Discover the Greek islands on a laid-back sailing adventure

A view of Amorgos. Image credit: Shutterstock/Pawel Kazmierczak

 

My journey on this magnificent, three-masted ship took me to Patmos, Amorgos, Naxos and Syros, with overnights in Amorgos and Syros. Perhaps because of the extra time in each, these two islands proved to be my highlights.

 

Amorgos cast a spell so absolutely intoxicating that even now, months later, I remain addicted to the fantasy of moving there. 

 

Almost nightly, I go online to check out long-term rentals, hoping that the just-before-bed exposure will animate those images during my sleep and transport me there at least until morning.

 

The island is a wanderer’s dream – and how I wandered. Down narrow cobbled streets, discovering tiny tavernas where locals sat talking over ice-cold Mythos beers, shielded from the sun beneath brightly coloured canopies; past a bakery that served Greek coffee so thick you could almost chew it; in and out of pottery shops that sold handmade this and that; going into churches to be comforted by the ritualistic lighting of candles for loved ones no longer with me.

Hozoviotissa monastery, Amorgos. Image credit: Shutterstock/Aneta Moscicka

 

What a day. Despite the sensible advice to climb to the Monastery of Hozoviotissa in the early morning or late afternoon, I sweated and sizzled my way to the top under the glare of a relentless midday sun. The reward when I reached this remarkable eight-floor structure, carved into the cliff-face 300m above sea level during the 11th century, made up for my efforts a hundredfold.

 

Greece’s second-oldest monastery is a labyrinth of rooms connected by the narrowest of steps, with an icon-laden chapel at its heart and views of the Aegean that stretch to infinity. 

 

It might not be so difficult to find God in such a place.

 

Back on Amorgos the next day, I took a walk along a barely trodden path that, after about 20 minutes of stumbling, seemed like it would lead to nothing. Ever the optimist, I continued, until I found the tiniest, shrubbiest beach and went for one of the best swims of my life.

 

The water was so clear and inviting, the scenery so picturesque, with Sea Cloud II hovering in the frame not far from a dazzling white church with its blue-domed cap. This was a place made for falling in love – with Greece, with your companion, with your own life.

 

What it’s like to sail with Sea Cloud Cruises

Sea Cloud II. Image credit: Islas Helicopters

 

The other islands provided similar opportunities for moments of complete contentment. There were more churches, including, on Patmos, the Cave of the Apocalypse where St John is said to have had the visions that would become the Book of Revelations. Plus more lazy beers in tavernas alongside aged men counting out the hours in backgammon games and staring, comfortably silent, out to sea.

 

Life on board the ship was equally mellow. In contrast to gargantuan floating resorts, Sea Cloud II and its sisters – Sea Cloud and Sea Spirit – bring calm, elegance and refinement to the oceans.

 

Gentle and genteel Sea Cloud II accommodates 94 passengers in 47 traditionally decorated cabins – polished dark wood, heavy full-length curtains, large windows with sea views and marble bathrooms – offering a design aesthetic that evokes the golden age of sail.

 

Its teak decks do not host yoga at dawn or sunset, nor tribute bands and bingo nights. Instead they have wooden tables and loungers where passengers can relax, catch the sun or catch up with reading.

 

The entertainment comes from conversations with fellow passengers, the occasional lecture and activities, including an olive oil tasting and a cocktail masterclass. The nightly live piano music on the Lido Deck is a joy – and for one night only, the passengers had a chance to join in, first by singing along to sea shanties and then prancing around to middle-aged classics from Abba, Tom Jones and Black Lace’s Agadoo, to which I most certainly Agadidn’t.

 

Other activities included climbing the rig, swimming off the ship within a safely demarcated area and enjoying the theatre of watching the crew releasing the 23 sails – a drama that never tires.

 

Given the ship’s dimensions, it was impossible not to meet people.

 

Mealtimes – with drinks included, even at breakfast where a bottle of fizz waited on ice alongside the fresh juices and smoothies – were a convivial affair as friendships formed around the dining tables, some of which sat 10.

 

The food at all times was superb: a generous buffet at lunch that always had a wonderful selection for vegetarians, as well as beautifully prepared whole fish, poultry and meat, even a roast hog at one sitting.

 

The dinners were sumptuous four-course affairs, except for the gala dinners, when that count went up to five. They lacked just one thing, though: the pomp and ceremony of evening dress. For someone like me, who is much more at home in walking shoes with a wardrobe ill-prepared for razzle-dazzling, this relaxed atmosphere was what elevated the cruise from excellent to absolutely perfect.

 

The teak deck on Sea Cloud II. Image credit: diginetmedia

 

 

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Book it

 

Sea Cloud Cruises’ Summer Breeze Through the Aegean costs from €4,550 and departs Piraeus, Athens, on July 17, 24 and 31, 2026. The cruise visits Amorgos and Milos in the Cyclades and Nafplio and Poros in the Peloponnese.

 

The all-inclusive fare covers all meals, including a nightly four-course meal and five-course gala dinner; wine with meals; complimentary drinks throughout the day; gratuities and port fees, a welcome bottle of champagne and some excursions.
seacloud.com

 

 

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Selling points of sailing cruises

 

Price: It’s certainly not cheap, but you would be very unlikely to find your clients a four-destination, five-star option on land that included all meals, drinks, gratuities and a few excursions for less money.

 

Convenience: The stress-free holiday existence starts from the minute clients get on board. There’s no need to pack and unpack or spend hours travelling by road or air – the journeys between islands are all part of the joy.

 

Variety: With four destinations to explore in one week, there’s enough time in each place to get a feel for the location and fit in shopping, swimming, visiting a museum or stopping to enjoy local snacks.

 

Relaxation: Once on board there is no pressure to always be doing or seeing something, guests can spend the hours just being – and appreciating the joy of this traditional mode of travel along the way.

 

Lead image credit: Shutterstock/Georgios Tsichlis