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The Cyclades before the July crush. Three islands with different personalities, small hotels a short walk from the water, and a schedule built around the swim-then-lunch rhythm that the islands themselves keep.
Trip at a Glance
- DestinationGreece
- DatesJun 6 – 15, 2027
- Duration9 Nights / 10 Days
- Group SizeMax 12 Travelers
- Travel StyleIslands, Sea, Very Slow
- Activity LevelEasy
- AccommodationThree islands, two ferries
Highlights
- Private caique day around the coastline with anchoring for swims
- Cooking with a yiayia who has never used a recipe
- Assyrtiko tasting at a vineyard where the vines grow in baskets on the ground
- Ancient Delos with an archaeologist, on the first boat of the day
- Sunset at a hillside taverna the guidebooks have not found
- A day so free of plans it feels illegal
Day by Day
10 days, 9 nights. Every day has an anchor and an escape hatch — nothing here is compulsory.
Transfer, evening walk under the Acropolis, dinner on a roof with the view.
Acropolis Museum in the morning, short flight to Naxos, first swim before dinner.
Marble villages, a cheese maker, and a long lunch inland. Beach afternoon.
Nothing. Actually nothing. We will happily suggest three beaches.
Morning ferry, harbour town base, evening in the old marble quarter.
Private boat around the coast with swim stops and lunch aboard.
Early boat to ancient Delos with an archaeologist, cooking class in the afternoon.
Afternoon crossing, cliffside hotel, sunset without the scrum.
Assyrtiko tasting, a walk on the caldera path, farewell dinner.
Flights home from Santorini via Athens.
What's Included
- 9 nights in small hotels, all a short walk from the sea
- All breakfasts, 6 dinners, 4 lunches
- All ferries and internal flights within Greece
- Private caique day, Delos guide, cooking class, wine tasting
- Transfers on every island
- Beach towels and a very good beach recommendation list
What's Not Included
- International flights
- Travel insurance
- Meals not listed
- Sun loungers and water sports
- Gratuities
We would rather show you this list than surprise you with it later.
Important Info
- PaceThe slowest trip we run. Most days have one thing in them.
- WeatherJune: 26–29°C, sea around 22°C, and the meltemi wind on a few afternoons.
- WalkingVillage lanes and steps, particularly in Santorini. Comfortable shoes, not sandals, for touring.
- SwimmingOptional everywhere, and never far away. Boat days have a ladder and calm anchorages.
- FerriesTwo crossings of 40–90 minutes, in reserved seats, with luggage handled.
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