I don’t begin planning by asking what someone wants to see, how many hours they have or, least of all, the size of car they want.
I begin by asking how they want the day to feel, and how much energy they realistically have to carry it.
Most planning in Santorini starts too late, after you’ve already half-decided what you want to see: attractions chosen, routes imagined, and expectations shaped by images and trending videos rather than experience.
By the time logistics enter the picture, the plan is already fragile.
The real problem I plan around
Santorini doesn’t lack good tours.
It lacks a clear starting point.
You’re shown dozens of private tours, each built around stops, duration, and inclusions. On paper, it looks like choice, but instead, you’re left stranded at a bus stop with lots of buses, chaos, and no clearly labeled routes.
In case that sounds like the main Fira Town terminal, that’s where I got this lightbulb moment from, trying to catch the right bus to work while lacking sleep and sanity.
Everyone asks:
“What do you want to see?”
Almost no one asks:
“How do you want the day to feel?”
“How much decision-making do you actually want to do?”
“How much energy do you have right now?”
That’s where things go wrong, fast.
What I pay attention to first
Before anything is designed, I look at a small set of realities that shape everything else on the island.
Energy
Some people arrive curious but depleted. Others arrive energized but unfocused. Trying to give them the same experience never works.
Scale
Santorini compresses everything–movement, attention, even privacy.
Rhythm
The island moves in pulses. Daily, weekly, seasonal. Fighting that rhythm creates friction that no itinerary can fix.
Visibility
Privacy always costs something here; if not money, then time and energy.
Feasibility
Many ideas sound simple but take way more work than they’re worth.
If these things aren’t named early, plans fall apart and people blame crowds, timing, or bad luck.
What I don’t optimize for
I don’t plan around:
- seeing everything
- maximizing stops
- squeezing value into every hour
- performing an experience for an audience
- pretending constraints don’t exist
Optimization creates pressure, and pressure is what drains people fastest.
How decisions are actually made
Planning, for me, is a process of adjustment, not accumulation.
That means:
- getting clear on what you want before deciding how to get it
- naming tradeoffs instead of hiding them
- choosing fewer elements and letting them breathe
- designing with the island, not against it
When decisions are aligned, fewer of them are needed.
Most people don’t need more options.
They need fewer decisions.
Where this approach comes from
This way of planning comes from years of working across tourism, hospitality, and actually coordinating things here in Greece.
It comes less from theory and more from watching what actually holds together here.
And from seeing where plans collapse, even when your idea was good and it really mattered to you.
Over time, I learned that doing less usually works better for your stay than the opposite.
How this turns into an experience
Some people want help thinking.
Others want that thinking carried for them, without having to navigate choices themselves.
That’s where Maria’s Choice comes from.
Instead of offering a menu of private tours, I design a single route, adjusted by energy and intention.
The pace shifts.
The emphasis changes.
The thinking stays the same.
Every time, it starts with one question:
How do you want the day to feel when it’s over?
What Maria’s Choice is (and isn’t)
It is:
- a private Santorini experience designed around energy, not checklists
- fewer decisions, carried for you
- a clear rhythm, without rushing or overfilling the day
It is not:
- a highlights race
- a customizable list of stops
- a performance of “doing Santorini right”
The goal is coherence, not coverage.
Who this approach works best for
This way of planning works well for people who:
- feel planning fatigue before they arrive
- want beauty without pressure
- prefer judgment and good taste over recommendations
- are willing to accept tradeoffs once they’re visible and trust their experience curator with their time
It’s not designed for speed, volume, or comparison shopping.
Where to go next
If you want to see how this thinking translates into a guided experience:
If you’re still orienting yourself:
→ Why “Simple” Retreats Fail in Santorini
Closing
Planning doesn’t need to be loud to be effective.
Sometimes the most helpful thing is simply starting in the right place.
With how you want to feel, rather than what you think you should do.