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Sailing holidays in the Caribbean with a local skipper

Sailing holidays in the Caribbean with a local skipper

Discover the magic of sailing holidays in the Caribbean! Get on board with a local skipper and live a unique adventure with your crew: learn to sail, explore incredible places, recharge your batteries and experience the local culture and gastronomy.

  • Sailing Holidays
  • Caribbean

COVID‑19

Additional guarantees on reservations, free cancellation and payment in tranches.

  • 8 reviews
    confirmed

    8 days catamaran cruise with hostess - all inclusive - Guadeloupe

    from 20 February - 7 nights
    Guadeloupe Caribbean
    Join in on this experience!
    1.700€ Per person
  • 8 reviews
    confirmed

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

    from 20 February - 7 nights
    Grenadines & Martinique Caribbean
    1 person interested
    in this holiday
    1.825€ Per person
  • 3 reviews
    confirmed

    From Guadeloupe to Martinique

    from 20 February - 7 nights
    Guadeloupe Caribbean
    1 person
    is on board
    735€ Per person
  • 8 reviews
    confirmed

    8 days catamaran cruise with hostess - all inclusive - Guadeloupe

    from 27 February - 7 nights
    Guadeloupe Caribbean
    Join in on this experience!
    1.700€ Per person
  • 2 discounted
    spots

    10 Days Sailing Cruise and Participation in the Heineken Regatta incl. breakfast and lunch on board

    from 27 February - 9 nights
    Saint Martin Caribbean
    Join in on this experience!
    1.851 1.799€ Per person
  • 8 reviews
    confirmed

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

    from 27 February - 7 nights
    Grenadines & Martinique Caribbean
    Join in on this experience!
    1.825€ Per person
  • 1 review
    confirmed

    Sailing in Guadeloupe - French West Indies - Antilles. Crew included

    from 27 February - 7 nights
    Guadeloupe Caribbean
    1 person
    is on board
    861€ Per person
  • confirmed

    Sailing course Pogo 12.50 - Towards the south, heading to the Grenadines

    from 28 February - 8 nights
    Grenadines & Martinique Caribbean
    3 people
    are onboard
    1.465€ Per person
  • 14 reviews

    Spend an ALL INCLUSIVE holiday with us sailing in Carribean! (meals and beverage included)

    from 1 March - 5 nights
    San Blas Islands - Panama Caribbean
    Join in on this experience!
    1.176€ Per person
  • confirmed

    Sailing course - Towards the south, heading for the Grenadines on RM 11.80

    from 1 March - 9 nights
    Grenadines & Martinique Caribbean
    3 people
    are onboard
    1.465€ Per person
  • Sailing course Pogo 12.50 - Towards the south, heading to the Grenadines

    from 1 March - 9 nights
    Grenadines & Martinique Caribbean
    Join in on this experience!
    1.465€ Per person
  • 1 discounted
    spot

    St Maarten Heineken Regatta 2021

    from 2 March - 5 nights
    Saint Martin Caribbean
    Join in on this experience!
    1.457 1.352€ Per person
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Why you should book a holiday with Sailsquare?

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Reserve a single spot, a cabin, or a whole boat just for you and your friends or family.

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Sailing holidays that suit all budgets

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Reviews - Sailing holidays in the Caribbean with a local skipper

177 reviews
20 / 10
Fabian M.

Fabian M.

review about 7 Days Sailing Cruise around St. Maarten and the BVI's incl. breakfast and lunch on board January 2021

10 / 10
First-class sailoring, first-class company, first-class sailing boat, first-class experience. Rob is an exceedingly competent skipper of a superb sailing yacht. On the human level, Rob and Jacky are absolutely delightful people who go out of their way to make you feel welcome and comfortable in every way. Cannot recommend more highly!
Fabian M.

Fabian M.

review about Christmas in the Caribbean ... a dream called the Grenadines December 2019

10 / 10
Michele is an excellent skipper -- technically sound, mature and responsible -- and an excellent host on board. He is also delightful company. I recommend him without qualification
Aleksandra Z.

Aleksandra Z.

review about ALL INCLUSIVE holiday at the Carribeans! (meals and beverage included & flexibles dates!)) February 2020

10 / 10
We had some amazing time with Giulia and Rodrigo in San Blas islands. They are most friendly and professional hosts that one can imagine. Giulias cooking is just great, while Rodrigo provides some fresh fish caught by himself. The boat was very comfortable and tidy. We can definitely recommend holidays with them!
Alex R.

Alex R.

review about Grenadines on a sailing boat with Skipper and Hostess among the pearls of the Caribbean - SUPER LAST MINUTE DISCOUNT January 2020

8 / 10
Sail fast, Live slow! 53 feet boat well updated with new sails and modern equipment without loosing the cachet of a vintage boat with tek-dek, etc. Designed to feel like home, all comforts on board, even TV and AC if it's what you're into and according to your budget. My bed was comfortable. If a couple, I would ask the master bedroom. With real shower and space that I never seen before in a sailing boat. We got an average of 8/9 knots of speed on the first day with picks of 12 knots! Great destinations. Beautiful spots. Clear waters full of fish and turtles. He delivers according whatever you are into and fixes whatever missing on board. Good host, Italian flair, recently reconverted in the Caribbeans, passionated, helpful and basic cooking. Does the best barracuda ceviche! Ask him to saber the Champagne ;) Check prices and what services are incl or not before booking, as with different languages, miscommunications happen. Also about moorings prices w service. Arrivée á bon port!
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!
Giulio M.

Giulio M.

review about Choose your dream destination. December 2019

10 / 10
Pierre is a good experienced skipper that can suggest you the best places to visit, he's also a good cook and will get your vacation very comfortable.
Luca D.

Luca D.

review about week at the San Blas Islands Panama - All inclusive March 2019

10 / 10
ROBERTO SKIPPER: supermitico supersimpantico e disponibile, profondo conoscitore delle SanBlas ti fa sentire a tuo agio e riesce a farti passare una vacanza indimenticabile. EQUIPAGGIO: molto cordiale e disponibile a supporto delle attivita' di bordo. BARCA: grande e spaziosa, molto vissuta, un refitting sarebbe consigliabile.
Silvia Q.

Silvia Q.

review about White week ... in flotilla in Cuba February 2019

10 / 10
Che dire? Altro giro altro regalo: quello di passare una fantastica settimana con Filo. Ormai sono tre anni che ho la fortuna di navigare tra i mari più belli che questo mondo ci regala, e la compagnia, il carisma, la simpatia e la competenza di filo possono solo rendere tutto estremamente perfetto!
Laura S.

Laura S.

review about Cruise 8 days on a Catamaran with hostess in Bahamas - All Inclusive February 2019

10 / 10
Sono partita da sola e non essendo un drago in inglese avrei potuto avere qualche difficoltà. Invece la disponibilità, la simpatia e la professionalità dell’equipaggio mi hanno subito messa a mio agio. Vacanza superiore alle aspettative, sia per i servizi offerti, sia per l’imbarcazione dotata di ogni comfort, sia per il personale, sia per l’itinerario svolto. Da ripetere!
Renato M.

Renato M.

review about Guadalupe sailing January 2019

10 / 10
Navigazione in sicurezza e con distanze ragionevoli. Ideale per vacanze tranquille e rilassanti e godere appieno dei posti. Stefano e Monica coccolano gli ospiti e lasciano godere della barca. Consigliato
Nelly Q.

Nelly Q.

review about Catamaran cruises in the Guadeloupean archipelago January 2019

8 / 10
Éric est un skipper attentif aux besoins de chacun et sait mettre ses connaissances humaines et de la mer au service des personnes qu’il accueille sur son bateau. Je suis ravie de cette croisière sur les îles guadeloupéennes.
Noëlle G.

Noëlle G.

review about Learning and relaxation in the Grenadines! January 2019

10 / 10
Semaine paradisiaque dans les Grenadines. Ce voilier est un bateau très performant qui permet de combiner plaisir de navigation et apprentissage. Hervé prend le temps d'expliquer chaque manoeuvre et répond à toutes les questions. Il est également bon cuisinier ! Il y avait une très bonne entente entre les différents équipiers, ambiance joviale sur le bord et mouillages exceptionnels.
Marzia M.

Marzia M.

review about New Year's in the Grenadines December 2018

10 / 10
Ciao, sono Marco,volevo ringraziare lo skipper Francesco e la skipper Anna per la professionalità,la cortesia e la gentilezza di come hanno accolto me e gli altri ospiti nella crociera di fine anno 2018. Francesco è un marinaio eccezionale ed esperto,ci siamo sempre sentiti in sicurezza in qualsiasi situazione. Un grazie di cuore per la stupenda vacanza che mi avete fatto passare. Ciao e buona fortuna
Aude K.

Aude K.

review about New Year's Eve cruise on a Catamaran in Guadalupe, Antigua, Barbuda, St. Kitts and Nevis December 2018

6 / 10
Vittorio est un excellent navigateur, un excellent cuisinier et son bateau est très grand, très propre spacieux et confortable. Cependant la communication n’est pas son fort et nous l’avons appris à nos dépens. Nous aurions en effet mettre au point qq détails avant le départ car nous avons été fort surpris d’apprendre qu’iI refusait de faire toute navigation nocturne. Et ce y compris pour les traversées les plus longues comme celle qui consiste à faire le tour de Guadeloupe ou celle entre la Guadeloupe et Antigua. Bilan nous avons fait à peine la moitié de l’itinéraire prévu : seulement Antigua-et-Barbuda alors que devions aller jusqu’à St Kitts puis Nevis et Montserrat (sur 10 jours c’était censé être faisable. Ce changement de programme a entraîné une assez mauvaise ambiance au sein du groupe de clients qui étaient d’autant plus déçus qu’a bord il y avait non seulement un autre membre d’équipage et parmi les clients il y avait aussi du monde pour assurer les 1/4 nocturnes !...
Elena P.

Elena P.

review about ABSOLUTE DISCOVERY - New Year's Eve at the Grenadines - Caribbean Islands December 2018

10 / 10
Navigare con Giammy al timone è una garanzia ! Attenzione e precisione ingegneristica unita ad una dose di simpatia e buonumore ! Un binomio perfetto!
BERNARD T.

BERNARD T.

review about What have you plan for New Year Eve? Get on board and enjoy the Caribbean December 2018

10 / 10
J’ai passé une superbe semaine à bord pour débuter cette nouvelle année. L’accueil et l’hospitalité combinés de Anna et Alfonso sont très appréciables Une semaine de tranquillité à profiter de la vie à bord animée par Anna, de la vie sur la mer et à tous vents skippé par Alfonso, avec la découverte de l’environnement terrestre des îles et de leurs habitants. En résumé prêt à repartir sur le voilier Buen vento e ci vediamo presto Bernard il francese
Carole D.

Carole D.

review about Tobago Cays and Grenadines in Catamaran December 2018

10 / 10
Amazing !!!!
Matteo C.

Matteo C.

review about Last minute - New Year in the Caribbean heat sailing between the Grenadines Islands! December 2018

10 / 10
Renato è un ottimo skipper è uno splendido compagno di viaggio. Con poche parole sa Farenite le indicazioni giuste per navigare e per passare del buon tempo tra persone in vacanza. Abbiamo scoperto insieme quei posti meravigliosi che sono i Caraibi Orientali. Il vento soffia sempre forte da quelle parti a dicembre ma non abbiamo mai fatto un passo indietro Grazie ancora Renato. A presto Matteo
Gonzalo B.

Gonzalo B.

review about The best of a sailing cruise in Carabbean with All Inclusive formula, in Guadeloupe island !! November 2018

8 / 10
Francesco it's a dedicated, passionate and experienced skipper. He always tries to fulfill all your expectations, changing the itinerary on the way if it's necessary. His boat is safe and comfortable.
Sergio V.

Sergio V.

review about ABSOLUTE DISCOVERY - Bahamas Exuma Cays in Catamaran April 2018

10 / 10
Anche in questa seconda esperienza di vacanza con Fabiano ho avuto modo di apprezzare la sua professionalità, esperienza e simpatia. Spero di poter navigare ancora presto al tuo fianco! Buon vento :-)
Francesca B.

Francesca B.

review about ABSOLUTE DISCOVERY - Bahamas Exuma Cays in Catamaran April 2018

10 / 10
Vacanza meravigliosa! Posti incredibili, equipaggio stupendo e skipper estremamente competente. Grazie
Antonio B.

Antonio B.

review about Come relax under Guadeloupean's coconut trees! April 2018

6 / 10
Didier ed Elisabeth hanno fatto quanto possibile per metterci a nostro agio e soddisfare le nostre esigenze quindi meritano i ns. rigraziamenti ed un giudizio complessivo positivo. Tuttavia le possibilità di migliorare il loro servizio sono veramente tante: Fare presente che parlate solo Francese. Verificate che i membri ospiti dell'equipaggio gradiscano la presenza di animali a bordo. Informatevi riguardo le abitudini alimentari dei vs. ospiti e fate la spesa insieme a loro o di comune accordo. utilizzate le ricevute per effettuare realmente i conti di cambusa porti e rifornimenti... Non è una tassa ma un rimborso spese. Infine ricordate che i vostri ospiti hanno scelto una vacanza su imbarcazione a vela... per veleggiare!
Fabiano C.

Fabiano C.

review about ABSOLUTE DISCOVERY - Bahamas Exuma Cays in Catamaran April 2018

10 / 10
Mitico Sergio! Assieme abbiamo navigato nei mari difficili delle Bahamas. Grazie alla sua competenza e al suo carisma ci siamo divertiti destreggiandoci in fiordi e canali di correnti molto complessi, in totale serenità! Grazie Sergio
Fabiano C.

Fabiano C.

review about ABSOLUTE DISCOVERY - Bahamas Exuma Cays in Catamaran April 2018

10 / 10
Grandissimo Goffredo! Abbiamo navigato assieme nel aradiso delle Bahamas. Grazie al suo aiuto abbiamo avuto vita facile nella gestione della navigazione nella acque difficili dei Caraibi. Grazie Goff!!
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6 reasons to choose the Caribbean for your next sailing holiday:

  • Warm winter under the tropical sun
  • Enjoy excellent sailing conditions to learn or improve
  • Relax in the beautiful coves where you can admire beautiful marine wildlife
  • Learn about Creole culture and discover a rich architectural and cultural heritage
  • Delight your taste buds with Creole flavours
  • Adapt your itinerary with your skipper, and experience numerous islands

The best destinations to visit during your sailing holidays in the Caribbean:

The Caribbean is a popular destination for sailing thanks to a warm year-round climate, stunning scenery, and dreamlike natural wonders. A sailing holiday is an ideal opportunity to discover the Caribbean Islands. Here are some of the most beautiful destinations to be discovered:

Guadeloupe: the islands with the beautiful waters

This extraordinary concentration of islands is a region rich in culinary tradition, colours and scents. The landscape is varied, with a dense tropical forest and lush vegetation, due to the very fertile volcanic soil. And then there are the beaches of white sand, met by a turquoise sea and coral reef. Between the wild Petite Terre, mythical Marie Galante and striking île des Saintes, there is much exploration to be done under the tropical sun.

Martinique: the island of flowers

The volcanic coast combines lush vegetation and turquoise lagoons dotted with small coves lined surrounded by palm trees. The southern part of Martinique is postcard picturesque, ideal for travellers looking for white sand beaches, coconuts, and warm waters. Martinique has a rich cultural heritage, expressed by its different forms of craftsmanship and delicious cuisine.

Saint Vincent and the Grenadines: the islands of Pirates of the Caribbean

Saint Vincent and the Grenadines are located in the southern part of the Caribbean. Aboard a sailboat or catamaran, you have the opportunity to explore a number of the 32 uninhabited, and over 600 uninhabited islands and islets of the archipelago. A true paradise made of fine white sand and turquoise water.

The British Virgin Islands:

A well preserved, wild archipelago where you can experience extraordinary catamaran sailing holidays. From the cultural and historic journey of the main islands, to the natural splendour of the 50 small islands, each anchorage having its own magic charm. Kick back in beautiful bays, on white sand beaches, snorkel with tropical fish, and explore the marinas and villages ashore as you go.

Cuba: the largest of the Caribbean islands

Enjoy the beautiful marine wildlife whilst sailing Cienfuegos the islands of Cayo Guano, Cayo Largo, Cayo Cantiles, just to name a few. Discover the untouched islands of paradise, swim in crystal clear waters, snorkel over beautiful reefs and spend days enjoying the relaxed atmosphere of irresistible Cuba. Find out why this vibrant country is an unmissable destination for sailing.

All you need to know about your next cruise in the Caribbean aboard a sailboat

The best time to go on a sailing holiday in the Caribbean

Sailing holidays in the Caribbean are best from November to April, during the European winter. This offers the opportunity to escape the colder part of the year, and to instead exchange it for a tropical sun and life aboard a sailboat. The season lasts until June, and then between July and September there are very few options as there is a significant risk of cyclones. However, areas such as the Grenadines are possible to visit during the European summer, as this part of the Antilles is not affected by these climatic events.

How much does it cost for a Caribbean?

It can be more accessible to board a sailboat or catamaran sailing adventure in the West Indies than you might think, for budgets of all inclusive experiences beginning from around €1,200 per person. This budget of such a holiday can be broken down into 3 parts: the plane ticket, the catamaran or sailboat, and the float cash (food, fuel, marina costs, etc). It is possible to find round trip plane tickets to Guadeloupe, Saint-Vincent or Martinique from €400 with a number of low-cost airlines The price of your Caribbean cruise will depend on the period, the services onboard (with or without cook and hostess), and whether it is a sailboat or catamaran. A catamaran sailing holiday in the Caribbean can be significantly more expensive than a sailboat trip given the higher level of comfort. You can find spots onboard catamaran holidays from €600 on Sailsquare and all-inclusive holidays from €1,000.

Transport options in the Caribbean

The Caribbean is home to many airports and there are a large number of different airlines, of different price brackets, connecting the Caribbean with the world. Transport pricing can vary depending on the seasons, with some peak in price around the Christmas holiday period. Transport to and from the Caribbean may be significantly cheaper during the months of November and January.

To travel the Caribbean on catamaran or sailboat - with or without skipper?

A Caribbean sailing holiday experience is a great opportunity to have quality time with family and friends. Do you already have your travelling group formed? No problem! There are a number of whole boat booking holiday listings that allow you to reserve the entire boat.

The best sailing holiday itineraries for your next adventure in the Caribbean with a skipper:

Across the Caribbean there are numerous sailing holiday itineraries available. Here are some of our favourites:

  • Guadeloupe:: even one week allows enough time to fully enjoy this sublime archipelago. From Pointe-à-Pitre, you make a first stop at Marie Galante, before discovering Les Saintes. Moments of pure relaxation and discovery. If you wish, you can also discover the aquatic fauna and flora of the Cousteau Reserve Marine Park.
  • Martinique, Saint Lucia & Saint Vincent:: a very beautiful adventure, comfortably doable in one week from Fort-de-France. At first you head for the volcanic island of Saint Lucia, then the lush island of St. Vincent, part of the Grenadines. So many wonderful places await you during this special holiday itinerary.
  • The BVI:: cross the British Virgin Islands, starting and ending in St. Martin. Your first stop will be Virgin Gorda, where the famous baths await you, before you pass onto Horse Shoe Reef, the Norman Island Caves, and a number of other natural wonders.
  • Guadeloupe, Antigua & Barbuda:: around 12 days sailing from Pointe-à-Pitre in Guadeloupe. You round the island from the west before going back to Antigua, then continue on to Barbuda and going on down to Pointe-à-Pitre, passing east of Antigua.
  • Cuba:: departing from Cienfuegos, you can take a week to sail the crystal clear waters surrounding Cayo Guano, Cayo Rosario, and Punta del Este.
  • Guadeloupe, Antigua & Barbuda:: a week-long holiday from Marsh Harbor. To the east of the island you can discover the neighbouring islands, colourful architecture of Elbow Cay, seven-mile beach of Great Guana Cay, passing by the famous sands of Treasure Cay, and deep bays Green Turtle Cay.

Caribbean: the most beautiful places to sail

  • Grenadines & Martinique (59)
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Caribbean: next departures

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Caribbean: best travel ideas

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