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La Storia by Jennifer Jacob · Jul 14, 2026

The 10 Questions I’d Ask Every Lake Como Client

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Jennifer Jacob · La Storia by Jennifer Jacob

The trip that finally taught me Lake Como, I brought my whole company with me. Back when I owned my travel agency, we held our annual retreat in Bellagio, and my days split cleanly in two. Mornings I spent scouting properties and trading ideas in meeting rooms with the lake filling every window. Afternoons melted into prosecco on a terrace across the water, and the evenings ended with a spritz at another grand old hotel while the light went down over the lake. I had been planning luxury trips for years by then, and I thought I knew this place. Como kept surprising me anyway, because it is not one destination you can learn in a weekend. It is a dozen different towns wrapped around a lake, and the one you land in decides the whole trip.

Most people say Lake Como the way they say Positano or Santorini, as if it were a single place with a single feeling. On the ground it is a Y-shaped lake with towns strung all along its arms, each with its own personality, its own pace, and its own answer to how a person will spend their days. Bellagio hums with boutiques and foot traffic. Varenna slows you down with a quiet promenade. A remote villa hotel wraps you in gardens and a boat ride to dinner. Where a client lands changes how much of the lake they see, how much they move, and whether the week feels like a rest or a puzzle. Almost none of that shows up in a photo of blue water and a bowl of pasta.

This is the next installment. Every one 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, and Venice came first. Lake Como gets ten, and here almost every one circles a single decision, matching a client to the right stretch of shoreline before they fall for a picture and book the wrong one.

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

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

The ten cover: whether they want a remote resort or a town at their doorstep, whether the room needs a lake view, whether they need a pool, whether they need a spa, what pace they are hoping for, what they want to do and whether Switzerland factors in, how they feel about skipping the car for boats and a driver, how much they want to eat around versus dine at the hotel, when they are going, and the Como they are picturing.

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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