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Greece flotilla: 14-nights Greek Cyclades flotilla


Join our legendary flotilla sailing adventure in Greece. For over 20 years we've been guiding our flotilla so you rest assured that you'll be part of a researched itinerary where you'll visit a mix of mythological, historical and stunningly beautiful islands. There are typically no more than six yachts on our flotillas so you'll have a more cultural sailing holiday delivered by our crew and guides. Along the way, you'll make new friends while sailing, relax on stunning beaches and savour the finest gastronomy and nightlife Greece has to offer! 

Greek writer Nikos Kazantzakis wrote "Happy is the person who has the good fortune to sail the Aegean Sea. Nowhere else can one pass so serenely from reality to dream."The dream is to immerse yourself in traditional Greek life and let each day bring a new port with a new adventure. 

What's special

  • 14-nights both the Saronic and Cyclades
  • Milos or Kithnos under the stars
  • Hydra no cars just donkeys
  • Ios beaches, bars and lots of fun
  • Santorini 2-nights on-shore excursion mid-way
  • Mykonos nightlife
  • Paros shopping and sites
  • Kea rural retreat

Flotilla info

  • Intermediate/advanced sailing
  • Experienced flotilla crew
  • Monohull or catamarans available
  • Yachts suitable for 2 or 10 people 
  • Unique cultural itinerary
  • Great sailing
  • Fun excursions and social activities
  • Wonderful restaurant guidance
Trip photo gallery

Each day your Greek island adventure will have planned excursions to make for an unparalleled adventure. 


Sailing is a fantastic way to see the Greek islands, but if you've never sailed before then watch this 5 minute video to see what it's all about. 


14-nights Athens to Athens
Athens-Aegina-Poros-Hydra-Milos or Kythnos and Sifnos-Ios-Schinoussa-Delos-Mykonos or Syros-Kea-Athens. 
The islands may vary due to weather but in general these are the groups of islands visited. 

Dates and rates

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Please note: Flotilla fee is a minimum fee and does not change if yachts do not stay together for the full duration. Itinerary is subject to weather and may change for safety and experience of the flotilla sailors. Pricing is subject to change without prior notice. Departure dates are subject to availability and discounts may change based upon the number of bookings received. A booking is not confirmed until a deposit payment is received and at that time no further discounts will be offered.


Your specialist for sailing holidays in Greece and sailing holidays in Croatia. 20 years experience in yacht charter and flotillas in Greece as well as yacht charter and flotillas in Croatia. We are recognized by the Greek National Tourist Organization US and Canadian offices.

Poseidon Charters | 1246 Bayview Drive | Woodlawn | Ontario | K0A 3M0 | Canada
Poseidon Charters INC is a Canadian federal chartered company
Company registration 3568792

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