Sailing Holiday
  • Yacht charter
  • Qualified skipper
  • Charter Pack
  • Air-conditioning
  • Linen & towels
  • Generator
  • Bow thruster
  • Damage waiver
  • Dinghy & Outboard
Not Included
  • Flights & transfers
  • Travel Insurance (mandatory)
  • Security bond (reduced to $950)
  • Fuel consumption
  • Berthing fees
  • Provisioning

$4,680 per person, twin share
Single supplement available

In conjunction with Charter World Yachting Holidays

Can't Join Us This Year?

If you can’t join us for this year’s sailing holiday, we’ve got you covered! Register your interest now for next year’s sailing adventure, and reserve your spot on the same boat, on the same dates, for another amazing journey through the Greek islands.

Island Hopping Through Greece,
But Knot As You Know It

Sailing The Cyclades

Soz, 2024 if full, Info on 2025 coming soon!


A Greek island holiday is high on many people’s lists, but to see true Greece, you need to sail through the islands. Picture it – waking up in the Mediterranean and jumping into its blue waters, docking up at a taverna serving smoked fish before sharing a shot of ouzo with local fishermen.

Greek culture revolves around boat crews and industry. Practice your sailing skills while embarking on an adventure of a lifetime. What more could you ask for? “Yamas!”

The Itinerary

Athens to Athens (14 day round trip)

Setting off from Athens, we’ll visit the stunning anchorages of the Cyclades — Hydra, Poros, Kea, Kythnos and more. With each trip being unique, no two sailings are the same, with the exception of fixed start and end points. We embrace the spontaneity of the Cyclades and we adapt the itinerary to suit the group’s preferences. While we strive to visit the desired locations, our priority is ensuring the safety and enjoyment of everyone on board. The itinerary may be adjusted or modified as necessary to ensure a smooth and pleasant sailing experience.

Poros is a charming island in the Saronic Gulf, known for its picturesque orange-roofed houses and vibrant harbour. Indulge in delicious Greek cuisine while enjoying breathtaking sea views at waterfront cafes and tavernas.

Hydra is a haven of traditional architecture, featuring stunning stone mansions and narrow cobblestone streets that create a charming atmosphere. With no cars or motorcycles, the island is known for its peaceful ambiance. Explore the vibrant waterfront bars, witness the donkeys gracefully traversing the streets, and create unforgettable memories by parking your boat at the square-shaped wharf, a unique experience that always leads to interesting stories. Hydra promises a delightful blend of history, tranquility, and vibrant coastal vibes.

Discover Kithnos, a hidden gem offering serene beaches and a laid-back atmosphere. Visit the island’s hot springs, relax in the therapeutic waters, and indulge in fresh seafood at tavernas located right on the beach.

Sail to Kea, a tranquil island with pristine beaches and hiking trails. Relax on the sandy shores, hike to ancient sites like the Lion of Kea, and enjoy a traditional meal at local tavernas overlooking the sea.

A captivating island famous for its unique rock formations and stunning beaches. Visit the remarkable Sarakiniko Beach, the catacombs of Milos, and the picturesque fishing village of Klima.

Our Yacht

Sail in Style on board the Jeanneau Sun Odyssey 519

The 52-foot yacht offers air-conditioned accommodation on a twin-share basis, with linen supplied. The yacht is handled by a qualified Skipper with years of experience. You choose your involvement level – sit back and relax or get involved in trimming and helming the yacht.

Client Experiences

“For good company, the best fun, excellent sailing, great Greek food and wines Terry’s Pacific Sailing School Greek Islands sailing holiday ticks every box. Not to be missed if you can possibly do it. Definitely all 5 Star and highly recommended.”

– Jonathan Bell, 2018 trip

“Where do I start…! The memories of sailing feel like it was just yesterday! Seamless transfers, an experienced and very knowledgeable crew made it a stress-free holiday filled with exploring ports, mixing with locals, many sunsets on board or in bars with a cocktail or two, and fun-filled inaugural yacht races in fancy dress. It was just magic! (Bed sheets came in handy… lol!) An experience you will hold onto for many years to come…! “

– Lee Gross

Jump aboard our Greek adventure

Register your interest in this year’s sailing holiday or secure your spot for next year’s (2024) sailing adventure by filling out the form below, and we’ll be in touch with more information.

Register Your Interest


Spaces are strictly limited, so get in quick!

Your name:

Your email:

Contact number:


A Glimpse into our 2018 Greek Islands Trip

Frequently Asked Questions

What experience do I need to have to join this sailing holiday?

No prior sailing experience is necessary. Our qualified skipper will guide you through everything you need to know and ensure you have a safe and enjoyable trip.

Can I bring a friend?

Absolutely! We encourage you to bring a friend along on this adventure. Many of our clients have years of sailing experience and often bring a friend or partner who may not be familiar with boats. Our experienced crew will ensure that everyone feels comfortable and has a fantastic time exploring the Greek Islands.

How many people can join the sailing holiday?

Our Jeanneau Sun Odyssey 519 can accommodate up to 10 people in three to five cabins, depending on the configuration.

Are flights and transfers included in the pricing?

No, flights and transfers are not included in the pricing. You will need to arrange your own travel to and from Athens.
Many guests choose to stay at Poseidon Athens Hotel, nearby to Alimos Marina where we will board the yacht on the start date of the sailing holiday.

How much sailing should I expect?

On our sailing holiday, you can expect a wonderful balance between sailing and relaxation. While it is a sailing holiday, we understand that it is also your vacation. The distance between the islands can vary from 10 to 48 miles, and the itinerary may slightly adjust based on weather conditions to ensure your safety and comfort.

We encourage everyone to get involved and be part of the sailing experience. Our crew fosters a team spirit and welcomes everyone to participate in navigating, hoisting sails, and steering the yacht. However, if you prefer to simply sit back, relax, and soak in the beautiful surroundings, that’s absolutely fine too. It’s your holiday, and we want you to enjoy every moment in a way that suits you best.

Is travel insurance mandatory?

Yes, travel insurance is mandatory for all participants.

Booking Conditions

  • Deposit $2,000 – non-refundable
  • Greek Islands Balance due 1st June 2024
  • Cancellations after the receipt of the deposit, which is non-refundable will be only made if an alternative replacement can be found and any refund of the balance of the cost of the holiday will be at a reduced rate to be determined by PSS. If no replacement can be found 60 days prior to the departure date, there will be no refund of the balance of the booking fee.

See our standard Booking Conditions