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!
Just returned from the Caribbean after a week with Gianluca and the Vivila sailing team. I had the most wonderfull experience, its hard to put into words.
Gianluca is a truly excellent captain and instructor, patient and considerate throughout, always happy to answer my 1000 and 1 questions on boats and sailing.
The itinerary that Gianluca created was extraordinary, we visited places that you just can't get to unless you are on a boat, the Tobego Cays and the island of Mayreau we two of the highlights.
It's important to note that unlike most of the experiences you will find on Sailsquare, Gianluca's trips arn't a commercial enterprise, rather, they are a chance for people outside of the Vivila sailing team to make up the numbers and cover the costs of chartering a boat. On this trip there were 16 people on 2 boats with 2 captains and crew from Italy, France, Germany and the UK.
It's my dream to sail with Gianluca and the Vivila team again, hoping to visit Croatia this summer.
5 stars and even more in Pier Paolo!!! Skipper and fantastic person, who managed with his professionalism, competence and sympathy to make this week even more indimentìcabile! He accompanied us with laughter and wonderful stories in these enchanted places; with simplicity it has always allowed us to make a group with cheerful evenings and chats, or to leave us to contemplate a little the landscapes immersed in our thoughts; also able to solve some small unexpected or to create valid alternatives, always meeting everyone's needs, always transmitting tranquility and security!
I cannot fail to mention Claudia who, with her delicious dinners, delicacies and lots of laughter, pampered us throughout the trip!!!
All the right ingredients to enjoy the Seychelles even more... Paradise beaches, an aquarium for everyone, surreal landscapes ...
We where 11 on a boat for 10, it was ok as i like to sleep outside (didnt have so to share the bed with another guy, i was not informed of that).
Susbcribing this Cruise, i expected ... to sail.
Sadly we motored during 3 days (2 hours genoa with engines). At this moment we had burned half the gas-tank.
the weather was sail-possible (you can check on windy), disapointing to see the waves running with boat ... ????
Finaly à left the boat the 4th Day, to change my plans.
I subscribed by sailsquare, not on motorsquare.
Olivier,
Crossing the Atlantic was a dream i had for a long time and Dominikus and Patricia made this dream come true in the best way ! Dominikus is a skipper you always feel safe with, he is also a captain who likes to share how things work on the boat and about the wind, sailing and the ocean. And more than this he always put good energy and fun in the crew ! Regarding Patricia, she also is the best. Very attentive of what you may need or how you feel, she cooked everyday (21days) some amazing fresh food, she takes very good care of the boat and make this trip a Luxury adventure ! If anyone dream of crossing the Atlantic or just want to spend time on spanish islands i recommand you join the Genia crew!!
Unforgettable holiday, to be repeated definitely!
Prepared and sociable skipper.
Inspiration for improvement: more formalism in the checkin process of the boat (which was rented and not 100%).
Unforgettable experience, Alessio puts his heart into what he does and does his best to make sure that everyone returns home with good memories ... super recommended!
ELISA? Fantastic! He gave us an unforgettable week in the Aeolian Islands. Kind, helpful and, above all, patient he accepted all our requests. We were guided by her and her experience. So young and so good. It was the putty of the group. A "crew" made up of (former) strangers who, thanks to her, managed to bond immediately. It was the perfect knot for a perfect holiday. Elisa, thanks to the undisputed beauty of the Aeolian archipelago, gave us postcard sunsets like that of Filicudi. He carefully chose the coves with crystal clear water to bathe and relax. But you know, the sea makes you hungry and even in that case Elisa managed to surprise us. Not only with advice on what to eat on board but also on land. I already have the magone. I would immediately leave the moorings to sail again. With her and her catamaran.
Very relaxing and fun holiday.
Roberta was a perfect Captain, attentive and scrupulous during the navigation and with the guests on board.
I recommend without delay to travel with her.
The boat is comfortable, clean and tidy!
I must say that the holiday met expectations
What a fantastic experience! Gianni is a very experienced skipper and a wonderful guy. He made us feel at home on his boat and took us to some of the most beautiful bays in Sardinia and Corsica, we swam, dived, waterskied, cooked, drank and laughed together.He has 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. Ha 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.
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.
