Catamaran CHALLENGE anchored in a blue cove

★★★★★ Season 2026 – 2027 · 14 days / 13 nights

The Caribbean under sail

Martinique → Saint Lucia → St. Vincent → the Grenadines. Two weeks among tropical islands, turquoise lagoons and white-sand beaches aboard a sailing catamaran.

Day-by-day route
14days under sail
9Caribbean islands
from €1,100for the whole trip
from 1guest — no group to wait for

Imagine this

Morning in a quiet Caribbean cove

You wake up aboard the catamaran. Palm trees, crystal-clear water and postcard islands all around. After breakfast we raise the sails and head off toward new adventures.

Ahead of us: desert islands, coral reefs, sea turtles, cosy Caribbean villages and unforgettable sunsets. This isn't just a holiday — it's a real sailing adventure you'll carry with you forever.

0days / 13 nights
0islands on the route
0Caribbean countries
0guest is enough to set sail

Day-by-day route

Where the wind takes us

Embarkation and disembarkation in Martinique, Le Marin. The captain may adjust the route depending on weather conditions.

MARTINIQUE SAINT LUCIA ST. VINCENT Bequia Mustique Canouan Tobago Cays Mayreau Union Island Le Marin Rodney Bay Soufrière · Pitons Wallilabou N CaribbeanSea AtlanticOcean

© EOX · Sentinel-2 cloudless 2016 · Copernicus · CC BY 4.0

Day 01 / 14Martinique, Le Marin
  1. 01

    Martinique · Le Marin

    Welcome aboard

    Boarding the catamaran, settling into your cabin, meeting the crew. Your first evening in the Caribbean.

  2. 02

    Martinique → Saint Lucia

    Rodney Bay

    Sailing to Rodney Bay. A first taste of the island, swimming and relaxing.

  3. 03

    Marigot Bay → Soufrière

    The volcanic Pitons

    Cruising along Saint Lucia's scenic coast. The famous volcanic Pitons, lush tropical scenery and beautiful bays.

  4. 04

    Saint Lucia → St. Vincent

    The “Pirates of the Caribbean” bay

    Sailing to Wallilabou Bay — the famous cove where scenes from “Pirates of the Caribbean” were filmed.

  5. 05

    St. Vincent → Bequia

    Admiralty Bay

    Colourful streets, local eateries and genuine Caribbean atmosphere.

  6. 06

    Bequia → Mustique

    Island of the celebrities

    One of the most famous islands in the Caribbean. White-sand beaches, luxury villas and the legendary Basil's Bar.

  7. 07

    Mustique → Tobago Cays

    A true tropical paradise

    Coral reefs, crystal-clear water and the chance to swim alongside sea turtles.

  8. 08

    Tobago Cays

    Among uninhabited islands

    A full day of snorkelling, swimming and relaxing. Weather permitting — the famous Petit Tabac.

  9. 09

    Tobago Cays → Mayreau → Union Island

    Salt Whistle Bay

    A picturesque bay, a stroll around the tiny island of Mayreau, then on to Union Island.

  10. 10

    Union Island → Canouan

    The quiet bays of the Grenadines

    Beautiful beaches, quiet bays and rest on one of the most scenic islands in the Grenadines.

  11. 11

    Canouan → Bequia

    Heading north again

    Heading back through the Grenadines. Swimming, relaxing and an evening on Bequia.

  12. 12

    Bequia → Saint Lucia

    A long sailing passage

    A real day at sea: sailing along the chain of Caribbean islands.

  13. 13

    Saint Lucia → Martinique

    Last evening aboard

    Back to Le Marin. Your last evening on the catamaran.

  14. 14

    Martinique

    See you at sea

    Breakfast, saying goodbye to the crew, and disembarkation.

What awaits you

Eight reasons to set sail

Every day brings a new bay, a new island, a new shade of water.

01

Swimming with sea turtles

02

Snorkelling among coral reefs

03

Desert islands and hidden coves

04

“Pirates of the Caribbean” filming locations

05

Real open-water passages under sail

06

Fishing on the open sea

07

Caribbean sunsets and evenings at anchor

08

Tropical fruit and local cuisine

Catamaran Fountaine Pajot Lipari 41 “CHALLENGE” at the dock

Our catamaran

Fountaine Pajot Lipari 41

«CHALLENGE»

A comfortable sailing catamaran with a spacious cockpit, a cosy saloon and double cabins. Everything you need is on board: a fully equipped galley, comfortable cabins, generous lounging areas — and the sea right outside, every single day.

  • 12 mlength
  • 6.6 mbeam — stability, no rolling
  • 2-berthcabins with portholes
  • Saloonwith galley and panoramic windows

2026 – 2027 sailing dates

Choose your 14 days

The cruise sets sail even with a single guest — no need to wait for a full group.

New Year cruise

December – January

28 Dec10 Jan

Welcome 2027 on the island of Bequia — under the stars, on the deck of the catamaran. More about the New Year cruise →

14 days / 13 nights

January 2027

13 Jan26 Jan

Dry season and steady trade winds — the perfect time for passages.

14 days / 13 nights

January – February 2027

29 Jan11 Feb

Sunshine, turquoise lagoons and the longest days at anchor.

14 days / 13 nights

February 2027

14 Feb27 Feb

Turtle season — we swim alongside them in Tobago Cays.

14 days / 13 nights

March 2027

2 Mar15 Mar

Blooming islands and warm water — closing out the Caribbean season.

14 days / 13 nights

Trip cost

14 days / 13 nights

Berth in a double cabin

0€ / person

€550 a week

  • The whole trip — 14 days
  • A berth in a cosy double cabin
  • Perfect if you're travelling solo
For couples and friends
Private double cabin

0€ / cabin

€950 a week

  • The whole trip — 14 days
  • The whole cabin is yours
  • For two — privacy and comfort
Ship's kitty

≈ 250€ / week per person

Shared costs for food, fuel, moorings, water and other trip expenses — based on a fully booked catamaran.

With fewer guests on board, the per-person kitty may increase.

Embarkation & disembarkationMartinique, Le Marin marina

Flexible routeThe captain adjusts it to the weather

Guaranteed departureThe cruise sails even with a single guest

And in spring — an ocean crossing

Caribbean → Azores

March 20, 2027departure from the Caribbean

A chance to join a real ocean passage under sail across the Atlantic. The captain will share the route, duration and cost in person.

Join us

Spots on the catamaran are limited

“The Caribbean isn't just a holiday. It's a real sailing adventure that will stay with you forever.”

Captain Konstantin

Leave your number — the captain will tell you about available cabins and help pick your dates