What Planning With Me Looks Like

I start with the flights, not the islands

Almost every Greece itinerary I'm shown by a prospective client has the same flaw: it was planned on a map. The islands look close together, so the route seems obvious — and then the flights don't exist, or they exist twice a week, and the whole thing has to be rebuilt.

So the first thing I do is find out what's actually flying on your dates. For Nora and Adam that meant two viable one-stop routings — into Santorini via Munich, or into Mykonos via London — and one that looked good on paper and wasn't: the island they most wanted to swim on needed two stops and a late arrival, which makes it a ferry leg in the middle of the trip rather than a place to land.

October is a thinning schedule in Greece. Knowing which routes survive into the second week of the month is what decides the shape of everything after it.

The route isn't a preference. It's whatever the flight schedule will actually support, arranged in the nicest possible order.

You get options, not one answer

This is the part that surprises people. I don't send back a single itinerary and ask what you think. I send several complete ways through the trip, each one built around a real arrival and a real departure, and each one with a different personality.

Nora and Adam got five. The design-forward one, built around the cliff hotel on Folegandros their friend had sent them. The most relaxing one, four nights on the swimming island. The best-food one. And two three-island routes that trade a couple of slower mornings for the full range — glamour, then village, then caldera.

Those five existed because of what they'd told me — an anniversary, a long flight they didn't want to repeat on the far end, one hotel they were already in love with, and a strong preference for swimming over sightseeing. Someone travelling with kids in July, or with four nights instead of ten, gets a completely different five. That's the point of doing it this way: the options are drawn from your answers, not picked off a list of routes I already had.

Each came with the nights split island by island, the ferry legs and their real durations, and one line on who that version is for. They picked in a day, because the choice was between five clear characters rather than a hundred hotels — and then we adjusted the one they chose until it was theirs.

The five pairings, written up in full →

Hotels, with a take on each

A list of hotels isn't advice. What you need is which one I'd put you in and why, including the ones I'd steer you away from — and what each actually costs, so the decision is real.

Here's roughly what that looked like on the Santorini page of their proposal. Rates are per night for early October, quoted at the time and indicative — they move, and I re-price before anything is booked.

Alongside that, the thing a rate sheet can't tell you: land in Santorini on day one and you're choosing from whatever has space that night. End there instead and the entire island is available. That single observation reshaped their route — and it's the sort of thing that only comes out of pricing all of it at once.

All 15 Santorini hotels, ranked →

The budget, weighted rather than spread

Nora and Adam had a fixed number for hotels and the instinct most people have, which is to divide it evenly by the number of nights. That's usually the wrong move, and it was here.

Islands don't reward the same nightly rate. On some of them the gap between a good hotel and the right one is the trip; on others that same money buys a slightly better view and nothing you'd remember.

Same total, weighted so the expensive nights are the ones earning it — and the rest of it spent on days rather than rooms.

The logistics, handled rather than listed

This is the least glamorous stage and the one that decides whether the trip feels effortless.

Ferries between the Cyclades go on sale in batches, and the good crossings on the good dates sell out early — so they get booked the day the schedules open, not the month before you travel. Private port transfers on both ends of every crossing, because a ferry arrival with luggage and no plan is where a good day comes apart. And a hard rule I don't bend: never a ferry on the same day as a flight. Cycladic boats cancel for wind with a few hours' notice, and a cancelled ferry on a flight day is a missed flight rather than an inconvenience.

Where the sea isn't the right answer at all, there's a helicopter — Athens to Santorini in under an hour through my partnership with Hoper, or a private boat directly between two islands whose public ferry schedule doesn't suit the day.

My Greek ferry rules →

Then it becomes an itinerary

Once the route is chosen and the hotels are confirmed, the proposal turns into the thing you actually travel with: every night, every transfer, every reservation and timing in one document, delivered about a week before you leave once everything is locked.

Dinner reservations at the tables that need booking weeks ahead. The guide meeting you at the Acropolis at the right hour rather than the crowded one. The boat charter that leaves before the day-trip fleet. All of it confirmed and timed around the rest of the day before you get on the plane.

See a finished sample itinerary →