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.
25,000+ happy travellers, and 10,000+ holidays in 110 destinations worldwide.
Get onboard solo, with your family, or your friends
Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.
Discover who’s already onboard
Introduce yourselves online, get to know each other onboard, and go home with a bunch of new friends.
Sailing holidays that suit all budgets
Rumour has it that sailing holidays are only for the rich or well-connected. With Sailsquare, that's no longer true. Come and discover a world you never thought was accessible!
Reviews - Flotilla yacht sailing holidays & tours in Greece
Raffa is the perfect skipper! Calm, never too intrusive or over the top, in short, in the meantime it transmits tranquility and confidence, which on the boat - especially for those who are at the first experience - is important. As soon as I saw it seemed to me the dj Luca Agnelli, oh well just a little lower ????. He is a sunny and sociable person, with whom you can talk about everything and it was nice to enter his world. He never shied away from partying with the crew at any time, with the excuse that he went out of his way to keep us entertained. Raffa, made us discover some wonderful coves. In short, I recommend him, for that calm madness of his.
Expert skipper, great historical, political and social culture of Greece. He knows all the excellences present in the territory, a great connoisseur of wines and typical foods. Great cook and organizer. He was a great colleague for organizing holidays out of standard.
If you are looking for a holiday that combines fun, adventure, relaxation and new friendships you have found what is right for you! My girlfriend and I boarded without knowing anyone from the crew and it was amazing. We got to make some great friends and have a lot of fun. The skipper was great! He took us to heavenly places and proved to be extremely helpful in all kinds of situations. During the day we moved to different places to swim and visit beautiful islands, while in the evening we usually ate in very special taverns. Good food and company made the evenings magnificent! I honestly recommend everyone to try such an experience! You will probably stop spending your holidays on crowded beaches to prefer the boat even in the following years. As already mentioned, the skipper was amazing and contributed a lot to making the holiday perfect! Thank you very much :) :) :)
Beautiful experience, our flotilla was made up of beautiful people, I have made a lot of connection with my boat, an experience that I will definitely do again. I left my comfort areas behind and spent 7 days of adventure, sharing and team spirit. A special thanks to Nicola who was a friend, a brother and a great captain for this week.
Leo was a skipper available from the beginning to facilitate the organization of the trip and during the holiday he showed us his competence and perfect knowledge of the places. Then the sympathy and the feeling did the rest... (also good food). great experience, which I recommend.
Andrea was very kind and professional already at the stage of describing the holiday weeks before leaving, helping me to understand what my first sailing holiday would have been like.
Throughout the holiday he even explained to me many notions about sailing and navigation.
Definitely a very good skipper.
I recommend it!
Claudio is a competent and reliable skipper.
He also turned out to be a really nice, welcoming and positive person!
My holiday went very well and therefore I recommend everyone a holiday with him (and Carmen)!
Thanks for everything Claudio! See you soon!
With his hand-rolled cigarette... his ugly sailor's glove... a love for the sea that exudes from every pore... the attention of the perfectionist
A true sailor but with a kind soul, ready to listen to everyone's needs and to make himself in 4 to support them; clearly master of his boat in all conditions; ad majora commander
As one of anonima founders, beside the fact that Pol is a great skipper, organizer and manager, most important are his skills as a DJ :) thanks to him, I've learned most important italian songs :)) he will assure and manage best parties on the beach! ..this was our second common trip and you will surely be very happy if you find yourself on his boat and company..thx Pol for all unforgettable moments in Greece, i'm looking forward to upcoming trips!
Being guided by Ema can only make you fall in love with the sailboat and this type of holiday! The passion for sailing, for the sea and for fun has a cascading effect on the whole crew, making the holiday a dream :)
I found myself very well with Luca, good people, good skipper and he knew how to better manage difficult situations.
I hope to get back on the boat with him .
Good ???? wind
The skipper of love! On his boat this year more couples than spritz (and there were so many!). Seriously Riccardo was a fantastic skipper, kind, present, prepared but not pressing. He taught us a lot without it sounding like a lesson and I had a great time. First experience on a sailboat promoted and to be repeated as soon as possible!
Choose a holiday of this type if you are looking for a week to live in a group, between boat parties, bisboccia in company and baths in the coves. The islands visited and the beaches chosen are very beautiful, although the program can be improved. Do not choose this holiday if you want to experience sailing: the organization assigns only one skipper per boat, sometimes even very young and at the first experiences, who will almost always choose to move by motor to respect the program of the beaches to visit and will hardly take the responsibility of leading the sailboat alone, if not in very easy wind and sea conditions. Sailing is another thing. The organization delegates to the guests the task of making a galley for a week, which is stimulating, but be prepared to make a big sweat as soon as you arrive at the marina after the trip. If you can reach the boarding by plane, the ferry trip from Ancona plus the transfer is challenging.
I've had other experiences in the past, but this one was really magnificent. I was on the boat with the skipper Paolo, who can see the strong PASSION for his work and the indisputable PROFESSIONALISM that make every day unique, making us live at the
better every place, emotion, fun in teaching life on a sailboat. The perfect combination that guarantees an unforgettable experience. We were in a flotilla with Fabio, equally professional, and together with the other boat it was fantastic, as the two skippers have very well created a playful, cheerful and equally adventurous atmosphere. With them everything is possible?????? It testifies to the last day, in which in the farewell between us there was a sweet emotion for the arrival of the end, although I am sure that it is the beginning of magnificent friendships. Paolo and Fabio are extraordinarily UNIQUE. To the next adventure..... good wind to all ????????????????????????????????
I will not dwell on his technical skills because they are impeccable! The Desa, a friend found almost by chance who made the 3 weeks spent in the flotilla a walk! Eh be yes eh!!
Trifo, the chic skipper who does not commit: absolute leadership of the boat without making it too heavy, great sailing experience, sense of security transmitted, sympathy and generosity. All this despite the fact that some crew members have practiced sleep deprivation experiments on him for a week. Indestructible!
Fabiano is often in the position of being the youngest and most experienced of all skippers, and knows how to manage this position with the wisdom of those with white hair. In a word: unparalleled!! I hope to return to sail with him very soon.
For our "First Officer" who like the Captain has a magical smile despite the photo published here by "sighting land we are almost there" "always on alert I'm", thanks for the irony and for "the boxer branded LECCE": lover of the sunset, dances and aperitifs and even patrolling by sea and on land. Skipper not by chance. Tireless eater excellent sailing companion and cleaning dishes with "scarpetta".
When you are quiet by sea you are a good skipper! I also confirm positivity and smile to which I add a dispassionate love for NUTELLA! Sun, sea, laughter and good wind!
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.
.
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.
