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Sailing trip Caribbean

Experience the ultimate sailing holiday in the Caribbean! Turquoise waters, white dream beaches and constant trade winds make your sailing trip in the Caribbean an unforgettable experience.

November - May

Martinique

4,9/5 Stars

Why choose caribbean for your next sailing adventure?

Weißer Sandstrand mit türkisem Meer und Segelbooten in der Karibik – segelreise karibik sailwithus

Dream beaches

Discover the most beautiful beaches in the world with sand as fine as powdered sugar and crystal-clear water in all shades of blue.

Bunte Holzhuetten und Strandbar unter Baeumen auf karibischer Insel – Segelreise Karibik sailwithus

Island culture

Immerse yourself in the relaxed Caribbean way of life with reggae rhythms, colorful markets and warm hospitality.

Luftbild drei Katamarane ankern an weißer Sandbank in türkisem Karibikwasser – segelreise karibik sailwithus

Perfect sailing conditions

Constant trade winds and sheltered anchorages make sailing a pure pleasure.

Caribbean sailing holiday - holiday in paradise

A sailing holiday in the Caribbean is an unforgettable experience that you shouldn't miss. Crystal clear waters, exotic islands and a warm climate make the Caribbean one of the best sailing destinations in the world.

Sailing the Caribbean with a skipper - your dream start in Martinique

Your unforgettable sailing trip in the Caribbean begins in Martinique. The small island is part of the French overseas department and belongs to the Lesser Antilles archipelago. It is located in the immediate vicinity of the islands of Barbados, Guadeloupe and Dominica.

When you arrive in Martinique, you will already have a very good feeling of what to expect on your Caribbean sailing trip. The island is the ultimate Caribbean dream. Tropical palm trees tower everywhere and hummingbirds buzz in the air. Behind the mangrove forests rise majestic, densely overgrown mountain ranges and the sweet scent of flowers covers the island like a veil.

As it is very mountainous due to the almost 1,400 meter high volcano Montagne Pelée, most of the beaches offer excellent views of the dense canopy of ancient forests that tower over the island.

Fantastic variety of islands on a Caribbean sailing trip

The Caribbean sailing trip of a lifetime begins in Martinique. An impressive spectacle of the Caribbean are the many different islands that are concentrated in a comparatively small area. You should definitely see the islands of the Caribbean once in your life.

From your starting point, you will find the ports of Tobago, St. Lucia or St. Vincent in the immediate vicinity. No matter where you end up, you won't be able to get enough of the white beaches and blue sea.

The sailing area with its many islands is so dreamy and relaxing. The period from November to May is particularly ideal for your Caribbean sailing tour.

Breathtaking underwater world while sailing the Caribbean

And don't miss the chance to take a look into the water. Whether from the yacht or up close on a little diving adventure. In the warm waters, you may well be able to observe all kinds of exotic animals.

Sea turtles, colorful coral reefs and tropical fish are just some of the many animal eye-catchers that await you on a Caribbean sailing trip with a skipper. The crystal-clear waters offer perfect visibility for unforgettable snorkeling and diving experiences.

The Tobago Cays are particularly well known for their spectacular underwater world and encounters with sea turtles in their natural environment.

Perfect sailing conditions - Caribbean sailing trip with flight

The Caribbean islands have a reputation for being stormy seas. But that couldn't be further from the truth. Almost nowhere else in the world will you find such a constant wind as here, which is also suitable for sailing beginners.

If you book a Caribbean sailing trip in winter, the Lesser Antilles experience the north-easterly trade winds at this time. The islands that particularly benefit from the north-easterly trade winds include Antigua, Guadeloupe, St. Lucia, Barbados, Grenada, Trinidad and Tobago.

Sailing the Caribbean is not just about relaxation, culinary delights and Caribbean music, but also many sailing experiences and nautical miles. You only need the motor here for anchoring in the bays or in the small harbors.

Sailing trip Caribbean with skipper - The Lesser Antilles

From Martinique you sail through the paradise of the Lesser Antilles. Perfect conditions for an unforgettable Caribbean sailing trip!

Route Martinique & Grenadines
🌴 Top destination

Route Martinique & Grenadines

Your Caribbean sailing trip starts in Martinique and takes you through the beautiful island world of the Grenadines. Experience white sand, turquoise blue sea and constant trade winds!

Route-Highlights

Martinique - French Caribbean flair with the Montagne Pelée volcano
St. Lucia - beautiful bays and the famous Pitons
Tobago Cays - crystal clear lagoons with sea turtles
St. Vincent - Anchoring in the Blue Lagoon
Grenada - exotic spices and untouched nature
Segelcharakter
Constant trade winds
Diverse islands and routes
Snorkeling and diving in numerous anchor bays
Tropical backdrop & easy vibes

Ready for your dream Caribbean sailing trip?

Make your Caribbean dream come true! Book your Caribbean sailing trip now and experience unforgettable moments in paradise with turquoise blue water and white dream beaches.

Frequently Asked Questions

Before Your Trip

Is sustainable travel possible?

Yes.

Some sailing destinations can be reached by train, ferry or long-distance bus.

Examples: Baltic Sea, Sardinia, France, Croatia.

Which insurance policies are useful?

Insurance is not mandatory, but recommended:

- Travel cancellation insurance

- International health insurance

- Accident insurance

- Liability insurance

How do I get from the airport to the marina?

All travel information is available by e-mail and here:

https://sailwithus.de/gut-zu-wissen/anreiseinformationen/

What is the best way to pack my travel bag or suitcase?

You can find packing tips here:

https://sailwithus.de/gut-zu-wissen/packliste/

When does the crew meet and can I come outside the recommended arrival time?

The crew usually meets between 2 and 4 p.m. in the marina or a nearby café.

From around 5 p.m., the skipper can board the yacht and carry out the handover. Meanwhile, the crew goes shopping.

Late arrival is possible in exceptional cases by arrangement.

Saturday is an organization day - sailing usually takes place on Sunday after the safety briefing.

Which piece of luggage is best?

A sports bag or hiking rucksack is best.

Please do not bring a hard-shell suitcase - there is no storage space for it and it is always in the way.

Recommendation: Packing list on the website.

YouTube:

- https://www.youtube.com/embed/5dPxMRSR9OM

- https://www.youtube.com/embed/JGboVfN5hVQ

What happens after I book my cruise?

After your booking, you will receive further information by email at regular intervals. This includes tips on packing, advice on meal planning, etc.

About a week before the start of the trip, we create a Whatsapp group where you can get to know each other as a crew and the skipper.

Approx. 5 days before the start of the cruise you will receive the final arrival information including a harbor plan and berth.

And then it's time to cast off!

Do I need a passport or identity card?

That depends on the area.

An identity card is sufficient in most districts.

A passport is required for overseas destinations (Thailand, Caribbean, Seychelles, etc.).

Recommendation: Check current information with the Federal Foreign Office.

Will I get to know my fellow sailors before departure?

Yes, a WhatsApp group will be created in the week before your trip. You can discuss travel and organization there.

Are there bed linen, pillows and towels on board?

Yes, you will be provided with bed linen and a towel.

But bring another towel yourself.

A beach towel is not necessary - you jump straight into the sea.

Frequently Asked Questions