Planning for Spontaneity: Southern Italy


Pilar Guzmán once wrote, in her editor’s letter for Condé Nast Traveler, “Sometimes a truly memorable trip is the one when the unexpected happens, when you get lost in a good way. But spontaneity takes planning, gathering, and the collective wisdom of travelers you trust.”

This felt so spot-on for me—planning for spontaneity; it’s how I like to approach traveling. In fact, I referenced this a few years back in an effort to solicit your collective wisdom before our trip to Italy, and was overwhelmed with the generous advice! Now, we’ve booked ticket to Rome once more, only with the goal of visiting new-to-us parts of the country, and I’m hoping I might ask for your suggestions once again.

Here’s what we know so far…

We’ll be flying in and out of Rome—with just over two weeks in between—during the second half of June. Though it’s tempting to do exactly as we did on our last trip to Italy (it was perfect!), we want to head south to Puglia, continuing on to Sicily. I don’t think we’ll stop in Naples or on the Amalfi coast this time, as much as I’d love to go back to Positano, so that we can give new places more attention.

Hudson will almost be 7, Skyler close to 4-1/2, which means that we will be keen to get most of our history lessons from the streets and the architecture, as opposed to museums—but I’m considering either a return to Pompeii or a visit to the ruins at Herculaneum or Paestum. In Puglia and Basilicata, we’re excited to see towns like Ostuni, Lecce, Polignano a Mare (above), and Otranto; to duck into the cave dwellings of Matera; and to feast on seafood and burrata. Initially, I thought it would be too much to consider going as far south as Sicily, but I think if we can figure out a one-way car rental or train combo, paired with a flight, it could work out. I’m wondering if we can both see some of the coast along the Ionian Sea as well as make a stop on the Aeolian Islands. Either way, a wonderful odyssey.

What can we actually fit in? Where should we stay? None of these practicalities are worked out yet.

Do you have experience traveling in Southern Italy? What advice would you give us? 

P.S. Our previous travelogues from Italy: Rome, Tuscany, and Positano (above). Also, our first visit to Italy together, pre-kids, and a stay on the island of Sardinia.

[Photos of Polignano a Mare via LondonKirsty; Matera via NY Times; Positano via Hither & Thither]


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