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Sailing the Caribbean

Caribbean islands holidays on the water
7 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 14 experiences
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Experience Inicio Plazas Price
Caribbean dreams: sailing adventures under palm trees
From 23 Mar to 6 Apr
23 Mar
15 days
8 More information Reserve for 1,860€
Sail seven days through the Caribbean aboard a sailboat
From 24 Mar to 30 Mar
24 Mar
7 days
4 More information Reserve for 951€
Sailboat navigation through San Blas Panama, with food included.
From 24 Mar to 26 Mar
24 Mar
3 days
2 More information Reserve for 1,200€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 25 Mar to 30 Mar
25 Mar
6 days
4 More information Reserve for 756€
Sailing trip in the Grenadines
From 25 Mar to 31 Mar
25 Mar
7 days
4 More information Reserve for 1,130€
Sail with us in the Paradise called Caribbean.
From 28 Mar to 7 Apr
28 Mar
11 days
1 More information Reserve for 1,500€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 1 Apr to 6 Apr
1 Apr
6 days
4 More information Reserve for 756€
Sailing trip in the Grenadines
From 1 Apr to 7 Apr
1 Apr
7 days
4 More information Reserve for 1,130€
Sail the Caribbean Sea by sailboat - Martinique and Grenadines
From 1 Apr to 8 Apr
1 Apr
8 days
2 More information Reserve for 800€
Sailboat navigation through San Blas Panama, with food included.
From 5 Apr to 7 Apr
5 Apr
3 days
2 More information Reserve for 1,200€
Caribbean dreams: sailing adventures under palm trees
From 6 Apr to 20 Apr
6 Apr
15 days
8 More information Reserve for 1,860€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 8 Apr to 13 Apr
8 Apr
6 days
4 More information Reserve for 756€
Sailing trip in the Grenadines
From 8 Apr to 14 Apr
8 Apr
7 days
4 More information Reserve for 1,130€
Sail with us in the Paradise called Caribbean.
From 11 Apr to 21 Apr
11 Apr
11 days
4 More information Reserve for 1,500€
Sailboat navigation through San Blas Panama, with food included.
From 12 Apr to 14 Apr
12 Apr
3 days
2 More information Reserve for 1,200€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 15 Apr to 20 Apr
15 Apr
6 days
4 More information Reserve for 756€
Sailing trip in the Grenadines
From 15 Apr to 21 Apr
15 Apr
7 days
4 More information Reserve for 1,130€
Sailboat navigation through San Blas Panama, with food included.
From 19 Apr to 21 Apr
19 Apr
3 days
2 More information Reserve for 1,200€
Nassau, Bahamas - West Palm Beach, USA
From 20 Apr to 3 May
20 Apr
14 days
6 More information Reserve for 1,125€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 22 Apr to 27 Apr
22 Apr
6 days
4 More information Reserve for 756€
Sailing trip in the Grenadines
From 22 Apr to 28 Apr
22 Apr
7 days
4 More information Reserve for 1,130€
Sail with us in the Paradise called Caribbean.
From 25 Apr to 5 May
25 Apr
11 days
4 More information Reserve for 1,500€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 29 Apr to 4 May
29 Apr
6 days
4 More information Reserve for 756€
Sailing trip in the Grenadines
From 29 Apr to 5 May
29 Apr
7 days
4 More information Reserve for 1,130€
SAN BLAS PANAMA, ISLAND HOPPING
From 29 Apr to 10 May
29 Apr
12 days
8 More information Reserve for 1,980€
Sailboat navigation through San Blas Panama, with food included.
From 3 May to 5 May
3 May
3 days
2 More information Reserve for 1,200€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 6 May to 11 May
6 May
6 days
4 More information Reserve for 756€
Sailing trip in the Grenadines
From 6 May to 12 May
6 May
7 days
4 More information Reserve for 1,130€
Sailboat navigation through San Blas Panama, with food included.
From 10 May to 12 May
10 May
3 days
2 More information Reserve for 1,200€
Sailing trip in the Grenadines
From 13 May to 19 May
13 May
7 days
4 More information Reserve for 1,130€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 13 May to 18 May
13 May
6 days
4 More information Reserve for 756€
Sailboat navigation through San Blas Panama, with food included.
From 17 May to 19 May
17 May
3 days
2 More information Reserve for 1,200€
Sailing trip in the Grenadines
From 20 May to 26 May
20 May
7 days
4 More information Reserve for 1,130€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 20 May to 25 May
20 May
6 days
4 More information Reserve for 756€
Sailboat navigation through San Blas Panama, with food included.
From 24 May to 26 May
24 May
3 days
2 More information Reserve for 1,200€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 27 May to 1 Jun
27 May
6 days
4 More information Reserve for 756€
Sailing trip in the Grenadines
From 27 May to 2 Jun
27 May
7 days
4 More information Reserve for 1,130€
Sailboat navigation through San Blas Panama, with food included.
From 31 May to 2 Jun
31 May
3 days
2 More information Reserve for 1,200€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 3 Jun to 8 Jun
3 Jun
6 days
4 More information Reserve for 756€
SAN BLAS PANAMA, ISLAND HOPPING
From 3 Jun to 14 Jun
3 Jun
12 days
8 More information Reserve for 1,980€
Sailing trip in the Grenadines
From 3 Jun to 10 Jun
3 Jun
8 days
4 More information Reserve for 1,130€
Sailboat navigation through San Blas Panama, with food included.
From 7 Jun to 9 Jun
7 Jun
3 days
2 More information Reserve for 1,200€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 10 Jun to 15 Jun
10 Jun
6 days
4 More information Reserve for 756€
Sailing trip in the Grenadines
From 11 Jun to 17 Jun
11 Jun
7 days
4 More information Reserve for 1,130€
Sailboat navigation through San Blas Panama, with food included.
From 14 Jun to 16 Jun
14 Jun
3 days
2 More information Reserve for 1,200€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 17 Jun to 22 Jun
17 Jun
6 days
4 More information Reserve for 756€
Sailing trip in the Grenadines
From 18 Jun to 24 Jun
18 Jun
7 days
4 More information Reserve for 1,130€
Sailboat navigation through San Blas Panama, with food included.
From 21 Jun to 23 Jun
21 Jun
3 days
2 More information Reserve for 1,200€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 24 Jun to 29 Jun
24 Jun
6 days
4 More information Reserve for 756€
Sailing trip in the Grenadines
From 25 Jun to 1 Jul
25 Jun
7 days
4 More information Reserve for 1,130€
Sailboat navigation through San Blas Panama, with food included.
From 28 Jun to 30 Jun
28 Jun
3 days
2 More information Reserve for 1,200€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 1 Jul to 6 Jul
1 Jul
6 days
4 More information Reserve for 756€
SAN BLAS PANAMA, ISLAND HOPPING
From 1 Jul to 12 Jul
1 Jul
12 days
8 More information Reserve for 1,980€
Sailing trip in the Grenadines
From 2 Jul to 8 Jul
2 Jul
7 days
4 More information Reserve for 1,130€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 8 Jul to 13 Jul
8 Jul
6 days
4 More information Reserve for 756€
Sailing trip in the Grenadines
From 9 Jul to 15 Jul
9 Jul
7 days
4 More information Reserve for 1,130€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 15 Jul to 20 Jul
15 Jul
6 days
4 More information Reserve for 756€
Sailing trip in the Grenadines
From 16 Jul to 22 Jul
16 Jul
7 days
4 More information Reserve for 1,130€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 22 Jul to 27 Jul
22 Jul
6 days
4 More information Reserve for 756€
Sailing trip in the Grenadines
From 23 Jul to 29 Jul
23 Jul
7 days
4 More information Reserve for 1,130€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 29 Jul to 3 Aug
29 Jul
6 days
4 More information Reserve for 756€
Sailing trip in the Grenadines
From 30 Jul to 5 Aug
30 Jul
7 days
4 More information Reserve for 1,130€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 5 Aug to 10 Aug
5 Aug
6 days
4 More information Reserve for 756€
SAN BLAS PANAMA, ISLAND HOPPING
From 5 Aug to 16 Aug
5 Aug
12 days
8 More information Reserve for 1,980€
Sailing trip in the Grenadines
From 6 Aug to 12 Aug
6 Aug
7 days
4 More information Reserve for 1,130€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 12 Aug to 17 Aug
12 Aug
6 days
4 More information Reserve for 756€
Sailing trip in the Grenadines
From 13 Aug to 19 Aug
13 Aug
7 days
4 More information Reserve for 1,130€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 19 Aug to 24 Aug
19 Aug
6 days
4 More information Reserve for 756€
Sailing trip in the Grenadines
From 20 Aug to 26 Aug
20 Aug
7 days
4 More information Reserve for 1,130€
Sailing trip from Martinique to Marie-Galante & Les Saintes
From 26 Aug to 31 Aug
26 Aug
6 days
4 More information Reserve for 756€
Sailing trip in the Grenadines
From 27 Aug to 2 Sep
27 Aug
7 days
4 More information Reserve for 1,130€
Caribbean dreams: sailing adventures under palm trees
From 2 Nov to 16 Nov
2 Nov
15 days
8 More information Reserve for 1,860€
Caribbean dreams: sailing adventures under palm trees
From 16 Nov to 30 Nov
16 Nov
15 days
8 More information Reserve for 1,860€
Caribbean dreams: sailing adventures under palm trees
From 30 Nov to 14 Dec
30 Nov
15 days
8 More information Reserve for 1,860€
Caribbean dreams: sailing adventures under palm trees
From 14 Dec to 28 Dec
14 Dec
15 days
8 More information Reserve for 2,100€
Family Sailing - Happy New Year in the Caribbean
From 26 Dec to 4 Jan (2025)
26 Dec
10 days
4 More information Reserve for 1,850€
NEW YEAR'S EVE IN THE CARIBBEAN .. SAILING BOAT
From 26 Dec to 7 Jan (2025)
26 Dec
13 days
8 More information Reserve for 1,521€
Explore the Caribbean in a relaxed manner - In the footsteps of Jack Sparrow (Grenadines)
From 4 Jan to 16 Jan (2025)
4 Jan
13 days
6 More information Reserve for 1,487€
Your yacht with friends or family in the Caribbean (with skipper)
From 18 Jan to 30 Jan (2025)
18 Jan
13 days
8 More information Reserve for 9,600€
Caribbean without compromises - premium vacation on sailing yacht GALINI
From 1 Feb to 8 Feb (2025)
1 Feb
8 days
6 More information Reserve for 16,000€
Caribbean without compromises - premium vacation on sailing yacht GALINI
From 8 Feb to 15 Feb (2025)
8 Feb
8 days
6 More information Reserve for 16,000€
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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