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Flotilla yacht sailing holidays & tours in Greece

Discover the magic of a sailing vacation in Greece! Flotilla: Come aboard together with your friends and experience an unforgettable summer. Find your dream cruise among thousands of experiences.

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The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Flotilla yacht sailing holidays & tours in Greece

435 reviews

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Sun & Fun Flotilla at the Ionian - Age 25/40

09/8/2024

Monica A.

First time for me on a sailing boat and I must say that it could not have gone better: I spent an unforgettable week! Formidable, balanced and well-assorted crew. Mattia has proven to be a super skipper, always professional, but "light" when necessary, an irreplaceable member of this wonderful crew! The only flaw: the difference between the boats in terms of size and comfort, an aspect that should be paid more attention to or at least clarified from the beginning (and that provides for any differences in rates).
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Sun & Fun Flotilla at the Ionian - Age 25/40

09/4/2024

Lorenzo B.

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Italy

A unique experience on a sailing boat, highly recommended for those who love the sea, life on a boat and fun. Beautiful Ionian islands, stellar crew, formidable Skipper (Mattia)! Lots of laughter and friendships born between a swim in the sea, a thousand toasts and a singing at the top of your lungs in the roadstead under the stars. What else? Marmaglia is on fire!
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Sun & Fun Flotilla at the Ionian - Age 25/40

09/4/2024

Giovanni D.

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Italy

An intense and exciting holiday that leaves its mark. Every day you visit a new cove, a place overlooking the sea like the famous windmills or you party directly on the boat and invite the whole flotilla. The organization is committed daily to creating opportunities for aggregation, fun and adventure. In those days the boat becomes their home and the crew their family. Seven days of intense experiences, with new friends who, once the holiday is over, you feel like you've known for a lifetime.
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Adventure Flotilla in the Gulf of Athens and Saronic Islands

09/3/2024

Federica N.

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Italy

everything perfect!

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6 reasons for a flotilla in Greece:

  • Meet new people and have the summer of your life
  • Let the sun shine on your face and the wind blow through your hair as you kick off the party with an aperitif aboard your yacht
  • Party the nights away while relaxing on deck during the day
  • Dance in the most famous clubs of the party islands like Mykonos and Co
  • Sail with many other party people and experience a week of fun, partying and laughter
  • Return with unforgettable memories and new friends

Places you should visit while flotilla sailing in Greece:

In the Aegean Sea are the Cyclades, the Dodecanese, the islands of the eastern and northern Aegean, and the Sporades. Between the Peloponnese and Attica are the Saronic Islands, and to the west toward Italy are the Ionian Islands.

The larger islands guarantee fun and entertainment. The smaller islands, on the other hand, have their quite unique charm, often consisting of just one small village, with a few typical restaurants along the seafront and characteristic bays where boats can dock. In the taverns ashore, unforgettable nights can be spent with typical Greek joie de vivre.

The Cyclades

If you are looking for an active and adventurous flotilla, the Cyclades are the right choice. The archipelago consisting of small islands of volcanic origin - located in the center of the Aegean Sea - attracts experienced sailors because of the good wind conditions. Typical for this region are white houses and monasteries perched on cliffs. Each island village awaits with its own unique charm and a perfect blend of narrow streets, historic buildings and golden sandy beaches.

Santorini, Naxos and Mykonos are among the best-known islands in the Cyclades, each known for its abundance of activities - from famous beaches to hip clubs. Small Cyclades like Ouzo, Metaxa and Mastika, on the other hand, are where you'll find traditional sirtaki dancing and soak up the local flavor.

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The Ionian Islands

If, on the other hand, you're looking for a gentler sailing experience for your flotilla in Ghent, the Ionian Islands are the perfect destination. The area is rich in ancient ruins and myths. Unlike the Cyclades and other areas of Greece, it is incredibly green here. The hills are dotted with olive groves, separated only by small dry stone walls.

The archipelago consists of seven major islands: Corfu, Paxos, Leucade, Ithaca, Kefalonia, Zakynthos and Cerigo, collectively known as Heptanese. Other smaller islands worth discovering are: Meganisi, Othonoi (also known as Fanò), Scorpio, Kalamos, Kastos, Atokos. The climate here is warm and the winds in the region are constant and mild - which is especially good for flotillas.

Everything you need to know about flotilla sailing in Greece:

  • Planning for a flotilla in Greece circa 700€ per person (plus travel to and from the island and local food and drink costs)
  • The arrival and departure is usually by plane as well as by ferry. Greece has a well-developed ferry network, which makes it easy to reach the starting point of the flotilla.
  • The best time for flotilla sailing in Greece is from May to September. The peak season is in July and August.

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