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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.
Up to $500 FREE Onboard Credit*+ 4 more offers
TCW EXCLUSIVE
Cunard

12-night Eastern Caribbean Cruise

Miami
San Juan
St. John's
Castries
Bridgetown (Barbados)
+3 more

Aboard

Queen Elizabeth

From

Miami, Florida

10 Sailings

Nov 6, 2025 - Nov 26, 2026

10 Sailings

Nov 6, 2025 - Nov 26, 2026

Published prices from

$1,399

per person*

taxes & fees included

Historic Acorn Street in Boston.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Royal Caribbean logo

7-night Boston To San Juan Cruise

Boston
Royal Naval Dockyard
St. John's
Roadtown
San Juan

Aboard

Brilliance of the Seas

From

Boston, Massachusetts

1 Sailing

Nov 2, 2025

1 Sailing

Nov 2, 2025

Published prices from

$698

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Buy One, Get One FREE Airfare*+ 5 more offers
Norwegian Cruise Line logo

7-night Caribbean Cruise: Barbados, Antigua & St. Lucia

San Juan
Roadtown
St. John's
Bridgetown (Barbados)
Castries
+2 more

Aboard

Norwegian Epic

From

San Juan, Puerto Rico

19 Sailings

Nov 23, 2025 - Apr 5, 2026

19 Sailings

Nov 23, 2025 - Apr 5, 2026

Published prices from

$650

per person*

taxes & fees included

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

10-night Eastern Caribbean Cruise

Ft. Lauderdale
San Juan
Roadtown
St. Maarten (Philipsburg)
St. John's
+2 more

Aboard

Celebrity Summit

From

Fort Lauderdale, Florida

1 Sailing

Nov 10, 2025

1 Sailing

Nov 10, 2025

Published prices from

$1,192

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

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.
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

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.
Norwegian ⚓ FREE Gratuities for Balcony & Above*+ 7 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo

7-night Caribbean Cruise: Great Stirrup Cay & Dominican Republic

Miami
Puerto Plata
St. Thomas (Charlotte Amalie)
Roadtown
Great Stirrup Cay

Aboard

Norwegian Aqua

From

Miami, Florida

44 Sailings

Nov 2, 2025 - Mar 28, 2027

44 Sailings

Nov 2, 2025 - Mar 28, 2027

Published prices from

$500

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. 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

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.
Buy One, Get One FREE Airfare*+ 5 more offers
Norwegian Cruise Line logo

7-night Caribbean Cruise: Great Stirrup Cay & Dominican Republic

Port Canaveral
Puerto Plata
St. Thomas (Charlotte Amalie)
Roadtown
Great Stirrup Cay

Aboard

Norwegian Joy

From

Port Canaveral, Florida

12 Sailings

Nov 15, 2025 - Apr 3, 2026

12 Sailings

Nov 15, 2025 - Apr 3, 2026

Published prices from

$449

per person*

taxes & fees included

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

26-night Crossing And Southern Caribbean Cruise

Barcelona
Tangier
Carambola Beach
Roadtown
San Juan
+8 more

Aboard

Seabourn Ovation

From

Barcelona, Spain

1 Sailing

Nov 18, 2025

1 Sailing

Nov 18, 2025

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.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

7-night Tortola, Antigua & Bahamas Cruise

Miami
Roadtown
San Juan
Puerto Plata

Aboard

Celebrity Beyond

From

Miami, Florida

12 Sailings

Nov 2, 2025 - Apr 19, 2026

12 Sailings

Nov 2, 2025 - Apr 19, 2026

Published prices from

$715

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.
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 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.
Buy One, Get One FREE Airfare*+ 5 more offers
Norwegian Cruise Line logo

10-night Transatlantic Cruise: St. Thomas & Philpsburg

Lisbon
Ponta Delgada (Azores)
Roadtown
St. Thomas (Charlotte Amalie)
San Juan

Aboard

Norwegian Epic

From

Lisbon, Portugal

1 Sailing

Nov 13, 2025

1 Sailing

Nov 13, 2025

Published prices from

$300

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*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

14-night Crossing To The Caribbean Cruise

Barcelona
Tangier
Carambola Beach
Roadtown
San Juan

Aboard

Seabourn Ovation

From

Barcelona, Spain

1 Sailing

Nov 18, 2025

1 Sailing

Nov 18, 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.
Up to $500 FREE Onboard Credit*+ 4 more offers
TCW EXCLUSIVE
Cunard

21-night Caribbean Cruise

Miami
San Juan
St. John's
Castries
Bridgetown (Barbados)
+8 more

Aboard

Queen Elizabeth

From

Miami, Florida

18 Sailings

Nov 6, 2025 - Nov 26, 2026

18 Sailings

Nov 6, 2025 - Nov 26, 2026

Published prices from

$2,919

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*+ 6 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo

11-night Caribbean Cruise: Dominican Republic & Antigua

Jacksonville
Grand Bahama Island
Puerto Plata
Roadtown
St. John's
+4 more

Aboard

Norwegian Gem

From

Jacksonville, Florida

2 Sailings

Dec 1, 2025 - Feb 17, 2026

2 Sailings

Dec 1, 2025 - Feb 17, 2026

Published prices from

$750

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

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 stunning aerial view of the turquoise waters and white-sand beaches around Paradise Island in Nassau, Bahamas, with the Atlantis resort visible in the distance.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Oceania Cruises

25-night Iberian & Island Dreams Voyage

Barcelona
Alicante
Malaga
Gibraltar
Seville (Cadiz)
+9 more

Aboard

Nautica

From

Barcelona, Spain

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

Published prices from

$6,699

per person*

taxes & fees included

An aerial view of the Kralendijk waterfront in Bonaire, showcasing the contrast between the deep blue ocean and the shallow turquoise water near the shore, with sailboats anchored offshore.
Up to FREE $2,000 Onboard Credit*
Seabourn logo

12-night Treasures Of Aruba, Bonaire & Curacao Cruise

San Juan
Oranjestad
Willemstad
Kralendijk
Trois Isles
+6 more

Aboard

Seabourn Ovation

From

San Juan, Puerto Rico

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

Published prices from

$15,999

per person*

taxes & fees included

An aerial view of the coastal city of Trapani, Sicily, with its scenic harbor filled with boats and a long sandy beach along the turquoise blue water.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

24-night Mediterranean Jewels & Atlantic Crossing Cruise

Rome (Civitavecchia)
Pompeii
Lipari
Mgarr (Victoria)
Valletta
+10 more

Aboard

Seabourn Ovation

From

Civitavecchia, Rome, Italy

1 Sailing

Nov 8, 2025

1 Sailing

Nov 8, 2025

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