The Cyclades · Excursion Guide
Santorini
Everything I’d actually book here — boats, wine, walks and tables — with what each one costs and who it’s for.
The Cyclades · Excursion Guide
Everything I’d actually book here — boats, wine, walks and tables — with what each one costs and who it’s for.
Read through, send me the ones you want, and I’ll build the days around them and hold the bookings that fill up first.
Santorini is small but slow — the roads are narrow and everything runs on the view. One anchor in the day and one good dinner is the right density.
The caldera villages are the reason you came, but the island behind them — vineyards, Pyrgos, the black-sand south — is where it stops feeling like a photograph.
Private boats and the handful of restaurants worth planning around go weeks ahead in summer. Tell me those first and the rest can stay loose.
Santorini is a crescent around a flooded volcano. Everything with a view sits along the west rim — Fira, Imerovigli, Oia — and everything else, the vineyards, the ruins and the black-sand beaches, is on the gentle slope behind. Tap any pin for what it is.
What I arrange by default for the airport and the ferry port. Athinios is a steep, chaotic switchback and the taxi queue there is genuinely unpleasant.
Worth it for the inland day — wineries, Pyrgos, the south coast. Not worth it for the rest: parking in Oia and Fira is close to impossible in season.
There are only a few dozen on the whole island and none you can hail. Have your hotel call ahead, or pre-book the driver for a dinner at the other end of the island.
Three hundred steps down, shared with donkeys. Walk down if you like, but book a car for the way back up — especially after lunch and wine.
You cannot understand Santorini from the rim — you have to be under it. Every boat below runs roughly the same circuit out of Ammoudi or the Old Port: along the caldera wall, out to the volcano and the hot springs, past the lighthouse to the red and white beaches, and back at sunset. What changes is how many people are on board with you.
A catamaran with a group, the full circuit, meal and drinks on board. Morning departures are calmer and cheaper; the sunset run is the one people remember. Boat size is what you’re really choosing — from fifty-five people down to fourteen.
If it’s your first time and you’re happy in company, this is the sensible booking.
From $87 per person
Same route, fourteen or twenty guests instead of fifty-five, more space on deck and a proper cooked meal rather than a buffet. The difference in the day is bigger than the difference in the price.
From $121 per person
The whole boat and crew for your group — up to fourteen, but just as good for two. You set the departure time, how long you stay in each cove, and whether you swim at the volcano or sail straight past it.
The best value on this page for a family or a group of friends.
From €1,000 for the boat
A different category altogether: a Pardo, a Wally or a Sunreef with a captain and a stewardess, three stops of your choosing, chef’s appetizers and good wine on board. Chauffeured to and from the boat, fuel and VAT included, no waiting at the dock.
Honeymoons, anniversaries, and anyone who’d rather have the day be the memory. Tell me the boat and I’ll get the date held.
From $1,430 for the yacht
Nea Kameni is still live — a short, hot climb over black rock to the crater rim, then a swim in the rust-colored sulphur water beside it. Wear something you don’t mind staining.
Down the steps to Ammoudi, a small boat around the headland, and lunch on the rocks at a table almost in the water. Barely an excursion, and still one of my favorite meals on the island.
Assyrtiko is grown here in a way it isn’t anywhere else — vines coiled into low baskets on the ground, no trellis, no irrigation, roots deep in volcanic ash and pumice. The wine that comes out is bone-dry, saline and unmistakable. Vassaltis is the one I send people to: modern, serious, and small enough that you’re looked after properly.
Four wines and four bites, each pairing made for the glass it comes with — current vintages plus a couple of rarer vinifications. A crash course in Assyrtiko and the easiest thing here to slot into an afternoon.
From $44 per person
Three courses meant to be shared, paired with tastings of three wines, at a table looking down the vine rows to the sea. Offered daily, and my pick if you want the wine to be lunch rather than an errand before it.
From $61 per person
A walk through the vineyard with one of the sommeliers — how they farm it, why the baskets, what the ash does — then a four-course lunch paired with four wines. The full afternoon, and worth building a day around.
From $99 per person
The old capital, stacked up the highest hill on the island inside its castle walls. Ten minutes of climbing lanes gets you a view over both coasts at once, and almost nobody is up there.
A Bronze Age town buried by the eruption and dug back out — three-story houses, paved streets, drainage, frescoes. It’s under a roof, which makes it the right call on a hot day or a rare wet one.
Vlychada for the wind-carved cliffs and near-empty sand, Perissa if you’d rather have a lounger and a taverna. Both are a different island from the rim — flat, hot, and gloriously ordinary.
There is almost no shade anywhere on this island. All three of these are morning walks — start by eight, carry water, and have a car meet you at the far end rather than walking back.
The signature walk, and the only way to understand the shape of the island: the whole crescent of the caldera on your left, Firostefani and Imerovigli, then a long empty stretch over the headland before Oia appears. Undulating and exposed — the hard part is the sun, not the climb.
Switchbacks up the Mesa Vouno headland to a Greek and Roman city strung along a ridge 350 metres above the sea, with Kamari on one side and Perissa on the other. Almost nobody walks it — and you can drive most of the way if you’d rather.
Not really a hike, but the best twenty minutes of walking on the island: the steps zigzag down the red cliff to a tiny fishing port with tavernas built onto the rock. Go down for a late lunch, and take a car back up.
The castle at Oia is famous, and by seven it is shoulder to shoulder with several thousand people. Every one of these is better.
Genuinely the best answer on the caldera side. A bottle, no crowd, and the light doing the work. Any hotel I book you into on the rim faces west for exactly this reason.
The short walk out to the old rock fortress puts you on the highest point of the rim with Oia in profile to the north. Twenty minutes from the village and a fraction of the people.
Looking back at the cliffs with the villages lighting up along the top of them. Every caldera cruise is timed for this, and it is a completely different picture from the land version.
The contrarian pick and my own favorite — from the castle you see the sun go down over the whole island rather than just the water, with the caldera villages glowing on the far ridge.
One of my favorite meals in all of Greece, and not on the caldera — which tells you how good the cooking is.
The big-occasion table, carved into the cliff face. Usually booked out — if you’re staying at Andronis I’ll have the concierge team try, and it’s worth asking early.
Beautiful fine dining, seafood-led, on the quietest stretch of the rim. The most elegant dinner on the island without being stiff about it.
Very authentic Greek dining, inland and unfussy, and where the island itself eats. No caldera view, which is exactly why it’s good. Tables go weeks ahead.
An authentic Greek fish tavern on the water at the bottom of the steps — a super cute spot, and the easy lunch on a day you’re not doing anything else.
Send me the ones you want and I’ll go through your hotel’s concierge to secure them. For anything on this list in July or August, three to four weeks ahead is not too early.
Three nights is the right length for Santorini. One day on the water, one day inland, and one day that asks nothing of you at all.
Arrive, do nothing, and let the island introduce itself. Walk Oia in the late afternoon before the sunset crowd arrives, then down the steps to Ammoudi for fish on the water and a car back up.
The caldera cruise, all day — volcano, hot springs, the red and white beaches, and the cliffs from below. Back late in the afternoon, and keep the evening close to home.
A car for the day. Akrotiri in the morning while it’s cool, lunch and wine at Vassaltis, then Pyrgos for the late light. Dinner inland at Metaxi Mas, which is where the island actually eats.
Reply with the ones you want and anything you’d skip, and I’ll build the days around them — boats held, tables booked, transfers arranged before you land.
Prices are operators’ published starting rates, converted from euros — final cost depends on date, group size and boat. I’ll quote exactly before anything is held.