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Road Tripping Italy’s Stiletto

Italy's  "stiletto heel" is home to some of its most beautiful sightsItaly’s shape is often referred to as a boot.


The heel of that boot bears the name Puglia, where the Adriatic and Ionian Seas shake hands.


It is a region most don’t visit because it is all the way down there. Puglia might be best explored by car for Italy adorns a big stiletto heel.


A road trip through some of Puglia’s small towns makes for an Italian escape away from the traditional itineraries of Tuscany and Rome.



First Stop: Castel del Monte—In the middle of nowhere it would seem, 29 kilometers south of Barletta, you can begin your trip through Puglia at Castel del Monte. Best reached by a car, the UNESCO approved structure raises up above the terrain of empty countryside, olive groves and sun scorched plains in summer. What makes Castel del Monte unique is its strange octagonal shape. Some believe Frederick II had the castle constructed in 1240 merely to showcase his power. Others think the castle to be a mathematical offering to the gods. The masterpiece of medieval architecture holds no fancy decorations or mosaics for it was looted after the king’s death.

Second Stop: Alberobello—The town of Alberobello holds the iconic structures of Puglia, trulli. The Zona dei Trulli sits on the western hill of Alberobello and has been deemed a UNESCO World Heritage site. 1,500 trulli stand here, dry stone buildings made of limestone from the 14th century. The conical roofs make the structures look more like pointy witch hats than Italian architectural masterpieces. No one really knows why these structures came to be. One theory is that they were built to avoid heavy taxes for they could be taken down easily. Others believe they were merely low maintenance homes for poor peasants. Despite the tourists, Alberobello is worth a look for the trulli or just to sit in one of the town’s squares sipping on a cocktail in the evening hours.

Third Stop: Locorotondo—White sheets wave in the wind on the blindingly white buildings of Locorotondo. On your way down the heel from Alberobello, drivers can cruise to what the town calls one of the “borghi piú belli d’Italia”, otherwise the most beautiful village in Italy. It is easy to see why Locorotondo thinks so highly of itself as you wander the streets of the centro storico. You can play I-Spy a trulli from the city as it perches up high on a hill. Wander those streets in summer and you will find locals dressed in that same bright white as pops of red flowers add a contrast to the monochromatic vision.

Fourth Stop: Otranto—From Locorotondo head deeper into Italy’s heel towards Otranto. What was once Italy’s main port to the Orient for 1,000 years not only lends history lessons but also overwhelming perspective. As Otranto gazes out on the Adriatic Sea, let history do the talking. Among the notable events in this port city, St. Peter supposedly held the first Western mass here. The Sack of Otranto took place on these grounds in 1480, when 18,000 Turks killed 800 Christians. The Greek looking buildings decorate in sapphire blue shutters. The Adriatic takes on a mint color so refreshing you might want to hop in for a taste.

Final Stop: Santa Maria di Leuca—Continue down from Otranto, past secret swimming coves and you will find yourself at the end of the world it would seem, or at least Italy’s world. Santa Maria di Leuca marks the meeting point of the Adriatic Sea and Ionian Sea, in other words, the lowest point of the Italian stiletto. While there isn’t really anything at this point of glory and amazement, it is still something for you have reached the very tip of Italy.

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