Santorini in 3 Days: The Lucalvry Itinerary
By Alex Marlowe · Updated 2026-05-17 · 12 min read
An hour-by-hour itinerary for three days in Santorini — Oia at sunrise to skip the cruise crush, the south-coast wineries between lunch and dinner, and the caldera-edge tavernas worth the booking.
Day 1
Fira arrival, caldera-rim walk, Imerovigli sunset
- Morning (10am arrival)
Land at JTR, transfer to your hotel in Imerovigli (35 minutes by private car, €70)
Land at JTR, transfer to your hotel in Imerovigli (35 minutes by private car, €70). Hotels in this strip release rooms from 2pm, so leave the bags at the front desk and walk the caldera path north toward Firostefani — a 25-minute level walk with the entire caldera arc in view. Coffee and bougatsa at Galini Café in Firostefani; the terrace is the calmest morning vantage on the cliff.
- Lunch (1pm)
Argo in Fira for grilled octopus and a glass of Assyrtiko — the kitchen is steady, the…
Argo in Fira for grilled octopus and a glass of Assyrtiko — the kitchen is steady, the prices are roughly half of the caldera-rim alternatives, and the booking is rarely difficult before 2pm. Skip the photographed cocktail bars on the same street; they pour from the same five bottles at three times the price.
- Afternoon (3pm)
Hotel check-in, a one-hour swim in the plunge pool (every serious Imerovigli stay has o…
Hotel check-in, a one-hour swim in the plunge pool (every serious Imerovigli stay has one), and a 5pm walk down to Skaros Rock — the volcanic outcrop that defines the Imerovigli skyline, with a flat 20-minute path and the strongest sunset vantage on the island that does not require an Oia reservation.
- Dinner (8:30pm)
Lauda at Andronis Boutique Hotel — one of the two serious tasting menus on the island,…
Lauda at Andronis Boutique Hotel — one of the two serious tasting menus on the island, paired with a deep Assyrtiko list and a caldera-rim terrace that handles 30 covers without feeling rushed. Book a fortnight ahead for window two; the seating is staggered to give every table the sunset.
Day 2
Akrotiri, southern wineries, Oia sunset
- Morning (8am)
Pre-booked taxi to Akrotiri (25 minutes, €35)
Pre-booked taxi to Akrotiri (25 minutes, €35). The site opens at 8am from April through October; arriving with the gate avoids the 10am cruise-ship swarm and the queue for the elevated walkway over the Bronze Age city. Allow 90 minutes including the small museum.
- Late morning (11am)
Walk down to Red Beach for a 30-minute swim — the cliffs are the most photographed on t…
Walk down to Red Beach for a 30-minute swim — the cliffs are the most photographed on the island after the caldera, and the water is calm enough for non-swimmers in the morning hours. Skip the lounger touts; the public end of the beach is fine.
- Lunch (1:30pm)
To Psaraki in Vlychada for grilled fresh fish at harbour-side prices
To Psaraki in Vlychada for grilled fresh fish at harbour-side prices. Order whatever was landed that morning and a half-litre of the house Athiri.
- Afternoon (3pm)
Two-winery loop along the south plateau: Domaine Sigalas in Oia (the Assyrtiko referenc…
Two-winery loop along the south plateau: Domaine Sigalas in Oia (the Assyrtiko reference, with the most polished tasting room on the island, €25 a flight) followed by Venetsanos overlooking the caldera at Megalochori (the most photographed cellar door, €20). Both take walk-ins after 3pm; the Sigalas tasting on the terrace is the more memorable seat.
- Sunset (7:15pm)
The Oia castle ruin is the postcard vantage and is correspondingly mobbed; arrive 90 mi…
The Oia castle ruin is the postcard vantage and is correspondingly mobbed; arrive 90 minutes early or skip it. The smarter alternative for a third-night sunset is the rooftop at the Atlantis Books in Oia, a 60-second walk from the castle, where the same arc is visible without the parapet shoving match.
- Dinner (9:30pm)
Ambrosia in Oia for the best post-sunset table on the caldera
Ambrosia in Oia for the best post-sunset table on the caldera. The veal cheek and the Assyrtiko-aged-on-lees pairing are the signatures; the kitchen runs late enough to accommodate a slow sunset and a slow walk back along the path.
Day 3
Caldera sail, slow afternoon, Selene farewell
- Morning (9:30am)
Pre-book a half-day private catamaran from Vlychada (Sunset Oia and Caldera Yachting bo…
Pre-book a half-day private catamaran from Vlychada (Sunset Oia and Caldera Yachting both run editor-level boats, €1,400 for a private 4-hour sail with a crew of two). The route is Vlychada → Red Beach → White Beach → the volcano hot springs at Palea Kameni, with three swim stops and lunch on board.
- Afternoon (2:30pm)
Return to the hotel for a slow plunge-pool reset and a one-hour spa booking — Andronis…
Return to the hotel for a slow plunge-pool reset and a one-hour spa booking — Andronis Concept and Vora both run their massage diaries thinly enough that same-day bookings are usually possible if you ask the concierge by 11am.
- Late afternoon (5pm)
A final caldera-path walk south from Imerovigli to Fira — the lighting between 5 and 6p…
A final caldera-path walk south from Imerovigli to Fira — the lighting between 5 and 6pm is the best of the trip and the path is at its emptiest as Oia pulls the crowds north.
- Dinner (8pm)
Selene in Pyrgos for the farewell
Selene in Pyrgos for the farewell. The most serious kitchen on the island for the last 25 years, now in a converted estate building 15 minutes inland from the caldera. The tasting menu is the right call (€140); the wine pairing leans heavily on small-volume Cycladic producers and is genuinely instructive about Greek viticulture beyond Assyrtiko.
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Editor-in-Chief
Alex MarloweAlex Marlowe is Lucalvry's Editor-in-Chief. Twelve years covering hotels and travel for Condé Nast Traveller, Monocle, and Wallpaper. Based between London and Lisbon.
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