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*Rates and offers are per person, in US Dollars, based on double occupancy, capacity controlled, subject to availability and confirmation, and may change without notice. Government taxes and fees are included. Rates and offers are available for select dates and categories only. Additional restrictions may apply. Call 1-800-377-9383 for full terms and conditions.

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

18-night Star Collector: Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica via the Panama Canal Cruise

Bridgetown (Barbados)
Bequia
Mayreau
St. George's
Kralendijk
+11 more

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Nov 18, 2025

1 Sailing

Nov 18, 2025

Rocky beach and palm trees in Barbados.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

7-night South Caribbean Cruise - Bridgetown To Bridgetown

Bridgetown (Barbados)
Castries
Fort de France
Gustavia
Roseau
+2 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Dec 8, 2025

1 Sailing

Dec 8, 2025

Published prices from

$5,800

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

16-night Caribbean Cruise

Cartagena (Colombia)
Santa Marta
Oranjestad
Kralendijk
Willemstad
+10 more

Aboard

Silver Shadow

From

Cartagena, Colombia

2 Sailings

Dec 19, 2025 - Feb 3, 2026

2 Sailings

Dec 19, 2025 - Feb 3, 2026

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

25-night Star Collector: Southern Caribbean Thanksgiving Jubilee Cruise

Lisbon
Bridgetown (Barbados)
Bequia
Mayreau
St. George's
+6 more

Aboard

Wind Spirit

From

Lisbon, Portugal

1 Sailing

Nov 4, 2025

1 Sailing

Nov 4, 2025

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

28-night Mediterranean & Caribbean Cruise

Lisbon
Funchal (Madeira)
Las Palmas (Gran Canaria)
Santa Cruz de Tenerife
Ft. Lauderdale
+9 more

Aboard

Silver Dawn

From

Lisbon, Portugal

1 Sailing

Dec 8, 2025

1 Sailing

Dec 8, 2025

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

21-night Caribbean & South America Cruise

Ft. Lauderdale
San Juan
St. Thomas (Charlotte Amalie)
Gustavia
St. John's
+12 more

Aboard

Silver Shadow

From

Fort Lauderdale, Florida

1 Sailing

Nov 10, 2025

1 Sailing

Nov 10, 2025

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

10-night Caribbean Cruise

Ft. Lauderdale
Virgin Gorda
St. John (U.S.V.I.)
St. John's
Deshaies
+5 more

Aboard

Silver Spirit

From

Fort Lauderdale, Florida

1 Sailing

Jan 16, 2026

1 Sailing

Jan 16, 2026

Published prices from

$7,300

per person*

taxes & fees included

A scenic Caribbean bay near Kingstown, Saint Vincent and the Grenadines, with small boats anchored in the turquoise water and lush green hillsides with colorful houses.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

12-night Eastern & Southern Caribbean Cruise

Ft. Lauderdale
San Juan
St. Thomas (Charlotte Amalie)
Gustavia
St. John's
+7 more

Aboard

Silver Shadow

From

Fort Lauderdale, Florida

1 Sailing

Nov 10, 2025

1 Sailing

Nov 10, 2025

Published prices from

$7,800

per person*

taxes & fees included

A snorkeler swims in the turquoise waters of the Baths National Park on Virgin Gorda, surrounded by massive granite boulders and palm trees.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

17-night Star Collector: Hidden Gems of the Caribbean Cruise

St. Maarten (Philipsburg)
Little Bay
Roseau
Castries
Mayreau
+10 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 14, 2026

1 Sailing

Jan 14, 2026

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

14-night Star Collector: Lovely Leewards Cruise

San Juan
Cruz Bay
Basseterre
Gustavia
St. Maarten (Philipsburg)
+8 more

Aboard

Star Pride

From

San Juan, Puerto Rico

13 Sailings

Nov 2, 2025 - Jan 3, 2027

13 Sailings

Nov 2, 2025 - Jan 3, 2027

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

11-night Caribbean Cruise

Bridgetown (Barbados)
Bequia
Castries
Deshaies
Roseau
+6 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

3 Sailings

Jan 5, 2026 - Feb 29, 2028

3 Sailings

Jan 5, 2026 - Feb 29, 2028

Published prices from

$5,600

per person*

taxes & fees included

A sunny, tropical beach on Grand Turk Island with multiple hot air balloons flying over the turquoise water and shoreline.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

14-night Caribbean Cruise

Ft. Lauderdale
Grand Turk
St. Thomas (Charlotte Amalie)
Basseterre
Roseau
+5 more

Aboard

Silver Dawn

From

Fort Lauderdale, Florida

1 Sailing

Dec 22, 2025

1 Sailing

Dec 22, 2025

Published prices from

$10,200

per person*

taxes & fees included

A scenic landscape view of Admiralty Bay in Bequia, St. Vincent and the Grenadines, with dozens of sailboats moored on the vibrant turquoise water, surrounded by lush green hills.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

10-night Blue Waters Of The Leeward Islands Cruise

St. Maarten (Philipsburg)
Little Bay
Roseau
Castries
Mayreau
+5 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 14, 2026

1 Sailing

Jan 14, 2026

A stunning panoramic view of Road Town on Tortola, British Virgin Islands, showing the harbor filled with boats and a small town surrounded by lush green hills overlooking the Caribbean Sea.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

21-night Caribbean Cruise

Bridgetown (Barbados)
Bequia
Castries
Deshaies
Roseau
+9 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

2 Sailings

Jan 5 - Feb 2, 2026

2 Sailings

Jan 5 - Feb 2, 2026

A vibrant panoramic view of Castries, St. Lucia, with colorful buildings nestled along the harbor and lush green hills in the background under a blue sky with white clouds.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

20-night Transatlantic Cruise

Lisbon
Funchal (Madeira)
Santa Cruz de La Palma
Sao Vicente (Mindelo)
Bridgetown (Barbados)
+7 more

Aboard

Silver Spirit

From

Lisbon, Portugal

1 Sailing

Nov 25, 2025

1 Sailing

Nov 25, 2025

A sunny view of the colorful waterfront of Willemstad, Curacao, with its iconic pastel-colored Dutch colonial buildings lining the Handelskade street and a ship docked in the port.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

55-night Star Collector: A Grand Caribbean Adventure Cruise

St. Maarten (Philipsburg)
Falmouth Harbour
Road Bay
Sopers Hole
Jost Van Dyke
+33 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

A sunny view of the colorful waterfront of Willemstad, Curacao, with its iconic pastel-colored Dutch colonial buildings lining the Handelskade street and a ship docked in the port.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

28-night Star Collector: The Best Of The Windward & Leeward Isles Cruise

St. Maarten (Philipsburg)
Falmouth Harbour
Road Bay
Sopers Hole
Jost Van Dyke
+19 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

A sunny view of the colorful waterfront of Willemstad, Curacao, with its iconic pastel-colored Dutch colonial buildings lining the Handelskade street and a ship docked in the port.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

11-night Columbian & Southern Caribbean Coastlines Cruise

Bridgetown (Barbados)
Bequia
Mayreau
St. George's
Kralendijk
+5 more

Aboard

Wind Spirit

From

Bridgetown, Barbados

1 Sailing

Nov 18, 2025

1 Sailing

Nov 18, 2025

An aerial view of Anse Mitan in Martinique, a beautiful Caribbean village with a bustling beach, sailboats moored in the bay, and lush green hills in the distance.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

21-night Star Collector: A Lesser Antilles Odyssey Cruise

St. Maarten (Philipsburg)
Falmouth Harbour
Road Bay
Sopers Hole
Jost Van Dyke
+13 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

A sunny view of the colorful waterfront of Willemstad, Curacao, with its iconic pastel-colored Dutch colonial buildings lining the Handelskade street and a ship docked in the port.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

9-night Southern Caribbean Cruise

Bridgetown (Barbados)
Soufriere
Bequia
Kralendijk
Willemstad
+4 more

Aboard

Silver Shadow

From

Bridgetown, Barbados

3 Sailings

Nov 22, 2025 - Jan 25, 2026

3 Sailings

Nov 22, 2025 - Jan 25, 2026

Published prices from

$5,500

per person*

taxes & fees included

An aerial panoramic view of a winding road overlooking Frigate Bay and the Caribbean Sea, with rolling green hills, a beach, and the town of Basseterre, St. Kitts.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

14-night Star Collector: Antilles Adventures Cruise

St. Maarten (Philipsburg)
Basseterre
Little Bay
Gustavia
Deshaies
+8 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 11, 2026

1 Sailing

Jan 11, 2026

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

7-night Eastern & Southern Caribbean Cruise

Bridgetown (Barbados)
Bequia
Fort de France
Gustavia
Roseau
+2 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Dec 15, 2025

1 Sailing

Dec 15, 2025

Published prices from

$5,200

per person*

taxes & fees included

An aerial view of the colorful waterfront of St. George's, Grenada, with the town's buildings nestled on a hillside and a long, rocky breakwater extending into the calm, turquoise water.
FREE Butler Service, Gourmet Dining & More*+ 1 more offer
Silversea logo

7-night Caribbean Cruise

Bridgetown (Barbados)
Castries
Fort de France
Gustavia
Roseau
+2 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

5 Sailings

Dec 22, 2025 - Mar 11, 2028

5 Sailings

Dec 22, 2025 - Mar 11, 2028

Published prices from

$3,800

per person*

taxes & fees included

A beautiful panoramic view of Roseau, Dominica, with a colorful town nestled between the deep blue Caribbean Sea and a backdrop of lush green, volcanic mountains.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

15-night Star Collector: Merry Christmas & Happy New Years From The Caribbean Cruise

Oranjestad
Willemstad
Kralendijk
St. George's
Mayreau
+7 more

Aboard

Wind Spirit

From

Oranjestad, Aruba, Caribbean

1 Sailing

Dec 20, 2025

1 Sailing

Dec 20, 2025

A scenic landscape view of Admiralty Bay in Bequia, St. Vincent and the Grenadines, with dozens of sailboats moored on the vibrant turquoise water, surrounded by lush green hills.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

8-night An ABC Christmas Cruise

Oranjestad
Willemstad
Kralendijk
St. George's
Mayreau
+3 more

Aboard

Wind Spirit

From

Oranjestad, Aruba, Caribbean

1 Sailing

Dec 20, 2025

1 Sailing

Dec 20, 2025