It is mid-summer, the temperatures are up in the high 30s and there can surely be no better way to explore the shimmering Aegean Sea than under sail. At this time of year the unpredictable Meltemi winds give gentle relief as we follow our Cycladic Journey, although we know they can turn wild at any moment.
I am on board Star Clipper, a luxury small cruise ship, traversing the waters surrounding the Cyclades Islands in Greece. So named because they form a ‘kiklos” or rough circle around the spiritual centre of Delos, the Cyclades bathe in history and legends that span thousands of years.
Our journey is a tapestry of biblical tales and ancient myths weaving together Gods, Kings, Emperors, Conquerors and Crusaders. The centuries seem to merge into one as I dip into the myriad of antiquity and civilisations. Stephen Fry’s Odyssey is my reliable companion throughout.

Roaming the isles
On our epic journey, we drop anchor to roam along the worn paved streets of the Roman Capital of Asia Minor that is Ephesus dating back over 3,000 years. We climb 269 steps to the 11th century Byzantine Monastery of Hozoviotissa in Amorgos and then drift back to the third millennium B.C. to wander amongst the Hellenist remains on the sacred island of Delos, dedicated to Apollo and Artemis.
Once the greatest commercial centre in the world, Delos bears witness to tales of destruction and death but there is still a sense of a prosperity among its proud decay.
In Greek mythology, Odysseus himself was marooned on one of these islands for seven years during his plight to find Penelope after the battle of Troy, with the pair finally reuniting in Ithaca.

The sense of bloody battles, piracy, misfortune and victories is never far from mind and our expert guides work hard to impart their knowledge of this powerful past. There is tangible evidence of great lives having been lived and lost wherever we go.
The origin of words such as agora-phobia (busy market and fear of crowds); acro-polis (city built in a high place) and pyro-graphy (fire and writing, meaning the art of burning words into wood) are all revealed by our guides.
Alongside all its history and evidence of a ‘glorious’ past, the Greek Islands’ quaint fishing villages; secluded coves; dazzling white and blue houses and iconic windmills also never disappoint. Crafts and culture remain high on the list of priorities for most visitors as do the traditional Greek tavernas with their grilled octopus and spit-roasted lamb.
Life onboard
For those who prefer dangling their toes over the Aegean to clambering over ancient ruins, life on board Star Clipper exceeds expectations too. Our elegant, stately, floating home for seven days proudly creaks in nautical history.
Built in 1992 along the lines of a 19th century sailing vessel, Star Clipper is a four-masted barquentine with 21 huge sails. The vessel’s teak decks, complex rigging, canvas sails and polished brass fittings give a sense of authentic luxury. The fleet is built to sail in nearly all conditions and the engines are only used when there is not enough wind for them to move independently. Its big sister, Royal Clipper, is listed as the largest square-rigged ship in service today.

White-uniformed officers and multi-national crew are always happy to chat and the cruise director is a mine of information on all things maritime, history and geography. This week we have 93 passengers (full capacity of 170) from 14 countries onboard.
The ship spirit is one of fun and relaxation with the added dimension of educational talks in the Library where charts and books are left out to pour over together. Optional educational excursions run every time the vessel sails into port and the queue for tenders is short and orderly. I hear one passenger describe the tone of the ship as “old school”.
Early risers can perch on the fore net to watch the sun rise and spot for dolphins, while the more energetic can climb up to the crow’s nest to take in the view. Two small pools are ideal for a quick dip and a shaded decking area is set out for relaxation. Open-air yoga, aqua aerobics and keep fit classes are a daily option.
Family affair
I estimate the average age of the other passengers is around the active sixty mark, but there is also a multi-generational family onboard, who I’m glad to see are making use of every activity on offer. Everyone is encouraged to get involved in the daily sailing routine onboard which can involve hoisting the sail and even taking the helm (under the watchful eye of the captain!)

On beach days the ‘fun team’ takes paddle boards and diving gear onto the shore, and with its draught of six metres, Star Clipper can slip into shallow depths where cruise ships would not dare to venture.
We take our meals in the Clipper Dining Room for a self-service buffet breakfast and lunch and waiter service in the evenings. Seating is informal and guests tend to move and mix in tables of up to eight.

There are theme nights and entertainment for those who want to join in, such as white nights, pirate nights and talent shows and the crew are always up for the fun. We spend our evenings around the Tropical Bar where dress is informal, dancing is expected and star-gazing is a must.
There is no question that ‘sailaways’ are the most iconic spectacle of our cruise. With everyone on deck as the anchor is weighed, Vangelis’ powerful Conquest of Paradise plays over the PA.
As the sails slowly unfurl the winds blow us back to our adventure.
Book it
Star Clipper sails year-round spending summer in the Mediterranean and winter in the Caribbean and Central America. Our Aegean Sea itinerary took us from Piraeus in Athens to Kusadasi, Patmos, Amorgos, Mykonos and Spetses.
In 2026 Star Flyer takes up the route with sailings on July 11, August 1 and 22 and September 12 calling in at Sifnos instead of Spetses. The cruise-only price based on two adults sharing leads in at £1,893pp.



