House Hunting in Puglia: A Scouting Trip with Backup on Speed Dial
- Caesar Sedek
- Aug 23
- 4 min read
Updated: Sep 29
When John and Linda (not their real names, but close enough) reached out about retiring in Italy, they had their sights set on Puglia. They weren’t alone—Puglia has been drawing retirees with its olive groves, affordable properties, and piazzas that still feel lived in rather than staged for tourists.
But wanting to “retire in Puglia” is a bit like saying you want to retire in California—too broad. Each town has its own rhythm, quirks, and realities. So before they packed their bags, I helped them frame their priorities and then built a shortlist of options:
Ceglie Messapica for its food culture and authentic year-round life.
Ostuni for the dramatic views and proximity to the Adriatic.
Martina Franca for its Baroque beauty and slightly larger infrastructure.
Cisternino for a quieter, small-town feel with a strong community.
The list gave them perspective, but it was Ceglie that stood out as the strongest contender based on their criteria: walkability, a lively piazza in all seasons, access to healthcare within 30 minutes, and real estate that didn’t require a billionaire’s budget.
Planning the Scouting Trip
Together, we built a custom itinerary. Not just property showings, but neighborhood walks, time in the piazza, grocery store visits, and chats with locals. Every day had a balance: exploration, reflection, and a little breathing room to let impressions settle.
My role? Not sitting at the café table with them in Puglia, but just a call or message away. I was their remote sounding board—fact-checking an agent’s pitch, explaining lease types (yes, 4+4 versus transitorio matters), and reminding them to pay attention not just to the house but to the town’s heartbeat.
On the Ground in Ceglie Messapica
Ceglie is the kind of place that doesn’t overwhelm you at first glance—it seeps in. The evenings in the piazza, with kids running across cobblestones and retirees playing cards at café tables, felt like the life they’d imagined. Restaurants buzzed, but with locals, not just summer tourists. By day three, the barista already remembered their order.
Of course, not everything was picture-perfect. Some homes looked charming in photos but revealed plumbing quirks or questionable renovations. That’s when the WhatsApps came flying in: “Should we even consider a trullo this old?” “How do deposits work here?” “Who’s responsible for septic upkeep?”
I was there to provide context and clarity—without sugarcoating. Better to be a little blunt now than surprised later.
The Bigger Picture
While Ceglie made the strongest case, the couple came home with a layered understanding. They saw what worked—and what didn’t—in real time. They confirmed that Ceglie might be “the one,” but they also knew that if things didn’t align perfectly there, Ostuni, Martina Franca, or Cisternino could step in as worthy Plan Bs.
Meanwhile, as they explored Puglia, I was also planning another scouting trip for a different couple bound for Liguria. Different coast, different priorities, but the same guiding principle: no two scouting trips are alike, and the process has to be as personal as the dream.
Why It Matters
A scouting trip isn’t a vacation. It’s an audition for your future life. That means looking past the Instagram views and asking the harder questions:
Does the piazza feel alive in February?
Is healthcare accessible without an odyssey?
Will the internet actually hold up on a Zoom call with your grandkids?
That’s why I support clients before, during, and after their trips. Sometimes it’s itinerary design. Sometimes it’s late-night texts from Italy about a too-good-to-be-true property. Sometimes it’s just reminding them that feeling nervous is part of the process—and that clarity always wins over speed.
John and Linda left Italy without buying anything. And that was a success. They returned with confidence that Ceglie was right for them, a clear idea of what their future home should look like, and peace of mind that they had options if things didn’t pan out.
Exploring the Local Culture
Understanding the local culture is crucial when considering retirement in Italy. Each town has its unique traditions, festivals, and culinary delights. For instance, Ceglie Messapica is famous for its rich culinary heritage. The local cuisine is a blend of flavors that reflect the region's history and agricultural bounty.
Culinary Delights
The food scene in Puglia is vibrant. From fresh pasta to locally sourced vegetables, the flavors are authentic and satisfying. John and Linda enjoyed exploring local markets, sampling fresh produce, and indulging in traditional dishes. They learned to appreciate the importance of food in Italian culture.
Festivals and Events
Puglia is known for its lively festivals. These events bring communities together and offer a glimpse into local traditions. Whether it’s a summer festival celebrating the harvest or a winter event showcasing local crafts, there’s always something happening.
Community Engagement
Engaging with the community is vital for a fulfilling retirement. John and Linda found that participating in local events helped them connect with residents. They attended cooking classes, art workshops, and even joined a local book club. These experiences enriched their understanding of life in Puglia.
Final Thoughts
Retiring in Italy is a dream for many, but it requires careful planning and consideration. John and Linda's journey illustrates the importance of thorough research and personal exploration. They learned that the right place is not just about beautiful homes but also about community, culture, and lifestyle.
👉 If you’re considering retiring in Italy, don’t leave it to chance. I’ll help you design a scouting trip that goes beyond brochures and Instagram—custom itineraries, vetted contacts, and ongoing support while you’re on the ground.
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