Caribbean – Lesser Antilles & Grenadines

The constant trade winds in the Lesser Antilles ensure perfect wind conditions and make the islands between the British Virgin Islands and the Grenadines a dream sailing area.
All cruises
Landingpage-Karten.indd
Perfectly stranded

Like a shimmering string of pearls, the Lesser Antilles stretch through the turquoise Caribbean Sea. The area between the British Virgin Islands in the north and the southern Grenadines provides perfect sailing conditions for windjammers and is a harmonious blend of lush greenery, picturesque beaches, relaxed sailing hubs, and vibrant underwater life.

Cruises
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
SUN-SOAKED ISLANDS TO SHAKE OFF WINTER

Retired NBC News correspondent Kerry Sanders will join this sailing.

Date: 11/27 – 12/04/2024
Ship: SEA CLOUD SPIRIT
Trip number: SCS-2445
Destination:
Lesser Antilles & Grenadines
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
Music cruise
Music cruise
Caribbean vibes and 80s’ spirit

Dive into the musical power of the 80s on our ‘SONGS ’N’ SAIL journey with Kai Wingenfelder & Christof Stein-Schneider (Fury in the Slaughterhouse).

Date: 12/04 – 12/11/2024
Ship: SEA CLOUD SPIRIT
Trip number: SCS-2446
Destination:
Lesser Antilles & Grenadines
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
A COLORFUL PRE-CHRISTMAS SEASON
Date: 12/11 – 12/21/2024
Ship: SEA CLOUD SPIRIT
Trip number: SCS-2447
Destination:
Lesser Antilles & Grenadines
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Pointe-à-Pitre/Guadeloupe –
Pointe-à-Pitre/Guadeloupe
ACROSS A SEA OF IDYLLIC ISLANDS
Date: 12/12 – 12/20/2024
Ship: SEA CLOUD II
Trip number: SCII-2442
Destination:
Lesser Antilles & Grenadines
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
TAKE A SUNNY BREAK FROM WINTER
Date: 12/13 – 12/20/2024
Ship: SEA CLOUD
Trip number: SC-2441
Destination:
Lesser Antilles & Grenadines
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
FESTIVE DAYS UNDER COCONUT PALMS
Date: 12/20/2024 – 01/03/2025
Ship: SEA CLOUD
Trip number: SC-2442
Destination:
Lesser Antilles & Grenadines
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Pointe-à-Pitre/Guadeloupe –
Pointe-à-Pitre/Guadeloupe
LAZY DAYS WITH SAND BETWEEN YOUR TOES
Date: 12/20/2024 – 01/03/2025
Ship: SEA CLOUD II
Trip number: SCII-2443
Destination:
Lesser Antilles & Grenadines
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
CARIBBEAN SUN FOR CHRISTMAS
Date: 12/21/2024 – 01/04/2025
Ship: SEA CLOUD SPIRIT
Trip number: SCS-2448
Destination:
Lesser Antilles & Grenadines
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
A TALL SHIP’S DREAM DESTINATION
Date: 01/03 – 01/10/2025
Ship: SEA CLOUD
Trip number: SC-2501
Destination:
Lesser Antilles & Grenadines
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Pointe-à-Pitre/Guadeloupe –
Philipsburg, St. Maarten
A STELLAR START TO THE NEW YEAR
Date: 01/03 – 01/14/2025
Ship: SEA CLOUD II
Trip number: SCII-2501
Destination:
Lesser Antilles & Grenadines
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Philipsburg, St. Maarten –
San Juan, Puerto Rico
Culinary cruise
Culinary cruise
ACROSS A SEA OF IDYLLIC ISLANDS

Chef Wilo Benet will join this sailing.

Date: 01/04 – 01/10/2025
Ship: SEA CLOUD SPIRIT
Trip number: SCS-2501
Destination:
Lesser Antilles & Grenadines
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Philipsburg, St. Maarten –
Bridgetown, Barbados
BAREFOOT THROUGH BALMY JANUARY
Date: 01/10 – 01/19/2025
Ship: SEA CLOUD
Trip number: SC-2502
Destination:
Lesser Antilles & Grenadines
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San Juan, Puerto Rico –
San Juan, Puerto Rico
Culinary cruise
Culinary cruise
A COLORFUL CARIBBEAN TIME-OUT

Chef Julie Carrión will join this sailing.

Date: 01/10 – 01/17/2025
Ship: SEA CLOUD SPIRIT
Trip number: SCS-2502
Destination:
Lesser Antilles & Grenadines
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Philipsburg, St. Maarten –
Bridgetown, Barbados
SAILING ALONG HISTORIC ROUTES
Date: 01/14 – 01/26/2025
Ship: SEA CLOUD II
Trip number: SCII-2502
Destination:
Lesser Antilles & Grenadines
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San Juan, Puerto Rico –
San Juan, Puerto Rico
Culinary cruise
Culinary cruise
A COLORFUL CARIBBEAN TIME-OUT

Chef Francis Guzman will join this sailing.

Date: 01/17 – 01/24/2025
Ship: SEA CLOUD SPIRIT
Trip number: SCS-2503
Destination:
Lesser Antilles & Grenadines
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San Juan, Puerto Rico –
Philipsburg, St. Maarten
Culinary cruise
Culinary cruise
ON THE SUNNY SIDE OF LIFE

Chef Mario Pagan will join this sailing.

Date: 01/24 – 02/01/2025
Ship: SEA CLOUD SPIRIT
Trip number: SCS-2504
Destination:
Lesser Antilles & Grenadines
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Philipsburg, St. Maarten –
Willemstad, Curaçao
COLORFUL CARIBBEAN FLAIR

Hillwood’s chief curator Dr. Wilfried Zeisler will join this sailing.

Date: 02/01 – 02/10/2025
Ship: SEA CLOUD SPIRIT
Trip number: SCS-2505
Destination:
Lesser Antilles & Grenadines
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Bridgetown, Barbados –
Bridgetown, Barbados
RELAX THE CARIBBEAN WAY
Date: 02/02 – 02/09/2025
Ship: SEA CLOUD
Trip number: SC-2505
Destination:
Lesser Antilles & Grenadines
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Bridgetown, Barbados –
Bridgetown, Barbados
RELAX THE CARIBBEAN WAY
Date: 02/09 – 02/16/2025
Ship: SEA CLOUD
Trip number: SC-2506
Destination:
Lesser Antilles & Grenadines
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Bridgetown, Barbados –
Philipsburg, St. Maarten
BLISSFUL IN THE LAP OF LUXURY

Dr. Peter Cressy will join this sailing.

Date: 02/18 – 02/25/2025
Ship: SEA CLOUD II
Trip number: SCII-2506
Destination:
Lesser Antilles & Grenadines
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Bridgetown, Barbados –
Philipsburg, St. Maarten
FROM REEF TO RAIN FOREST
Date: 02/23 – 03/02/2025
Ship: SEA CLOUD
Trip number: SC-2508
Destination:
Lesser Antilles & Grenadines
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
SAILING ON THE TRADE WINDS
Date: 02/25 – 03/07/2025
Ship: SEA CLOUD II
Trip number: SCII-2507
Destination:
Lesser Antilles & Grenadines
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
PIRATE BAYS & JET SET HARBORS AWAIT
Date: 03/02 – 03/11/2025
Ship: SEA CLOUD
Trip number: SC-2509
Destination:
Lesser Antilles & Grenadines
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
Bucket Regatta St Barths
Bucket Regatta St Barths
A SAILING EVENT IN A CLASS OF ITS OWN
Date: 03/07 – 03/17/2025
Ship: SEA CLOUD II
Trip number: SCII-2508
Destination:
Lesser Antilles & Grenadines
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
Bucket Regatta St Barths
Bucket Regatta St Barths
FRONT-ROW AT THE BUCKET REGATTA
Date: 03/11 – 03/20/2025
Ship: SEA CLOUD
Trip number: SC-2510
Destination:
Lesser Antilles & Grenadines
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
SUN, SEA, AND SERENITY
Date: 03/17 – 03/24/2025
Ship: SEA CLOUD II
Trip number: SCII-2509
Destination:
Lesser Antilles & Grenadines
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
A TALL SHIP’S DREAM DESTINATION
Date: 03/20 – 03/27/2025
Ship: SEA CLOUD
Trip number: SC-2511
Destination:
Lesser Antilles & Grenadines
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
Special event included
Special event included
SAVE THE BEST FOR LAST
Date: 03/27 – 04/03/2025
Ship: SEA CLOUD
Trip number: SC-2512
Destination:
Lesser Antilles & Grenadines
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
CARIBBEAN FLAIR AWAY FROM THE EVERYDAY
Date: 11/26 – 12/04/2025
Ship: SEA CLOUD SPIRIT
Trip number: SCS-2542
Destination:
Lesser Antilles & Grenadines
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
PIRATE ISLANDS AND SAILORS’ HAUNTS
Date: 12/04 – 12/11/2025
Ship: SEA CLOUD SPIRIT
Trip number: SCS-2543
Destination:
Lesser Antilles & Grenadines
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