Cruising the Greek Islands never appealed to me. This trip changed my mind

Istanbul cruise terminal knocks Istanbul airport for six. Sleek as a contemporary art museum, it looks over the hum and chug of one of the world’s most historic harbours. It’s an anteroom to the Mediterranean.Plaka on the island of Milos.iStockThe first thrill – technically, not quite the Mediterranean – is sailing out of Istanbul as an orange sun collapses onto the turrets of Topkapi palace. Next morning my ship, Explora II, squeezes through the Dardanelles and into the Aegean. How can you not be delighted to be on a luxury ship in a place so rich in maritime lore?Greece was the first place I visited as an independent adult. I’d just turned 18 and rumbled about the mainland in buses, hitchhiked when I needed to and racketed around the Greek islands on ferries that stank of oil and rust.I never thought I’d be cruising the Greek islands. I’m not sure I knew cruise ships existed because I grew up far from the coast. Eventually when I did know, I thought they’d never be for me.Things have moved on, not least my open mindedness, greater need for comfort and lowered patience for travel’s irritations. While I’d never travel exclusively by cruise ship, they’re an enjoyable respite from do-it-yourself galumphing.Sign up for the Traveller Deals newsletterGet exclusive travel deals delivered straight to your inbox. Sign up now.Case in point, getting from Istanbul to Milos with sophisticated cruise line Explora Journeys, which takes no effort on my part. We sail into Milos’ well-concealed bay, which has a narrow entrance but widens out between parched brown hillsides scattered with white buildings. The ride ashore via tender takes only minutes.Hard not to feel smug on the deck of this ship as I see sweaty travellers hauling suitcases down the gangway of an inter-island ferry, looking tired and harassed. Sure, you can do the Mediterranean on your own and much cheaper but, if you have the choice, why would you?The naysayers who criticise cruising have seldom been on a cruise. And look, there are aspects of cruising – like any form of travel – that I don’t like either. You can be cut off from the local experience, but that argument doesn’t cut it in the Greek islands.Sitting in a resort won’t get you a more local experience. Nor will doing it by ferry or plane, but it will take up a great chunk of your holiday time. Not so on a cruise ship. The tedious transportation is taken care of while you sleep, and next day you’re somewhere new in an abracadabra of ease.You can be off the ship all day and slurp up all the local experiences you want. In Milos I’m off on the public bus to hilltop Plaka for a gloriously scenic walk that I share with only two other tourists. Then I walk down to Klima through dilapidated fields that smell of rosemary and goat, and don’t meet a single person.The fishing village of Klima on Milos.iStockThe experiences you have wherever you go, whether by cruise ship or otherwise, is the result of your choices. A cruise ship is merely the facilitator. Besides, it presents you with a maritime perspective you won’t otherwise get. You never see the bad side of Greek islands from a cruise ship.All you get is blue sea, rusty rock, golden cliffs, hot skies. Over the centuries, islanders have added blue-domed chapels and whitewashed windmills, castles and fishing ports. You won’t see an airport terminal or a carpark. Almost every view is worthy of being featured on a postcard or printed calendar, if such things still exist.The ship is well-matched to the Greek islands. It is light-filled, breezy, unfussy and serene. Its subdued decor doesn’t try to compete with the explosion of colour outside.The ship has no formal dress code, hardly any tablecloths, and little fuss despite the luxury levels. Who would want to sail here and squeeze into a dinner jacket?Comfort and ease aren’t the only reasons that cruising is the way to go in Greece. Most islands can be appreciated in a single day, and you get an overview of several in a short time. They’re often further from the crowds than you might think.You aren’t going to escape the tourist hordes in Greece all of the time, and that time is Rhodes on my cruise. But choose an itinerary that takes in less well-known islands, too, and you’ll be richly rewarded.Samos is one of the Greek Islands that hasn’t yet been overwhelmed by tourists.iStockMilos, Samos and Paros haven’t as yet been carbuncled with luxury resorts and nightclubs. Life here hasn’t been overwhelmed by the jetsetters and Instagrammers who play and party on Santorini and Mykonos.You can head into the interior and hike amid landscapes that would make a petulant Greek god smile. Hills are stitched together by dry stone walls. Windmills are white, church domes blue, the window frames of houses green and red. Chapel interiors glimmer gold. In the village of Podromos on Paros I eat in a cafe surrounded by retirees swinging worry beads.As the ship sails away, I can enjoy a sunset without being jostled, as the blue-and-white colours of the Cyclades morph into orange and red. As evening falls, there are no thumping nightclubs and raucous stag parties, just a twinkle of stars, the muted burble of a fishing boat’s engines, the black outline of islands and a good dinner.One of Explora II’s four pools. Explora II has numerous restaurants, and no complaints about that. I can hop from Japan to France to the American West for an aged black Angus steak from a fine beast that might have been lassoed by a cowboy.But I keep wandering back to Med Yacht Club. For a start, I like its jaunty nautical theme: model ships, porthole-shaped windows only far larger, contemporary contours.I like its cuisine, too. The menu rambles gently across the Mediterranean, sometimes unexpectedly, such as in tomato and strawberry salad with burrata. I can have a Greek meal here: shrimp saganaki, grilled octopus, some fine fish with a splash of lemon and herb salad. No baklava for dessert, but I’m not grumbling about the hazelnut semifreddo.Nothing about the ship will irritate anyone, not even the princess with her pea. But I have to admit that one annoying thing is the bed because I seldom want to get out of it. I dare say it’s the best bed at sea.But still, it can’t compete with the Greek islands. I wrestle with my urge to snuggle down and amp up early, ready for the next arrival. I never thought I’d cruise the Greek islands, but never say never is a good philosophy to travel by.THE DETAILSCruiseExplora Journeys offers various cruises in the Greek islands on regular departures until mid-November 2026 and resumes from March 2027. None match the itinerary described here but each is similar in spirit.A seven-day “Journey Through Mythical Isles” cruise between Piraeus (Athens) and Istanbul visits Nafplio, Paros, Skiathos, Volos and Kusadasi. Departs May 10, 2027, from $6950 a person twin share including dining, beverages, Wi-Fi and gratuities. See explorajourneys.comMorevisitgreece.grThe writer travelled as a guest of Explora Journeys.Brian Johnston seemed destined to become a travel writer: he is an Irishman born in Nigeria and raised in Switzerland, who has lived in Britain and China and now calls Australia home.From our partners