Santorini · already booked
Already booked
your hotel?
Send me what you’ve booked and I’ll build the rest of the trip around it — the reservations, the boat day, the drivers, the ferries.
Santorini · already booked
Send me what you’ve booked and I’ll build the rest of the trip around it — the reservations, the boat day, the drivers, the ferries.
The hotel is the easy part. What makes or breaks a Santorini trip is everything around it.
The dinner you couldn’t get a table for, the boat day that sold out, the winery afternoon nobody told you to book a driver for, the ferry that was cancelled the morning you were supposed to fly home. That’s the part I take on. Send me your hotel confirmation and your dates, and I’ll come back with a plan for the days around it — tables held at the restaurants worth going to, a private boat on the right morning, a driver for the wine afternoon, and transfers that account for what the Aegean does in August. You keep the room you booked. I build the trip around it.
I spent four weeks across the Cyclades touring nearly every luxury hotel on Santorini and eating, sailing, and driving my way around the island, so none of this comes off a list — it comes from having done it. Still deciding on the hotel? Start with my Santorini hotel rankings or the Santorini guide.
The thing to lock in the same day you book your room
Santorini’s best tables go earlier than almost anywhere else I’ve been in Greece. From mid-June through mid-September, the sunset-facing tables at the top restaurants are gone weeks out, and what’s left is 6:00pm or 10:30pm. Tell me your dates and I’ll book the nights that matter before they’re gone — including the rooms that are effectively closed to walk-ins.
Omnia at Canaves Epitome. The best meal I had in Greece, and where I’d send you for sunset — Epitome faces an actual sunset into the Aegean rather than a caldera view. It’s also one of the harder tables to get at the hour worth having, which is why I go after it first.
Lycabettus at Andronis. The famous cliffside room. If you’re at Andronis I book this the moment your suite is confirmed; if you’re not, it’s still worth an evening, and I’ll tell you which night to give it.
Varoulko at Grace, Imerovigli. Michelin-starred chef Lefteris Lazarou’s seafood tasting menu, and he personally visits tables. Distinctly Greek yet modern — the strongest part of the Grace experience.
Selene, Fira. The island’s benchmark for a serious modern Greek tasting menu — Santorini fava, white eggplant, tomatoes, Assyrtiko. Worth the night away from Oia, and worth the driver I’ll arrange to get you back.
Ammoudi Bay, below Oia. Grilled fish at the water’s edge. Go at lunch instead of sunset — same food, a fraction of the crowd, and you won’t be climbing 300 steps in the dark.
One good rule: two big dinners across a three-night stay, and let the rest be long lunches. Send me your dates and I’ll tell you which of those nights are already tight and what I can still get — usually within a day.
The best half-day on the island, chartered properly
Seeing the caldera from the water is the one excursion I’d put on essentially every Santorini trip. I book these privately with the crews I use myself — not through a booking site — and I place the day where it won’t get wrecked by wind or collide with your dinner.
Saint Yachting. My pick at the top end. Crewed, genuinely five-star service, and they’ll do overnight and multi-day charters if you want to fold in another island — worth asking me about early, because the good boats go first.
Oia Sunset Cruise. The one I book for a classic private sunset sail out of Ammoudi — well run, and the right call if you want the experience without a full yacht budget.
Private over shared, always. Shared catamarans run 40–50 people. A private charter is 4–5 hours with the hot springs, Red and White Beach, a meal aboard and an open bar — at your pace. I’ll match the boat to your budget rather than the other way around.
Consider a morning departure. Calmer water, far fewer boats at the swim stops, and you keep your sunset free for dinner or your own terrace.
The Meltemi is real. Summer wind can cancel or reroute a sail with little notice, so I place the charter early in your stay with room to move it — which you can’t do once you’ve prepaid a fixed date online.
Tell me your dates and who’s coming and I’ll price the right boat for the right morning — and hold it before the good crews fill up.
One is plenty — and it needs a driver and a booking
Something most first-timers don’t realize: there’s no swimming from the caldera. The beaches are on the opposite side of the island, 25–40 minutes from Oia, and they’re black or red volcanic sand rather than the white sand people picture. Worth one day, planned — not worth improvising on a cruise-ship morning.
Theros Wave Bar, Vlychada. The most design-driven beach club on the island and the one I’d book first. Roughly 15 minutes from Fira, open May through October, and beds go quickly in peak season.
Perivolos & Perissa. The long black-sand stretch on the southeast coast where most of the island’s beach club scene lives. Easy, lively, and a genuine change of pace from Oia.
Kamari and Red Beach. Both are worth seeing once. Neither is worth a full day — Red Beach in particular is more photograph than swim, which is the kind of thing worth knowing before it eats your only beach day.
Front-row beds sell out by mid-morning. In July and August a walk-in at the better clubs is a lost afternoon — so I reserve the beds and the car together, and place the day where it doesn’t collide with your dinner.
One beach day is plenty on Santorini. If beaches are actually the point of the trip, that’s an argument for adding Milos or Paros — which I’ll build in rather than talk you out of.
Your hotel confirmation and your dates are enough. I’ll come back with what I’d book around them — and what’s already getting tight on your nights.
Santorini’s vines are grown in volcanic ash and trained into low baskets against the wind. The wine is unlike anything else in Greece, and a half-day is all it takes — booked in the right order, with someone else at the wheel.
Don’t drive this yourself. The roads between the estates are narrow, the tastings are generous, and the whole point is not to be watching the clock. I book the tastings in the right order and put a driver on the afternoon — it’s one line on your itinerary and nothing for you to arrange.
Two or three nights, not a layover
Most people treat Athens as a gateway to the islands. I think that’s a mistake. Give yourself two or three nights and you’ll discover one of Europe’s most exciting food cities, incredible luxury hotels, and neighborhoods that feel completely different from one another. It’s the perfect way to begin or end a trip through Greece.
Put it at the end, not the beginning. Flying home out of Athens gives you a buffer against a cancelled ferry or a delayed island flight — and you arrive in the city already unwound.
Two nights is the minimum that works. One night is an airport hotel with extra steps. Three is genuinely great.
Book the Acropolis early. Timed entry, and the first slot of the morning is the only one worth having in summer.
Read the full Athens guide for where I’d stay and how I’d spend the days.
The island I recommend more every year — beaches, restaurants, and villages that never feel overly polished.
Read the guide →
Volcanic cliffs, white rock formations, and hidden coves — the island to add if you want to actually swim.
Read the guide →Santorini is three to four nights for most people. If you have more time, add a single island and actually settle into it — three islands in seven nights is really three travel days. Both of these are a straightforward ferry, and I can arrange a private boat transfer if the schedules don’t cooperate.
Rules I’d give any client
You’ve done the hard part by choosing the hotel. Send me the confirmation and let me handle the rest of it.
I’ll build the rest.
Haven’t locked in the hotel yet? See the Santorini rankings — booking through me includes a space-available upgrade, daily breakfast, and a €100 hotel credit.