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La Storia by Jennifer Jacob · Jul 21, 2026

The 10 Questions I'd Ask Every Puglia Client

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Jennifer Jacob · La Storia by Jennifer Jacob

I have never been to Puglia. I want to say that out loud before I say anything else, because I have planned it, priced it, argued with clients about the rental car, and heard how it went when they came home. Here is the reason I have not made it there. Puglia sits far enough from everything else in Italy that it demands a trip of its own, a dedicated stretch of days, its own flights, its own commitment, and I have not been able to make that happen yet. Every year I look at it and think this is the year. Every year the calendar wins and I go somewhere that will share a trip with three other places. That is the confession, and it is also the whole point of this piece, because the reason I keep not going is the same reason your client’s Puglia will fall apart if you plan it like the rest of Italy.

Puglia has been the up-and-coming region for a while now, and it stays up-and-coming for one reason. It is hard to reach. There is no direct flight from the States, the towns sit far apart from each other, and it sits a long way from everywhere your client already wants to go. So it never quite tips over into the mainstream, which is part of what makes it wonderful and all of what makes it tricky.

Here is the line I would put on the wall. Puglia is not a place you add to a trip. It is the trip. It asks for a dedicated stretch of days, its own set of flights, and a client who wants olive groves and white towns and long roads between them more than they want to check another region off a list. The people who give it that come home talking about it for years. The ones who try to bolt it onto a week in Rome come home wondering what everyone was going on about.

This is the next installment. Everyone hands you the high-impact questions for a single Italian destination, the exact ones I would ask before I planned a thing, each with a note on what the answer is telling you, all built to copy straight onto your intake form. The coast, Rome, Venice, and Lake Como came first. Puglia is the first one where the logistics decide whether the trip should happen at all, which is why almost every question here is quietly asking the same thing. Is this client ready to commit to it?

Here is exactly what is on the other side of this:

The ten questions I would ask before I planned a day in Puglia, organized to lift straight onto your intake form, each with a note on what the answer tells you.

The ten cover: what is drawing them and what they are picturing, whether Puglia is the whole trip or a piece of a bigger one, which airport they should fly into and out of, how they feel about driving themselves or paying for a driver every day, whether they want a town at their door or a masseria in the middle of nowhere, whether their days belong at the beach or in the countryside, how much of the region they want to see and how many bases that takes, how they want to eat when dinner is mostly at the property, when they are going, and the pace they are expecting once they learn that nothing here is next door.

A paid subscription to La Storia is $8 a month, or $80 for the year, which comes out to less than one client gift. The annual is the one I would choose.

Read the original on lastoria.substack.com

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