Greek Island Hopping and Sailing cruises

Posted by on June 15th, 2015 | Leave a comment | Back to overview

Admittedly sailing is the best way to see the Greek Islands. Greece is one of the greatest sailing hubs in the Mediterranean Sea with thousands of islands counting for up to a 20% of the total land and a 9000 mile coastline. There are just unlimited gems to explore from hidden bays and marinas, uninhabited islands, late night beach parties, secret tavernas (only known to locals) and so much more.

There’s just something about sailing from island to island that is unique; each has it’s own quite different character ( and local “characters”!) ; it’s own idiosyncrasies and ambiance. Be it a luxury yacht, catamaran or superb wooden Sailing Boat this is the best way to explore this country. So on your next trip to Greece be sure to make ‘space’ in your itinerary for the famous Greek Island Hopping.

Here are some of our favorite islands to explore on your sailing:

Sailing in Sifnos
Sifnos is a very hip, cosmopolitan island and its big port hosts hundreds of boats every summer. The most popular bay for docking is that of Vathy; well protected from the winds and the scenery is beautiful, with the long sandy beach and the three small taverns by the water.

Pinterest sailing in sifnos

Sailing in Serifos
Serifos is definitely not a cosmopolitan island, but it does have 72 stunning beaches. This is the island with an authentic Cycladic feel. Some of its beaches are only accessible by boat and they are definitely worth a visit. Livadi, where the main port is located, is a lively little seaside town. A little before sunset the bay of Livadi is filled with sailing boats that rock in the emerald waters.

pinterest sailing in serifos

Sailing in Spetses
Spetses is also a historical, cosmopolitan island, which boasts two ports. The main and the old one. Hundreds of sailing boats and yachts crowd the well organized marina, especially in June and September, when the famous Armata celebration takes place.

Sailing in Spetses

Sailing in Symi
Few islands have Symi’s crisp brightness and its amphitheatre ambiance of Neoclassical mansions, in soft ochre or traditional deep shades, stacked one on top of the other right up the barren hill sides. During the afternoon numerous ferries bring loads of tourist, but when these invaders depart, the sailing fraternity – flying flags from all nationalities – takes over, and the boulevard rejoices in a more gentil and relaxed air.

Pinterest Port of Symi Island

Sailing in Ios
The alternative corner of the Aegean during the 70s and 80s. Its fans have grown up now and have proper jobs but something of the atmosphere of those days is still preserved on the island. The whitewashed houses of Hora, its main village, hide some beautiful little shops and tavernas and a frenetic nightlife; yet there seems to be a movement towards serving for more sophisticated travelers. So watch this space. Its beaches are at par with the best in Cyclades and indeed the whole country (be sure to visit Manganari).

Pinterest Ios

Sailing in Hydra
Hydra is a historical, yet very cosmopolitan island. No beaches to show for and no vegetation. However, this rock with the amphitheatrically built mansions overlooking the small bay is breathtaking. Sailing and motor boats, as well as luxurious yachts crowd the marina and the entire bay between May and October.

Pinterest Hydra2

Pinterest Hydra

Sailing in Santorini
Santorini is one of the most popular destinations in Greece, renowned for the natural beauty of its volcanic origin. Sailing tours to the volcano and the hot springs make sailing a romantic exploration through the island’s history, offering travelers a lifetime experience. Nothing beats sailing during sunset around the volcanic little isles of Santorini.

Nisha Ravji5 Santorini

Nisha Ravji3

Nisha RAvji 4

Nikos Gogas5

Nikos Gogas3

Nikos Gogas2

Sailing in Mykonos
A cross between Capri and Ibiza (in its good days) but with a very cycladic feel, Mykonos boasts of the best beaches in the country, the craziest nightlife and the most luxurius yachts you’ll come across in the Greek Islands. Bring along the best pieces of your wardrobe (preferably white), all your energy and credit cards. The fact that world famous Japanese restaurant Nobu set up shop first in Mykonos and a few years later in Athens says a lot about the kind of holiday you should expect here.


Include some island hopping or cruising in your wedding plans.

Images compliments of: Andrea & Marcus // Nikos Gogas // Nisha Ravji // Pinterest



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