About this trip
Ten days sailing around the Cyclades, starting in Santorini and following the wind toward Mykonos and other islands, mixing ancient towns with quiet coves.
Days are shaped by the boat and the weather — swimming stops in clear water, fresh seafood and local wine on shore, and a skipper who raises the sails whenever conditions allow.
You'll mostly overnight in small island marinas rather than at anchor, with a local leader steering you toward the right spots on land.
What you'll do
- Sail the Aegean between Santorini, Mykonos and smaller Cycladic islands
- Swim and cool off in turquoise coves along the route
- Eat freshly caught seafood and try local wines ashore
- Overnight in small island marinas most nights
- Explore ancient towns and laid-back island life on foot
- You live and sleep on a real yacht, so cabins, bathrooms and living space are shared and can feel compact
- You need to be comfortable moving around the boat, including stairs — sea sickness medication is worth packing
- Sound carries easily on board, so late nights are best spent ashore rather than on the yacht
Cheapest live departure per day, in £, recorded by our tracker since 18 Jul. Never a brochure “was” price.
Your free day in Santorini
Landing early, staying on, or filling free time? The best-rated day experiences in Santorini — you book on Viator (we may earn a commission).
Worth it if you want hands-on sailing with exceptional local guides in stunning islands. Think twice if you need land-based comfort or prefer minimal sea time.
- Skippers George and Orestis were genuinely knowledgeable, safety-focused, and made the trip fun with Greek history insights.
- Afternoons and evenings exploring different islands while mornings spent sailing gives real variety across ten days.
- Budget two days minimum to adjust to constant boat life; this isn't a resort experience.
- Daily briefings with island info and dining recommendations help maximise time ashore at each stop.
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 £1,365, about 44% 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 Santorini · 24 Jul – 25 Jul
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