My Trip Coach

In the heart of southern Italy, the hilltop towns of Locorotondo, Alberobello, Ostuni, and Matera showcase the very soul of Puglia. Locorotondo – A whitewashed hilltop village known for its perfectly circular historic center (“the round place”), narrow lanes, and balconies draped with flowers. It’s one of the “Borghi più belli d’Italia” (most beautiful villages of Italy).
Alberobello – Famous for its fairytale-like trulli houses—white conical-roofed dwellings unique to this part of Puglia and a UNESCO World Heritage Site. The town feels like stepping into an open-air museum.
Ostuni – Nicknamed “La Città Bianca” (The White City), Ostuni perches dramatically on a hilltop overlooking olive groves and the Adriatic Sea. Its maze of sun-bleached alleys, baroque churches, and panoramic terraces make it one of Puglia’s most iconic towns. Matera – Straddling the border of Basilicata and Puglia, Matera is famed for its ancient Sassi cave dwellings carved into limestone cliffs. Once considered one of Italy’s poorest areas, it’s now a UNESCO World Heritage Site and a European Capital of Culture, with boutique cave hotels, rock-hewn churches, and cinematic views at every turn.

We began our exploration of Puglia at Masseria Le Torre, tucked among centuries-old olive groves, and immediately felt the slow rhythm of Puglia wrap around us. The whitewashed stone buildings, once a working farmhouse, are now blend rustic charm with understated luxury. Mornings began with breakfast under a pergola scented with jasmine; afternoons were for lounging by the serene pool. Evenings brought candlelit dinners of fresh, local ingredients and, of course, wine. The owners, Mimi and Silvana, made every guest feel like precious friends and made our stay feel both authentic and indulgent, a perfect escape into the heart of Puglia.

A magical trip draws to a close. We said farewell to the Dolomites on the most picturesque ride of my life — skimming the mountainsides and down along the sparkling coast of Lake Garda. We wandered the charming streets of Riva before boating across the lake to Vecchia Malcesine for a Michelin-star feast.

Our local guides, Ricardo and Alberto, thought of every detail: unique nights in agriturismos, five-star hotels, and a Relais & Châteaux property. We biked alongside a chef who later prepared an unforgettable dinner, rode electric mountain bikes to a hidden waterfall, hiked, pedaled through vineyards, tasted exquisite local wines, and explored Lake Garda by boat.

I can’t imagine experiencing this breathtaking region any other way. Our new friends made the trip special…especially the All You Can Eat bike club, with an average age of 78(inspirational), my uphill biker pal Penny and my favorite biker of all time David! Huge thanks to DuVine and their team for crafting such a perfect trip!