Sailing the Caribbean

Choose from 45 experiences

1,690€

per spot

Discover the world: Caribbean northwards – from Martinique to St. Martin

Port of departure: Martinique

3 reviews

Next departure: 20 mar 2027

1,690€
1,690€

per spot

Discover the world: Grenadines round trip from Martinique – Tobago Cays and back

Port of departure: Martinique

3 reviews

Next departure: 6 mar 2027

1,690€
2,450€

per spot

Caribbean Catamaran Vacation with a Chef: Guadeloupe, Antigua, and Barbuda

Port of departure: Pointe-à-Pitre, Guadeloupe

Next departure: 22 apr 2027

2,450€
890€

per spot

Caribbean sailing trip: From Martinique to the Virgin Islands

Port of departure: Martinique

6 reviews

Next departure: 28 november

890€
2,700€

per spot

Guadeloupe, Antigua and Barbuda in a flotilla of 3 catamarans with a chef

Port of departure: Pointe-à-Pitre, Guadeloupe

Next departure: 22 apr 2027

2,700€
1,690€

per spot

Discover the world: Pure Caribbean – from St. Martin to Martinique

Port of departure: St. Martin

3 reviews

Next departure: 16 jan 2027

1,690€
From 1,600€

cabin

Island Hopping by Sailboat in San Blas, Panama

Port of departure: San Blas, Panama

Next departure: 28 november · 2 dates available

From 1,600€
1,750€

per spot

Caribbean sailing trip | 9 days discovering Martinique and the Grenadines

Port of departure: Le Marin, Martinique

44 reviews

Next departure: 6 jan 2027 · 3 dates available

1,750€
2,199€

per spot

Caribbean Sailing Vacation: St. Martin and the Lesser Antilles

Port of departure: Sint Maarten

1 review

Next departure: 13 feb 2027 · 1 dates available

2,199€
1,990€

per spot

Travel the world: Antigua Sailing Week – Regatta week starting from St. Martin

Port of departure: St. Martin

3 reviews

Next departure: 17 apr 2027

1,990€
From 1,390€

per spot

14 days in the Caribbean island paradise on a catamaran

Port of departure: Martinique

2 reviews

Next departure: 28 november · 4 dates available

From 1,390€
From
1,350€
1,215€

per spot

San Blas Islands Sailing Cruise

Port of departure: Guna Yala, Panama

2 reviews

Next departure: 24 mar 2027 · 3 dates available

From 1,350€ 1,215€

Show more experiences

A Guide to Sailing and Catamaran Vacations in the Caribbean

In this practical guide, we answer the most frequently asked questions about sailing in the Caribbean: from the best times to depart to must-see destinations, to life on board and the features of the various cruises. All the information you need to choose the Sailwiz itinerary that best suits your expectations and plan your Caribbean vacation.

By Alicia Iglesias

21 October, 2026

Upcoming Caribbean trips

Experience	Start	Plazas		Price
Caribbean, Colombia and Panama on a catamaran fleet	From 20 Nov to 11 Dec 20 Nov 22 days	4	More information	Reserve for 2,900€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 21 Nov to 28 Nov 21 Nov 8 days	6	More information	Reserve for 3,600€ More information
A week in Saint Martin on a Catamaran with everything included	From 21 Nov to 28 Nov 21 Nov 8 days	2	More information	Reserve for 3,510€ More information
A week on the Grenadines by catamaran with everything included	From 21 Nov to 28 Nov 21 Nov 8 days	0	More information	No availability More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 21 Nov to 28 Nov 21 Nov 8 days	6	More information	Reserve for 1789.25€ More information
Sail the Caribbean on a catamaran from Martinique to Saint Blaise	From 21 Nov to 30 Nov 21 Nov 10 days	4	More information	Reserve for 2,400€ More information
A week in the Bahamas (Exumas) on a Catamaran with everything included	From 21 Nov to 28 Nov 21 Nov 8 days	4	More information	Reserve for 3,744€ More information
11-day trip through the Caribbean Sea on a Catamaran with everything included	From 22 Nov to 2 Dec 22 Nov 11 days	6	More information	Reserve for 2605.25€ More information
Catamaran route from Martinique to Sint Maarten	From 26 Nov to 1 Dec 26 Nov 6 days	7	More information	Reserve for 2,080€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 28 Nov to 5 Dec 28 Nov 8 days	2	More information	Reserve for 4,090€ More information
A week in Saint Martin on a Catamaran with everything included	From 28 Nov to 5 Dec 28 Nov 8 days	4	More information	Reserve for 3,510€ More information
A week on the Grenadines by catamaran with everything included	From 28 Nov to 5 Dec 28 Nov 8 days	6	More information	Reserve for 3,900€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 28 Nov to 5 Dec 28 Nov 8 days	0	More information	No availability More information
14 days in the Caribbean island paradise on a catamaran	From 28 Nov to 12 Dec 28 Nov 15 days	2	More information	Reserve for 1,390€ More information
A week in the Bahamas (Exumas) on a Catamaran with everything included	From 28 Nov to 5 Dec 28 Nov 8 days	4	More information	Reserve for 3,512€ More information
Caribbean sailing trip: From Martinique to the Virgin Islands	From 28 Nov to 7 Dec 28 Nov 10 days	6	More information	Reserve for 890€ More information
Island Hopping by Sailboat in San Blas, Panama	From 28 Nov to 7 Dec 28 Nov 10 days	2	More information	Reserve for 1,600€ More information
Bahamas Calling – 14 Days of Sailing Adventure in the Aquarium of the Caribbean	From 1 Dec to 15 Dec 1 Dec 15 days	4	More information	Reserve for 2,790€ More information
11-day trip through the Caribbean Sea on a Catamaran with everything included	From 2 Dec to 12 Dec 2 Dec 11 days	6	More information	Reserve for 4343.5€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 5 Dec to 12 Dec 5 Dec 8 days	6	More information	Reserve for 1,964€ More information
A week in Saint Martin on a Catamaran with everything included	From 5 Dec to 12 Dec 5 Dec 8 days	12	More information	Reserve for 1789.25€ More information
A week on the Grenadines by catamaran with everything included	From 5 Dec to 12 Dec 5 Dec 8 days	4	More information	Reserve for 3,900€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 5 Dec to 12 Dec 5 Dec 8 days	12	More information	Reserve for 1789.25€ More information
A week in the Bahamas (Exumas) on a Catamaran with everything included	From 5 Dec to 12 Dec 5 Dec 8 days	0	More information	No availability More information
Catamaran Vacation in the San Blas Islands	From 7 Dec to 13 Dec 7 Dec 7 days	0	More information	No availability More information
Island Hopping by Sailboat in San Blas, Panama	From 9 Dec to 18 Dec 9 Dec 10 days	4	More information	Reserve for 1,600€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 12 Dec to 19 Dec 12 Dec 8 days	2	More information	Reserve for 3,272€ More information
A week in Saint Martin on a Catamaran with everything included	From 12 Dec to 19 Dec 12 Dec 8 days	6	More information	Reserve for 1789.25€ More information
A week on the Grenadines by catamaran with everything included	From 12 Dec to 19 Dec 12 Dec 8 days	10	More information	Reserve for 2,106€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 12 Dec to 19 Dec 12 Dec 8 days	6	More information	Reserve for 3,159€ More information
11-day trip through the Caribbean Sea on a Catamaran with everything included	From 12 Dec to 22 Dec 12 Dec 11 days	6	More information	Reserve for 4343.5€ More information
A week in the Bahamas (Exumas) on a Catamaran with everything included	From 12 Dec to 19 Dec 12 Dec 8 days	0	More information	No availability More information
Catamaran Vacation in the San Blas Islands	From 14 Dec to 20 Dec 14 Dec 7 days	0	More information	No availability More information
Caribbean Grenadines under sail - all-inclusive 2 weeks, Aura 51	From 15 Dec to 27 Dec 15 Dec 13 days	4	More information	Reserve for 3,655€ More information
Catamaran adventure in San Blas, Guna Yala (Panama)	From 16 Dec to 23 Dec 16 Dec 8 days	6	More information	Reserve for 2,500€ More information
A week on the Grenadines by catamaran with everything included	From 19 Dec to 26 Dec 19 Dec 8 days	6	More information	Reserve for 4,365€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 19 Dec to 26 Dec 19 Dec 8 days	4	More information	Reserve for 4,365€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 19 Dec to 26 Dec 19 Dec 8 days	0	More information	No availability More information
A week in the Bahamas (Exumas) on a Catamaran with everything included	From 19 Dec to 26 Dec 19 Dec 8 days	12	More information	Reserve for 3,744€ More information
A week in Saint Martin on a Catamaran with everything included	From 19 Dec to 26 Dec 19 Dec 8 days	12	More information	Reserve for 1967.75€ More information
14 days in the Caribbean island paradise on a catamaran	From 20 Dec to 2 Jan 20 Dec 14 days	6	More information	Reserve for 2,290€ More information
Post-ARC Caribbean Cruising	From 20 Dec to 27 Dec 20 Dec 8 days	9	More information	Reserve for 505€ More information
Sailing trip in the Las Perlas archipelago – 120+ islands on a 56-foot catamaran	From 21 Dec to 2 Jan 21 Dec 13 days	8	More information	Reserve for 2,580€ More information
Catamaran Vacation in the San Blas Islands	From 21 Dec to 27 Dec 21 Dec 7 days	6	More information	Reserve for 2,376€ More information
A week on the Grenadines by catamaran with everything included	From 26 Dec to 2 Jan 26 Dec 8 days	4	More information	Reserve for 5,290€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 26 Dec to 2 Jan 26 Dec 8 days	4	More information	Reserve for 5,290€ More information
Discover the world: New Year's Eve & New Year's Day – from Martinique to St. Martin	From 26 Dec to 6 Jan 26 Dec 12 days	8	More information	Reserve for 1,690€ More information
Caribbean Grenadines under sail - all-inclusive 2 weeks, Aura 51	From 26 Dec to 7 Jan 26 Dec 13 days	4	More information	Reserve for 5,025€ More information
Catamaran Vacation in the San Blas Islands	From 28 Dec to 3 Jan 28 Dec 7 days	0	More information	No availability More information
Island Hopping by Sailboat in San Blas, Panama	From 30 Dec to 8 Jan 30 Dec 10 days	2	More information	Reserve for 1,600€ More information
Catamaran adventure in San Blas, Guna Yala (Panama)	From 31 Dec to 7 Jan 31 Dec 8 days	8	More information	Reserve for 2,500€ More information
A week in the Bahamas (Exumas) on a Catamaran with everything included	From 2 Jan to 9 Jan (2027) 2 Jan 8 days	12	More information	Reserve for 3,600€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 2 Jan to 9 Jan (2027) 2 Jan 8 days	6	More information	Reserve for 3,616€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 2 Jan to 9 Jan (2027) 2 Jan 8 days	0	More information	No availability More information
A week on the Grenadines by catamaran with everything included	From 2 Jan to 9 Jan (2027) 2 Jan 8 days	2	More information	Reserve for 4,320€ More information
Catamaran adventure in San Blas, Guna Yala (Panama)	From 3 Jan to 10 Jan (2027) 3 Jan 8 days	6	More information	Reserve for 2,500€ More information
Sailing trip in the Las Perlas archipelago – 120+ islands on a 56-foot catamaran	From 4 Jan to 15 Jan (2027) 4 Jan 12 days	10	More information	Reserve for 1,990€ More information
A week in Saint Martin on a Catamaran with everything included	From 4 Jan to 11 Jan (2027) 4 Jan 8 days	4	More information	Reserve for 4,110€ More information
Catamaran Vacation in the San Blas Islands	From 4 Jan to 10 Jan (2027) 4 Jan 7 days	2	More information	Reserve for 2,376€ More information
Caribbean sailing trip \| 9 days discovering Martinique and the Grenadines	From 6 Jan to 14 Jan (2027) 6 Jan 9 days	10	More information	Reserve for 1,750€ More information
11-day trip through the Caribbean Sea on a Catamaran with everything included	From 7 Jan to 17 Jan (2027) 7 Jan 11 days	4	More information	Reserve for 5,920€ More information
The Caribbean by boat, the Grenadines and Tobago Cays	From 9 Jan to 16 Jan (2027) 9 Jan 8 days	0	More information	No availability More information
A week in the Bahamas (Exumas) on a Catamaran with everything included	From 9 Jan to 16 Jan (2027) 9 Jan 8 days	12	More information	Reserve for 3,600€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 9 Jan to 16 Jan (2027) 9 Jan 8 days	12	More information	Reserve for 3,616€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 9 Jan to 16 Jan (2027) 9 Jan 8 days	12	More information	Reserve for 3391.5€ More information
A week on the Grenadines by catamaran with everything included	From 9 Jan to 16 Jan (2027) 9 Jan 8 days	6	More information	Reserve for 4,470€ More information
From Grenada to Martinique – Caribbean sailing	From 10 Jan to 23 Jan (2027) 10 Jan 14 days	6	More information	Reserve for 1,980€ More information
A week in Saint Martin on a Catamaran with everything included	From 11 Jan to 18 Jan (2027) 11 Jan 8 days	4	More information	Reserve for 4,110€ More information
Catamaran Vacation in the San Blas Islands	From 11 Jan to 17 Jan (2027) 11 Jan 7 days	0	More information	No availability More information
The Caribbean by boat, the Grenadines and Tobago Cays	From 16 Jan to 23 Jan (2027) 16 Jan 8 days	6	More information	Reserve for 845€ More information
Catamaran sailing week in the Caribbean	From 16 Jan to 23 Jan (2027) 16 Jan 8 days	8	More information	Reserve for 2,000€ More information
A week in the Bahamas (Exumas) on a Catamaran with everything included	From 16 Jan to 23 Jan (2027) 16 Jan 8 days	4	More information	Reserve for 3,600€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 16 Jan to 23 Jan (2027) 16 Jan 8 days	12	More information	Reserve for 3,616€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 16 Jan to 23 Jan (2027) 16 Jan 8 days	4	More information	Reserve for 4,040€ More information
A week on the Grenadines by catamaran with everything included	From 16 Jan to 23 Jan (2027) 16 Jan 8 days	10	More information	Reserve for 4,068€ More information
Caribbean sailing trip \| 9 days discovering Martinique and the Grenadines	From 16 Jan to 24 Jan (2027) 16 Jan 9 days	10	More information	Reserve for 1,750€ More information
Discover the world: Pure Caribbean – from St. Martin to Martinique	From 16 Jan to 30 Jan (2027) 16 Jan 15 days	5	More information	Reserve for 1,690€ More information
11-day trip through the Caribbean Sea on a Catamaran with everything included	From 17 Jan to 27 Jan (2027) 17 Jan 11 days	6	More information	Reserve for 5,508€ More information
Catamaran adventure in San Blas, Guna Yala (Panama)	From 17 Jan to 24 Jan (2027) 17 Jan 8 days	6	More information	Reserve for 2,500€ More information
Sailing trip in the Las Perlas archipelago – 120+ islands on a 56-foot catamaran	From 18 Jan to 29 Jan (2027) 18 Jan 12 days	10	More information	Reserve for 1,990€ More information
A week in Saint Martin on a Catamaran with everything included	From 18 Jan to 25 Jan (2027) 18 Jan 8 days	6	More information	Reserve for 4,160€ More information
Catamaran Vacation in the San Blas Islands	From 18 Jan to 24 Jan (2027) 18 Jan 7 days	4	More information	Reserve for 1,980€ More information
The Caribbean by boat, the Grenadines and Tobago Cays	From 23 Jan to 30 Jan (2027) 23 Jan 8 days	6	More information	Reserve for 845€ More information
Catamaran sailing week in the Caribbean	From 23 Jan to 30 Jan (2027) 23 Jan 8 days	8	More information	Reserve for 2,000€ More information
A week in the Bahamas (Exumas) on a Catamaran with everything included	From 23 Jan to 30 Jan (2027) 23 Jan 8 days	0	More information	No availability More information
A week in the British Virgin Islands on a Catamaran with everything included	From 23 Jan to 30 Jan (2027) 23 Jan 8 days	12	More information	Reserve for 3,800€ More information
A week on the Grenadines by catamaran with everything included	From 23 Jan to 30 Jan (2027) 23 Jan 8 days	10	More information	Reserve for 4,580€ More information
Caribbean dream: 14 days of island hopping from Martinique	From 23 Jan to 6 Feb (2027) 23 Jan 15 days	4	More information	Reserve for 1,900€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 23 Jan to 30 Jan (2027) 23 Jan 8 days	6	More information	Reserve for 4,080€ More information
Caribbean dream: 14 days of island hopping from Martinique	From 23 Jan to 6 Feb (2027) 23 Jan 15 days	4	More information	Reserve for 1,900€ More information
Catamaran adventure in San Blas, Guna Yala (Panama)	From 24 Jan to 31 Jan (2027) 24 Jan 8 days	6	More information	Reserve for 2,500€ More information
A week in Saint Martin on a Catamaran with everything included	From 25 Jan to 1 Feb (2027) 25 Jan 8 days	6	More information	Reserve for 3,789€ More information
Catamaran Vacation in the San Blas Islands	From 25 Jan to 31 Jan (2027) 25 Jan 7 days	6	More information	Reserve for 1,980€ More information
11-day trip through the Caribbean Sea on a Catamaran with everything included	From 27 Jan to 6 Feb (2027) 27 Jan 11 days	10	More information	Reserve for 5,598€ More information
Caribbean sailing trip \| 9 days discovering Martinique and the Grenadines	From 27 Jan to 4 Feb (2027) 27 Jan 9 days	10	More information	Reserve for 1,750€ More information
A week in the Bahamas (Exumas) on a Catamaran with everything included	From 30 Jan to 6 Feb (2027) 30 Jan 8 days	6	More information	Reserve for 3,648€ More information
A week in the British Virgin Islands on a Catamaran with everything included	From 30 Jan to 6 Feb (2027) 30 Jan 8 days	12	More information	Reserve for 3,968€ More information
A week through the islands of Guadeloupe on a Catamaran with everything included	From 30 Jan to 6 Feb (2027) 30 Jan 8 days	2	More information	Reserve for 4,230€ More information
A week on the Grenadines by catamaran with everything included	From 30 Jan to 6 Feb (2027) 30 Jan 8 days	10	More information	Reserve for 4,266€ More information
Pure Caribbean: From Martinique to the ABC Islands	From 31 Jan to 13 Feb (2027) 31 Jan 14 days	6	More information	Reserve for 1,980€ More information

Show all dates

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.
Why should you consider a sailing trip through the Caribbean?
Sailwiz's concept is based on the "shared boat" principle. You don't have to rent an entire boat; you can simply book a berth. This offers you numerous advantages:
- Experienced skippers: Our skippers are experts in their area. They know the safest anchorages, the best beach bars, and the most secret snorkeling spots.
- Safety & Trust: Sailwiz vets all providers. Genuine reviews from Sailwiz users give you the assurance that your sailing trip will deliver on its promises.
- No sailing experience necessary: The skippers take care of the boat. However, if you wish, you can learn a lot about navigation and sailing techniques.
- Community: You meet like-minded people and share the costs and the experience, which makes a Caribbean sailing trip significantly more affordable than a private charter.
How do I book my sailing holiday in the Caribbean with Sailwiz?
Sailwiz makes your dream holiday easy to find:
- Choose activity: Search our platform for a suitable date and area.
- Direct contact: Ask the skipper any questions about the route, provisions or equipment in advance via our messaging system.
- Secure booking: Reserve your spot with a deposit directly through our encrypted website.
- Confirmation: You will immediately receive all travel details and booking confirmation via email.
Trust in the experience of thousands of sailors who have already explored the world's oceans with Sailwiz. Start your adventure now and experience sailing in the Caribbean at its finest!
How much does a sailing holiday in the Caribbean with a skipper cost?
The cost of a Caribbean sailing trip varies depending on the duration, type of vessel (sailboat or catamaran), and the chosen route. At Sailwiz, we prioritize price transparency so you can accurately plan your budget.

Price overview and services:
- Beginner sailing trips & short trips (3 to 5 days): These offers are usually priced between €600 and €900 per person. Ideal for getting to know sailing in the Caribbean or as an exclusive addition to a hotel stay.
- Standard sailing week (7 to 10 days): The classic option for a comprehensive sailing trip in the Caribbean. Prices typically range between €1,200 and €1,800 per person. This timeframe allows for in-depth exploration of island groups such as the Grenadines or the British Virgin Islands.
- Premium Experiences & Long-Term Cruises (14 days or more): For true adventurers who want to fully enjoy sailing in the Caribbean, these trips start from €2,500. They often include special extras such as full board or special diving excursions.
What is included in the price?
When you book with Sailwiz, an experienced skipper is already included in the price. This means maximum safety and local expertise without additional personnel costs. Depending on the offer, accommodation in the booked cabin, use of the galley, and safety equipment are also included.

Note: In the activity description, pay attention to the "kitty" (for food, fuel, and port fees), which is usually divided among the participants on site. This ensures your vacation remains flexible and fairly priced.
What our customers say about sailing trips in the Caribbean: Customer experiences and skipper tips

Here are insights from guests and skippers who have explored the Caribbean with Sailwiz:
"While it was snowing in Germany, we were sitting on the beach in Bequia with a Punch. The decision to book a cabin with Sailwiz was the best of my year. I arrived as a stranger and left as a friend of the crew." – Sarah K., Sailing in the Grenadines

"I thought the pictures were edited, but the water really is that clear. Our skipper knew exactly when we needed to be at the Tobago Cays to avoid the crowds." – Thomas L., catamaran trip.

Insider tips from the Sailwiz skippers:
"Don't miss the local 'lobster dinner' on the beach. There's nothing more authentic than grilling fresh lobster right over the fire as the sun sets." – Skipper Marc.

"Between January and March we often hold our breath – the chance of seeing whales near Dominica is huge during this time!" – Skipper Elena.
Which boats can I rent to explore the Caribbean?
At Sailwiz we offer two main types of ships that are perfectly suited to Caribbean conditions:
- The catamaran: Almost 80% of our Caribbean cruises take place on catamarans. Why? Because their shallow draft allows them to get extremely close to the beaches. They offer huge deck areas for sunbathing, a stable position (no rocking), and a spacious saloon. Ideal for groups and families.
- The sailing yacht: For purists who love the true feeling of sailing. A monohull glides sportily through the trade winds and is often the more affordable option for adventurers who focus on the sailing itself.
Duration & Planning: How long should your sailing holiday last?
A flight to the Caribbean is a long journey – therefore we recommend taking your time. Here are the most common formats at Sailwiz:
- The classic sailing week (7–9 days): The standard for cruising areas like the BVI or Antigua. Enough time to see the main islands of a group without rushing.
- The intensive island-hopping trip (10–14 days): Our most frequently booked duration for the Martinique – Grenadines route. Since you pass many islands (St. Lucia, St. Vincent, Bequia, Mayreau), 12 or 14 days are worthwhile to allow for an extra day in a beautiful bay.
- Transatlantic & Long-Distance (21+ days): For those with truly grand dreams. We also offer legs from Europe to the Caribbean (Atlantic crossing) – the ultimate adventure for sailing enthusiasts.

Choose from 45 experiences

Upcoming Caribbean trips

What routes are available for a Caribbean boat holiday?

Preguntas frecuentes para sailing the Caribbean

⭐ ¿Por qué realizar un crucero por el Caribe?

✅ ¿Por qué viajar al Caribe en barco?

✍ ¿Qué islas del Caribe podré visitar durante la travesía?

✍ ¿Cómo puedo reservar una travesía al Caribe?

Quanto dura una vacanza in barca a vela ai Caraibi?

Posso prenotare solo una cabina o devo noleggiare tutta la barca?

Dove andare ai Caraibi in barca a vela?

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?

Why should you consider a sailing trip through the Caribbean?

How do I book my sailing holiday in the Caribbean with Sailwiz?

How much does a sailing holiday in the Caribbean with a skipper cost?

What our customers say about sailing trips in the Caribbean: Customer experiences and skipper tips

Which boats can I rent to explore the Caribbean?

Duration & Planning: How long should your sailing holiday last?