Every Question I Wish I'd Asked My Amalfi Coast Clients

Years ago I built an itinerary for a client that looked, on paper, like a smart Amalfi Coast trip. Five nights in Sorrento as the comfortable, better-value base, a day trip to Capri so she could see the island without paying to sleep there, and three nights in Positano at the end to splurge. It was the kind of itinerary I would have been proud to show anyone. She came home and told me Sorrento felt too long, that she had wanted more to do. With a pool and a view like the one she had, I would happily sit still for five days and call it the best week of my life, and I understood her completely anyway. None of it was a mistake. I had simply never asked her the one thing that would have changed the whole trip, which is how much she needed to be moving to feel like she was on vacation.

That is the thing about the coast. It can be the most restful week of someone’s life or the most restless, and the deciding factor is rarely the hotel. It is the person. One traveler unwinds on a terrace with a book and a spritz for days and never once feels stuck. Another needs a town underfoot, a boat to catch, a reason to get dressed. Both of those are wonderful trips. They are just not the same trip, and the coast will happily hand a client the wrong one if nobody asks first.

The questions that get you to the right one are not about budget or logistics. You have those handled. They are about how this particular person experiences a place, and on the coast, where the towns are so different from one another, the cost of guessing is high.

This is the first of something I have wanted to build for a while. Every installment, I am handing you ten high-impact questions for one Italian destination, the exact ones I would ask before I booked a single night, each with a short note on what the answer is telling you. They are written to be copied straight onto your intake form. Lake Como, Venice, Florence, Rome, and Puglia are all coming. I am starting on the coast because it is where the gap between what a client pictures and what they book is the widest.

People also tend to lump the whole region together. Sorrento and Capri both get called the Amalfi Coast, and technically neither one is. I break down exactly what is and is not the Amalfi Coast here: What “Is” And What “Is Not” The Amalfi Coast. Because clients group them anyway, this first set covers Sorrento and the coast towns, and I am adding three bonus questions for Capri at the end.

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

The ten questions I would ask every Amalfi Coast client, organized so you can copy them straight onto your own intake form, each with a short note on what the answer tells you. Then three bonus questions for Capri.

The ten cover: what enjoying themselves looks like and how much structure they want, what they picture when they say Amalfi Coast, how much steep walking they can take and how flexible they are on the town, motion and seasickness, what five-star versus value means to them, what they picture when they say beach, how much the food matters, whether they want the buzz or to feel removed, how important getting in the water is and what season fits, and where the coast should fall in the larger trip.

Plus three bonus questions for Capri, and the script for the one moment you will need it, when a client brings up renting an Airbnb on the coast.

This is what every installment in the series will give you: ten questions, ready to use before your next client call.

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.