I Was Researching It for a Client. Then I Found the Castle.
Why Puglia stopped me mid-scroll, and the exact process I use to plan a trip that actually delivers.
Photo by Marcel PirnayYou know that feeling when you see a place and your entire body just exhales? That was me and Puglia.
I stumbled onto it while researching a women's retreat in Italy for a client. One minute I was doing my job. The next I was deep in olive groves and whitewashed hilltop towns and renovated castle villas with a gorgeous ocean view backdrop, completely forgetting what I was supposed to be working on.
Puglia is the heel of Italy's boot, and it is the Italy most tourists have not found yet. Masserie, the ancient fortified farmhouses of Puglia, many converted into stunning private villas and boutique hotels, dot the countryside alongside olive groves that have been producing oil for centuries. Villages so different from each other you could spend a week driving between them and never run out of things to discover. Alberobello with its iconic trulli, those cone-shaped stone rooftops that look like something out of a fairy tale.
Ostuni, the White City, perched on a hilltop so blindingly beautiful it looks like it was lifted straight from a Greek island.
Photo by Robert Bye
And then my contact sent over a renovated castle. An actual castle, restored into a private villa with all of its history still intact and all the comfort of a luxury stay layered on top.
I booked a one way flight with points before I could talk myself out of it. Dan is coming. He just does not fully understand how yet.
How I actually plan a trip like this
Whether I am planning for a client or for myself, my process is exactly the same. Here is how it works from start to finish.
Step 1 — Flights First
I start with Google Flights to get a sense of routes, price ranges, and which airlines are operating the best options. I check one-way versus round trip because sometimes the math surprises you. The key is letting the prices and availability dictate the dates rather than the other way around. Flexibility here saves you significantly.
Step 2 — Points Strategy
Once I know the routes I jump to my preferred airline, American Airlines, and pull up the miles calendar with the business class filter on. I try to avoid connections where possible but if I must connect, I look for a city worth stopping in and book a night or two. Why suffer through a long layover when you can turn it into a mini adventure?
Step 3 — The Right Property
Once flights are locked I reach out to my contacts who know my taste. I love rustic with refined. Beautiful bones, gorgeous views, quaint enough for personal service, a top notch concierge who actually knows the area rather than reading off a list, a nice bar and restaurant, unique amenities, and a setting I genuinely want to spend time in. The hotel is never just a place to sleep.
Step 4 — Experiences Worth Showing Up For
With the property confirmed my contacts help narrow down activities. I always start with a food tour to get a real feel for the culture and pick up the best local restaurant recommendations. From there I look for a cooking class, a workshop, a bike or horse tour, something out of the ordinary that most people would not find on their own.
Step 5 — Food Research
I make a short list of non-negotiable restaurants, ideally incredible food with an equally incredible view, and leave the rest open for local recommendations I pick up along the way. Over-booking dinners is the fastest way to kill the spontaneity of a trip.
Step 6 — Check the Weather. Then Shop.
Once everything is locked I check the forecast for the travel window and the outfit planning begins. This is not a small part of the process. This is the reward.
What comes next
This fall I am heading to Puglia with Dan to experience it firsthand. Because the only way I can recommend a destination to my clients, or organize a future group retreat there, with full conviction is to go myself.
I am already thinking about what a small group of women in a Puglia villa could look like. Morning markets, long lunches under olive trees, village hopping, evenings on a terrace with local wine and a view that makes everything feel very far away and very right.
Stay close. More on that after the research trip.
This is exactly the process I use for every client trip I plan. You bring the destination, the dream, or even just a vague feeling of "I need to go somewhere." I handle everything from flights to the final dinner reservation.
