Imagine this: stone-walled lanes, endless vegetable gardens, infinite groves of olive trees (some known to be thousands of years old)––filling the horizon and reaching out to the subtle waves of the sparkling Adriatic Sea. While we weave our ways in and out of tiny white-washed villages, we pause along the way to sit, talk, nibble Southern delights and sip wine with some of Puglia’s most prestigious wine makers. This is our Journey Through Italy’s  Puglia: The Heel of the Boot

This past Fall, we ran a relaxed, highly cultural version of our Puglia itinerary. It was a modified version of our usual trip in this glorious region–sans hiking–but equally exciting and chock full of rich, fascinating daily experiences.

The first part of this unique trip – with a focus on the cities of Lecce and Otranto (and areas in between) immediately inspired appreciation and delightful curiosity within our group.

As we tooled around the tiny, narrow, magical lanes of Puglia, we were surrounded by groves of gigantic, twisted, gnarly, olive trees, vastly different than those they’d seen on past visits to Tuscany. The countryside has large swaths of agriculture with tilled fields of rich, delicious red soil. After a welcoming, historical walk through the city of Lecce with our passionate local guide we spent hours in the kitchen with Gianna, a local chef and sommelier where we not only learned the ins and outs of how to prepare local dishes, but we learned many tricks, short-cuts, and pure kitchen magic from this lovely maestra.


Gianna working her magic in the kitchen during our cooking lesson

Next we explored the colorful fish market and cliff walks around Gallipoli. We stopped at wineries where we tasted and adored incredible, high quality wines including ones made with ancient, recently re-introduced grape varieties (Susumaniello, Zagarese Primitivo and Aglianico Hellenic).

Fresh fish at the Gallipoli market

Fishermen cleaning and untangling their nets after a morning at sea 

Our visits also included an exploration of the work of local artisans in the town of Maglie:  

a visit with a family of stonemasons (who work with the local Lecce stone); three generations of  hat makers whose dedicated work and passion is sewing Southern Italian beret style caps, and lastly a delectable visit with a famous local chocolatier. 


We had the honor of visiting the beautiful cantina and part of the private family villa of the Duke Carlo Guarini. Afterwards we sat and enjoyed a multi-course meal with him in the villa’s lemon-adorned garden. Unforgettable.

With our joyful group happily enthralled with Puglia, the landscapes, history and the beautiful local people, we transferred further north from the southern tip of Italy’s “heel.” This area is referred to as the Altopiano delle Murge or the Murge plateau.

After settling into our luxurious masseria (a fortified farmhouse or country house on an estate) we spent the following days touring, eating, tasting wines and exploring the white-washed, quintessential Pugliese villages of Locorotondo, Ostuni, Monopoli and of course, the fantastical village of Alberobello, famous for its Trulli, unique dry stone huts with conical shaped roofs, seen only in this area.

Lovely set of Trulli homes set against the blue sky of Puglia

At week’s end, we bid our group a special farewell on our last evening in the port city of Brindisi (the word brindisi in Italian actually means “to toast in celebration”). It was a perfect ending to a highly educational, culturally focused one-of-a-kind Journey Through Italy adventure, in one of our favorite Southern Italian destinations. Viva la Puglia!