Discover the magic of skippered catamaran holidays, an original
holiday idea to share a comfortable adventure with family or
friends in a little bit of luxury. Catamaran holidays in the
Caribbean including the Grenadines, Seychelles, Martinique, Antigua
and Barbuda, and Cuba - as well as in the Mediterranean including
Greece, Croatia, Corsica, and Sardinia. The world’s best travel
destinations await you.
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.
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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!
What a fantastic experience! Gianni is a very experienced skipper and a wonderful guy, He made us feel at home on Marelia and took us to some of the most beautiful bays in Sardinia and Corsica, we swam, dived, waterskied, cooked, drank and laughed together. Marelia is an amazing catamaran, spacious, brand new and with all the comforts including air con and sound system. I can’t wait to sail again with Gianni and the #Lagoon’sLovers ??
#bagnetto #birretta
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Che esperienza fantastica! Gianni è uno skipper molto esperto e un ragazzo meraviglioso ?? ci ha portato in alcuni dei posti più belli della Sardegna e della Corsica, abbiamo nuotato, fatto immersioni e sci d’acqua, abbiamo cucinato, bevuto e riso insieme. Marelia è un catamarano bellissimo, spazioso, nuovo e dotato di tutti i comfort, aria condizionata e sound system inclusi! Non vediamo l’ora di poter veleggiare di nuovo con Gianni e i #LagoonLovers ??
#bagnetto #birretta
Mari & Carlo
Relaxing holiday, in close contact with nature and eco-sustainability.
It was nice to approach the world of sailing in a catamaran version; Elisa made us so involved, always safely!
Beautiful holiday with our skippers Massimo and Giovanni ?????????????? in the name of ???? sun of the sea '???? of relaxation in navigation ?? ,of the aperitifs ???????? of good wine???? ???? of ???????? beer of the Venetian, Tuscan, Emilian, Genoese accent, of the dives in the blue ??????? and in the intense blue of the sea,??????? great food???????????????? with our men refined chefs and how to forget the evening challenges to briscola called in 8 with the Treviso cards ????,which in reality none of us crew has yet understood well to the end ... ????
Our week on Vincent's catamaran was great!
Vincent is really good captain, with a lot of experience, you can learn a lot if you want - do things on the boat - or not, depends from you. He will explain everything (he also has a groups for sail training). Apart from this, he is a really interesting person with many great stories from his life, really easy going and with good recommendation always. Normally at night you can have a dinner in a restaurant, on your own or go with the captain and the rest of the crew, we always chose the second option, as dinner with them was great and the selection of the place perfect!
Melanie, his partner, was helpful, and funny! You just have great time with her! And a lot of ice-creams :)
The boat is comfortable, and they do not take more than 4 people although there is one cabin unocupied so the group is more comfortable.
The area of Ionian Islands was above our expectations. Wonderful views, really beautiful places with clear water.
I recommend it!!!
Well what can I say... Andrea is a really nice person and a prepared skipper! It makes everyone feel at ease, takes care of the problems on board, and involves everyone without exclusion!
Full rating, fun holiday to repeat absolutely..
Bravo Captain!
Professionalism, availability and friendliness were decisive for the success of the holiday!
Thanks to Daniele and Chiara !
I'm already thinking about when to repeat a holiday with the commander!
AMAZING!
Thanks to Giuseppe and his outstanding service and fantastic catamaran, we had a fantastic time.
Very knowledgeable, he was able to listen and adapt to our needs to make sure we could relax, see incredible places and get the best out of an unforgettable week.
We got spoiled with a perfect catamaran, delicious tuna (Giuseppe is a great cook too!), a tour of Marettimo, Levanzo, Favignana but also San Vito lo Capo (one of the best beaches in the whole Italy).
I can't thank enough Giuseppe for all his efforts and attention to every single details. We cannot wait to book another week with him!
A trained, professional Skipper capable of handling any situation. Enrico is also great at partying and satisfying the crew for any need. There were problems in the management of the holiday not to be attributed to the Skipper, but to the owners.
For Enrico chapeaux!!!
Beautiful scenery, great company, skipper friendly and helpful, but did not speak Italian, did not know the area and had no experience driving a catamaran.
Skipper attentive, professional, experienced, able to live the experience in the right way, good advice on what was better to visit. Very good and attentive also the hostess, nice, good cook who was able to share with us this beautiful experience.
Bad assistance of Tajana, which contacted from the day before boarding, has never responded to our requests for information, neither via sailsquare, nor via whatsapp nor via phone. We were totally abandoned, looking for photos in hand for two hours inside the port of Trogir, asking right and missing if someone knew her, as we had not been given any info on what the charter company was, much less the name of the boat until someone managed to tell us something. The other guests were black for the fact that we did not arrive,they wanted to leave,but without us they could not. I was promised and assigned the stern cabin straight side and I had bow left side! Very bad experience.
Skipper and catamaran Top, equipped with every good of god... Sup, canoe, diving equipment etc ... Fabio in addition to an excellent preparation is very good at teaching a little sailing to those interested, it seems strange, but in Charter it is a rare thing. Recommended for those who want to spend a week of relaxation in the name of sea sailing and lots of nature. Do not forget the cute Jack, the delicious sailor dog, always looking to be pampered by everyone, the mascot of the boat!
Claudio is a competent and reliable Skipper, attentive to the needs and desires of the whole group. The holiday was well organized with various reservations of restaurants, aperitifs and buoys x moorings in the most beautiful and strategic places, for this I thank Valentina, a perfect organizer. As far as I'm concerned the holiday exceeded expectations! I would definitely do a holiday with Claudio again!
Nathalie and Jonathan are very pleasant people and make sure that the guests lack nothing. Nathalie cooks very well and Jonathan is very careful and the safety of the guests comes first.
Jonathan organized everything well. The plans for the next day were discussed with the whole crew and everyone could contribute their wishes and suggestions.
This sailing turn in the Seychelles was very nice and we would repeat it immediately!
The week training is very useful. Jos is a quite relaxed teacher that lets you sail and manouver the boat most of the time. The organization of the holiday and training is not perfectly clear, but that lets space for the crew to decide part of it.
What can I say... an unforgettable holiday like the whole crew! Thank you all for this beautiful experience that I will carry forever with me!
Thank you Skipper and thank you guys!!!!!
Truly bubbly holiday, with crazy travel companions, upwind sails with more than 20 knots of wind, white beaches, swimming in incredible bays, breathtaking sunsets and evenings of joy and fun
Thanks to the group of tireless skippers who organized our stages perfectly, but even more for our skipper Samuele who proved to be very professional, nice and willing to satisfy our whims.
Definitely see you next time.... Good wind to all
The skipper is a very helpful person, attentive to the needs of customers and with great experience at sea. He will welcome you in his beautiful boat (well-kept, clean and spacious) making you feel immediately at ease and giving you if you want also some nautical knowledge. Thanks to his friendliness and kindness in the end you will not want to go down!
Experienced skipper always ready to involve us and teach us the basics of sailing and life on board.
Comfortable and clean catamaran, equipped with all the necessary accessories for a comfortable chartering.
Cosimo is a fantastic, fun and extremely correct skipper, with a real passion for what he does and for beautiful things, nature, food and friends! He managed to lead the group in a harmonious way, always attentive and ready to satisfy our every request.. when possible!
We spent a wonderful week, in an earthly paradise. All this was fundamental for two who, like us, had never ventured into a week-long experience on the sea. Despite all the fears we spent 7 days of pure fun, freedom, relaxation, laughter, sea, sun .. in short, of LIFE!!!
Highly recommended!!
Thanks Cosimo and good wind!!!!
Antonio L. (Modena)
7 reasons to go on a sailing holiday on a catamaran with a skipper
A catamaran is described by many as a floating house: comfortable, spacious, bright, and very well equipped.
Ideal for families with children, with room and the environment that is more secure than a monohull sailboat.
A new way of travelling that allows you to discover islands and paradisiacal beaches that are only accessible by boat - the catamaran has a weak draft, allowing it to go where other boats cannot.
The opportunity to get stuck into a book, nap on the deck with a warm sea breeze, or trampoline on the netting that sits at the front of the boat.
A catamaran is more stable than a sailboat, therefore they are a great way for first time sailors to discover the magic of sailing holidays, without the fear of seasickness!
A catamaran usually has 4 large cabins, which will allow you to cast off with your family or your best friends, with plenty of space for all.
Everything you need to know to organise your next catamaran sailing holiday
The advantages of a catamaran sailing holiday with Skipper
If you have an existing group of travellers (of family or friends), we highly recommend reserving an entire catamaran with skipper. In such cases, it is often possible to receive a discount on you booking (from 10% of the total booking cost upwards), this is more likely to be the case if you are booking in advance or in less busy periods of the year. In addition to saving money, reserving a skippered catamaran allows you maximum flexibility in itineraries, with skippers often willing to be very accommodating to your wishes. Reserving a whole catamaran also allows maximum privacy, if you are looking to share some quality time with your family or friends.
If you are travelling as a couple or solo, bare in mind that you can book either a single berth or an entire cabin. A cabin allows for much more privacy and more personal space. Either way, you have the ability to share your sailing experience with other like-minded travellers - an excellent opportunity to meet new people and make new friends!
Catamarans: the comfort of a house, on the water!
Many describe catamarans as floating houses, for the extensive space and facilities they have onboard. After a long day of adventure, you can rest in large, well-equipped cabins, that are complete with a full size double bed. There are usually 2 cabins each for the 2 floats, or sides of the boat. These are then separated by a bathroom, complete with a shower and toilet. The common area of the catamaran including the lounge and kitchen are then located in the middle-upper part of the boat, in between each float.
Catamarans are generally very spacious and bright, with large windows that overlook the sea, a perfect view when cooking or relaxing! They are very social and friendly due to how the design of the boat. Finally, it is true that the bridge offers lots of charm to the catamaran, this area of the boat is the main area for relaxing and enjoying time on the deck!
What are the differences between a sailboat or catamaran?
A sailboat may be better for people looking to learn the practice of sailing, or to sharpen their skills, where as the catamaran is the most comfortable and luxurious way to enjoy a holiday at sea. Here are a few advantages and disadvantages of each:
Sailboat: ideal for sailing, less emphasis on comfort, cheaper, less spacious, more user-friendly
Catamaran: less motion impact on the stability of the boat, more comfortable, more expensive, more spacious
The 8 best destinations for a catamaran sailing holiday
The Mediterranean, Caribbean, Indian oceans - some destinations are ideal for a skippered catamaran sailing holiday. For those who dream of a trip in the Caribbean, it is full of ideal different destinations for a catamaran trip. We mainly recommend the Grenadines (which normally set sail from the port of Marin in Martinique), Guadeloupe, and Cuba.
The Mediterranean Sea is another paradise for catamaran trips. We recommend a week between Corsica and Sardinia to explore the famous Lavezzi Islands and the Maddalena Archipelago, but there is also the wonderful Greek archipelago of the Cyclades or the Ionian Islands. Last but not least, who does not dream of discovering the paradisiacal landscapes of Seychelles aboard the catamaran with a local skipper? An adventure to treasure for your entire life.
All you need to know for your next skippered catamaran cruise
The demand for skippered catamaran holidays can be very high compared to the number of offers. We recommend booking several months in advance - January or February for summer trips in the Mediterranean and September or October for winter trips in the Caribbean.The best time for a catamaran holiday in the Mediterranean is from May to October. For a Caribbean holiday, between November and April.
The price of a catamaran sailing holiday can be much higher than a sailing holiday on a monohull because of the extra comfort and the limited availability. You can find experiences between €600 and €1,200 per week depending on the destination and the period of the year.
The best destinations for catamaran holidays are: Antilles (Grenadines, Guadeloupe, Cuba, British Virgin Islands), Seychelles and the Mediterranean (Greece, Corsica, Sardinia, Croatia). Booking an entire catamaran with a skipper is a brilliant option for holidays with family or friends.
