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A Two-Week Southern Italy Itinerary, By Land

You’ve traveled the world and you’ve visited Northern Italy. You’ve hit the Italian “big three,” Venice-Florence-Rome, and you’re ready for something different. You enjoy Italy well enough, but you wouldn’t mind lower prices and smaller crowds. I’ve got two words for you: go south.

Southern Italy offers a chance to explore parts of the country often ignored by tourists, despite being equally beautiful, full of historic and artistic treasures, and brimming with excellent food and wine. Not only that, it manages to offer all this at (often) a fraction of the prices you’ll see in the north. It’s a great option for long-term travelers keen on seeing Europe without spending a fortune.

With only one week, I’d probably just tell you to split your time between Naples and Palermo, basing yourself in those two cities and doing day trips. But to get a real taste of Southern Italy – to vacation where the Italians do, to find out where all those long-lost Italian bargains still lurk – spend a couple of weeks hitting more than just a few highlights. You’ll still barely scratch the surface.

Things to note about this itinerary:

  • It’s not really an itinerary. And nothing’s set in stone, really. Each of these destinations merits more time than you’ll have in two weeks, so do a bit of research and reading to see which ones are more interesting to you. You’ll spend more time at some, and perhaps skip others.
  • The assumption is that you’re starting in Rome and ending in Palermo. If you need a round-trip back to Rome, factor in time for a return flight, train or bus.
  • I’m sticking to places you can reach relatively easily by train or bus, but keep in mind that much of Southern Italy is best visited with your own wheels. Rent a car and you’ll have much more flexibility about where you get to go.


Take the train from Rome to Naples. The high-speed trains get you there in just over an hour, giving you plenty of time to get settled and start exploring the historic center of this frenetic city. Eat pizza. Poke your head into churches. Visit the impressive archaeological museum. Dodge scooters. Note the three straight roads that run through the web-like center (they’re ancient Roman roads), and marvel at how many people have walked down those roads in the past 2,000+ years.

Budget hotels in Naples cost less than similar properties up north, but there’s also an awesome hostel near the water that’s still not far from the historic center. Spend a few days based in Naples and you can take a half-day trip to Pompeii and Herculaneum, then spend another day hopping along the Amalfi Coast. Sun-lovers may want to splurge for one overnight on the coast just to soak up more of the spectacular views.

Puglia and Basilicata

ARC Trulli shops Alberobello

The fastest trains in Italy only go to Bari from Rome, so if you’re traveling from Naples, be prepared to sit back and enjoy the views for the rest of the trip. Naples-Bari can take between 3.5-6 hours, and there’s always a connection involved. Basing yourself in Bari for a couple days gives you a chance to dip your toes in the Adriatic Sea (having done the same in the Tyrrhenian Sea off the Amalfi Coast, you’re already up to two seas on this trip), and there are a couple of excellent day trips you can take from Bari.

Visit Alberobello to see the famous Pugliese “trulli” – white-washed conical buildings with pointed tile roofs. They’re very much in use today, and if you want, you can stay the night in one. Bari-Alberobello is about 1.5 hours on the train.

You can also visit Matera (which is actually in the neighboring Basilicata region) to see the “sassi” – cave residences that date back a couple thousand years. If you want to stay the night in Matera, there are some B&B-type lodging options in the sassi themselves. Bari-Matera is also about 1.5 hours on the train.

>> If you’re all Italy-ed out by this point, note that Bari is a jumping-off point for Croatia by ferry.


Tropea - two week itinerary southern Italy

I’m going to be completely honest here and say that the next major destination on this Southern Italian tour is Sicily. But check out a map of Italy – see all that space between Bari and Sicily? Sure, you could get an inexpensive flight from Bari to Catania, but where’s the slow-travel adventure in that?

Instead, plot a course through Calabria en route to Sicily, taking 3-4 days to work your way to the tip of Italy’s toe, stopping along the way in places like Santa Maria Dell’Isola (pictured), Cosenza, Catanzaro, Tropea, and Reggio Calabria. Incidentally, zig-zagging from side to side of the region means you’ll get to touch yet another big body of water – the Gulf of Taranto. That’s three on this trip, if you’re counting.


You used to be able to take the train from Calabria to the island of Sicily. Yes, the train, and yes, across a body of water. How? The train rolled onto specially-designed ferries with train tracks built into the floor. It took ages longer than a simple ferry crossing, so it was completely impractical, but now the service has been discontinued, and it’s a shame really, as it was an odd experience worth having and now you have to take the train, then the ferry, then the train again.

For the rest of your trip, work your way around the island of Sicily, starting in Catania and ending up in Palermo. Along the way, you can include things like a hike on Europe’s biggest active volcano (Mt. Etna), a visit to one of Italy’s most popular beach resorts (Taormina), and a tour of some of the best-preserved Greek ruins – yes, I said Greek ruins – on earth (at Siracusa and Agrigento). Finish up with a few days in Palermo, eating enough cannoli to last you until your next visit.

Train service on Sicily isn’t as fast or easy as in Northern Italy, but you can get to all of the destinations listed above without renting a car. Plus, circumnavigating Sicily gives you an opportunity to add two more bodies of water to your list – the Straits of Sicilia off the coast of Agrigento, and the Mediterranean Sea.

Meanwhile, on your trip from Sicily to wherever the winds (planes or trains) carry you next, you can figure out how and when you’ll return to Southern Italy to pick up where you left off. Italy warrants more time than any of us will ever have.

About the Author: Jessica Spiegel is a Portland-based writer, Italy expert, and social media enthusiast. She’s pretty sure she could subsist on gelato and pizza alone.

Photo Credits: Arts Illustrated Studios, and Creative Commons License.

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