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Sailing the Caribbean

Caribbean islands holidays on the water
2 reviews
Go sailing in the Caribbean for your next holiday. Bask in the sun on board as the boat cuts through the clearest blue waters, take a dip when you please and spend some time exploring on shore. Choose the part of the Caribbean you wish to explore and enjoy a holiday in paradise.
Choose from 19 experiences
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Next plans
Experience InicioPlazasPrice
PANAMA - CUBA
From 1 Dec to 15 Dec
1 Dec
15 days
6 More information Reserve for 1,499€
Caribbean dreams: sailing adventures under palm trees
From 2 Dec to 16 Dec
2 Dec
15 days
8 More information Reserve for 1,860€
Caribbean dreams: sailing adventures under palm trees
From 16 Dec to 30 Dec
16 Dec
15 days
8 More information Reserve for 2,100€
Happy New Year in the Caribbean
From 27 Dec to 9 Jan (2024)
27 Dec
14 days
6 More information Reserve for 1,572€
Caribbean dreams: sailing adventures under palm trees
From 30 Dec to 13 Jan (2024)
30 Dec
15 days
8 More information Reserve for 2,100€
Discover the best islands in the Caribbean by catamaran for 7 days
From 1 Jan to 7 Jan (2024)
1 Jan
7 days
8 More information Reserve for 1,320€
Discover the best islands in the Caribbean by catamaran for 7 days
From 8 Jan to 14 Jan (2024)
8 Jan
7 days
6 More information Reserve for 1,320€
CIENFUEGOS CUBA to CANCUN MEXICO
From 8 Jan to 21 Jan (2024)
8 Jan
14 days
7 More information Reserve for 1,980€
Caribbean dreams: sailing adventures under palm trees
From 13 Jan to 27 Jan (2024)
13 Jan
15 days
8 More information Reserve for 1,860€
Explore the Caribbean in a relaxed manner - in the footsteps of Jack Sparrow
From 13 Jan to 25 Jan (2024)
13 Jan
13 days
6 More information Reserve for 1,657€
Discover the best islands in the Caribbean by catamaran for 7 days
From 15 Jan to 21 Jan (2024)
15 Jan
7 days
8 More information Reserve for 1,320€
Discover the best islands in the Caribbean by catamaran for 7 days
From 22 Jan to 28 Jan (2024)
22 Jan
7 days
8 More information Reserve for 1,320€
CANCUN MEXICO TO CIENFUEGOS, CUBA
From 25 Jan to 11 Feb (2024)
25 Jan
18 days
7 More information Reserve for 1,980€
CANCUN MEXICO TO CIENFUEGOS, CUBA
From 25 Jan to 11 Feb (2024)
25 Jan
18 days
7 More information Reserve for 1,980€
Caribbean dreams: sailing adventures under palm trees
From 27 Jan to 10 Feb (2024)
27 Jan
15 days
8 More information Reserve for 1,860€
Discover the best islands in the Caribbean by catamaran for 7 days
From 29 Jan to 4 Feb (2024)
29 Jan
7 days
8 More information Reserve for 1,320€
Sail the Caribbean Sea by sailboat - Martinique and Grenadines
From 1 Feb to 8 Feb (2024)
1 Feb
8 days
4 More information Reserve for 800€
Discover the best islands in the Caribbean by catamaran for 7 days
From 5 Feb to 11 Feb (2024)
5 Feb
7 days
8 More information Reserve for 1,320€
Sail seven days through the Caribbean aboard a sailboat
From 5 Feb to 11 Feb (2024)
5 Feb
7 days
4 More information Reserve for 951€
Caribbean dreams: sailing adventures under palm trees
From 10 Feb to 24 Feb (2024)
10 Feb
15 days
8 More information Reserve for 1,860€
Discover the Caribbean from a fantastic sailing yacht
From 10 Feb to 24 Feb (2024)
10 Feb
15 days
6 More information Reserve for 1,755€
Discover the best islands in the Caribbean by catamaran for 7 days
From 12 Feb to 18 Feb (2024)
12 Feb
7 days
8 More information Reserve for 1,320€
Sail on a sailboat in the Caribbean between Martinique and The Grenadines
From 13 Feb to 13 Mar (2024)
13 Feb
30 days
6 More information Reserve for 1,490€
Sail 3 months in the Caribbean, from Granada to Panama
From 13 Feb to 23 Apr (2024)
13 Feb
71 days
10 More information Reserve for 5,000€
Sail seven days through the Caribbean aboard a sailboat
From 13 Feb to 19 Feb (2024)
13 Feb
7 days
4 More information Reserve for 951€
CUBA CIENFUEGOS ARCHIPELAGO DE CANARREOS
From 13 Feb to 24 Feb (2024)
13 Feb
12 days
7 More information Reserve for 1,980€
Discover the best islands in the Caribbean by catamaran for 7 days
From 19 Feb to 25 Feb (2024)
19 Feb
7 days
8 More information Reserve for 1,320€
Sail seven days through the Caribbean aboard a sailboat
From 21 Feb to 27 Feb (2024)
21 Feb
7 days
4 More information Reserve for 951€
Caribbean dreams: sailing adventures under palm trees
From 24 Feb to 9 Mar (2024)
24 Feb
15 days
8 More information Reserve for 1,860€
With Sunshine Reggae through the British Virgin Islands
From 24 Feb to 10 Mar (2024)
24 Feb
16 days
6 More information Reserve for 1,757€
Sail on a sailboat from Martinique to Panama
From 25 Feb to 6 Mar (2024)
25 Feb
11 days
6 More information Reserve for 1,400€
Discover the best islands in the Caribbean by catamaran for 7 days
From 26 Feb to 3 Mar (2024)
26 Feb
7 days
8 More information Reserve for 1,320€
Sail seven days through the Caribbean aboard a sailboat
From 29 Feb to 6 Mar (2024)
29 Feb
7 days
4 More information Reserve for 951€
Sail seven days through the Caribbean aboard a sailboat
From 8 Mar to 14 Mar (2024)
8 Mar
7 days
4 More information Reserve for 951€
Caribbean dreams: sailing adventures under palm trees
From 9 Mar to 23 Mar (2024)
9 Mar
15 days
8 More information Reserve for 1,860€
St. Martin to Luperon, Dominican Republic Caribbean cruise
From 9 Mar to 22 Mar (2024)
9 Mar
14 days
6 More information Reserve for 1,187€
Sail seven days through the Caribbean aboard a sailboat
From 16 Mar to 22 Mar (2024)
16 Mar
7 days
4 More information Reserve for 951€
Caribbean dreams: sailing adventures under palm trees
From 23 Mar to 6 Apr (2024)
23 Mar
15 days
8 More information Reserve for 1,860€
Luperon, Dominican Republic - George Town, Bahamas Caribbean cruise
From 23 Mar to 5 Apr (2024)
23 Mar
14 days
6 More information Reserve for 1,187€
Sail seven days through the Caribbean aboard a sailboat
From 24 Mar to 30 Mar (2024)
24 Mar
7 days
4 More information Reserve for 951€
Caribbean dreams: sailing adventures under palm trees
From 6 Apr to 20 Apr (2024)
6 Apr
15 days
8 More information Reserve for 1,860€
George Town - Nassau, Bahamas
From 6 Apr to 19 Apr (2024)
6 Apr
14 days
6 More information Reserve for 1,187€
Nassau, Bahamas - West Palm Beach, USA
From 20 Apr to 3 May (2024)
20 Apr
14 days
6 More information Reserve for 1,125€
Caribbean dreams: sailing adventures under palm trees
From 2 Nov to 16 Nov (2024)
2 Nov
15 days
8 More information Reserve for 1,860€
Caribbean dreams: sailing adventures under palm trees
From 16 Nov to 30 Nov (2024)
16 Nov
15 days
8 More information Reserve for 1,860€
Caribbean dreams: sailing adventures under palm trees
From 30 Nov to 14 Dec (2024)
30 Nov
15 days
8 More information Reserve for 1,860€
Caribbean dreams: sailing adventures under palm trees
From 14 Dec to 28 Dec (2024)
14 Dec
15 days
8 More information Reserve for 2,100€
Show all dates
Frequent questions
  • ⭐ ¿Por qué realizar un crucero por el Caribe?
    Viajar al Carube es la mejor opción para desconectar de la rutina y recargar energías. Además, podrás conocer a gente nueva autóctona de las islas, visitar nuevos lugarees y disfrutar del mar como nunca antes.
  • ✅ ¿Por qué viajar al Caribe en barco?
    Viajar al Caribe en barco es la mejor opción para disfrutar de la naturaleza y descubrir lugares recónditos que, si no fuese en barco, serían imposibles de acceder.
  • ➡️ ¿Cuál es la mejor época del año para viajar al Caribe en velero?
    La mejor temporada para hacer una travesía por el Caribe es entre diciembre y mayo, momento en el que el tiempo es algo más fresco, seco y menos húmedo.
  • ✍ ¿Qué islas del Caribe podré visitar durante la travesía?
    Las zonas más frecuentadas por los navegantes son Cuba y República Dominicana, Antigua, Guadalupe, Martinca y Dominica, Trinidad y Tobago, y Panamá.
  • ✍ ¿Cómo puedo reservar una travesía al Caribe?
    Tienes que entrar en la actividad que te interesa, consultar con el patrón todas las dudas que puedan surgirte y reservar a través de la web previo pago. Una vez completada la reserva, recibirás la confirmación en tu email.
  • ⚡ ¿Cuánto cuesta una travesía por el Caribe?
    Los precios de las travesías por el Caribe varían en función del tipo de embarcación, la duración de la experiencia, la época del año en la que desees navegar y la zona de embarque y desembarque.
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  • Why go on a Caribbean sailing holiday?

    Caribbean travel entails completely disconnecting from the accelerated pace we are used to every day. In this region there is no rush and the locals here are cheerful, happy and carefree.
    The Caribbean is a favorite destination for many people, both because of the desirable environment and warm weather as well as the warm welcome of the local people.

    For a holiday in the Caribbean aboard a sailboat or a catamaran, the experience is truly unique, as this arrangement allows you to visit extraordinary places and enjoy the sea, the sun and the breeze at all times.
  • When is the best time to travel around the Caribbean aboard a sailboat?

    The best time to sail in the Caribbean is between December and May, at which time the weather is somewhat cooler (especially in the north), drier and less humid. It is also the time that European tourists flock to the Caribbean paradise to escape winter in their home countries.
    The best months are December and January, when the trade winds are much more established.
  • Flora and Fauna you will see in the Caribbean aboard a sailboat

    In the Caribbean, there are 38 recognized locations where you can dive to observe marine life, areas with underwater lava flows, black sand, large strands of black coral, summits of underwater mountains, thousands of fish, etc.
    The biodiversity of the Caribbean coast is unique and offers a lively spectacle full of color for lovers of nature.
  • Why travel the Caribbean on a sailboat or catamaran?
    Exploring the Caribbean islands aboard a sailboat or catamaran is an excellent idea if you want to enjoy nature in its purest form. You can reach the nooks most hidden from the world and the speed ​​of the boats allows a peaceful itinerary so you can soak up the stunning and pristine bays and coves.
  • How do I book a Caribbean sailing holiday?
    On Sailwiz we make it easy for you to book your dream vacation in the Caribbean. You simply have to enter into the activity that interests you, ask the skipper any questions you may have and book through the website. Once the booking is complete, you will receive a confirmation email.
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