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Sailing the Caribbean

Caribbean islands holidays on the water
45 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 27 experiences
Show more experiences
caribbean cruise
The Caribbean seas have always been one of the desired sailing areas due to the incredible scenery and gorgeous climate. You can experience this beauty for yourself with the sailing plans that we have available in Sailwiz.
  • IMG-20190701-WA0118
By Álvaro Casanova
1 October, 2025
Next plans
Experience Start Plazas Price
14 days in the Caribbean island paradise on a catamaran
From 20 Dec to 3 Jan
20 Dec
15 days
6 More information Reserve for 2,290€
A week on the Grenadines by catamaran with everything included
From 20 Dec to 27 Dec
20 Dec
8 days
0 More information No availability
Post-ARC Caribbean Cruising
From 21 Dec to 28 Dec
21 Dec
8 days
9 More information Reserve for 530€
Cruise in the Las Perlas Archipelago – +200 islands on a 56-foot catamaran
From 22 Dec to 9 Jan
22 Dec
19 days
2 More information Reserve for 2,980€
Happy New Year! Across the Caribbean – Sailing, Sun, Paradise
From 26 Dec to 6 Jan
26 Dec
12 days
2 More information Reserve for 1,436€
Cruises to the Grenadines - Caribbean (Martinique - Martinique)
From 26 Dec to 5 Jan
26 Dec
11 days
0 More information No availability
A week on the Grenadines by catamaran with everything included
From 27 Dec to 3 Jan
27 Dec
8 days
0 More information No availability
14 days in the Caribbean island paradise on a catamaran
From 3 Jan to 17 Jan (2026)
3 Jan
15 days
4 More information Reserve for 1,390€
A week on the Grenadines by catamaran with everything included
From 3 Jan to 10 Jan (2026)
3 Jan
8 days
0 More information No availability
A week in Saint Martin on a Catamaran with everything included
From 3 Jan to 10 Jan (2026)
3 Jan
8 days
0 More information No availability
A week in the British Virgin Islands on a Catamaran with everything included
From 3 Jan to 10 Jan (2026)
3 Jan
8 days
0 More information No availability
Sailing charter in the nautical paradise of the British Virgin Islands (BVI)
From 3 Jan to 9 Jan (2026)
3 Jan
7 days
10 More information Reserve for 1,400€
Sail around the Caribbean - British Virgin Islands (BVI)
From 3 Jan to 9 Jan (2026)
3 Jan
7 days
10 More information Reserve for 1,400€
11-day trip through the Caribbean Sea on a Catamaran with everything included
From 6 Jan to 16 Jan (2026)
6 Jan
11 days
0 More information No availability
Bahamas sailing adventure with a professional Dutch catamaran skipper
From 7 Jan to 14 Jan (2026)
7 Jan
8 days
6 More information Reserve for 1,299€
A week on the Grenadines by catamaran with everything included
From 10 Jan to 17 Jan (2026)
10 Jan
8 days
4 More information Reserve for 4,340€
A week through the islands of Guadeloupe on a Catamaran with everything included
From 10 Jan to 17 Jan (2026)
10 Jan
8 days
0 More information No availability
A week in Saint Martin on a Catamaran with everything included
From 10 Jan to 17 Jan (2026)
10 Jan
8 days
0 More information No availability
A week in the British Virgin Islands on a Catamaran with everything included
From 10 Jan to 17 Jan (2026)
10 Jan
8 days
0 More information No availability
Sailing charter in the nautical paradise of the British Virgin Islands (BVI)
From 10 Jan to 16 Jan (2026)
10 Jan
7 days
8 More information Reserve for 1,400€
A week in the Bahamas (Abacos) on a Catamaran with everything included
From 10 Jan to 17 Jan (2026)
10 Jan
8 days
4 More information Reserve for 2,142€
Sail around the Caribbean - British Virgin Islands (BVI)
From 10 Jan to 16 Jan (2026)
10 Jan
7 days
10 More information Reserve for 1,400€
We discover the world: A dream British Virgin Islands & Puerto Rico
From 11 Jan to 22 Jan (2026)
11 Jan
12 days
1 More information Reserve for 1,690€
Cruises to the Grenadines - Caribbean (Martinique - Martinique)
From 12 Jan to 25 Jan (2026)
12 Jan
14 days
0 More information No availability
Bahamas sailing adventure with a professional Dutch catamaran skipper
From 14 Jan to 21 Jan (2026)
14 Jan
8 days
6 More information Reserve for 1,299€
11-day trip through the Caribbean Sea on a Catamaran with everything included
From 16 Jan to 26 Jan (2026)
16 Jan
11 days
2 More information Reserve for 4,736€
A week on the Grenadines by catamaran with everything included
From 17 Jan to 24 Jan (2026)
17 Jan
8 days
2 More information Reserve for 4,340€
A week through the islands of Guadeloupe on a Catamaran with everything included
From 17 Jan to 24 Jan (2026)
17 Jan
8 days
0 More information No availability
A week in Saint Martin on a Catamaran with everything included
From 17 Jan to 24 Jan (2026)
17 Jan
8 days
2 More information Reserve for 2,345€
A week in the British Virgin Islands on a Catamaran with everything included
From 17 Jan to 24 Jan (2026)
17 Jan
8 days
2 More information Reserve for 4,390€
Sailing charter in the nautical paradise of the British Virgin Islands (BVI)
From 17 Jan to 23 Jan (2026)
17 Jan
7 days
10 More information Reserve for 1,400€
A week in the Bahamas (Abacos) on a Catamaran with everything included
From 17 Jan to 24 Jan (2026)
17 Jan
8 days
2 More information Reserve for 4,200€
Sail around the Caribbean - British Virgin Islands (BVI)
From 17 Jan to 23 Jan (2026)
17 Jan
7 days
10 More information Reserve for 1,400€
Bahamas sailing adventure with a professional Dutch catamaran skipper
From 21 Jan to 28 Jan (2026)
21 Jan
8 days
6 More information Reserve for 1,299€
A week on the Grenadines by catamaran with everything included
From 24 Jan to 31 Jan (2026)
24 Jan
8 days
2 More information Reserve for 4,340€
A week through the islands of Guadeloupe on a Catamaran with everything included
From 24 Jan to 31 Jan (2026)
24 Jan
8 days
0 More information No availability
A week in Saint Martin on a Catamaran with everything included
From 24 Jan to 31 Jan (2026)
24 Jan
8 days
0 More information No availability
A week in the British Virgin Islands on a Catamaran with everything included
From 24 Jan to 31 Jan (2026)
24 Jan
8 days
0 More information No availability
We discover the world: A dream in Puerto Rico & British Virgin Islands
From 24 Jan to 5 Feb (2026)
24 Jan
13 days
2 More information Reserve for 1,690€
A week in the Bahamas (Abacos) on a Catamaran with everything included
From 24 Jan to 31 Jan (2026)
24 Jan
8 days
0 More information No availability
Sail around the Caribbean - British Virgin Islands (BVI)
From 24 Jan to 30 Jan (2026)
24 Jan
7 days
10 More information Reserve for 1,400€
Guadeloupe to Martinique
From 24 Jan to 6 Feb (2026)
24 Jan
14 days
4 More information Reserve for 1,463€
11-day trip through the Caribbean Sea on a Catamaran with everything included
From 26 Jan to 5 Feb (2026)
26 Jan
11 days
2 More information Reserve for 5,920€
Cruise in the Las Perlas Archipelago – +200 islands on a 56-foot catamaran
From 26 Jan to 6 Feb (2026)
26 Jan
12 days
4 More information Reserve for 1,980€
Bahamas sailing adventure with a professional Dutch catamaran skipper
From 28 Jan to 4 Feb (2026)
28 Jan
8 days
6 More information Reserve for 1,299€
Cruises to the Grenadines - Caribbean (Martinique - Martinique)
From 29 Jan to 10 Feb (2026)
29 Jan
13 days
6 More information Reserve for 1,300€
A week on the Grenadines by catamaran with everything included
From 31 Jan to 7 Feb (2026)
31 Jan
8 days
6 More information Reserve for 2214.25€
A week through the islands of Guadeloupe on a Catamaran with everything included
From 31 Jan to 7 Feb (2026)
31 Jan
8 days
0 More information No availability
A week in Saint Martin on a Catamaran with everything included
From 31 Jan to 7 Feb (2026)
31 Jan
8 days
2 More information Reserve for 3,910€
A week in the British Virgin Islands on a Catamaran with everything included
From 31 Jan to 7 Feb (2026)
31 Jan
8 days
4 More information Reserve for 4,114€
Ocean School/Travel/Mile building: Caribbean Sea (BVI to Martinique)
From 31 Jan to 8 Feb (2026)
31 Jan
9 days
8 More information Reserve for 1,400€
Ocean School/Travel/Mile building: Caribbean Sea (Full Antilles)
From 31 Jan to 15 Feb (2026)
31 Jan
16 days
6 More information Reserve for 2,400€
A week in the Bahamas (Abacos) on a Catamaran with everything included
From 31 Jan to 7 Feb (2026)
31 Jan
8 days
4 More information Reserve for 2,044€
Bahamas sailing adventure with a professional Dutch catamaran skipper
From 4 Feb to 11 Feb (2026)
4 Feb
8 days
6 More information Reserve for 1,299€
11-day trip through the Caribbean Sea on a Catamaran with everything included
From 5 Feb to 15 Feb (2026)
5 Feb
11 days
2 More information Reserve for 6,120€
A week on the Grenadines by catamaran with everything included
From 7 Feb to 14 Feb (2026)
7 Feb
8 days
10 More information Reserve for 3,906€
A week through the islands of Guadeloupe on a Catamaran with everything included
From 7 Feb to 14 Feb (2026)
7 Feb
8 days
2 More information Reserve for 3,519€
A week in Saint Martin on a Catamaran with everything included
From 7 Feb to 14 Feb (2026)
7 Feb
8 days
2 More information Reserve for 3,910€
A week in the British Virgin Islands on a Catamaran with everything included
From 7 Feb to 14 Feb (2026)
7 Feb
8 days
12 More information Reserve for 4,114€
A week in the Bahamas (Abacos) on a Catamaran with everything included
From 7 Feb to 14 Feb (2026)
7 Feb
8 days
2 More information Reserve for 3,808€
Martinique to Guadeloupe
From 7 Feb to 20 Feb (2026)
7 Feb
14 days
5 More information Reserve for 1,463€
Ocean School/Travel/Mile building: Caribbean Sea (Martinique to BVI)
From 8 Feb to 15 Feb (2026)
8 Feb
8 days
8 More information Reserve for 1,400€
Cruise in the Las Perlas Archipelago – +200 islands on a 56-foot catamaran
From 9 Feb to 20 Feb (2026)
9 Feb
12 days
4 More information Reserve for 1,980€
Bahamas sailing adventure with a professional Dutch catamaran skipper
From 11 Feb to 18 Feb (2026)
11 Feb
8 days
6 More information Reserve for 1,299€
A week on the Grenadines by catamaran with everything included
From 14 Feb to 21 Feb (2026)
14 Feb
8 days
10 More information Reserve for 3,906€
A week in Saint Martin on a Catamaran with everything included
From 14 Feb to 21 Feb (2026)
14 Feb
8 days
4 More information Reserve for 3,910€
A week in the British Virgin Islands on a Catamaran with everything included
From 14 Feb to 21 Feb (2026)
14 Feb
8 days
2 More information Reserve for 4,990€
A week in the Bahamas (Abacos) on a Catamaran with everything included
From 14 Feb to 21 Feb (2026)
14 Feb
8 days
12 More information Reserve for 3,360€
11-day trip through the Caribbean Sea on a Catamaran with everything included
From 15 Feb to 25 Feb (2026)
15 Feb
11 days
2 More information Reserve for 6,120€
Cruises to the Grenadines - Caribbean (Martinique - Martinique)
From 15 Feb to 26 Feb (2026)
15 Feb
12 days
6 More information Reserve for 1,200€
We discover the Caribbean: Relaxing through the northern Antilles
From 15 Feb to 26 Feb (2026)
15 Feb
12 days
7 More information Reserve for 1,790€
A week on the Grenadines by catamaran with everything included
From 21 Feb to 28 Feb (2026)
21 Feb
8 days
10 More information Reserve for 3,906€
A week through the islands of Guadeloupe on a Catamaran with everything included
From 21 Feb to 28 Feb (2026)
21 Feb
8 days
4 More information Reserve for 3,128€
A week in Saint Martin on a Catamaran with everything included
From 21 Feb to 28 Feb (2026)
21 Feb
8 days
2 More information Reserve for 3,910€
A week in the British Virgin Islands on a Catamaran with everything included
From 21 Feb to 28 Feb (2026)
21 Feb
8 days
2 More information Reserve for 4,990€
Sailing charter in the nautical paradise of the British Virgin Islands (BVI)
From 21 Feb to 27 Feb (2026)
21 Feb
7 days
10 More information Reserve for 1,400€
A week in the Bahamas (Abacos) on a Catamaran with everything included
From 21 Feb to 28 Feb (2026)
21 Feb
8 days
12 More information Reserve for 3,510€
Sail around the Caribbean - British Virgin Islands (BVI)
From 21 Feb to 27 Feb (2026)
21 Feb
7 days
10 More information Reserve for 1,400€
Gudeloupe - St. Martin
From 21 Feb to 6 Mar (2026)
21 Feb
14 days
5 More information Reserve for 1,463€
Cruise in the Las Perlas Archipelago – +200 islands on a 56-foot catamaran
From 23 Feb to 6 Mar (2026)
23 Feb
12 days
7 More information Reserve for 1,980€
11-day trip through the Caribbean Sea on a Catamaran with everything included
From 25 Feb to 7 Mar (2026)
25 Feb
11 days
2 More information Reserve for 5,202€
A week on the Grenadines by catamaran with everything included
From 28 Feb to 7 Mar (2026)
28 Feb
8 days
2 More information Reserve for 4,240€
A week through the islands of Guadeloupe on a Catamaran with everything included
From 28 Feb to 7 Mar (2026)
28 Feb
8 days
2 More information Reserve for 3,820€
A week in Saint Martin on a Catamaran with everything included
From 28 Feb to 7 Mar (2026)
28 Feb
8 days
4 More information Reserve for 3,247€
A week in the British Virgin Islands on a Catamaran with everything included
From 28 Feb to 7 Mar (2026)
28 Feb
8 days
12 More information Reserve for 4,491€
Ocean School/Travel/Mile building: Caribbean Sea (BVI to Martinique)
From 28 Feb to 8 Mar (2026)
28 Feb
9 days
8 More information Reserve for 1,400€
Ocean School/Travel/Mile building: Caribbean Sea (Full Antilles)
From 28 Feb to 15 Mar (2026)
28 Feb
16 days
8 More information Reserve for 2,400€
A week in the Bahamas (Abacos) on a Catamaran with everything included
From 28 Feb to 7 Mar (2026)
28 Feb
8 days
2 More information Reserve for 4,114€
Cruises to the Grenadines - Caribbean (Martinique - Martinique)
From 3 Mar to 15 Mar (2026)
3 Mar
13 days
6 More information Reserve for 1,300€
A week in the British Virgin Islands on a Catamaran with everything included
From 7 Mar to 14 Mar (2026)
7 Mar
8 days
0 More information No availability
A week on the Grenadines by catamaran with everything included
From 7 Mar to 14 Mar (2026)
7 Mar
8 days
10 More information Reserve for 3,744€
11-day trip through the Caribbean Sea on a Catamaran with everything included
From 7 Mar to 17 Mar (2026)
7 Mar
11 days
2 More information Reserve for 5,960€
A week through the islands of Guadeloupe on a Catamaran with everything included
From 7 Mar to 14 Mar (2026)
7 Mar
8 days
12 More information Reserve for 3,366€
A week in Saint Martin on a Catamaran with everything included
From 7 Mar to 14 Mar (2026)
7 Mar
8 days
12 More information Reserve for 3,366€
A week in the Bahamas (Abacos) on a Catamaran with everything included
From 7 Mar to 14 Mar (2026)
7 Mar
8 days
2 More information Reserve for 5,000€
Ocean School/Travel/Mile building: Caribbean Sea (Martinique to BVI)
From 8 Mar to 15 Mar (2026)
8 Mar
8 days
8 More information Reserve for 1,400€
We discover the world: A dream British Virgin Islands & Puerto Rico
From 8 Mar to 20 Mar (2026)
8 Mar
13 days
6 More information Reserve for 1,790€
Cruise in the Las Perlas Archipelago – +200 islands on a 56-foot catamaran
From 9 Mar to 20 Mar (2026)
9 Mar
12 days
7 More information Reserve for 1,980€
A week in the British Virgin Islands on a Catamaran with everything included
From 14 Mar to 21 Mar (2026)
14 Mar
8 days
12 More information Reserve for 4,990€
A week in Saint Martin on a Catamaran with everything included
From 14 Mar to 21 Mar (2026)
14 Mar
8 days
12 More information Reserve for 3,366€
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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