Sail the Legendary Greek Isles: Top Islands to Explore by Boat

More than 6,000 islands surround mainland Greece, though only about 230 are inhabited. Beach lovers flock to the pebble shores of Corfu, the dazzling white sands of Kefalonia’s Myrtos and the dramatic black-sand beaches of Santorini.

Food is a major draw on the islands. Regional specialties, freshly caught fish served in local tavernas, and an array of soft cheeses — from salty feta to sweet mizithra and peppery kopanisti — define the culinary scene. Don’t forget the briny Kalamata olives that appear on nearly every table.

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History enthusiasts will find castles, ancient ruins and whitewashed churches clinging to cliffs. A popular pilgrimage is the 223 stone steps up to the church of Agios Ioannis, made famous by the film Mamma Mia! After sightseeing, relax at a seaside taverna with chilled ouzo or a local microbrew and enjoy traditional bouzouki music. Plate smashing, once a folk ritual for good luck, became a modern-era party custom after Zorba the Greek, though it was later banned in tavernas for safety reasons.

Each island group has its own personality. The Ionian Islands, including Corfu, on Greece’s west coast evoke a charming, slightly old-fashioned tropical vibe. The Argo-Saronic islands (Salamis, Aegina, Poros, Hydra and Spetses) hug the east coast and serve as popular weekend escapes for Athenians. The northeastern Aegean islands are rugged and forested, with a wealth of archaeological sites. The Dodecanese, anchored by Rhodes, feature medieval walled towns and Crusader-era monuments. The Cyclades — a 56-island chain — include famous destinations such as Mykonos, Folegandros and Santorini. Crete, the largest island, lies roughly midway between Athens and North Africa and is rich in archaeological treasures, including the Bronze Age palace of King Minos.

Crete, Mykonos and Santorini are among the best diving destinations in Greece. Divers find reefs, caves, wrecks and protected marine parks. Certified centers offer night dives to witness bioluminescent plankton, nocturnal squid, octopus and morays, and to explore modern wrecks like the freighter Kyra Eleni (1978), the paddle steamer Patris (1868), the British submarine Perseus (1941) and the famed HMHS Britannic, sister ship to the Titanic, which sank in 1916 near Kea. Note that diving to ancient wrecks is prohibited.

How you experience the Greek islands depends on your interests, time and budget. From rugged, low-key isles to luxurious private-yacht charters, there’s something for every traveler.

Pontos Imperial Yachts, Ltd. caters to high-end clients seeking exceptional service. This third-generation, family-owned company offers lavish charters with chauffeur transfers from hotels to yachts, helicopter flights to remote islands, personal assistants and concierge access to top restaurants. Onboard amenities include king-bedded master cabins, his-and-hers bathrooms, indoor and outdoor dining areas served by private chefs, and an array of water toys — Sea-Doos, water skis, wake-surf boards and stand-up paddleboards — plus a crew to instruct guests. Experienced captains navigate Greek waters and tailor itineraries for secluded swimming spots, clifftop villages, dramatic canyon hikes or leisurely sunbathing on deck.

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Abercrombie & Kent runs intimate 10-day island cruises aboard chartered small ships that accommodate about 148 guests. These cruises feature private balconies, butler service and expert onboard teams including local guides and archaeologists. Typical itineraries mix iconic islands like Mykonos and Santorini with less-visited gems such as Patmos, Delos and Syros. Excursions often include exclusive wine tastings, behind-the-scenes museum visits, meetings with artisans, beach breaks with service on sheltered shores, and hands-on experiences like cooking classes at local farms and tavernas.

Silversea introduced the Silver Moon, a new ship with 298 suites and a 1:1 crew-to-guest ratio. Silver Moon’s S.A.L.T. (Sea and Land Taste) program focuses on culinary immersion: S.A.L.T. Labs host tastings and workshops with local chefs, S.A.L.T. Kitchen serves regionally inspired dishes and ashore excursions visit cheese makers, olive mills and local growers. Food-focused activities are curated to showcase island flavors and traditions.

Sailing remains the most romantic way to explore the islands. Windstar operates elegant sailing vessels and small all-suite ships that call at hidden Aegean ports such as Nafplio, Monemvassia and Patmos. Star Clippers’ tall ships recreate the golden age of sailing with teak decks and classic rigging; passengers can interact with the crew and even climb to the crow’s nest under supervision. Sea Cloud Cruises sails the historic Sea Cloud and Sea Cloud II, offering an atmosphere of old-world glamour with refined interiors and menus influenced by the islands.

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For those seeking quieter, less-developed islands, take a ferry, catamaran or hydrofoil to the small Cyclades like Iraklia, Schinoussa and Ano Koufonissi. These islands are simple and unpretentious: clean, modest accommodations and rustic tavernas, limited internet, more donkeys than cars, and few organized activities beyond swimming, lingering over meals and watching tranquil sunsets. A basic grasp of Greek and a flexible schedule help, and while luxury is scarce, the islands’ unspoiled charm is increasingly attracting visitors from Italy and Northern Europe.

INFO TO GO
Most international flights arrive at Athens International Airport. From there you can take a taxi or limousine to the port of Piraeus (about an hour) to board a cruise, or spend a night in Athens before departing. For independent island-hopping, several ferry companies operate inter-island services, offering options for schedules and budgets.