Let me help with everything that comes next.
The hotel is the easy part. What actually makes or breaks a Santorini trip is everything around it — the dinner you couldn't get a table for, the catamaran 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.
I spent four weeks across the Cyclades touring nearly every luxury hotel on Santorini and eating, sailing, and driving my way around the island. Below is what I'd tell a friend who already has their room confirmed and just wants the rest of it handled well.
If you'd like me to actually build the itinerary, make the reservations, and arrange the transfers, that's what I do. Scroll to the bottom, tell me where you're staying, and I'll take it from there.
Still deciding on the hotel? Start with my Santorini hotel rankings or the Santorini destination guide.
Book these the same day you book your room
Reserve · 4–8 Weeks Ahead In High Season
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 the ones that are left are at 6:00pm or 10:30pm. If dinner matters to you, this is the single thing worth locking in before you land.
Omnia at Canaves Epitome. The best meal I had in Greece. It's also where I'd send you for sunset — Epitome faces an actual sunset into the Aegean rather than a caldera view.
Lycabettus at Andronis. The famous cliffside room, and the reservation I tell every Andronis guest to make the moment they confirm their suite.
Varoulko at Grace, Imerovigli. Michelin-starred chef Lefteris Lazarou's seafood tasting menu, and he personally visits tables. The food felt 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.
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. Santorini rewards slowing down, not chasing every restaurant on a list.
The best half-day on the island
Best For · Honeymoons, Anniversaries, Anyone Skipping The Sunset Crowds
Seeing the caldera from the water is the one excursion I recommend to essentially everyone. It's also the cleanest way to avoid the Oia sunset scrum — you get the same golden hour with a glass of Assyrtiko and roughly two hundred fewer people around you.
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.
Oia Sunset Cruise. The one I recommend 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 usually 4–5 hours with the hot springs, Red Beach and White Beach, a meal aboard, and an open bar — and you set the pace.
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. Book the cruise on your first full day so there's room to move it.
Skip the crowded sunset viewpoints and enjoy golden hour from your hotel instead, or via a private sunset cruise. Every time.
All the way across the island — and worth one day
Best For · A Break From The Caldera, Long Lunches, Younger Couples
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. They're worth seeing — just don't build your trip around them.
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.
Book loungers ahead in July and August. Front-row beds at the better clubs sell out by mid-morning, and a walk-in on a cruise day is a lost afternoon.
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 rather than staying put.
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.
Start in the north of the island at the winery I send almost everyone to first. Modern, unfussy, and focused on the wine rather than the view — which is exactly the right way to begin before your palate is three tastings deep.
The serious stop. Paris Sigalas built the estate that made the world take Santorini Assyrtiko seriously, and the seated tastings run deep — old-vine bottlings, aged Nykteri, barrel Vinsanto — paired with small plates. Add lunch here and let the afternoon stretch.
Finish on the cliff above Athinios port, cut straight into the rock, with the caldera opening up in front of you. It's the view stop — and a far calmer one than Santo Wines, which fills with cruise groups at exactly the hour you'd want to be there.
Hire a driver for the afternoon. The roads between the wineries are narrow, the tastings are generous, and the whole point is not to be watching the clock. I arrange this as part of the itinerary.
Two or three nights, not a layover
Best For · Bookending The Trip, Food Lovers, First-Time Greece
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.
Add One Island, Not Three
The island I recommend more every year — beaches, restaurants, and villages that never feel overly polished
Volcanic cliffs, white rock formations, and hidden coves — the island to add if you want to actually swim
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.
If it cancels, there's nothing behind it.
Build in a night. The Aegean does not care about your itinerary.
Three islands in seven nights is three travel days.
Slow ones don't, as often. Pack motion sickness patches either way.
Private transfers are the easiest way to travel between the airport, ferry port, and your hotel — especially in Oia, where the drop-off point and your room can be a few hundred stairs apart. I also arrange private helicopter transfers through my partnership with Hoper, as well as private boat transfers, for travelers combining Santorini with nearby islands.
Santorini is one of those rare destinations that truly lives up to the hype. The secret isn't seeing more, it's slowing down. Wake up early, linger over long lunches, and enjoy the caldera from your own terrace instead of chasing every viewpoint. If your hotel is already booked, everything below that line is what I can take off your plate.
Send Your Hotel & Dates And I'll Take It From There
Haven't locked in the hotel yet? See Keith's Santorini Hotel Rankings for all 10 properties, ranked — booking through me includes a space-available upgrade, daily breakfast, and a €100 hotel credit.