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.
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SeaCloud_Kreuzfahrten_Caribbean-Lesser-Antilles-Grenadines_Map
Caribbean – Lesser Antilles & Grenadines

The Lesser Antilles stretch through the turquoise Caribbean Sea like a dazzling string of pearls. The area between Puerto Rico, the Virgin Islands in the north and the Grenadines in the south offers perfect sailing conditions for windjammers and is a perfect mix of lush green nature, picturesque beaches, relaxed sailor lifestyle and colorful underwater world.

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FAMOUS SAILORS AND YACHTSMEN’S HAUNTS

Reliable trade winds and countless hours of sunshine provide ideal sailing conditions in the Caribbean. No wonder that enthusiastic “Yachties” from all over the world meet here. The SEA CLOUDs anchor in places that many small sailing yachts from all over the world are also drawn to. In the quaint beach bars of the U.S. and British Virgin Islands, you will quickly get into conversation and be infected by the carefree lifestyle.

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PICTURE BOOK BEACHES AND DREAM BAYS

The Caribbean – that also means a very special attitude to life. When the sun twinkles through the palm fronds and your toes sink into the warm sand, you will notice: Doing nothing can also be a great occupation. The U.S. and British Virgin Islands, the Tobago Cays and Puerto Rico enchant with tropical dream beaches. After a swim in the sea, it is also a great place to relax at a beach barbecue.

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GREEN ISLANDS AND TROPICAL PARADISES

Volcanic lakes, waterfalls and gardens with tropical plants: On the more southern islands of the Antilles and Grenadines, the Caribbean shows a completely different aspect with its lush, green nature. While on St. Lucia the green double volcanoes welcome the SEA CLOUDs from afar, the natural beauty of Dominica fascinates somewhat more serenely with its lush national parks. The spice island of Grenada was not given its name for nothing – the aromas of cinnamon and nutmeg linger in the air.

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FASCINATING SNORKELING SPOTS

Around the Lesser Antilles, the crystal clear water entices you to swim and snorkel; relaxed enjoyment awaits you at the barbecue on board or on the beach. For water sports enthusiasts, snorkeling equipment, stand-up paddles and towable tubes are available for activities from the beach or ship.

Cruises
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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
14 nights sailing trip per person from
11,985 $
Cruise details Request
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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
7 nights sailing trip per person from
5,995 $
Cruise details Request
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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
11 nights sailing trip per person from
9,420 $
Cruise details Request
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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
6 nights sailing trip per person from
6,425 $
Cruise details Request
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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
9 nights sailing trip per person from
4,140 $
Cruise details Request
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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
7 nights sailing trip per person from
5,995 $
Cruise details Request
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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
12 nights sailing trip per person from
10,265 $
Cruise details Request
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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
7 nights sailing trip per person from
5,995 $
Cruise details Request
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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
8 nights sailing trip per person from
6,855 $
Cruise details Request
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Philipsburg, St. Maarten –
Willemstad, Curaçao
MORE TIME FOR ISLAND DREAMS

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
9 nights sailing trip per person from
7,695 $
Cruise details Request
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Philipsburg, St. Maarten –
Panama City (Colón), Panama
MORE TIME FOR ISLAND DREAMS
Date: 02/01 – 02/18/2025
Ship: SEA CLOUD SPIRIT
Trip number: SCS-250506
Destination:
Lesser Antilles & Grenadines
17 nights sailing trip per person from
13,095 $
Cruise details Request
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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
7 nights sailing trip per person from
5,995 $
Cruise details Request
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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
7 nights sailing trip per person from
5,995 $
Cruise details Request
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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
7 nights sailing trip per person from
5,995 $
Cruise details Request
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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
7 nights sailing trip per person from
5,995 $
Cruise details Request
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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
10 nights sailing trip per person from
4,610 $
Cruise details Request
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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
9 nights sailing trip per person from
7,695 $
Cruise details Request
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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
10 nights sailing trip per person from
8,565 $
Cruise details Request
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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
9 nights sailing trip per person from
7,695 $
Cruise details Request
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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
7 nights sailing trip per person from
3,230 $
Cruise details Request
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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
7 nights sailing trip per person from
5,995 $
Cruise details Request
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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
7 nights sailing trip per person from
3,440 $
Cruise details Request
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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
8 nights sailing trip per person from
4,610 $
Cruise details Request
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
Music cruise
Music cruise
Caribbean vibes and 80s’ spirit

After a successful debut in 2024, Songs’N’Sail will set sail for its second edition in 2025.

Date: 12/04 – 12/11/2025
Ship: SEA CLOUD SPIRIT
Trip number: SCS-2543
Destination:
Lesser Antilles & Grenadines
7 nights sailing trip per person from
4,035 $
Cruise details Request
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
Sailing Together
Sailing Together
A SUNNY BREAK FROM WINTER BLUES
Date: 12/10 – 12/20/2025
Ship: SEA CLOUD II
Trip number: SCII-2546
Destination:
Lesser Antilles & Grenadines
10 nights sailing trip per person from
15,375 $
Cruise details Request
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
Sailing Together
Sailing Together
RENDEZVOUS OF TWO WINDJAMMERS
Date: 12/11 – 12/21/2025
Ship: SEA CLOUD SPIRIT
Trip number: SCS-2544
Destination:
Lesser Antilles & Grenadines
10 nights sailing trip per person from
5,760 $
Cruise details Request
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
Sailing Together
Sailing Together
CHRISTMAS CARIBBEAN STYLE
Date: 12/20/2025 – 01/03/2026
Ship: SEA CLOUD II
Trip number: SCII-2547
Destination:
Lesser Antilles & Grenadines
14 nights sailing trip per person from
13,985 $
Cruise details Request
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Philipsburg, St. Maarten –
Philipsburg, St. Maarten
Sailing Together
Sailing Together
HAPPY SUNNY HOLIDAYS
Date: 12/21/2025 – 01/04/2026
Ship: SEA CLOUD SPIRIT
Trip number: SCS-2545
Destination:
Lesser Antilles & Grenadines
14 nights sailing trip per person from
8,070 $
Cruise details Request
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Philipsburg, St. Maarten –
San Juan, Puerto Rico
ON THE SUNNY SIDE OF LIFE
Date: 01/04 – 01/12/2026
Ship: SEA CLOUD SPIRIT
Trip number: SCS-2601
Destination:
Lesser Antilles & Grenadines
8 nights sailing trip per person from
7,995 $
Cruise details Request
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San Juan, Puerto Rico –
San Juan, Puerto Rico
A COLORFUL CARIBBEAN TIME-OUT
Date: 01/12 – 01/19/2026
Ship: SEA CLOUD SPIRIT
Trip number: SCS-2602
Destination:
Lesser Antilles & Grenadines
7 nights sailing trip per person from
6,995 $
Cruise details Request
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Our cruise team

With high levels of passion and expertise, our cruise team members are aways there to help you. Whether you are just getting to know us and need some basic advice, or you are an old sea dog with clear ideas on your next adventure, our team will be at your side to organise the perfect trip for you.

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