Greek island cruises

About Greek island cruises

By the ULTIMATE Athens Editorial Team

The Greek islands were made to be seen from the sea. Whether you sail into Santorini’s volcanic caldera on a cruise liner, drop anchor in a quiet Cycladic bay on a small ship, or set your own course on a sailing yacht, here is everything you need to know: the different ways to cruise, the classic itineraries, the best time to go and the companies to book with.

Three ways to sail the islands

Seen from the deck of a ship, the Greek islands make sense in a way they never do on a map: one after another they rise out of the sea, each with its own harbour, its own white town and its own story. There are three very different ways to do it. A cruise liner is the easiest, with your hotel, restaurants and entertainment sailing with you. A small ship or motor cruiser takes you to quieter islands and lets you swim from the side of the boat. And under sail, on a tall ship or a yacht of your own, you travel the way the Greeks have for thousands of years, with the wind deciding the pace.

Cruise liners: the classic Aegean voyage

Piraeus is one of the busiest cruise ports in the Mediterranean, and every summer week dozens of ships set out from here or call on longer voyages around the Eastern Mediterranean. The favourite stops are Mykonos and Santorini, often with Crete, Rhodes or Patmos, and sometimes Kuşadası in Turkey for the ruins of Ephesus.

Seen from the deck of a ship, the Greek islands make sense in a way they never do on a map.

The Greek line Celestyal specialises in these waters, with short cruises of three to seven nights from Piraeus, while the big international lines, such as Royal Caribbean, Norwegian, Celebrity, MSC and Princess, include Greek islands on week-long or longer Eastern Mediterranean itineraries. At the luxury end, smaller ships from Silversea, Seabourn and Ponant can reach islands the big ships cannot.

Arriving at Santorini is unforgettable. Big ships cannot dock, so they anchor in the flooded volcanic caldera and passengers are taken ashore by tender boats to the old port below Fira. From there you climb to the town by cable car, by the long stepped path, or, as tradition has it, on a donkey, though many visitors now choose to walk. On busy days the queues for the cable car can be long, so go ashore early or book a shore excursion that includes your transfer.

Small ships and motor cruisers

If you would rather wake up in a little harbour than in a big port, a small-ship cruise is the answer. Greek family companies such as Variety Cruises sail small ships with a few dozen cabins around the Cyclades, calling at islands such as Milos, Folegandros, Sifnos and Delos that big ships rarely visit, and stopping in quiet bays for a swim from the boat. The atmosphere is relaxed, the dress code is casual and you get to know your fellow passengers.

For complete freedom, you can charter a crewed motor yacht from the marinas of Alimos or Glyfada, with a captain, a crew and often a cook, and design the route yourself: a long lunch in a bay on Kea, a night in Hydra’s harbour, a dawn swim off Milos.

Under sail

There is nothing quite like the islands under sail. Star Clippers sails tall ships, modern square-riggers with billowing white sails, on summer voyages in Greek waters, and passengers can help with the sails or simply lie in the nets over the bowsprit and watch the sea. Windstar’s small ships, some with sails, offer a similar romance with a little more luxury.

Many visitors charter a sailing yacht. Companies such as Kiriacoulis, Istion, Sunsail and The Moorings have fleets at Alimos and Lavrio, near Athens. You can hire a yacht bareboat, if you hold a recognised sailing licence and have the experience to handle Aegean conditions, take a skipper who knows the waters, or book a fully crewed yacht and simply relax. Sailing from Lavrio, the western Cyclades are within easy reach: Kea, Kythnos, Serifos and Sifnos make a wonderful week.

Sample itineraries

Short liner cruise, three to four nights: Piraeus, Mykonos, Kuşadası for Ephesus, Patmos or Rhodes, Crete and Santorini, then back to Piraeus. A great taste of the islands if you have only a few days.

Small-ship week in the Cyclades: from Piraeus to Syros, Mykonos and Delos, Paros or Naxos, Santorini, Folegandros and Milos, with swimming stops along the way. Each day brings a new island, and you unpack only once.

Sailing week from Lavrio: Kea, Kythnos, Serifos and Sifnos, then back by way of quiet anchorages. When the summer wind is strong, the sheltered Saronic Gulf, with Aegina, Poros and Hydra, is a gentler alternative.

When to go

The cruise season runs from April to October, and the best months are May, June and September, when the sea is warm and the islands are calmer. In July and August, the meltemi, a strong north wind, blows across the Aegean, which can make the sea rough, change a ship’s route or keep sailing yachts in port for a day. Big cruise ships are rarely affected, but if you are sailing, build some spare time into your plans.

Cruise or ferry?

A cruise is perfect if you want to see several islands without packing and unpacking, with everything organised. The downside is time: on a liner you often have only a few hours ashore, and you arrive with thousands of other passengers. Island hopping by ferry, as in our ultimate island hop, lets you stay longer, sleep on the islands and discover them at your own pace. Many people do both: a short cruise for a first taste, then a return trip by ferry to the islands they loved.

Our advice: book early for summer, especially for small ships and yacht charters, which sell out. On a liner, check how long you will have at each port, and at Santorini go ashore on the first tenders. On a sailing holiday, pack light and soft-sided, bring reef-safe sun cream and a hat, and always listen to your skipper about the weather.

Cruising at a glance

Cruise and charter itineraries change every year; check the latest routes and dates with each company before you book.

Opening hours, prices and seasonal openings change, so please check with Greek island cruises before you go.