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Two Week Southern Italy Road Trip Itinerary

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A road trip through Southern Italy is the perfect way to explore stunning coastlines, historic towns, and incredible food. From the Amalfi Coast to the rugged landscapes of Puglia, this guide takes you through the best stops, must-see sights, and travel tips to make the most of your journey. Ready to hit the road? Let’s go! Updated January 2025

However, if you are anything like me and enjoy exploring hidden gems, then maybe a Southern Italy road trip is the perfect way to see the South of Italy’s best. 

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Standing in the middle of pompeii

Southern Italy Road Trip

Car Hire in Italy

Important note: Many cities are off-limit to parking in the city centre walls to protect the historic towns. It would help if you researched each city before entering; many sites will give you the correct information on parking.

Visa in Italy

Travel insurance in Italy

Southern Italy Road Trip Planner

southern italy

Southern Italy Road Trip Route

Day 1: Naples

Day 2: Naples to Pompei

Day 3: Naples to Capri

Day 4: Capri to Amalfi Coast

Day 5: Explore Amalfi Coast

Day 6:Explore Almafi Coast

Day 8: Explore Lamezia Terme

Day 10: explore Reggio Calabria

Day 11: Reggio Calabria to Messina

Day 13: explore Taormina

Day 14: explore Taormina

Road Trip Around Italy For Two Weeks

Southern Italy Road Trip: Day 1 Naples

Arriving in Naples is easy; follow the signs to pick up your car, check your Tripit app for the address of your accommodation in Naples, and begin your road trip to Southern Italy. 

Things to do in Naples

What better way to kick off your Southern Italy Road trip than a day in grungy Naples? This city might seem dirty from the outside, but it has some southern Italian charm once you start exploring. 

Standing tall at Naples Port’s edge, you will find Castel Nuovo (new castle), an impressive medieval Renaissance fortress. The Castel Nuovo is open from Monday to Saturday: 8:30 am to 6 pm and 10 am to 1 pm on Sunday. 

Another fascinating must-see is the Castel dell’Ovo (Egg Castle), which has defended the city, become a prison and was once a royal residence. It is said that poet Virgil hid a magical egg here, and if someone broke the egg, he promised that the city would suffer great catastrophes.

I’m unsure if anyone ever found the egg, but the name stuck! The entry is free, so there is no need to book online. 

Accommodation in Naples

standing in the centre of naples

Southern Italy Road Trip: Day 2 Naples to Pompeii

Travel time from Naples to Pompeii

Travelling from Naples to Pompei will take approximately 30 minutes, but if you are touring the southern part of Italy during summer, Pompei can be very hot! So I highly recommend arriving early or late in the afternoon to save you from the midday sun as there is no shelter.

Things to do in Pompeii

My son on a rock in pompeii
 

Southern Italy Road Trip: Day 3 Naples to Capri

Travel time from Naples to Capri

Car Parking

Things to do on the island of Capri

Suppose you would rather not spend the night on Capri and instead make a day trip and head over on a tour of this beautiful island (including the Blue Grotto). Here, you will go on a guided tour of this magical island without worrying about parking the car for the night. 

Hire a boat from the dock as soon as you arrive on Capri; many companies offer a trip out to the Grottoes. These are not tours but a trip to the Grottos, where you pay another person with a small dingy to visit the actual Grottos. 

The Blue Grotto is the most well-known for its history of witches, monsters, and Emperor Tiberius’ personal swimming hole; this spectacular cave is blue beyond blue! Why? Because sunlight passes through the underwater cavity, this reflection illuminates and makes the water so blue that it is breathtaking. 

On the other side of the island of Capri, you will find the Grotta Verde (Green Grotto). The colour in each Grotto is determined by the unique combination of water clarity, light source, cave depth, and Grotto’s size. 

The Grotta Bianca (white cave) has white limestone rocks set against the crystal blue sea, combined with the density of the water and the stalactites and stalagmites, which gives it that spectacular look.

This is just a reminder that all caves will depend on the season and the rise of the ocean, so check before you go. If the sea is too high, you will not have access to the caves. 

Accommodation: near Capri

sailing to Capri

Southern Italy Road Trip: Day 4 to Day 6 Capri to Amalfi Coast

Travel time from Naples to Positano

From one slice of heaven to another, today, you will head back to Naples, pick up the car and drive to the Amalfi Coast. Just a short 1.5 hours away from the Naples Port will have you there in time to relax on the beach and enjoy a heartful Italian lunch.

Things to do in Positano 

Spend the entire day relaxing in this beautiful part of Southern Italy. Lay on the beach, enjoy a long lunch and take it easy. You have plenty of time to explore the Amalfi Coast. 

The Amalfi Coast was listed in 1977 as a UNESCO World Heritage Site, consisting of 13 towns in the region. So there are a lot of exciting areas to explore.

The drive along the Amalfi coastal road is one of the most breathtaking views in Italy. However, it can be slightly terrifying as you zigzag along the coastal road.

Spending time on the water may seem luxurious on the Amalfi coast, and to some, it probably is. But you have to experience Amalfi and Positano on a boat tour, where you will stop to explore the towns, swim in the crystal clear ocean and enjoy time snorkelling, amongst other things.

Accommodation in Positano

sitting on a rock on the beach

Southern Italy Road Trip: Day 7 and 8 Positano to Lamezia Terme

Travel time from Positano to Lamezia Terme

The route from Positano to Lamezia is your longest drive, with approximately 4.5 to 5 hours of driving time (whether you take the coastal road or go the more direct inland route), so you are best to start the day early. 

Things to do in Lamezia Terme

Accommodation in Lamezia Terme

standing in front of an old house

Southern Italy Road Trip: Day 9 to 10 Lamezia Terme to Reggio Calabria

Travel time from Lamezia Terme to Reggio Calabria 

During this 1.5-hour drive, there isn’t much to see of this part of Calabria, as it is less travelled by tourists, with most opting to pass through Calabria and head straight to Sicily. 

Things to do in Reggio Calabria

Or spend the day at one of Calabria’s many beautiful beaches. The beaches are clean, the water is crystal clear, and the area is less crowded (even in summer). 

Accommodation in Reggio Calabria

View of the sea

Southern Italy Road Trip: Day 11 Reggio Calabria to Messina

Travel time from Reggio Calabria to Messina

Driving from Reggio Calabria to the Villa San Giovanni ferry pier is approximately 15 minutes. However, be warned that there can be a long wait to get onto the ferry, so arrive early and check the ferry times before you arrive. 

Things to do in Messina

Accommodation in Messina

on the ferry to messina with the car

Southern Italy Road Trip: Day 12 Messina to Taormina

Travel time from Messina to Taormina

The drive from Messina town centre to Taormina will have you there within the hour. As the trip is such a short distance, this allows you to spend the morning relaxing, as taking off too early isn’t necessary for your final journey on this southern Italy road trip. 

Things to do in Taormina

Oh, Taormina, what a wonderful place to finish your two-week southern Italy road trip. This ancient town in Sicily is beautiful to the eye and magical to the soul. Why? Well, it is hard to describe what makes this part of Italy so unique; for some reason, it makes my heart sing. 

Spend the day lying on the sunbeds, swimming in the ocean and eating incredible food. If that isn’t enough, go for a walk through The Corso Umberto, the main street of Taormina, and you will see why it has been christened “the Sicilian Saint Tropez“.

Spend the afternoon right in the centre of Corso Umberto at Piazza IX Aprile, where many cafes exist to rest your tired legs. 

Accommodation in Taormina

standing in front of the steps

Southern Italy Road Trip Day 13 and Day 14: Explore Taormina

Whether your last days are spent solely in Taormina (I don’t blame you here) or you feel like exploring this beautiful area is more your thing. It is totally up to you, but here are some great ideas for day trips from Taormina if you choose the latter. 

Taormina day trips 

Mount Edna

Savoca and Forza d’Agrò 

Etnaland

standing in front of the etnaland sign

Thanks for taking the time to read my blog. I hope this post has given you the information you need. If you have any recommendations, tips or advice, I would love to share them in the comment section below!

 

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  • Paula Barreca Barnes

    So 17 years ago, my husband and I set off with our little family in tow, embarking on a short-term assignment in Taiwan. Although without any knowledge of expat life or the Taiwanese culture, we took the chance and decided this would be an exciting little adventure; little did we know it changed the direction of our lives forever.

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