About this trip
Ten days sailing the Cyclades aboard a 57 ft yacht, starting and finishing in Mykonos. There's no fixed itinerary — where you go depends on the weather and your skipper's read of it, so the route flexes day to day.
Expect a mix of island time and time on the water: wandering ruins, stopping for a local brew, or doing nothing much on a good beach. You'll sail through Santorini's caldera and get the windmills-of-Mykonos view from where it counts, out on the water.
This is a small-group sail rather than a fixed island-hopping ferry route, with a private room aboard and a fully guided setup throughout.
What you'll do
- Sail the Cyclades aboard a 57 ft yacht
- See Mykonos' windmills from the water
- Sail through Santorini's caldera
- Explore ancient ruins on island stops
- Stop at a local microbrewery to taste
- Relax on beaches along the route
- Route is weather-dependent and set by the skipper, not fixed in advance
- Private room aboard the yacht, but you're living on a boat with a small group for 10 days
- Pace is easy — built around sailing and island stops rather than packed sightseeing
Worth it if you want genuine sailing and island access smaller ships can't reach. Think twice if you're a complete beginner expecting luxury or extensive instruction.
- Access to tiny islands and snorkel spots (WWI plane wreck, sea caves) larger boats simply cannot reach.
- Captain Phil/Kristina genuinely skilled sailors who create group cohesion; dinners on board were standout moments.
- Torn genoa sail on day one with no spare; skipper communication gaps meant experienced sailors had to teach basics.
- Not a luxury floating hotel—you're actually living on a working sailboat with basic creature comforts.
Distilled from real traveller reviews on TourRadar — we don't edit out the bad bits.
The same-vibe trips, side by side — price, value per day, and how each is moving. Only we can lay two operators' trips out honestly.
Sorted by fit — never by who paid. Price moves and availability come from our own daily tracking.
Departing in Jul is cheapest — from £1,095, about 77% below the priciest month (Jun).
Getting there
Opens Trip.com, pre-filled — one-way so you can book your return whenever. Prices & booking shown there.
Where to stay
A night before your tour in Mykonos · 20 Jul – 21 Jul
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