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Greece

Sailing Greece - Santorini to Santorini

Start & end in Santorini 10 days Up to 10

About this trip

Ten days aboard a 57ft yacht, sailing round-trip from Santorini through the Greek islands. Days mix time at the helm with stops to swim, hike and wander harbour towns.

Expect a rhythm of sailing, snorkelling stops, and evenings ashore at taverna-lined harbours, with fresh seafood and a glass of ouzo part of the routine.

This is a small group trip with a private cabin for you, moderate in pace — active enough with hikes and time on deck, but built around the sailing itself rather than a packed itinerary.

What you'll do

  • Sail round-trip from Santorini aboard a 57ft yacht
  • Snorkel in coves and bays along the route
  • Hike stretches of coastline and island trails
  • Visit ancient archaeological sites
  • Eat fresh seafood in taverna-lined harbours
  • Try ouzo in a harbourside taverna
Good to know
  • Moderate pace — a mix of sailing, hiking and downtime rather than constant activity
  • Private cabin included, but you're sharing yacht life with the rest of the group
  • Days are shaped by wind and weather as much as by plan
What travellers actually say

Worth it if you're keen on sailing, don't mind tight quarters, and want a skipper-led adventure. Think twice if you need privacy or creature comforts.

  • Skippers are genuinely excellent teachers—guests learned hands-on sailing, navigation, and mooring, not just sightseeing.
  • Small group dynamic works. Solo travellers and strangers bonded quickly; skippers knew local spots and arranged meals, swimming, snorkelling.
  • Cabin accommodation is austere and spartan; expect bunk-style sleeping quarters, not comfortable private cabins.
  • Trip avoids tourist crowds by design; you get quieter islands and authentic experiences, not Santorini town bustle.

Distilled from real traveller reviews on TourRadar — we don't edit out the bad bits.

Tour dupe
Same trip, less money
£315 less all-in
Sailing Greece - Mykonos to Santorini
4.6from £9098 days
The trade-off: 2 fewer nights, and a different operator.
See the dupe
How it compares

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.

Best month to go

Departing in Aug is cheapest — from £1,210, about 63% below the priciest month (Jun).

Aug
Sep
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Aug

Getting there

Santorini
One-way · arrive 9 Aug 26

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 · 9 Aug10 Aug

Booked on their own sites, separate from your tour. We may earn a commission — it never changes your price.

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