Trullo Agathea
The Traditional Trullo: Trullo Agathea
Amid the low hills and ancient olive groves of Puglia’s Valle d’Itria is a unique architectural structure found nowhere else in the country: the trullo. With whitewashed stone dwalls and distinctive cone-shaped roofs made from stacked limestone, trulli (plural of trullo) are little Puglian marvels rooted in centuries of rural history. Orginally designed to be easily dismantled and reassembled as a means to avoid property taxes, trulli were typically built by farmers and laborers with just stones and no mortor. The unique design had other benifits too, as trulli are ingeniously suited to the hot southern climate, keeping inhabitants cool all summer long.
Over time, the quirky appearance and brilliant functionality made trulli synonymous with the Puglia’s identity, especially around the UNESCO-listed town of Alberobello. Staying in a trullo isn’t just about aesthetics though, it’s about experiencing the region in an only-in-Puglia fashion. Trullo Agathea, only available through The Thinking Traveller, offers one of the finest interpretations of this ancient building style.
Located just outside Cisternino, one of Puglia’s most atmospheric hill towns known for its excellent butchers, Trullo Agathea blends historical charm and modern comfort. Designed to sleep up to four guests in two bedrooms, each with their own en suite bathroom, the villa unfolds across a small cluster of conical-roofed buildings that have been carefully restored to retain their original features. Thick stone walls provide natural insulation, keeping interiors cool even in high summer, while vaulted ceilings and softly curved walls lend a sense of cocooned tranquility to each room. The decor is rustic with wood furniture, local ceramics and natural linens in a palette of whites, creams and olive greens.
What makes Trullo Agathea particularly special is the surrounding landscape. The home is nestled within a well-tended olive grove, thriving with ancient trees, Mediterranean herbs, and even a few fruit trees. A pergola-shaded dining area makes the most of the peaceful views and is ideal for long, lazy lunches. The private pool is perfectly proportioned and shaded terraces invite afternoon snoozes or sunset spritzes.
Location-wise, Trullo Agathea is ideal for exploring the region: It’s just outside of Cisternino, and the towns of Ostuni, Martina Franca, and Locorotondo are all within easy reach, while beaches along the Adriatic coast are also within reach.
Trullo Agathea by The Thinking Traveller sleeps up to 4 and starts at $654 per night ($4,583 per week).
Masseria La Residenza
The Masseria Masterpiece: Masseria La Residenza
Like a trullo, a masseria (plural masserie) is a fortified farmhouse traditionally found in Puglia’s countryside. Orginally built to serve as a rural home and community hub for landowners, workers and even livestock, most masserie in Puglia date back to the 16th through 19th centuries. Today, many have been beautifully restored into stylish retreats—both as hotels and private homes.
Masseria La Residenza was built in the early 1800s, though it was recently refurbished to include all the creature comforts needed. Set among almond and olive groves just outside the town of Fasano, the villa inclues a social-media-ready L-shaped swimming pool; manicured gardens; and multiple al fresco dining spots under pergolas and on terraces. There’s also a fantastic outdoor gym. With five beautifully appointed suites dressed with chandeliers, baroque antiques and luxurious headboards, expect high-end vibes and no shortage of comfort.
Masseria La Residenza by A&K Villas sleeps up to 10 and starts at $21,967 per week ($3,138 per night).
Villa Monte Caliolo
A Modern Marvel: Villa Monte Caliolo
Nestled in the heart of Valle d’Itria and a short drive from Carovigno, Ostuni and the Costa Merlata, Villa Monte Caliolo is a very modern take on a masseria. It comfortably sleeps eight across two buildings with four bedrooms (two en‑suite and two sharing a spacious shower room).
Interiors are minimalist and elegant, with locally hewn furniture and natural materials. Outside, the infinity pool is the star of the show, overlooking olive groves and glimpses of the blue Adriatic. A team is available to organize excursions, meals or wellness services tailored to your tastes.
Villa Monte Caliolo by The Luxury Travel Book sleeps up to 8 and starts at $743 per night ($5,201 per week).
Casino Doxi Stracca
An Old‑World Wonder: Casino Doxi Stracca
It doesn’t get more old-world glamorous than Casino Doxi Stracca. An aristocratic 18th-century villa set within five acres of landscaped gardens, groves and vineyards, Casino Doxi Stracca is steeped in history and undeniably luxurious after a sensitive recent restoration. Original architectural features include a chapel, frescoed ceilings and grand reception rooms, but it’s the unbelievable 59-foot-long pool that will have sunworshippers besotted.
In addition to the Instagram-ready pool, there’s also a plunge pool and plenty of shaded areas. It accommodates up to 14 guests in seven bedrooms, so there’s no shortage of space and privacy, especially for multigenerational gatherings or for groups of friends. There’s a well-equipped kitchen for self-catering, but the concierge services can also arrange for private chefs, cooking classes and local wine tastings.
Casino Doxi Stracca by The Thinking Traveller sleeps up to 14 and starts at $10,413 ($1,487 per night). (Note: Casino Doxi Stracca also has a reduced price avaible upon request, during the shoulder season, for groups up to 8, needing only 4 bedrooms.)
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