Amazing Experiences You Will Collect While Sailing the Greek Islands

by Julia on July 2, 2018

Beach Boys, Chris Janson, and Jimmy Buffett songs have all romanticized the sailing lifestyle; after all, something about boats brings out the inner adventurer in everyone! While sailing may not be for everyone, it is one of the best ways to gain new experiences – including collecting amazing Greek experiences.

At the mention of Greece, most people think white-washed houses, romantic sunsets, Mediterranean flavors and beautiful turquoise waters as far as the eye can see. This imagery is what makes the Greek Islands Europe’s most popular sea destination.

Greece is the proud host of more than 5,000 islands and islets; therefore, making a list of the most beautiful can be extremely difficult. To help you attain the most amazing experiences, here are some of the favorite Greek Islands that are worth checking out during your next flotilla holiday, click here for more details.


The first choice of Greek Island sailing destination is the famous and classic Santorini. If you are looking for a destination with plenty of water, some romance and a bit of nightlife, this is the island for you.

The area features ruggedly black sand beaches created from volcanic activity, and in stark contrast with the blue sea and Fira’s white houses. Fira is the village perched on the island’s western side where you can take in breathtaking views of sunsets.

Some of the best beaches in Santorini include the Red Beach, so named for its lava-colored sand. Other beaches you should stop at include Perissa, Kamari and White Beach.


Mykonos is Greece’s most famous cosmopolitan island that offers guests a glimpse into paradise on earth, right in the heart of Cyclades. Mythology says that Hercules created the island out of petrified bodies of the giants he killed. Plus, did you know that the island’s name is derived from Apollo’s grandson Mykonos?

Sail to the island and take on a journey that takes you through a fascinating world where simplicity meets glamour. Once on the island, families, college students and celebrities mingle to create a big celebration of the Greek summer. If you are an entertainment junkie or a history buff, Mykonos has something to offer everyone.

Unlike other Cycladic capitals, Hora, the island’s capital, spreads over an extensive area. Hora is home to some of the best examples of Cycladic architecture, narrow marble streets and whitewashed houses. A walk through the shopping streets reveals plenty of brand name stores, stylish restaurants, and charming cafes.

Mykonos is a paradise for the water sports enthusiast in you. While sailing, you can set dock at some secluded spots like Meyali, Kalafatis, and Korfos.


Myth describes the area around Icaria as the place where Daedalus’ son landed after his wax wings were burnt by the sun. It’s also said that Icarus rests to eternity on the Nikari islet. That is not all, Icaria is also linked to Bacchus; especially the area to the east of Drakano where it’s said the god was born.

Icaria is not only known for its associated myths, but it is also an island that offers visitors an exceptional hiking experience. The pristine land is largely mountainous and covered by a carpet of oak, cypress and pine trees. Under this carpet, the slopes of the island maintain their moisture, allowing wild goats to graze freely.

Some of the best natural attractions in Icaria are:

  • The forest of Radi

  • Chalaris’ Canyon

  • Aeolian park

If you are looking for high mountains and thick vegetation within reach of your sailboat, Icaria is the destination for you. The place is also known for gorgeous gorges and enchanting rivers.

Another thing Icaria is known for is its numerous feasts. The feasts happen almost daily in summer, either for social or religious reasons.

Locals create their own red, full-bodied wine from their vineyards. Also, the inhabitants boil or roast wild goat meat that’s consumed with potatoes and salads. In return, the visitors or islanders not taking part in preparing the feast pay a token price that goes into financing public works.


Callimachus, in the epic Ogygia, says that Calypso’s island was Gavdos. In fact, any local will lead you to the palace of the nymph near a cave.

Apart from its mythological background, Gavdos is known for hosting some of the most famous Greek fighters, including Markos Vafiadis, Aris Velouchiotis, and Partsalidis. Moreover, their houses remain standing up until today.

The island is one of southern Europe’s unique gems that is away from a bustling civilization with crystal blue waters, wild beauty, amazing beaches and breathtaking sunsets. Gavdos is the island where cedars reach the sea and definitely whose beauty deserves discovery any time you are sailing Greek islands.

The island is home to about 98 permanent residents, with the population easily hitting 3,500 in summer. Gavdos’ port is Karave, the capital village Kastri and is a good fishing place. Despite the low population, the island is home to some famous beaches, including:

  • Agiannis beach

  • Pyrgos beach

  • Potamos beach

  • Tripiti beach

  • Beach Diana at Aspecs


Paxi (or Paxoi) is a tiny island found in the Ionian Sea just south of Corfu. The island is famous for its exotic beaches that are close to the largely uninhabited island of Antipoxas. Paxi features three small seaside villages where fishing and sailing boats moor in summer.

The villages are full of studios and fish taverns. If you do not have your own boat, take advantage of the daily boats that depart from Gaios, Paxi’s main village to Antipaxos. While holidaying in Paxi, make sure you include Corfu and the opposite coasts into your itinerary.

Despite its small size, Paxi is a fairly cosmopolitan location with a huge range of accommodation options. The capital has a huge selection of charming guesthouses, villas, and studios where you can stay if you prefer staying on land.

The other villages on the island are Lakka and Logos. Paxi is home to many beautiful beaches with many of them located along the northern and eastern part while Antipaxos feature exotic waters. Other things to do and highlights around the island include:

  • Gaios village

  • Lakka village

  • Monodendri beach


If you are into adventure travel and looking to explore Greek’s rich wildlife, then the mountains and rough back roads of this island are a must-visit. While on Tilos Island, you have a unique opportunity to come into close contact with exotic birds and dwarf elephants. While the beaches are difficult to access and rocky, you will still get to enjoy the peace and quiet nature it has to offer – even at peak season.

The best beaches in Tilos are San Antonio, Red Beach, and Eristos. There is no airport service in the island, so the only way to get there is by boat from Athens, Mykonos or Pireo.


According to millions of tourists and travelers, these are the top destinations in Greece. Fortunately, most of the islands have not given up all their secrets yet, so there is still a chance for you to discover them. With a sailboat, you can reach all the islands, and fall even deeper in love than you had anticipated.

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