Santorini: The Caldera, Slowly
Most people get six hours on Santorini and spend four of them queuing in Oia. We give it a week: the caldera path at dawn, the assyrtiko vineyards inland, Thirassia by fishing boat, and the Akrotiri excavation with an archaeologist rather than an audio guide.
- Days
- 7
- 6 nights
- Group size
- 6–10
- Hard cap
- Difficulty
- Easy
- See the day-by-day below
- From, per person
- $2,340
- Land price, no flights
The 7 days, in order
Written by the guide who runs it. Where a day is hard, it says so.
Arrive Thira, settle in Imerovigli
Day 1 of 7Twenty minutes from the airport to Imerovigli, which is on the rim but not on the cruise route. Sunset from the terrace, dinner in the village.
Night: Cave house, ImerovigliMeals: DThe caldera path, north
Day 2 of 7Imerovigli to Oia along the rim, ten kilometres of it, starting at half six so you finish before the heat and the coaches. Swim at Ammoudi, then the long lunch you have earned at the bottom of the 300 steps.
Night: Cave house, ImerovigliMeals: B · LAkrotiri with an archaeologist
Day 3 of 7The Bronze Age town under the ash roof, walked with someone who has worked the site — two hours that reframe the whole island. Afternoon at the Red Beach and Vlychada.
Night: Cave house, ImerovigliMeals: BAssyrtiko, and the vines that grow in baskets
Day 4 of 7Inland to Pyrgos and the vineyards, where the vines are trained into low koulara baskets against the wind. Three estates, a barrel tasting, and tomatokeftedes at a kafenio in Emporio.
Night: Cave house, ImerovigliMeals: B · LThirassia by fishing boat
Day 5 of 7Across the caldera to the island Santorini used to be: one village, one road, no hotels to speak of. Swim off the boat at the hot springs on the way back.
Night: Cave house, ImerovigliMeals: B · LAncient Thera and the east coast
Day 6 of 7Up Mesa Vouno to the Dorian city on the ridge, with the whole island laid out either side. Afternoon free — most people sleep. Farewell dinner in Megalochori.
Night: Cave house, ImerovigliMeals: B · DFly out
Day 7 of 7Transfer to Thira for your flight, or on to the ferry port if you are carrying on through the Cyclades.
Depart todayMeals: B
Santorini, month by month
Average daily high and average monthly rainfall. Our own recommendation is May, June, September and early October.
Average high temperature
15–30 °C across the year
| Month | Average high (°C) |
|---|---|
| Jan | 15°C |
| Feb | 15°C |
| Mar | 17°C |
| Apr | 20°C |
| May | 24°C |
| Jun | 28°C |
| Jul | 30°C |
| Aug | 30°C |
| Sep | 27°C |
| Oct | 23°C |
| Nov | 19°C |
| Dec | 16°C |
Average rainfall
1–90 mm a month
VerdictSweet spot: May–June — the sea is already swimmable, rainfall is effectively nil, and the caldera path is yours before the August crowds and the 30 °C afternoons.
What is and is not in the price
Included
- 6 nights in a caldera-facing cave house, twin share
- Guide throughout, and a site archaeologist at Akrotiri
- Private fishing boat to Thirassia and the hot springs
- Three-estate wine tasting with the growers
- All site entries: Akrotiri, Ancient Thera, the museum
- Breakfast daily, 4 lunches, 2 dinners
- Airport transfers on both days
Not included
- Flights to and from Thira (JTR)
- Travel insurance — required
- Meals not listed, and all drinks outside the tastings
- The cable car and donkey path in Fira
- Tips
Oia, Santorini, Greece
Centred on where the trip is based. OpenStreetMap, so nothing is requested from a third party that sets cookies.
Before you book Santorini
When is the best time to visit Santorini?
May, June, September and early October. Sweet spot: May–June — the sea is already swimmable, rainfall is effectively nil, and the caldera path is yours before the August crowds and the 30 °C afternoons. The two charts in the "best time to visit" block above plot the average daily high and the average monthly rainfall for all twelve months, so you can judge it against your own tolerance for heat and rain rather than taking our word for it.
How hard is the Santorini trip?
We rate it easy. It runs 7 days with a group of 6–10, and the day-by-day itinerary above says exactly what each day asks of you. If a particular day looks like too much, say so when you book — sitting one out is normal and costs nothing.
What is included in the Santorini price?
6 nights in a caldera-facing cave house, twin share; Guide throughout, and a site archaeologist at Akrotiri; Private fishing boat to Thirassia and the hot springs — and more; the full list is in the inclusions above. Flights are not included.
What is the cancellation policy?
Free cancellation for 14 days after booking, with the deposit refunded in full. After that: cancel more than 60 days before departure and you lose the 20% deposit only; between 60 and 30 days, 50% of the trip price; inside 30 days, the full amount. If we cancel a departure — too few travellers, or a route genuinely closed — you choose between a full refund and a transfer to any other date.