Sailing the Caribbean

Choose from 15 experiences

From 890€

per spot

14 days in the Caribbean island paradise on a catamaran

Port of departure: Martinique

1 review

Next departure: 18 october · 5 dates available

From 890€
1,690€

per spot

We discover the world: A dream in Puerto Rico & British Virgin Islands

Port of departure: San Juan, Puerto Rico

2 reviews

Next departure: 24 jan 2026

1,690€
2,290€

per spot

⛵☀️ 14 days Caribbean with luxury catamaran - sailing holiday in 2025

Port of departure: Martinique

Next departure: 1 november

2,290€
1,690€
1,605€

per spot

Across the Caribbean – Sailing, Sun, Paradise

Port of departure: Martinique

2 reviews

Next departure: 26 december

1,690€ 1,605€
1,550€

per spot

New Year's Eve in the Caribbean on a Catamaran: Martinique, Saint Vincent and the Grenadines

Port of departure: Le Marin, Martinique

6 reviews

Next departure: 3 jan 2026

1,550€
From 3,573€

cabin

A week in the Bahamas on a Catamaran with everything included

Port of departure: Palm Cay Marina

Next departure: 25 october · 5 dates available

From 3,573€
2,400€
2,160€

per spot

Sail the Caribbean on a catamaran from Martinique to Saint Blaise

Port of departure: Martinica

Next departure: 18 november

2,400€ 2,160€
From 1,060€

cabin

A week through the islands of Guadeloupe on a Catamaran with everything included

Port of departure: Pointe-à-Pitre, Guadeloupe

Next departure: 11 october · 21 dates available

From 1,060€
1,690€

per spot

We discover the world: A dream British Virgin Islands & Puerto Rico

Port of departure: St Maarten

2 reviews

Next departure: 11 jan 2026

1,690€
From 1,001€

cabin

A week on the Grenadines by catamaran with everything included

Port of departure: Le Marin, Martinique

Next departure: 6 september · 27 dates available

From 1,001€
From 2,709€

cabin

A week in Saint Martin on a Catamaran with everything included

Port of departure: Anse Marcel, Saint Martin

Next departure: 1 november · 19 dates available

From 2,709€

Show more experiences

Discover the Caribbean aboard a sailboat

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.

By Álvaro Casanova y Jason Loughnane

21 November, 2019

Next plans

Experience	Start	Plazas		Price
A week on the Grenadines by catamaran with everything included	From 6 Sep to 13 Sep 6 Sep 8 days	10	More information	Reserve for 1,144€ More information
11-day trip through the Caribbean Sea on a Catamaran with everything included	From 11 Sep to 21 Sep 11 Sep 11 days	10	More information	Reserve for 1368.5€ More information
Cruise in the Las Perlas Archipelago – +200 islands on a 56-foot catamaran	From 15 Sep to 26 Sep 15 Sep 12 days	7	More information	Reserve for 1,980€ More information
A week on the Grenadines by catamaran with everything included	From 27 Sep to 4 Oct 27 Sep 8 days	10	More information	Reserve for 1,001€ More information
11-day trip through the Caribbean Sea on a Catamaran with everything included	From 1 Oct to 11 Oct 1 Oct 11 days	10	More information	Reserve for 2,771€ More information
A week on the Grenadines by catamaran with everything included	From 4 Oct to 11 Oct 4 Oct 8 days	10	More information	Reserve for 1,144€ More information
A week on the Grenadines by catamaran with everything included	From 11 Oct to 18 Oct 11 Oct 8 days	10	More information	Reserve for 1,248€ More information
11-day trip through the Caribbean Sea on a Catamaran with everything included	From 11 Oct to 21 Oct 11 Oct 11 days	10	More information	Reserve for 1,712€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 11 Oct to 18 Oct 11 Oct 8 days	12	More information	Reserve for 1,060€ More information
Cruise in the Las Perlas Archipelago – +200 islands on a 56-foot catamaran	From 13 Oct to 24 Oct 13 Oct 12 days	7	More information	Reserve for 1,980€ More information
A week on the Grenadines by catamaran with everything included	From 18 Oct to 25 Oct 18 Oct 8 days	10	More information	Reserve for 2405.5€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 18 Oct to 25 Oct 18 Oct 8 days	12	More information	Reserve for 3,040€ More information
14 days in the Caribbean island paradise on a catamaran	From 18 Oct to 1 Nov 18 Oct 15 days	6	More information	Reserve for 1,390€ More information
11-day trip through the Caribbean Sea on a Catamaran with everything included	From 21 Oct to 31 Oct 21 Oct 11 days	10	More information	Reserve for 3306.5€ More information
A week on the Grenadines by catamaran with everything included	From 25 Oct to 1 Nov 25 Oct 8 days	10	More information	Reserve for 2711.5€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 25 Oct to 1 Nov 25 Oct 8 days	12	More information	Reserve for 2,439€ More information
A week in the Bahamas on a Catamaran with everything included	From 25 Oct to 1 Nov 25 Oct 8 days	12	More information	Reserve for 3,730€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 25 Oct to 1 Nov 25 Oct 8 days	12	More information	Reserve for 2,924€ More information
11-day trip through the Caribbean Sea on a Catamaran with everything included	From 31 Oct to 10 Nov 31 Oct 11 days	10	More information	Reserve for 3,706€ More information
A week on the Grenadines by catamaran with everything included	From 1 Nov to 8 Nov 1 Nov 8 days	10	More information	Reserve for 3,190€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 1 Nov to 8 Nov 1 Nov 8 days	12	More information	Reserve for 2,709€ More information
A week in Saint Martin on a Catamaran with everything included	From 1 Nov to 8 Nov 1 Nov 8 days	12	More information	Reserve for 2,709€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 1 Nov to 8 Nov 1 Nov 8 days	12	More information	Reserve for 3,321€ More information
14 days in the Caribbean island paradise on a catamaran	From 1 Nov to 15 Nov 1 Nov 15 days	4	More information	Reserve for 1,390€ More information
⛵☀️ 14 days Caribbean with luxury catamaran - sailing holiday in 2025	From 1 Nov to 15 Nov 1 Nov 15 days	8	More information	Reserve for 2,290€ More information
Cruise in the Las Perlas Archipelago – +200 islands on a 56-foot catamaran	From 3 Nov to 7 Nov 3 Nov 5 days	6	More information	Reserve for 999€ More information
A week on the Grenadines by catamaran with everything included	From 8 Nov to 15 Nov 8 Nov 8 days	10	More information	Reserve for 3,540€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 8 Nov to 15 Nov 8 Nov 8 days	12	More information	Reserve for 3,186€ More information
A week in Saint Martin on a Catamaran with everything included	From 8 Nov to 15 Nov 8 Nov 8 days	12	More information	Reserve for 3,186€ More information
A week in the Bahamas on a Catamaran with everything included	From 8 Nov to 15 Nov 8 Nov 8 days	12	More information	Reserve for 3,970€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 8 Nov to 15 Nov 8 Nov 8 days	12	More information	Reserve for 3,970€ More information
11-day trip through the Caribbean Sea on a Catamaran with everything included	From 10 Nov to 20 Nov 10 Nov 11 days	10	More information	Reserve for 4,960€ More information
A week on the Grenadines by catamaran with everything included	From 15 Nov to 22 Nov 15 Nov 8 days	10	More information	Reserve for 3,186€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 15 Nov to 22 Nov 15 Nov 8 days	12	More information	Reserve for 3,540€ More information
A week in Saint Martin on a Catamaran with everything included	From 15 Nov to 22 Nov 15 Nov 8 days	12	More information	Reserve for 3,540€ More information
A week in the Bahamas on a Catamaran with everything included	From 15 Nov to 22 Nov 15 Nov 8 days	12	More information	Reserve for 3,970€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 15 Nov to 22 Nov 15 Nov 8 days	12	More information	Reserve for 3,970€ More information
14 days in the Caribbean island paradise on a catamaran	From 15 Nov to 29 Nov 15 Nov 15 days	0	More information	No availability More information
Sail the Caribbean on a catamaran from Martinique to Saint Blaise	From 18 Nov to 29 Nov 18 Nov 12 days	6	More information	Reserve for 2,160€ More information
11-day trip through the Caribbean Sea on a Catamaran with everything included	From 20 Nov to 30 Nov 20 Nov 11 days	10	More information	Reserve for 4,960€ More information
A week on the Grenadines by catamaran with everything included	From 22 Nov to 29 Nov 22 Nov 8 days	10	More information	Reserve for 3,186€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 22 Nov to 29 Nov 22 Nov 8 days	12	More information	Reserve for 3,186€ More information
A week in Saint Martin on a Catamaran with everything included	From 22 Nov to 29 Nov 22 Nov 8 days	12	More information	Reserve for 3,186€ More information
A week in the Bahamas on a Catamaran with everything included	From 22 Nov to 29 Nov 22 Nov 8 days	12	More information	Reserve for 3,933€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 22 Nov to 29 Nov 22 Nov 8 days	12	More information	Reserve for 3,933€ More information
A week on the Grenadines by catamaran with everything included	From 29 Nov to 6 Dec 29 Nov 8 days	10	More information	Reserve for 3,186€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 29 Nov to 6 Dec 29 Nov 8 days	12	More information	Reserve for 3,186€ More information
A week in Saint Martin on a Catamaran with everything included	From 29 Nov to 6 Dec 29 Nov 8 days	12	More information	Reserve for 3,540€ More information
A week in the Bahamas on a Catamaran with everything included	From 29 Nov to 6 Dec 29 Nov 8 days	12	More information	Reserve for 3,573€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 29 Nov to 6 Dec 29 Nov 8 days	12	More information	Reserve for 3,573€ More information
14 days in the Caribbean island paradise on a catamaran	From 29 Nov to 13 Dec 29 Nov 15 days	6	More information	Reserve for 1,390€ More information
11-day trip through the Caribbean Sea on a Catamaran with everything included	From 30 Nov to 10 Dec 30 Nov 11 days	10	More information	Reserve for 4,960€ More information
A week on the Grenadines by catamaran with everything included	From 6 Dec to 13 Dec 6 Dec 8 days	10	More information	Reserve for 3,186€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 6 Dec to 13 Dec 6 Dec 8 days	12	More information	Reserve for 3,186€ More information
A week in Saint Martin on a Catamaran with everything included	From 6 Dec to 13 Dec 6 Dec 8 days	12	More information	Reserve for 3,540€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 6 Dec to 13 Dec 6 Dec 8 days	12	More information	Reserve for 3,970€ More information
11-day trip through the Caribbean Sea on a Catamaran with everything included	From 10 Dec to 20 Dec 10 Dec 11 days	10	More information	Reserve for 4,464€ More information
A week on the Grenadines by catamaran with everything included	From 13 Dec to 20 Dec 13 Dec 8 days	10	More information	Reserve for 3,186€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 13 Dec to 20 Dec 13 Dec 8 days	12	More information	Reserve for 3,186€ More information
A week in Saint Martin on a Catamaran with everything included	From 13 Dec to 20 Dec 13 Dec 8 days	12	More information	Reserve for 3,186€ More information
A week in the Bahamas on a Catamaran with everything included	From 13 Dec to 20 Dec 13 Dec 8 days	12	More information	Reserve for 3,573€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 13 Dec to 20 Dec 13 Dec 8 days	12	More information	Reserve for 3,573€ More information
14 days in the Caribbean island paradise on a catamaran	From 13 Dec to 20 Dec 13 Dec 8 days	6	More information	Reserve for 890€ More information
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€ More information
A week on the Grenadines by catamaran with everything included	From 20 Dec to 27 Dec 20 Dec 8 days	10	More information	Reserve for 4,239€ More information
Cruise in the Las Perlas Archipelago – +200 islands on a 56-foot catamaran	From 22 Dec to 9 Jan 22 Dec 19 days	4	More information	Reserve for 2,980€ More information
Across the Caribbean – Sailing, Sun, Paradise	From 26 Dec to 6 Jan 26 Dec 12 days	8	More information	Reserve for 1,605€ More information
New Year's Eve in the Caribbean on a Catamaran: Martinique, Saint Vincent and the Grenadines	From 27 Dec to 3 Jan 27 Dec 8 days	0	More information	No availability More information
A week on the Grenadines by catamaran with everything included	From 27 Dec to 3 Jan 27 Dec 8 days	10	More information	Reserve for 5,140€ More information
New Year's Eve in the Caribbean on a Catamaran: Martinique, Saint Vincent and the Grenadines	From 3 Jan to 10 Jan (2026) 3 Jan 8 days	1	More information	Reserve for 1,550€ More information
14 days in the Caribbean island paradise on a catamaran	From 3 Jan to 17 Jan (2026) 3 Jan 15 days	6	More information	Reserve for 1,390€ More information
A week on the Grenadines by catamaran with everything included	From 3 Jan to 10 Jan (2026) 3 Jan 8 days	10	More information	Reserve for 4,140€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 3 Jan to 10 Jan (2026) 3 Jan 8 days	12	More information	Reserve for 4,140€ More information
A week in Saint Martin on a Catamaran with everything included	From 3 Jan to 10 Jan (2026) 3 Jan 8 days	12	More information	Reserve for 3,357€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 3 Jan to 10 Jan (2026) 3 Jan 8 days	12	More information	Reserve for 3,951€ More information
11-day trip through the Caribbean Sea on a Catamaran with everything included	From 6 Jan to 16 Jan (2026) 6 Jan 11 days	10	More information	Reserve for 5,328€ More information
A week on the Grenadines by catamaran with everything included	From 10 Jan to 17 Jan (2026) 10 Jan 8 days	10	More information	Reserve for 3,906€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 10 Jan to 17 Jan (2026) 10 Jan 8 days	12	More information	Reserve for 3,906€ More information
A week in Saint Martin on a Catamaran with everything included	From 10 Jan to 17 Jan (2026) 10 Jan 8 days	12	More information	Reserve for 3,519€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 10 Jan to 17 Jan (2026) 10 Jan 8 days	12	More information	Reserve for 4,390€ More information
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€ More information
11-day trip through the Caribbean Sea on a Catamaran with everything included	From 16 Jan to 26 Jan (2026) 16 Jan 11 days	10	More information	Reserve for 5,328€ More information
A week on the Grenadines by catamaran with everything included	From 17 Jan to 24 Jan (2026) 17 Jan 8 days	10	More information	Reserve for 3,906€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 17 Jan to 24 Jan (2026) 17 Jan 8 days	12	More information	Reserve for 3,906€ More information
A week in Saint Martin on a Catamaran with everything included	From 17 Jan to 24 Jan (2026) 17 Jan 8 days	12	More information	Reserve for 3,519€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 17 Jan to 24 Jan (2026) 17 Jan 8 days	12	More information	Reserve for 3,951€ More information
A week on the Grenadines by catamaran with everything included	From 24 Jan to 31 Jan (2026) 24 Jan 8 days	10	More information	Reserve for 3,906€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 24 Jan to 31 Jan (2026) 24 Jan 8 days	12	More information	Reserve for 3,906€ More information
A week in Saint Martin on a Catamaran with everything included	From 24 Jan to 31 Jan (2026) 24 Jan 8 days	12	More information	Reserve for 3,519€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 24 Jan to 31 Jan (2026) 24 Jan 8 days	12	More information	Reserve for 4,149€ More information
We discover the world: A dream in Puerto Rico & British Virgin Islands	From 24 Jan to 5 Feb (2026) 24 Jan 13 days	6	More information	Reserve for 1,690€ More information
11-day trip through the Caribbean Sea on a Catamaran with everything included	From 26 Jan to 5 Feb (2026) 26 Jan 11 days	10	More information	Reserve for 5,328€ More information
Cruise in the Las Perlas Archipelago – +200 islands on a 56-foot catamaran	From 26 Jan to 6 Feb (2026) 26 Jan 12 days	7	More information	Reserve for 1,980€ More information
A week on the Grenadines by catamaran with everything included	From 31 Jan to 7 Feb (2026) 31 Jan 8 days	10	More information	Reserve for 3,906€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 31 Jan to 7 Feb (2026) 31 Jan 8 days	12	More information	Reserve for 3,906€ More information
A week in Saint Martin on a Catamaran with everything included	From 31 Jan to 7 Feb (2026) 31 Jan 8 days	12	More information	Reserve for 3,519€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 31 Jan to 7 Feb (2026) 31 Jan 8 days	12	More information	Reserve for 4,356€ More information
11-day trip through the Caribbean Sea on a Catamaran with everything included	From 5 Feb to 15 Feb (2026) 5 Feb 11 days	10	More information	Reserve for 5,508€ More information
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€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 7 Feb to 14 Feb (2026) 7 Feb 8 days	12	More information	Reserve for 3,906€ More information

Show all dates

Why go on a Caribbean sailing holiday?

When is the best time to travel around the Caribbean aboard a sailboat?

Flora and Fauna you will see in the Caribbean aboard a sailboat

Why travel the Caribbean on a sailboat or catamaran?

How do I book a Caribbean sailing holiday?