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Catamaran yacht sailing holidays & skippered tours

Catamaran yacht sailing holidays & skippered tours

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.

  • Sailing Holidays
  • Catamaran

FLEXIBLE CANCELLATION.

Stress-free booking: you can cancel up to 24 hours before departure!

  • AEOLIAN ISLANDS: sea, sun and relaxation - Brand new 15-metre Lagoon 50 Catamaran

    from 15 April - 7 nights
    Aeolian Islands Italy
    Join in on this experience!
    651€ Per person
  • PREMIUM 16 reviews
    confirmed

    MALDIVES Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

    from 16 April - 7 nights
    The Maldives Indian Ocean
    Join in on this experience!
    2.015€ Per person
  • PREMIUM 16 reviews
    confirmed

    Dream Caribbean Premium - 11 days in catamaran ALL INCLUSIVE with hostess / cook

    from 16 April - 10 nights
    Grenadines & Martinique Caribbean
    Join in on this experience!
    2.510€ Per person
  • PREMIUM 16 reviews
    confirmed

    BAA & RAA Dream Premium - ALL INCLUSIVE catamaran with hostess / cook

    from 16 April - 10 nights
    The Maldives Indian Ocean
    Join in on this experience!
    2.540€ Per person
  • PREMIUM 16 reviews
    confirmed

    PRASLIN Dream Premium - ALL INCLUSIVE catamaran with hostess / cook

    from 17 April - 7 nights
    Seychelles Indian Ocean
    Join in on this experience!
    2.025€ Per person
  • PREMIUM 16 reviews
    confirmed

    SILHOUETTE Dream Premium - ALL INCLUSIVE catamaran with hostess / cook

    from 17 April - 10 nights
    Seychelles Indian Ocean
    Join in on this experience!
    2.595€ Per person
  • 12 reviews
    almost
    confirmed

    Four days sailing on a catamaran between Genoa Cinque Terre and Portovenere

    from 21 April - 4 nights
    Liguria Italy
    2 people
    are onboard
    350€ Per person
  • 8 reviews
    4 discounted
    spots

    April 25th in Costa Smeralda on a Catamaran among the colors of spring

    from 21 April - 4 nights
    Northern Sardinia Italy
    Join in on this experience!
    599 570€ Per person
  • PREMIUM 16 reviews
    confirmed

    PHUKET Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

    from 22 April - 7 nights
    Phuket, Krabi and Phi Phi Islands Thailand
    Join in on this experience!
    1.345€ Per person
  • PREMIUM 16 reviews
    confirmed

    ST. BARTH Dream Premium - 8 days in catamaran ALL INCLUSIVE with hostess / cook

    from 22 April - 7 nights
    Saint Martin Caribbean
    Join in on this experience!
    1.740€ Per person
  • PREMIUM 16 reviews
    confirmed

    BORA BORA Dream - 8 days in catamaran ALL INCLUSIVE with hostess / cook

    from 22 April - 7 nights
    French Polynesia Pacific Ocean
    Join in on this experience!
    2.295€ Per person
  • PREMIUM 16 reviews
    confirmed

    GUADELOUPE Dream Premium - ALL INCLUSIVE catamaran with hostess / cook

    from 22 April - 7 nights
    Guadeloupe Caribbean
    1 person interested
    in this holiday
    1.575€ Per person
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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 - Catamaran yacht sailing holidays & skippered tours

647 reviews
18 / 10
Antony N.

Antony N.

review about Sailing Caribbean: Grenadines and Tobago Cays March 2023

10 / 10
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.
Alice F.

Alice F.

review about LAST MINUTE! - Catamaran cruise to the SEYCHELLES - Cook on board! November 2022

10 / 10
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 ...
Olivier C.

Olivier C.

review about Christmas on a Catamaran in Phuket in Thailand - LAST PLACE FOR WOMEN December 2022

6 / 10
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,
Lucie D.

Lucie D.

review about Crossing the Atlantic on a catamaran November 2022

10 / 10
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!!
Davide G.

Davide G.

review about Maddalena Park and Costa Smeralda in premium catamaran and sailing boat - WEEK 1 August 2022

8 / 10
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%).
Roberta D.

Roberta D.

review about Flotilla between the Gulf of Naples and the Pontine Islands - week 1 August 2022

10 / 10
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!
Michele D.

Michele D.

review about LAST MINUTE - AEOLIAN IN CATAMARAN: relaxation, nature, good food, many sunsets and volcanic eruptions! July 2022

10 / 10
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.
LUCA B.

LUCA B.

review about LAST MINUTE! Discovering CILENTO by CATAMARAN! July 2022

10 / 10
THANKS ANTONIO AND FRANCESCA A WEEK FROM GOD, TO BE RELIVED AS SOON AS POSSIBLE .... WONDERFUL BOAT IN EVERY DETAIL .... THANK YOU, THANK YOU
Federica L.

Federica L.

review about Let's explore the Maddalena archipelago by catamaran June 2022

10 / 10
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
Valerio P.

Valerio P.

review about Catamaran sailing to the island of Elba June 2022

10 / 10
Experienced captain, attentive to the needs of the crew and very kind in the ways. What more could you ask for? grade 10 laude
Marialuisa S.

Marialuisa S.

review about Sailing in the Maddalena archipelago and southern Corsica on a brand new Lagoon46 August 2021

10 / 10
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 ———— 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
Valentina C.

Valentina C.

review about Aeolian Islands in Catamaran: lots of relaxation, good food and adventures September 2021

10 / 10
More than a holiday it was a journey within a journey! Contact with the sea is assured and not at the expense of comfort. To be redone!
MariaVittoria D.

MariaVittoria D.

review about Sailing CAT-Away! Parks, waterfall and culture August 2021

8 / 10
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!
Loredana P.

Loredana P.

review about Ponza, Ventotene, Palmarola: nature, history and culture on a catamaran August 2021

10 / 10
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 ... ????
Aleksandra K.

Aleksandra K.

review about By catamaran in the heart of the Ionian Islands July 2021

10 / 10
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!!!
Nicola F.

Nicola F.

review about By catamaran to the Pontine islands ... with a super price !! June 2021

10 / 10
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!
Mariano D.

Mariano D.

review about Aeolian Islands on Bali 48 of 2021 with skipper and hostess all inclusive June 2021

10 / 10
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!
Benedetta G.

Benedetta G.

review about Two days in Porto Azzurro ELBA departure and return aboard the catamaran, Captain Marco's sailing ship June 2021

10 / 10
Beautiful weekend, wonderful places and an excellent captain. I will definitely be back.
Luca B.

Luca B.

review about CRUISE WITH CATAMARAN CROSSING IN SARDINIA - Bridge of 2 JUNE (28 May -4 Jun) May 2021

10 / 10
Simply fantastic
Salvatore B.

Salvatore B.

review about Experience the Egadi Islands, an archipelago of beauties. September 2020

10 / 10
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!
Elena S.

Elena S.

review about Late Summer Flotilla on the Pontine Islands September 2020

10 / 10
Fantastic skipper, serious and attentive, but also available to teach how to go sailing, cheerful and ready to party.
Ignazio D.

Ignazio D.

review about Relax and navigation from the Egadi islands to Palermo September 2020

10 / 10
great Skipper, great holiday.
Francesco M.

Francesco M.

review about Pontine Islands in 20 meters catamaran with private bathroom August 2020

10 / 10
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!!!
Filippo Z.

Filippo Z.

review about Special Wind of Sardinia in sailing catamaran August 2020

6 / 10
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.
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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.
  • The best way to discover the exotic islands of the Caribbean, including the Grenadines, Martinique, Guadeloupe, Cuba, and the British Virgin Islands.

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.

Catamaran: best destinations

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