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Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Carnival Cruise Line

8-night Eastern Caribbean Cruise

Miami
Princess Cays®
San Juan
St. Maarten (Philipsburg)
St. Thomas (Charlotte Amalie)

Aboard

Carnival Magic

From

Miami, Florida

35 Sailings

Nov 1, 2025 - Mar 11, 2028

35 Sailings

Nov 1, 2025 - Mar 11, 2028

Published prices from

$674

per person*

taxes & fees included

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

12-night Carnival Journeys Cruise - Southern Caribbean

New York City
St. Thomas (Charlotte Amalie)
St. Croix
Oranjestad
Curacao
+3 more

Aboard

Carnival Venezia

From

New York, New York

1 Sailing

Nov 8, 2025

1 Sailing

Nov 8, 2025

Published prices from

$769

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Royal Caribbean logo

7-night Eastern Caribbean & Perfect Day Cruise

Miami
Perfect Day at CocoCay
San Juan
St. Thomas (Charlotte Amalie)

Aboard

Independence of the Seas

From

Miami, Florida

19 Sailings

Nov 2, 2025 - Apr 18, 2027

19 Sailings

Nov 2, 2025 - Apr 18, 2027

Published prices from

$658

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
Carnival Cruise Line

14-night Carnival Journeys Cruise - Southern Caribbean

Baltimore
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Basseterre
Oranjestad
+3 more

Aboard

Carnival Pride

From

Baltimore, Maryland

4 Sailings

Nov 2, 2025 - Jan 10, 2027

4 Sailings

Nov 2, 2025 - Jan 10, 2027

Published prices from

$1,644

per person*

taxes & fees included

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

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Royal Caribbean logo

8-night Eastern Caribbean & Perfect Day Cruise

Ft. Lauderdale
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
San Juan
Perfect Day at CocoCay

Aboard

Allure of the Seas

From

Fort Lauderdale, Florida

14 Sailings

Nov 8, 2025 - Sep 19, 2026

14 Sailings

Nov 8, 2025 - Sep 19, 2026

Published prices from

$866

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

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Royal Caribbean logo

7-night Eastern Caribbean Cruise

Miami
St. Maarten (Philipsburg)
St. Thomas (Charlotte Amalie)
Nassau

Aboard

Symphony of the Seas

From

Miami, Florida

12 Sailings

Nov 2, 2025 - Apr 12, 2026

12 Sailings

Nov 2, 2025 - Apr 12, 2026

Published prices from

$758

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Dining, Onboard Activities & More*
Royal Caribbean logo

7-night Southern Caribbean Cruise

San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
St. Croix
Fort de France
+2 more

Aboard

Jewel of the Seas

From

San Juan, Puerto Rico

24 Sailings

Nov 8, 2025 - Apr 18, 2026

24 Sailings

Nov 8, 2025 - Apr 18, 2026

Published prices from

$692

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

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Holland America logo

14-night Eastern & Western Caribbean: San Juan & Mexico Cruise

Miami
Grand Turk
San Juan
St. Thomas (Charlotte Amalie)
Half Moon Cay
+4 more

Aboard

Zuiderdam

From

Miami, Florida

1 Sailing

Nov 1, 2025

1 Sailing

Nov 1, 2025

Published prices from

$2,139

per person*

taxes & fees included

*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.

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 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*+ 2 more offers
TCW EXCLUSIVE
Carnival Cruise Line

7-night Eastern Caribbean Cruise

Miami
Celebration Key
San Juan
St. Thomas (Charlotte Amalie)

Aboard

Carnival Celebration

From

Miami, Florida

92 Sailings

Nov 9, 2025 - Mar 26, 2028

92 Sailings

Nov 9, 2025 - Mar 26, 2028

Published prices from

$609

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*+ 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 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 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.
FREE Dining, Onboard Activities & More*
Royal Caribbean logo

7-night Eastern Caribbean & Perfect Day Cruise

Port Canaveral
Perfect Day at CocoCay
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)

Aboard

Star of the Seas

From

Port Canaveral, Florida

42 Sailings

Nov 2, 2025 - Apr 18, 2027

42 Sailings

Nov 2, 2025 - Apr 18, 2027

Published prices from

$1,261

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*+ 2 more offers
TCW EXCLUSIVE
Holland America logo

28-night Panama Canal & Eastern Caribbean Cruise

San Diego
Puerto Vallarta
Huatulco
Chiapas
Puerto Quetzal
+14 more

Aboard

Koningsdam

From

San Diego, California

1 Sailing

Nov 1, 2025

1 Sailing

Nov 1, 2025

Published prices from

$4,374

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*+ 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 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 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

$1,357

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.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Royal Caribbean logo

7-Night Eastern Caribbean & Perfect Day Cruise

Miami
St. Maarten (Philipsburg)
St. Thomas (Charlotte Amalie)
Perfect Day at CocoCay

Aboard

Icon of the Seas

From

Miami, Florida

13 Sailings

Nov 8, 2025 - Apr 25, 2026

13 Sailings

Nov 8, 2025 - Apr 25, 2026

Published prices from

$1,521

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.
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

$922

per person*

taxes & fees included

A sunny, idyllic beach scene in Amber Cove, Dominican Republic, with a small boat and paddle resting under a palm tree beside the turquoise ocean and a clear blue sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

14-night Eastern Caribbean: Bahamas & San Juan Cruise

Ft. Lauderdale
Half Moon Cay
Grand Turk
Amber Cove
Bimini
+3 more

Aboard

Eurodam

From

Fort Lauderdale, Florida

4 Sailings

Nov 9, 2025 - Mar 8, 2026

4 Sailings

Nov 9, 2025 - Mar 8, 2026

Published prices from

$2,559

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
Holland America logo

7-night Eastern Caribbean: San Juan & St. Thomas Cruise

Miami
Grand Turk
San Juan
St. Thomas (Charlotte Amalie)
Half Moon Cay

Aboard

Zuiderdam

From

Miami, Florida

4 Sailings

Nov 1, 2025 - Apr 11, 2026

4 Sailings

Nov 1, 2025 - Apr 11, 2026

Published prices from

$834

per person*

taxes & fees included