HOW IT WORKS

Start with the trip. The itinerary comes second.

Before I recommend a hotel, a route, a tour, or the restaurant you absolutely have to try, I want to understand what the trip is supposed to do for you: what matters, what doesn’t, what would make it feel successful, and what constraints we need to respect. Then we build outward from there.

A grand historic library with floor-to-ceiling bookshelves beneath a long arched wooden ceiling.

I ask “why?” before I ask “which hotel?”

A honeymoon, a family homecoming, a week to decompress, and a milestone birthday can all happen in the same destination and still need completely different trips. The useful starting point is not a list of things to book. It’s understanding what you’re actually trying to accomplish.

That habit comes directly from my strategic communication background: objective first, tactics flow from there. Once we know the objective and parameters, we have something useful to calibrate against. Is the itinerary getting too ambitious? Is the splurge worth it? Do you want another guided day or room to wander? Is the default destination actually the right one?

The payoff is coherence.

Hotels, pacing, transportation, experiences, budget, and free time stop being separate decisions and start working together as one trip.

ONE TRIP, NOT A PILE OF RESERVATIONS

For Briggs and Sonja’s anniversary road trip through Sicily, the work wasn’t simply finding good hotels and tours. It was designing the route so the driving days, ferries, parking, places to linger, splurge decisions, food experiences, and unscheduled time all supported one another. Any one of those reservations could have been made independently. The value was that they were designed together.

Briggs and Sonja smiling together on a ferry during their anniversary trip through Sicily.

Big decisions first, then we zoom in.

My planning usually moves from the choices with the biggest ripple effects toward the finer details. That is deliberate: it’s much easier to pick the right hotel once we know the route, or the right tour once we know how much time you’ll have in a place. We can change course when something new surfaces, but the process is designed to avoid chicken and egg dilemmas or rebuilding the whole trip every time a smaller decision changes.


1 / UNDERSTAND

What matters, who is traveling, budget, preferences, constraints, must-dos, and the reason for the trip.


2 / SHAPE

Build the shell: destination, dates, routing, pacing, and the major contours. Decide what belongs — and what does not.


3 / CALIBRATE

Fine-tune lodging, experiences, guided vs. independent time, pre-booked vs. spur of the moment, splurge vs. save, together vs. apart, and the tradeoffs between them.


4 / COORDINATE

You make the meaningful choices. I coordinate the agreed pieces, manage supplier communication, and keep the whole picture aligned.


5 / PREPARE

Reconfirm where it matters, organize the particulars, flag what you need to know, and make sure you have easy access to contacts and important details.

FLEXIBLE DOES NOT MEAN GOING IN CIRCLES

If a genuinely better option appears or priorities change, of course we’ll adjust. But the reason I start with the big picture is to surface the decisions with downstream consequences early. The goal is a process that keeps moving forward — not an endless loop of drafts.

SCOPE + FEES, UP FRONT

Before the deep work, we agree on the scope.

The first conversation is just a conversation. If the trip calls for substantial planning, I’ll outline my approach, the expected timeline, and any planning fee before I dive in. If the need is straightforward, we can keep the process straightforward too.

Planning should build excitement, not drain it.

1. Four travelers wearing aviation headsets and smiling together inside a helicopter.

You stay the decision-maker. I take on the research, comparison, follow-up, and coordination that can turn anticipation into administration. My job is to bring you the choices that are actually worth making, explain the tradeoffs, and give you a point of view.

Some clients want to be deeply involved in every hotel and experience. Others give me a broad brief and would rather react to a thoughtfully narrowed set of recommendations. Most land somewhere in between. Using an advisor does not mean giving up the parts of planning you enjoy.


“Michael was so patient and regularly checked in to give us the push we needed to make decisions! Planning… can be overwhelming, but Michael helped to reduce that stress!”

— Crystal, family trip to London + Dublin

Plan enough that you can stop thinking about the plan.

JUST ENOUGH PLANNING

I’ve always liked the idea of “just enough planning:” rigorous enough that the important pieces are handled, but not so rigid that the trip cannot breathe. Before departure, I reconfirm the pieces that warrant it, organize the useful information, flag anything you need to know, and make sure the practical handoffs make sense.

The goal is not an hour-by-hour script. It is to do enough thinking in advance that, once you are there, you can have the long lunch, wander into the market you did not know existed, change your mind about the afternoon, or simply stop looking at your phone.

SUPPORT THAT GETS YOU TO THE FASTEST SOLUTION

I make sure you leave with confirmation numbers, supplier contact information, and clear instructions for the parts of the trip that may need them. If something simple goes sideways while you are traveling, the hotel, driver, tour operator, or local partner in front of you can often fix it faster than I can from several time zones away. I never want to be the roadblock between you and the resolution you need in the moment.

The point is that you’re not on your own. I remain a resource for booking or supplier issues and an advocate when my involvement can help. On some trips, I may recommend working with someone who can be an on-the-ground partner. I’ll always send you out prepared, with the right people reachable and with me in your corner when I am that useful person to involve.

Questions? Good.

The process is flexible, but a few practical questions come up a lot. Open whatever is useful; ignore the rest.

When does the fun part start?

Right here, ideally. Tell me what you are thinking about, and we can start turning the idea into something you will actually look forward to — including the planning itself.

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