction of Pompei. This drive usually takes around 27 min.

When you're ready for some sights, head to Archaeological Park Of Pompeii, an interesting archeological site in Pompei. Explore its picture-perfect features at your own pace before you continue your journey to your next attraction, Amphitheatre Of Pompeii. This popular archeological site is a top recommendation in the area.

Once you're ready to continue your road trip, it's time to buckle up and drive, eagerly anticipating your arrival in Positano. This drive usually takes around 1 hour 10 min, without any stops or traffic disruptions.

Enjoy sightseeing at your own pace and allow yourself time to explore the beautiful surroundings. Take your self-guided tour to Spiaggia Di Positano Marina Grande, an often recommended beach that everyone visiting Positano should see.

Set your GPS to Alberi and hit the road. Expect a journey of approximately 32 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Alberi beckons with new experiences!

One of our top recommendations for your sightseeing is Belvedere Sorrento. Spend some time admiring the romantic features of the observation deck before you continue to your next stop.

At the end of the day, you will drive to Sorrento, 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 Sorrento's most popular restaurants, and connect with friendly locals for a true cultural experience.

Enjoy a lovely dining experience at Frankie's Pizza Bar Sorrento Brunch & Vegan, a popular restaurant in Sorrento. This acclaimed establishment has earned the admiration of countless food lovers in the city. Alternatively, experience a taste of Sorrento at Bougainvillea, 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 Banana Split. It’s yet another ideal choice to enhance your time in Sorrento tonight.

After your delicious meal, get a taste of the vibrant nightlife with a visit to Leone Rosso Café, known for its inviting atmosphere. Hotel Antiche Mura Sorrento is another great option if you’re looking for a place to get the night started.

Say good night to Sorrento and look forward to another great day of your road trip in Italy!

Day3

Day 3

Sorrento
Montepulciano
Siena
Florence
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Drive 550 km, 7 hours 2 min

Porta al Prato
Porta Camollia, Siena
Cathedral of Santa Maria del Fiore
Ponte Vecchio
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On day 3 of your exciting self-drive vacation in Italy, you’ll soak in the magnificence of 3 destinations, including Montepulciano, Siena, and Florence. When you’re not sightseeing, take time to relax at your chosen hotel in Florence, where you’ll be staying for 1 night.

When you’ve had your share of Sorrento, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Montepulciano. Your travel time is around 4 hours 37 min.

Our first attraction recommendation in Montepulciano is Porta Al Prato, an increasingly popular monument that draws attention for its history-steeped features.

Continue your road trip and head to your next destination, Siena. This car ride takes around 1 hour 3 min.

Porta Camollia, Siena is an up-and-coming monument we recommend visiting today. Discover its culturally significant features before continuing your self-guided tour.

When you’re ready to jump back into the car and say goodbye to Siena, you’ll hit the road in the direction of Florence. This drive usually takes around 1 hour 7 min.

For a more meaningful self-guided tour of the town's best attractions, visit Cathedral Of Santa Maria Del Fiore, an astonishing church that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Ponte Vecchio and admire its majestic features.

When you’re done exploring for the day, you’ll drive to your hotel in Florence. Check in and relax before you head out to tour 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 Florence, it's often a good idea to reserve a table in advance.

Treat yourself to a wonderful meal at Ristorante Oliviero 1962, a top-rated dining spot in Florence. If you're in the mood for something new, try Di Poneta Novoli, another premier location with a delectable menu. You might also want to book a table at Caffe San Firenze. Known for its consistently satisfied patrons, it’s a perfect choice to elevate your evening in Florence.

After enjoying a fulfilling meal, continue your evening at Manifattura, ideal for those looking to unwind with a drink in a comfortable setting. Alternatively, Se·sto On Arno Rooftop Bar offers a welcoming atmosphere for easing into the nightlife. Similarly, Il Vinile provides an excellent environment for a relaxed and enjoyable evening.

As the sun sets, rest up and recharge for the next leg of your road trip in Italy.

Day4

Day 4

Florence
Pisa
Siena
Naples
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Drive 641 km, 7 hours 31 min

Leaning Tower of Pisa
Fontebranda
piazza del Campo
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Your itinerary for day 4 of your road trip in Italy includes 2 stops and features some of the highlights of Pisa and Siena. At the end of the day, enjoy the comforts of a top-rated hotel in Naples, where you'll spend 1 night.

Set your GPS to Pisa and hit the road. Expect a journey of approximately 1 hour 18 min without stops. Soak in the beautiful landscapes as you drive and look forward to exploring your next destination. Pisa beckons with new experiences!

Spend your afternoon discovering Leaning Tower Of Pisa, a world-famous monument known for its breathtaking features.

When you’ve had your share of Pisa, prepare for your next destination. Admire the views and listen to some good music as you drive in the direction of Siena. Your travel time is around 1 hour 48 min.

For a more meaningful self-guided tour of the city's best attractions, visit Fontebranda, an intriguing historical landmark that is sure to impress. Take in the surroundings and enjoy the freedom of exploring at your own pace before you continue your journey. Next, head to Piazza Del Campo and admire its visually striking features.

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

Naples is a place where the culinary landscape is as diverse as its attractions. So before the day ends, treat your palate to a taste of local cuisine at one of the best restaurants in Naples.

Dine in style at Antica Pizzeria Di Matteo, a top recommendation for dinner tonight. Or, for a change of pace, Mercure Napoli Centro Angioino boasts a menu that's sure to impress. Also, be sure to check out La Lazzara Trattoria e Pizzeria. Known as a local hotspot, it’s a great choice for tonight in Naples.

Following your dinner, dive into the local bar culture at Archivio Storico - Cocktail Bar & Wonderfood. Enjoy this evening's relaxed ambiance with delightful drinks. Alternatively, go to Archeobar, the perfect place for those looking to experience the best of the nightlife. Similarly, Babette Pub provides excellent drinks and a great atmosphere, ensuring a memorable night out.

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

Day5

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, we recommend visiting Ovo Castle, a history-steeped castle before you head out.

For a shopping spree in Naples, we recommend the lively Via Toledo. Here, you'll find a range of shops you can browse for some souvenir shopping.

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

Dine in style at Opera Restaurant, a top recommendation for dinner tonight. Or, for a change of pace, Trattoria San Ferdinando boasts a menu that's sure to impress.

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.

We guarantee

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

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