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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.

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Active & Retired Military Members Save up to $200*+ 1 more offer
Celebrity Cruise Line logo

7-night St. Kitts, San Juan & Puerto Plata Cruise

Port Canaveral
Puerto Plata
San Juan
Basseterre

Aboard

Celebrity Apex

From

Port Canaveral, Florida

11 Sailings

Nov 8, 2025 - Apr 11, 2026

11 Sailings

Nov 8, 2025 - Apr 11, 2026

Published prices from

$1,249

per person*

taxes & fees included

Colorful colonial balconies in Cartagena.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
MSC Cruises logo

21 nights West Caribbean

Miami
Falmouth (Jamaica)
Cartagena (Colombia)
Colon (Panama)
Puerto Limon
+9 more

Aboard

MSC Divina

From

Miami, Florida

4 Sailings

Nov 9, 2025 - Mar 1, 2026

4 Sailings

Nov 9, 2025 - Mar 1, 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
St. Maarten (Philipsburg)
Dominica
Bridgetown (Barbados)
St. George's
+4 more

Aboard

Grand Princess

From

San Juan, Puerto Rico

20 Sailings

Nov 9, 2025 - Mar 22, 2026

20 Sailings

Nov 9, 2025 - Mar 22, 2026

Published prices from

$2,329

per person*

taxes & fees included

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

Published prices from

$6,609

per person*

taxes & fees included

 Speicherstadt Warehouse District in Hamburg.
Access Exclusive Savings with Cunard World Club*+ 1 more offer
Cunard

21-night Transatlantic Crossing And Eastern Caribbean Cruise

Hamburg
London (Southampton)
New York City
St. Maarten (Philipsburg)
Roseau
+4 more

Aboard

Queen Mary 2

From

Hamburg, Germany

1 Sailing

Nov 17, 2025

1 Sailing

Nov 17, 2025

Statue of Liberty and Manhattan skyline.
Access Exclusive Savings with Cunard World Club*+ 1 more offer
Cunard

28-night Transatlantic Crossing And Eastern Caribbean Cruise

Hamburg
London (Southampton)
New York City
St. Maarten (Philipsburg)
Roseau
+4 more

Aboard

Queen Mary 2

From

Hamburg, Germany

1 Sailing

Nov 17, 2025

1 Sailing

Nov 17, 2025

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

26-night Transatlantic Crossing And Eastern Caribbean Cruise

London (Southampton)
New York City
St. Maarten (Philipsburg)
Roseau
Bridgetown (Barbados)
+3 more

Aboard

Queen Mary 2

From

Southampton (London), England

1 Sailing

Nov 19, 2025

1 Sailing

Nov 19, 2025

A night-time view of the iconic Bayonne Bridge in New Jersey, brightly lit against a dark sky, reflecting its lights on the still water of the Kill Van Kull waterway.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Royal Caribbean logo

11-night Eastern Caribbean Cruise

Cape Liberty Cruise Port (Bayonne
St. Maarten (Philipsburg)
St. John's
Basseterre
San Juan

Aboard

Odyssey of the Seas

From

Cape Liberty Cruise Port (Bayonne, NJ)

3 Sailings

Nov 5, 2025 - Jan 3, 2027

3 Sailings

Nov 5, 2025 - Jan 3, 2027

Published prices from

$1,464

per person*

taxes & fees included

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

10-night Eastern Caribbean With Tortola Cruise

Ft. Lauderdale
Princess Cays®
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
St. John's
+3 more

Aboard

Caribbean Princess

From

Fort Lauderdale, Florida

2 Sailings

Nov 7, 2025 - Apr 8, 2026

2 Sailings

Nov 7, 2025 - Apr 8, 2026

Published prices from

$1,329

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

$3,889

per person*

taxes & fees included

A high-angle view of the bustling harbor of Marigot, St. Martin, with boats and yachts docked along the coast and colorful buildings nestled against the green hills.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

14-night Star Collector: Lovely Leewards Cruise

San Juan
St. George's
Bequia
Pigeon Island
Iles des Saintes
+8 more

Aboard

Star Pride

From

San Juan, Puerto Rico

12 Sailings

Nov 9, 2025 - Jan 3, 2027

12 Sailings

Nov 9, 2025 - Jan 3, 2027

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

21 Sailings

Nov 9, 2025 - Mar 29, 2026

21 Sailings

Nov 9, 2025 - Mar 29, 2026

Published prices from

$1,154

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

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*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

11-night Eastern Caribbean With St. Thomas Cruise

Ft. Lauderdale
Amber Cove
St. Thomas (Charlotte Amalie)
Basseterre
St. Maarten (Philipsburg)
+3 more

Aboard

Coral Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 13, 2025

1 Sailing

Nov 13, 2025

A wide-angle view of the bustling harbor of Charlotte Amalie, St. Thomas, with many sailboats and yachts docked in the tranquil blue water, and the town's buildings climbing the lush green hills.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

20-night Caribbean Explorer Holiday Cruise

Ft. Lauderdale
Princess Cays®
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
St. John's
+6 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

3 Sailings

Nov 13 - Dec 27, 2025

3 Sailings

Nov 13 - Dec 27, 2025

Published prices from

$4,998

per person*

taxes & fees included

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

7-night Eastern Caribbean Voyage

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+3 more

Aboard

Azamara Quest

From

Bridgetown, Barbados

2 Sailings

Nov 15 - Nov 29, 2025

2 Sailings

Nov 15 - Nov 29, 2025

Published prices from

$659

per person*

taxes & fees included

A view of the stunning architecture of the Hassan II Mosque in Casablanca, Morocco, featuring a long series of ornate stone arches and a spacious courtyard.
FREE $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers
Azamara logo

25-night Transatlantic Cruise: Lisbon To Miami

Lisbon
Casablanca
Miami
San Juan
St. John (U.S.V.I.)
+6 more

Aboard

Azamara Onward

From

Lisbon, Portugal

1 Sailing

Nov 17, 2025

1 Sailing

Nov 17, 2025

A wide-angle view of the bustling harbor of Charlotte Amalie, St. Thomas, with many sailboats and yachts docked in the tranquil blue water, and the town's buildings climbing the lush green hills.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

7-night St. Thomas, St. Kitts & Puerto Plata Cruise

Miami
Puerto Plata
St. Thomas (Charlotte Amalie)
Basseterre

Aboard

Celebrity Beyond

From

Miami, Florida

11 Sailings

Nov 9, 2025 - Apr 12, 2026

11 Sailings

Nov 9, 2025 - Apr 12, 2026

Published prices from

$847

per person*

taxes & fees included

An aerial view of a luxurious resort and pristine sandy beach on the coast of Puerto Plata, Dominican Republic, with turquoise waters, lush green hills, and a cityscape in the background.
FREE Dining, Onboard Activities & More*
Royal Caribbean logo

10-night Southern Caribbean Cruise

Port Canaveral
Puerto Plata
San Juan
Basseterre
Castries
+3 more

Aboard

Adventure of the Seas

From

Port Canaveral, Florida

1 Sailing

Nov 12, 2025

1 Sailing

Nov 12, 2025

Published prices from

$1,245

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

10-night Eastern Caribbean With Tortola Cruise

Ft. Lauderdale
Princess Cays®
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
St. John's
+3 more

Aboard

Enchanted Princess

From

Fort Lauderdale, Florida

3 Sailings

Nov 13, 2025 - Mar 7, 2026

3 Sailings

Nov 13, 2025 - Mar 7, 2026

Published prices from

$2,339

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

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.
Military Families Save 10%*+ 1 more offer
MSC Cruises logo

18 nights South Caribbean

Rotterdam
London (Southampton)
Paris/Normandy (Le Havre)
Ponta Delgada (Azores)
Bridgetown (Barbados)
+6 more

Aboard

MSC Virtuosa

From

Rotterdam, The Netherlands

1 Sailing

Nov 19, 2025

1 Sailing

Nov 19, 2025

Published prices from

$834

per person*

taxes & fees included

A panoramic view of Fort-de-France, Martinique, showing a bustling bay filled with boats and yachts, with colorful houses nestled on the surrounding green hillsides and the deep blue Caribbean Sea beyond.
Military Families Save 10%*+ 1 more offer
MSC Cruises logo

17 nights South Caribbean

Rotterdam
London (Southampton)
Paris/Normandy (Le Havre)
Ponta Delgada (Azores)
Bridgetown (Barbados)
+5 more

Aboard

MSC Virtuosa

From

Rotterdam, The Netherlands

1 Sailing

Nov 19, 2025

1 Sailing

Nov 19, 2025

Published prices from

$623

per person*

taxes & fees included

Boats on a canal in Fort Lauderdale.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

21-night Eastern & Southern Caribbean: Leeward & Abc Islands Cruise

Ft. Lauderdale
St. Maarten (Philipsburg)
St. John's
Castries
Roseau
+9 more

Aboard

Koningsdam

From

Fort Lauderdale, Florida

1 Sailing

Nov 18, 2025

1 Sailing

Nov 18, 2025

Published prices from

$3,259

per person*

taxes & fees included

Boats on a canal in Fort Lauderdale.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

11-night Eastern Caribbean: Windward & Leeward Islands Cruise

Ft. Lauderdale
St. Maarten (Philipsburg)
St. John's
Castries
Roseau
+4 more

Aboard

Koningsdam

From

Fort Lauderdale, Florida

5 Sailings

Nov 18, 2025 - Feb 14, 2026

5 Sailings

Nov 18, 2025 - Feb 14, 2026

Published prices from

$1,477

per person*

taxes & fees included