About this trip
Eight days sailing through the Cyclades, moving between the boat, quiet beaches and small Greek villages between Mykonos and Santorini.
Days settle into swimming, time on white-sand beaches, good food and wandering coastal villages with plenty of history behind them. Evenings bring sunsets and overnight stops in small island marinas, with the boat as your base throughout.
This is life on a real working yacht, guided by a skipper who sails whenever conditions allow, so plans can shift a little with the weather.
What you'll do
- Sail between Mykonos, Amorgos, Naxos, Small Cyclades and Ios on to Santorini
- Swim in turquoise water and stop at white-sand beaches along the way
- Explore coastal villages shaped by centuries of history and mythology
- Watch the sunset from the deck most evenings
- Sleep aboard the boat, mostly moored in small island marinas
- You'll need to be steady on your feet moving around the boat, including stairs, and comfortable sharing cabins, bathrooms and living space with other passengers
- Sleeping quarters are compact, though most of your time is spent above deck in the open air
- Sound travels easily on board, so a late night is better spent ashore in town than back at the boat
Worth it if you want an intimate, island-hopping sailing experience with genuinely excellent skippers. Think twice if you need seamless pre-trip logistics or prefer less rustic boat living.
- Skippers Fotis and Rita consistently create inclusive, warm team environments with deep local knowledge.
- Seven Greek islands with distinct cultural styles visited; well-researched itinerary delivers genuine discovery.
- Intrepid's pre-trip communication is slow; expect 3-day waits for responses and wrong starting location info.
- Boat living requires resilience; sailing is not for everyone, despite skipper excellence making it doable.
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 Sep is cheapest — from £1,100, about 38% below the priciest month (May).
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 · 25 Sept – 26 Sept
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