About this trip
Eight days sailing through the southern Cyclades, from Mykonos to Santorini, aboard a 57 ft yacht with a skipper doing the actual work.
Days are shaped around the wind and the coastline rather than a fixed itinerary — swimming off the boat, wandering lesser-known island villages, and eating well in between. It's a slower, sea-based way to see islands most people fly past.
Good for a group who want the Cyclades without the ferry timetables, and don't mind sharing a boat as home base for the week.
What you'll do
- Sail between Mykonos and Santorini via the southern Cyclades
- Swim and relax on quiet, less-visited island beaches
- Wander historic ruins along the route
- Eat and drink in small local villages
- Sleep aboard a 57 ft yacht with your own private room
- Pace and route depend on wind and weather, guided by your skipper
- You're based on the boat throughout, so it suits people happy with close quarters and shared spaces
Worth it if you want genuine sailing (not just ferrying) with flexibility to explore hidden spots and don't mind an early learning curve. Think twice if you need guaranteed Santorini port access or prefer a tightly scheduled, age-matched group.
- You actually sail and choose where to go next, hitting hidden caves and WW2 snorkel sites tourists never see.
- Skippers teach you sailing tasks if you're keen; anchoring at remote beaches beats standard ferry-hopping itineraries.
- You finish on Thirasia, not Santorini port itself; water taxi and bus transfers required, so clarify logistics beforehand.
- Meals and group cohesion less organized than expected; age mix can feel wide, so clarify your crew vibe upfront.
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 Aug is cheapest — from £909, about 61% below the priciest month (Jul).
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 · 31 Jul – 1 Aug
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