The Exact Framework I Used To Design My Best Client Trips

Back when I started selling travel, I built package deals through wholesaler sites and promoted them on Facebook. I didn’t have any clients yet, and I was doing everything to educate people on what I could do for them. They were great for getting people interested. What they never did was make anyone feel seen, because every trip is a fingerprint, unique to the person taking it, and a package is built for nobody in particular.

The same lesson arrived from the other direction, too. The request I heard more than any other in my years as a travel advisor started the same way every time: “My friend went to Italy and had the best time. I want to do exactly what they did.” And I understood it. The friend came home glowing, the photos were gorgeous, the restaurant list was already typed up. But the moment I asked a few questions about their interests, their pace, and their family, the friend’s itinerary fell apart in their hands. It was built for someone else. I am sure everyone who posts their trip on Pinterest had a great time. They are not you, and their itinerary was never yours.

That’s the first quiet truth underneath disappointing Italy trips. The second is where they break: at the seams. When friends come home from Italy underwhelmed, the complaints are almost never about the Colosseum. The Airbnb sat in the wrong neighborhood, or had no air conditioning in July. They felt scrambled hauling luggage onto a train, or flustered and frustrated between the rental car counter and every parking garage after it. Or they stayed somewhere wonderful on the first leg, let it set their expectations, and then finished in a subpar property in the destination they’d saved for last, wrong location or missing amenities, and the place they were most excited about got tarnished by the room they slept in. The trip breaks between the highlights, and most of those breaks happen in transit.

But one thing I absolutely nailed, even in the package era: I approached every single trip with the same formula in place. Every trip came out different, and every one was built the same way, and that’s what this article is.

When I look back at the client trips I’m still proud of, the ones where people came home and sent the long thank-you email, they had wildly different destinations, budgets, and travelers, and the same skeleton underneath every one. The trips that work aren’t the ones with the best ideas in them. They’re the ones built in the right order, because the order is what protects the seams. The feeling comes before the region. The math comes before the map. The transportation comes before the hotels. Get the order wrong and you end up decorating a broken frame.

So this week I’m handing over the whole frame. Two weeks ago I gave you the eleven checks I run on a finished first-timer itinerary, and a few of these rules will rhyme with those on purpose, because the audit and the blueprint should agree with each other. What follows is the exact framework, ten rules in the order I applied them to every client trip I’d still put my name on, from the blank page forward.

Behind the paywall today:

The framework itself, all ten rules in the sequence I applied them, so your next itinerary builds in the right direction from the first decision.

The first-leg rule that decides where a trip opens, and why I put the most relaxing destination at the start when everyone else saves it for the finale.

The permission slip, the rule about saying no that protects your reputation more than any booking you’ll ever make.

If you build Italy trips, this is the framework that sits underneath everything else I’ve written here. It’s $8 a month, or $80 for the year, and the annual is less than one client gift. Come on in.