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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.

Rocky beach and palm trees in Barbados.
FREE Dining, Waterparks, Entertainment & More*+ 1 more offer
Carnival Cruise Line

14-night Southern Caribbean Cruise

Port Canaveral
St. Thomas (Charlotte Amalie)
St. John's
Castries
St. George's
+5 more

Aboard

Carnival Venezia

From

Port Canaveral, Florida

2 Sailings

Nov 30, 2025 - Feb 22, 2026

2 Sailings

Nov 30, 2025 - Feb 22, 2026

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers
Princess Cruises logo

14-night Southern Caribbean Adventurer Cruise

San Juan
Bridgetown (Barbados)
Dominica
St. John's
St. Maarten (Philipsburg)
+4 more

Aboard

Grand Princess

From

San Juan, Puerto Rico

21 Sailings

Nov 2, 2025 - Mar 22, 2026

21 Sailings

Nov 2, 2025 - Mar 22, 2026

Published prices from

$2,329

per person*

taxes & fees included

Statue of Liberty and Manhattan skyline.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Regent Seven Seas

15-night Auburn Sunsets, Turquoise Seas Cruise

New York City
Royal Naval Dockyard
Gustavia
Castries
Bridgetown (Barbados)
+7 more

Aboard

Seven Seas Splendor

From

New York, New York

1 Sailing

Nov 2, 2025

1 Sailing

Nov 2, 2025

Published prices from

$13,299

per person*

taxes & fees included

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

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Oceania Cruises

12-night Curated Caribbean Voyage

Miami
Oranjestad
Willemstad
Kralendijk
St. George's
+4 more

Aboard

Allura

From

Miami, Florida

1 Sailing

Nov 16, 2025

1 Sailing

Nov 16, 2025

Published prices from

$4,999

per person*

taxes & fees included

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.
FREE $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers
Azamara logo

14-night Eastern Caribbean Voyage

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+9 more

Aboard

Azamara Quest

From

Bridgetown, Barbados

3 Sailings

Nov 15 - Dec 13, 2025

3 Sailings

Nov 15 - Dec 13, 2025

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

An aerial view of the colorful waterfront of St. John's, Antigua, with a long pier extending into the calm, blue sea and the town's charming buildings and marina in the background.
FREE Dining, Onboard Activities & More*
Royal Caribbean logo

7-night Southern Caribbean Cruise

San Juan
Roadtown
St. John's
St. George's
St. Vincent (Kingstown)
+2 more

Aboard

Brilliance of the Seas

From

San Juan, Puerto Rico

18 Sailings

Nov 9, 2025 - Apr 12, 2026

18 Sailings

Nov 9, 2025 - Apr 12, 2026

Published prices from

$655

per person*

taxes & fees included

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 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

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

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.
Up to FREE $2,000 Onboard Credit*
Seabourn logo

20-night Southern Caribbean Discovery Cruise

San Juan
Oranjestad
Willemstad
Kralendijk
Trois Isles
+12 more

Aboard

Seabourn Ovation

From

San Juan, Puerto Rico

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

Published prices from

$11,499

per person*

taxes & fees included

A panoramic view of the coastal city of Roseau in Dominica, with its colorful buildings nestled between the Caribbean Sea and lush, mountainous terrain under a beautiful sky.
Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers
Princess Cruises logo

7-night Southern Caribbean with Barbados Cruise

San Juan
St. Maarten (Philipsburg)
Dominica
Bridgetown (Barbados)
St. George's
+2 more

Aboard

Grand Princess

From

San Juan, Puerto Rico

22 Sailings

Nov 2, 2025 - Mar 29, 2026

22 Sailings

Nov 2, 2025 - Mar 29, 2026

Published prices from

$1,154

per person*

taxes & fees included

A cruise ship navigating through the Gatun Locks of the Panama Canal, an important navigational route and popular tourist destination.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Regent Seven Seas

16-night Southern Caribbean Beauty Cruise

Miami
Florida Strait
Cozumel
Costa Maya
Harvest Caye
+11 more

Aboard

Seven Seas Splendor

From

Miami, Florida

1 Sailing

Nov 17, 2025

1 Sailing

Nov 17, 2025

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Oceania Cruises

19-night Caribbean Spectrum Voyage

Miami
Oranjestad
Willemstad
Kralendijk
St. George's
+8 more

Aboard

Allura

From

Miami, Florida

1 Sailing

Nov 16, 2025

1 Sailing

Nov 16, 2025

Published prices from

$6,499

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 $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers
Azamara logo

7-night Southern Caribbean Voyage

San Juan
Virgin Gorda
St. John's
St. Pierre
Port Elizabeth (Bequia)
+3 more

Aboard

Azamara Quest

From

San Juan, Puerto Rico

3 Sailings

Nov 8 - Dec 6, 2025

3 Sailings

Nov 8 - Dec 6, 2025

Published prices from

$609

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.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

14-night Circle the Caribbean Cruise

Ft. Lauderdale
St. Maarten (Philipsburg)
Basseterre
Fort de France
Bridgetown (Barbados)
+5 more

Aboard

Island Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 7, 2025

1 Sailing

Nov 7, 2025

A scenic view of Devil's Island, a small tropical island in French Guiana, completely covered by a dense forest of palm trees.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Regent Seven Seas

30-night Caribbean Shores to Rio's Marvels Cruise

Miami
Florida Strait
Cozumel
Costa Maya
Harvest Caye
+20 more

Aboard

Seven Seas Splendor

From

Miami, Florida

1 Sailing

Nov 17, 2025

1 Sailing

Nov 17, 2025

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.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

14-night Circle Caribbean Cruise

Ft. Lauderdale
Basseterre
Fort de France
Castries
Bridgetown (Barbados)
+5 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

2 Sailings

Dec 3, 2025 - Dec 3, 2026

2 Sailings

Dec 3, 2025 - Dec 3, 2026

Published prices from

$2,206

per person*

taxes & fees included

An aerial view of the colorful waterfront of St. John's, Antigua, with a long pier extending into the calm, blue sea and the town's charming buildings and marina in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Oceania Cruises

25-night Call Of The Amazon Voyage

Miami
St. John's
Castries
St. George's
Scarborough
+10 more

Aboard

Insignia

From

Miami, Florida

1 Sailing

Nov 12, 2025

1 Sailing

Nov 12, 2025

Published prices from

$6,999

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 $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers
Azamara logo

14-night Eastern Caribbean Voyage

San Juan
Virgin Gorda
St. John's
St. Pierre
Port Elizabeth (Bequia)
+9 more

Aboard

Azamara Quest

From

San Juan, Puerto Rico

2 Sailings

Nov 8 - Nov 22, 2025

2 Sailings

Nov 8 - Nov 22, 2025

Published prices from

$3,689

per person*

taxes & fees included

An aerial view of Kingston Beach, a residential suburb near Hobart, Tasmania, Australia. The image shows the curved white-sand beach and the adjacent neighborhood of houses and streets, bordering the calm, blue waters of the River Derwent estuary.
Military Families Save 10%*+ 1 more offer
MSC Cruises logo

24 nights South Caribbean

Rotterdam
London (Southampton)
Paris/Normandy (Le Havre)
Ponta Delgada (Azores)
Bridgetown (Barbados)
+9 more

Aboard

MSC Virtuosa

From

Rotterdam, The Netherlands

1 Sailing

Nov 19, 2025

1 Sailing

Nov 19, 2025

Published prices from

$1,479

per person*

taxes & fees included

A scenic coastal view in Curaçao featuring houses with orange roofs on a cliffside overlooking a rocky beach with beautiful turquoise Caribbean water.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

14-night Circle Caribbean Cruise

Ft. Lauderdale
St. Maarten (Philipsburg)
Basseterre
Dominica
Fort de France
+5 more

Aboard

Coral Princess

From

Fort Lauderdale, Florida

3 Sailings

Nov 24, 2025 - Oct 15, 2026

3 Sailings

Nov 24, 2025 - Oct 15, 2026

Published prices from

$2,309

per person*

taxes & fees included