Thalassa Sailing

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Thalassa Sailing Daily and private sailing cruises around the Santorini caldera. Enjoy our delicious “meze” and sip renowned Santorini w**e.

For those adventurous souls seeking an authentic connection to the unique history of the volcanic island of Santorini, we sail off into the deep blue waters on our cruise featuring stunning and breathtaking views of the water-filled caldera and the golden sun sinking into the sea. Dive into crystal clear blue waters and lough with newfound friends as the fascinating shoreline of the island slips by the side of the boat.

This sailing season’s closure is here with today’s story uploaded being a reminder and also proof that people who took o...
05/10/2026

This sailing season’s closure is here with today’s story uploaded being a reminder and also proof that people who took our sunset cruise were not only passengers, but dear guests. Many of them became friends by sharing a quiet, yet vivid friendship aura throughout the years.
Filoxenia /filoksen’ia/ at its sailing edition by sharing love and memories created on board filled by the mesmerising scenery of Santorini, the aegean breeze and colorful sunsets.

THANK YOU all very much for joining us this year, in the past or both! You are the reason we love what we do as hosts!

Take care sailors! 😉

See you in 2027!

Over And Out ❤️

Just in thy mould and beauteous in thy form,Gentle in roll and buoyant on the surge,Light as the sea-fowl rocking in th...
13/09/2026

Just in thy mould and beauteous in thy form,
Gentle in roll and buoyant on the surge,

Light as the sea-fowl rocking in the storm,

In breeze and gale thy onward course we urge,

My water-queen!

Lady of mine,

More light and swift than thou none thread the sea

With surer keel or steadier on its path,

We brave each waste of ocean-mystery

And laugh to hear the howling tempest’s wrath,

For we are thine.

My brigantine!

Trust to the mystic power that points thy way,

Trust to the eye that pierces from afar;

Trust the red meteors that around thee play,

And, fearless, trust the Sea-Green Lady’s star,

Thou bark divine!

From the “Water Witch”- J. F. Cooper 1789-1851

There is a crack in everything, that ‘s how the light gets in
08/09/2026

There is a crack in everything, that ‘s how the light gets in

Mind the gaps. They are full of Sunset 🌅
22/08/2026

Mind the gaps. They are full of Sunset 🌅

Oia’ s Castle on the top serving its purpose: watching out for possible pirate invasions.Beware! Pirates Are Coming ⚓️ ...
11/08/2026

Oia’ s Castle on the top serving its purpose: watching out for possible pirate invasions.
Beware! Pirates Are Coming ⚓️

Sunkissed
10/07/2026

Sunkissed

Nothing beats sunset’s orange
30/05/2026

Nothing beats sunset’s orange

Sky above, sea below, sailing in between
14/09/2025

Sky above, sea below, sailing in between

06/08/2025

Dakoutros Travel is...

🛳 Ferries/Air Tickets
🛌 Accommodation
🌋 Sea Excursions
⛵ Catamaran Cruises
🚐 Tours
🏄‍♀️ Activities
🍷 Experiences
📸 Services
..and so many more!

Contact us for anything you need on or off Santorini island.
👉 http://bit.ly/4m4qgY1

It takes two to pirate tango ☠️⚓️
29/07/2025



It takes two to pirate tango ☠️⚓️

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Fira
Firá
84700

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