My Best, Breezy Southern Italy Itinerary

Ciao, friends! I already took you with me on a whirlwind 2-day trip to Rome, but this time around  I figured I’d share a longer itinerary, for when you want to explore Italy’s southern cities. There’s so much more to this country than the Colosseum! 

Italy is one of the most romantic countries in Europe, thanks to stylish spots like Venice, Florence, and of course Rome, but don’t forget about everything to see down south! While Northern Italy may be known for its cosmopolitan, classic vibe, Southern Italy brings you closer to the sea with its picturesque, whitewashed towns. With delicious seafood everywhere you turn, it’s well worth a longer stay!

Day 1-3: Hanging In Naples and Sorrento

Sorrento in southern italy

Odds are, you’re starting off by flying into Rome. Flights into the capital city are remarkably cheap, especially from other European capitals, so if you’d like to start off by exploring where you land, then by all means, go ahead! I’ve already got a city guide all typed up for you, so feel free to add a couple of days in order to do as the Romans do.

Otherwise, go ahead and hop on a train to Naples, or fly straight there if that’s in your budget. Now, everybody has different priorities while they travel, so your choice here is to base your next couple days in Naples or in nearby, smaller Sorrento. Going to Naples will give you a bigger city vibe, with a fair share of grit as well as delicious food and historical buildings. You can get a taste of classic Neapolitan pizza, visit the National Archeological Museum and Museo Capodimonte, and so much more.

Choosing Sorrento offers a smaller and simpler city experience, with easy ferries to Capri or Ischia Island. You can take day trips to Naples so you don’t miss out on the museums and pizza, then come back to a breezy cliffside city.

You really can’t go wrong with either! Choose the spot where you’ll be most comfortable for a couple days of initial jet lag and day trips, in addition to exploring the cities themselves.

Now, once you’ve settled in, here’s where you can explore before moving on to our next spot: Pompeii and the ruins of this historically thriving town, swept under the eruption of Mt. Vesuvius all the way back in 79 AD. Go on your own self-guided tour through the city, or hire a tour guide for extra historical context. You can even hike Mount Vesuvius itself, another UNESCO world heritage site, for a touch of nature with your trip back in time.

Closer to Sorrento, Positano is another good choice for a day trip, as it can be expensive and touristy, making it less pleasant for a longer stay. Hang out in this gorgeous city along the famed Amalfi Coast, window shop at the posh stores, and relax on a glittering beach.

Days 4-5: Exploring Matera

matera in southern italy

After a couple of days near Naples, it’s time to move on! Just a 2-3 hour drive away is the city of Matera, in the Basilicata region. This is the midpoint between our initial Napoli / Amalfi Coast exploration and our final destination, Puglia. Note to those who decided to rent a car for a full road trip: Matera roads are only open to residents, so check with your hotel or Airbnb host for places to park your car while you explore the city!

Matera is an ancient cave city, with stone houses and grottos piled together over rolling hills. The main districts of the old town are: Sasso Barisano and Sasso Caveoso. The first, Sasso Barisano, is a lively area full of narrow streets, a cathedral with a panoramic view, a ravine studded with paleolithic caves, and Palombaro Lungo, a palatial underground cistern. Don’t forget to take pictures!

After you’ve fully explored Sasso Barisano and had a bite to eat, take your second day to nose around Sasso Caveoso, the far less developed area of ancient Matera. Here, you’ll find perfectly preserved cave dwellings, that Matera’s residents continued to live in all the way to the 1950s. You can take tours of this sasso, check into a hotel or Airbnb full of cave rooms, and have dinner in atmospheric restaurants dug into the cliff walls. When the sun goes down, spend a bit of time at the Piazza Pascoli for an overhead view of the city lit up in streetlights!

Days 67: Finishing Up In Puglia

puglia in southern italy

After a couple days in Matera, we’re going to truck on over to Puglia, the last region on our trip—unless you’d like to stick around longer! I’ll give you some tips for extra stops at the end of this article.

About an hour’s drive from Matera is Alberobello, UNESCO World Heritage Site and home to conical trulli houses. These whitewashed huts date all the way back to the 1500’s, when local feudal rulers forced their peasants to build these dwellings without mortar, so they could be torn down quickly upon visits from the King. Why? Tax evasion, of course!

Incredibly, many of these temporary homes still exist today, peppered throughout Alberobello. At this point, most of the city’s residents don’t live in the trulli, but they do serve as restaurants, shops, and even Airbnb’s for rent. Meander about all by yourself, or take a guided walking tour. Visit the Museo del Territorio for a better idea of this quaint town’s history, the Parrocchia Sant’Antonio di Padova for a simple trullo church (the only one in the world!), the less commercialized Rione Aia Piccola district, and more.

Of course, Alborello can be full of tourists, meaning the small town is crowded in the spring and early summer. Time this itinerary for the off-season if you’d like some extra peace and quiet!

After a day and night in Alberobello, your last step is to make your way to Bari and fly away via the Bari International Airport. The great part about this last step is that nearly the entire drive takes place along the coast, meaning you’ll pass through such picturesque towns as Monopoli, Pogliano e Mare, and others. If you drive straight on, it’ll only take you about an hour to arrive in Bari. 

Still, I’d highly recommend you stop and take some extra time in these gorgeous beach towns with stunning cliff sides, fresh seafood, boat trips, and white-washed houses!

Got Some Extra Time? 

If you’re working with one week of vacation time, this itinerary will get you everywhere you want to go! However, if you’re looking to tack on a few extra days, here’s my recommendation.

Swing back to the island of Sicily via train, plane, or another long road trip! Enjoy sightseeing around Syracuse and Palermo, swimming in the Mediterranean Sea, admiring Greek and Roman architecture, and even touring the filming locations for the Godfather. I love this island, so it’s just a matter of time until I write a whole post devoted to it one day

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