Places to Stay

My Favorite Airbnb: A Cozy Trullo Among the Olive Groves in Puglia

For an authentic Puglian stay, nothing beats bedding down in one of the locale's iconic conical homes.
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April is my favorite month, and this year we had long, sunlit days in Italy with temperatures that almost made it feel like summer. When a two-day gap opened up in my calendar, heading south felt inevitable. As much as I love the Amalfi Coast and Sicily, they’re not the easiest for a fleeting escape, so I turned to Puglia. It’s the perfect balance between countryside and seaside—especially the area around Ostuni, where you have endless stretches of olive groves, and the coastline of Monopoli, with Savelletri nearby for an impromptu swim.

I opened Airbnb in search of a villa that felt rooted in local architecture yet offered the ease of a private home, and came across Masseria Silentio. I was immediately drawn to the little cluster of trulli they have on-site, as there is nothing more emblematic of Puglia than those little cone-shaped houses. So I went ahead and booked it, took an easy train from Florence to Brindisi, and within a 30-minute drive from Brindisi, I was at the property.

A canopy over the beds adds Italian flair

Lucrezia Worthington

Views out to the olive groves

Lucrezia Worthington

The moment I arrived, driving through the gate, I realized that I could easily spend an entire week here, disconnecting from reality. The only sounds were the birds, rustling leaves in the soft breeze, and insects buzzing around from flower to flower. I also had another thought: I need to come back in September when the fig trees will be fruiting, and I can indulge in prosciutto e fichi at every meal.

The sun going down over the trulli

Lucrezia Worthington

A perfect setting for cake

Lucrezia Worthington

Set between Ostuni and Ceglie Messapica and surrounded by silvery olive groves, the Masseria Silentio is a former Masseriola, or rural farmhouse, dating back to the 18th century. When the current owners first purchased the property, they added a few touches to the main villa, including a charming little conservatory with a dining table where the light filters in from sunrise to sunset.

Inside, there’s a living room, kitchen, two bedrooms, and two bathrooms, while outside, a stone staircase leads up to the rooftop for views that stretch across the valley (highly suggest popping up at dawn or golden hour). My favorite bedroom is the one towards the back of the property, as even though the other has an en suite, this one has a door that leads directly to the garden. It’s also cozy, with blue drapes hanging over the bed, and had enough storage space to hang up my clothes.

The pool, set in idyllic surroundings

Lucrezia Worthington

Simplicity is a common theme, and much of the furniture is sourced from antique markets or inherited from the owner's family. The layout follows that of a traditional masseria, with the main villa flanked by Trullo Castelluccio, a five-coned trullo where the farmers used to live. This space houses a stone alcove bed, additional sleeping space, a generous kitchen, and a beautiful bathroom of stone and cocciopesto.

I barely left the villa, but dragged myself away to visit Ostuni—a must-visit if you’re a first timer in Puglia. For the beach, head out to Monopoli or Savelletri, where you can find a handful of beach clubs, sandy bays, or rocky inlets for a swim and tanning session. Instead of lying in the sand, I spent my weekend dipping in and out of the swimming pool, which sits between the two buildings, framed by olive trees, rosemary bushes, and wild herbs, while beyond, a two-and-a-half-acre garden unfolds with lemon, fig, and almond trees.

Lunchtime with a view

Lucrezia Worthington

The interiors are authentically Puglian

Lucrezia Worthington

There’s also an outdoor kitchen with a wood-fired oven, perfect for a pizza night if cooking is your love language. I didn’t use it this time (certainly a great excuse to come back), but I did have a sublime aperitivo at sundown. We sat at the little table by the trulli, popped open a bottle of prosecco, and nibbled on taralli, olives, and mozzarella. This is my favorite time of day, and the memory of spending it in this very spot will live with me forever.

This article was originally published on Condé Nast Traveller.