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Catamaran sailing holidays with a skipper

Catamaran sailing holidays with a skipper

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

COVID‑19

Book without stress paying a small deposit, cancellation is free!.

  • 17 reviews

    Easter cruise on a luxury catamaran to the Maddalena Archipelago and Corsica

    from 2 April - 3 nights
    Northern Sardinia Italy
    Join in on this experience!
    490€ Per person
  • 8 reviews
    Discounted
    spots until 3 Jan.

    8 days catamaran cruise with hostess - all inclusive - Guadeloupe

    from 3 April - 7 nights
    Guadeloupe Caribbean
    Join in on this experience!
    1.485 1.410€ Per person
  • 8 reviews
    Discounted
    spots until 3 Jan.

    Premium 8 days on Catamarans with hostesses aboard the Grenadines - All Inclusive

    from 3 April - 7 nights
    Grenadines & Martinique Caribbean
    Join in on this experience!
    1.516 1.440€ Per person
  • JESOLO VENEZIA - Sailing on a brand new Lagoon 450 CATAMARAN

    from 4 April - One day
    Venice and the Gulf of Trieste Italy
    Join in on this experience!
    90€ Per person
  • 8 reviews
    Discounted
    spots until 10 Jan.

    Premium 8 days on Catamarans with hostesses aboard the Grenadines - All Inclusive

    from 10 April - 7 nights
    Grenadines & Martinique Caribbean
    Join in on this experience!
    1.516 1.440€ Per person
  • JESOLO VENEZIA - Sailing on a brand new Lagoon 450 CATAMARAN

    from 11 April - One day
    Venice and the Gulf of Trieste Italy
    Join in on this experience!
    90€ Per person
  • 8 reviews
    Discounted
    spots until 17 Jan.

    Premium 8 days on Catamarans with hostesses aboard the Grenadines - All Inclusive

    from 17 April - 7 nights
    Grenadines & Martinique Caribbean
    Join in on this experience!
    1.516 1.440€ Per person
  • 17 reviews

    April 25 on a luxurious catamaran to the Maddalena Archipelago

    from 22 April - 3 nights
    Northern Sardinia Italy
    Join in on this experience!
    390€ Per person
  • 8 reviews
    Discounted
    spots until 24 Jan.

    8 days catamaran cruise with hostess - all inclusive - Guadeloupe

    from 24 April - 7 nights
    Guadeloupe Caribbean
    Join in on this experience!
    1.485 1.410€ Per person
  • 8 reviews
    Discounted
    spots until 24 Jan.

    Premium 8 days on Catamarans with hostesses aboard the Grenadines - All Inclusive

    from 24 April - 7 nights
    Grenadines & Martinique Caribbean
    Join in on this experience!
    1.516 1.440€ Per person
  • 2 reviews

    An incredible journey sailing among the most enchanting islands of Greece

    from 24 April - 7 nights
    Ionian Islands Greece
    Join in on this experience!
    750€ Per person
  • JESOLO VENEZIA - Sailing on a brand new Lagoon 450 CATAMARAN

    from 25 April - One day
    Venice and the Gulf of Trieste Italy
    Join in on this experience!
    90€ Per person
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Reviews - Catamaran sailing holidays with a skipper

430 reviews
18 / 10
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
Fantastico skipper, Serio e attento, ma anche disponibile a insegnare ad andare in barca a vela, allegro e pronto a fare festa.
Ignazio D.

Ignazio D.

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

10 / 10
ottimo Skipper, ottima vacanza.
Francesco M.

Francesco M.

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

10 / 10
Uno Skipper preparato, professionale capace di gestire qualsiasi situazione. Enrico é grande anche nel fare festa ed accontentare l'equipaggio per qualsiasi esigenza. Ci sono stati dei problemi nella gestione della vacanza non da imputare allo Skipper, ma agli armatori. Per Enrico chapeaux!!!
Filippo Z.

Filippo Z.

review about Special Wind of Sardinia in sailing catamaran August 2020

6 / 10
Scenari splendidi, ottima compagnia, Skipper gentile e disponibile, ma non parlava italiano, non conosceva la zona e non aveva esperienza alla guida di un catamarano.
Paolo B.

Paolo B.

review about Croatia - Gastro Route on a catamaran with hostess / Half-board included August 2020

10 / 10
Skipper attento,professionale,esperto,in grado di far vivere l'esperienza nel modo giusto,buon consigliere sul cosa fosse meglio visitare.Molto brava ed attenta anche la hostess,simpatica,brava cuoca che ha saputo condividere con noi questa bella esperienza. Pessima l'assistenza di Tajana,la quale contattata dal giorno prima dell'imbarco,non ha mai risposto alle nostre richieste di informazioni,ne via sailsquare,ne via whatsapp ne via telefono.Siamo stati totalmente abbandonati,alla sua ricerca foto alla mano per due ore all'interno del porto di Trogir,chiedendo a destra e manca se qualcuno la conoscesse, in quanto non ci era stata data alcuna info su quale fosse la compagnia di charter,tantomeno il nome della barca fino a quando qualcuno è riuscito a dirci qualcosa.Gli altri ospiti erano neri per il fatto che non arrivavamo,volevano partire,ma senza di noi non potevano.Mi era stata promessa ed assegnata la cabina di poppa lato dritto ed ho avuto prua lato sinistro!Pessima esperienza.
Luca P.

Luca P.

review about Ulysses' course, August 2020

10 / 10
Skipper e catamarano Top, fornito di ogni ben di dio... Sup, canoa, attrezzatura da sub etc... Fabio oltre ad un'ottima preparazione è molto bravo a insegnare un po' di vela agli interessati, sembra strano, ma nei Charter é cosa rara. Consigliato a chi desidera passare una settimana di relax all'insegna di mare vela e tanta natura. Da non dimenticare il simpatico Jack, il cane marinaio buonissimo, sempre alla ricerca di essere coccolato da tutti, la mascotte della barca!
Barbara S.

Barbara S.

review about Aeolian catamaran: a week between relaxation and nature August 2020

10 / 10
Claudio è uno Skipper competente ed affidabile, attento alle esigenze e ai desideri di tutto il gruppo. La vacanza è stata ben organizzata con prenotazioni varie di ristoranti, aperitivi e boe x ormeggi nei posti più belli e strategici, per questo ringrazio Valentina, un organizzatrice perfetta. Per quanto mi riguarda la vacanza ha superato le aspettative! Sicuramente rifarei una vacanza con Claudio!
Ruppert G.

Ruppert G.

review about Join Us on a Seychelles Winter Escape - Private, Small Group Charter on Luxury Catamaran February 2020

10 / 10
Nathalie and Jonathan sind sehr angenehme Personen und schauen dass es den Gästen an nichts fehlt. Nathalie kocht sehr gut und Jonathan ist sehr vorsichtig und die Sicherheit der Gäste steht an erster Stelle. Jonathan hat alles gut organisiert. Die Pläne für den nächsten Tag wurden mit der ganzen Crew besprochen und jeder konnte sein Wünsche und Vorschläge einbringen. Dieser Segelturn auf den Seychellen war sehr schön und wir würden es sofort wiederholen!
Giorgio N.

Giorgio N.

review about Vacation on a luxury catamaran in Tenerife February 2020

8 / 10
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.
Cristina F.

Cristina F.

review about Discovering the Grenadines by catamaran December 2019

10 / 10
Perfetto organizzatore, molto preparato e preciso...come sempre, una garanzia!
Veronica C.

Veronica C.

review about 3 Catamarans for 2 Weeks in Flottiglia in the Wonderful Maddalena - South Corsica August 2019

10 / 10
Che dire... una vacanza indimenticabile come tutto l'equipaggio! Grazie a tutti per questa bellissima esperienza che porterò per sempre con me! Grazie Skipper e grazie ragazzi!!!!!
Daniela A.

Daniela A.

review about Greece - The Summer Flotilla among the Ionian Islands week 3 August 2019

10 / 10
Vacanza veramente spumeggiante, con compagni di viaggio pazzi , veleggiate di bolina con piu di 20 nodi di vento, spiagge bianche, bagni in baie incredibili, tramonti mozzafiato e serate all'insegna dell'allegria e del divertimento Un ringraziamento al gruppo di skipper instancabili che ha organizzato le nostre tappe in maniera perfetta, ma ancora di più per il nostro skipper Samuele che si è dimostrato molto professionale, simpatico e disponibile ad accontentare i nostri capricci. Sicuramente alla prossima....Buon vento a tutti
Francesca B.

Francesca B.

review about Flotilla of 2 Catamarans in Greece. The Chalkidiki peninsula and the remote island of Limnos August 2019

10 / 10
Ho fatto varie vacanze in barca ma uno skypper come Luca non l ho mai trovato. Attento a tutto, rispettoso del mare e di chi ci vive. Prima di essere uno skypper è un marinaio con uno spirito genuino e bello. Uno che ama il mare e lo trasmette.. Viaggio organizzato alla perfezione con un team alle spalle impeccabile. Ripartirei subito!
Mauro M.

Mauro M.

review about Catamaran vacation in Corsica with skipper August 2019

10 / 10
È stata una settimana fantastica, abbiamo navigato in un mare stupendo, facendo tanti bagni in calette e spiagge magnifiche! A bordo si è creata una complicità unica... ripartirei immediatamente!
Sara F.

Sara F.

review about 4 days Côte d'Azur August 2019

10 / 10
Lo skipper è una persona molto disponibile, attenta alle esigenze dei clienti e con grande esperienza in mare. Vi accoglierà nella sua splendida barca (curata, pulita e spaziosa) facendovi sentire immediatamente a vostro agio e donandovi se lo vorrete anche qualche conoscenza nautica. Grazie alla sua cordialita’ e gentilezza alla fine non vorrete più scendere!
Alfredo C.

Alfredo C.

review about Tour of the two Sardinia Parks on a 2019 catamaran with chef - Meals included August 2019

6 / 10
Mauro, lo skipper, è una persona cortese e preparata. Lo chef lo è altrettanto, la barca è davvero bella. Purtroppo la vacanza si vende come "giro dei due parchi", ma non lo è. Il parco è solo uno (quello dell'Asinara, niente Maddalena) ed il percorso è meno della metà di quello dichiarato, non per colpa dello skipper o dello chef, ma dell'armatore (Lorenzo) che dettaglia un percorso non realizzabile. Le bevande (escluso acqua) sono a pagamento, i prezzi sono in linea con una ristorazione media, ma non è permesso portare bevande da casa. Quindi 5 stelle allo skipper e allo chef, 1 all'armatore, media 3
Antonio L.

Antonio L.

review about Catamaran holiday at the Aeolian 2019 August 2019

10 / 10
Skipper espertissimo sempre pronto a coinvolgerci e ad insegnarci le basi della vela e della vita a bordo. Catamarano comodo e pulito, dotato di tutti gli accessori necessari per un chartering confortevole. Cosimo è uno skipper fantastico, divertente ed estremamente corretto, con una vera passione per quello che fa e per le cose belle, natura, cibo e amici! È riuscito a guidare il gruppo in maniera armoniosa, sempre attento e pronto a soddisfare ogni nostra richiesta..quando possibile! Abbiamo trascorso una settimana splendida, in un paradiso terrestre. Tutto ciò è stato fondamentale per due che come noi non si erano mai cimentati in un’esperienza sul mare lunga una settimana. Nonostante tutte le paure abbiamo trascorso 7giorni di puro divertimento, libertà, relax, risate, mare, sole..insomma di VITA!!! Straconsigliato!! Grazie Cosimo e buon vento!!!! Antonio L. (Modena)
Virginia C.

Virginia C.

review about Sardinia catamaran 20 meters with private bathroom August 2019

10 / 10
Siamo appena tornati dalla settimana su Flash! Che dire un'esperienza positivissima! Il catamarano definito dalle skipper(proprietario) vintage è comodo e funzionale. Gli spazi dove potersi rilassare sono tanti ed enormi, la cabina comodissima, una cucina più che abitabile! Insomma non sarà un ultimo modello ma del tutto confortevole! Davide e Stefania due persone splendide che hanno provato a trasferire al gruppo il loro amore per il mare, per la vela e le loro conoscenze in questo ambito! Grazie al maestrale che ci ha fatto compagnia per tre giorni abbiamo navigato più volte a vela, un' esperienza unica!! Era la prima volta che facevo una vacanza con gente sconosciuta e su una imbarcazione a vela ed onestamente la consiglio a tutti. Una vacanza a stretto contatto con il mare e la sua tranquillità, aperitivi al tramonto, cene sotto le stelle e notti in rada, tutto quello che cercavo!Ovviamente complice l'equipaggio con cui si è instaurato un bel feeling sin da subito!
Yves C.

Yves C.

review about Comfort week at the BALEARIES on catamaran 440 July 2019

10 / 10
EXCELLENT ! ***** Pour ceux qui veulent autant partager une expérience de navigation, qu’un grand moment de convivialité : Edouardo est aux « petits soins » (bagage perdu à l’aéroport : il s’est chargé d’appeler pendant plus d’une heure et demi pour le récupérer, il a soigné des piqure d’oursins, de petites plaies... ????...), et partage son expérience avec passion. Bateau très confortable. Nous étions 7 (avec 2 sympathiques coéquipiers rencontrés à l’occasion) Nous le rappellerons avec plaisir pour une prochaine croisière. Une belle rencontre, pour une très belle nav’ (Formentera et Ibiza) Grazie e Buon Vento Edoardo !
Roberta F.

Roberta F.

review about Island of Elba by catamaran July 2019

10 / 10
Una bellissima esperienza grazie anche alla professionalità, alla simpatia e alle capacità dello skipper e del grande Alberto.
Federica B.

Federica B.

review about Spring rifle flotilla in the Seychelles April 2019

10 / 10
Prima esperienza con Marmaglia con un ottimo risultato. Bellissima vacanza, posti meravigliosi, mare cristallino, musica e tanto divertimento . Un ringraziamento allo skipper Massimo, col quale ho diviso la nostra spaziosissima dinette ???? Equipaggio perfetto, bellissima l’esperienza in flottiglia. Esperienza da ripetere! Buon vento a tutti e alla prossima vacanza ???? Federica
Nicola Luca A.

Nicola Luca A.

review about Special Easter and April 25th in Sailing Catamaran in the Seychelles April 2019

10 / 10
Ottima esperienza con Stefano. Competente, esperto efficiente e di compagnia... Ma sopratutto disponibile e attento alle esigenze di tutto l'equipaggio. Consigliatissimo! Grazie Stefano, alla prossima.
Alessandro D.

Alessandro D.

review about Seychelles in catamaran April 2019

10 / 10
Lorenzo e’ uno skipper di grande esperienza e professionalità . Ci ha fatto trascorrere una vacanza unica: preparatissimo sui posti più belli da vedere, sempre disponibile con tutti gli ospiti , molto simpatico e professionale al tempo stesso. Senza di lui non sarebbe stata la stessa vacanza !
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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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