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263 Results

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Two colorful striped beach chairs sit on the white sand beach of Great Stirrup Cay, Bahamas, facing the clear turquoise water under a bright blue sky with palm fronds overhead.
Norwegian Cruise Line logo.

7-night Caribbean Cruise: Great Stirrup Cay, Dominican Republic & Tortola From Miami, Florida

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

Aboard

Norwegian Luna

From

Miami, Florida

1 Sailing

Oct 31, 2026

1 Sailing

Oct 31, 2026

Published prices from

$609

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.
50% Off + Kids Sail FREE + FREE Pre-Paid Tips*
Norwegian Cruise Line logo.

7-night Caribbean Cruise: Great Stirrup Cay & Dominican Republic From Port Canaveral, Florida

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

Aboard

Norwegian Prima

From

Port Canaveral, Florida

1 Sailing

Nov 1, 2026

1 Sailing

Nov 1, 2026

Published prices from

$509

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

14-night An Extended Journey Into Island Delights, Hidden Coves & Chic Coastlines From San Juan, Puerto Rico

San Juan
Roadtown
Basseterre
Gustavia
Road Bay
+6 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Nov 1, 2026

1 Sailing

Nov 1, 2026

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

7-night A Journey Into Caribbean Exploration & Island Delights From San Juan, Puerto Rico

San Juan
Roadtown
Basseterre
Gustavia
Road Bay
+2 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Nov 1, 2026

1 Sailing

Nov 1, 2026

Published prices from

$6,750

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Royal Caribbean logo

7-night Southern Caribbean Cruise From San Juan, Puerto Rico

San Juan
Roadtown
St. John's
Fort de France
St. Vincent (Kingstown)
+2 more

Aboard

Vision of the Seas

From

San Juan, Puerto Rico

42 Sailings

Nov 1, 2026 - Apr 16, 2028

42 Sailings

Nov 1, 2026 - Apr 16, 2028

Published prices from

$521

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

47-night Footsteps of Columbus Voyage From Barcelona, Spain

Barcelona
Palma de Mallorca
Alicante
Cartagena (Spain)
Malaga
+24 more

Aboard

Insignia

From

Barcelona, Spain

1 Sailing

Nov 2, 2026

1 Sailing

Nov 2, 2026

Published prices from

$28,049

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Viking

10-night West Indies Explorer Cruise From San Juan, Puerto Rico

San Juan
Roadtown
Basseterre
Castries
Bridgetown (Barbados)
+4 more

Aboard

Viking Sea

From

San Juan, Puerto Rico

25 Sailings

Nov 5, 2026 - Jan 29, 2029

25 Sailings

Nov 5, 2026 - Jan 29, 2029

Published prices from

$3,599

per person*

taxes & fees included

The ancient stone ruins of a majestic Mayan temple or pyramid, featuring historic architecture at an archaeological site in Mexico's Costa Maya region.
Cunard

21-night Caribbean Cruise From Miami, Florida

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

Aboard

Queen Elizabeth

From

Miami, Florida

3 Sailings

Nov 5 - Nov 26, 2026

3 Sailings

Nov 5 - Nov 26, 2026

Published prices from

$1,808

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
Cunard

12-night Eastern Caribbean Cruise From Miami, Florida

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

Aboard

Queen Elizabeth

From

Miami, Florida

2 Sailings

Nov 5 - Nov 26, 2026

2 Sailings

Nov 5 - Nov 26, 2026

Published prices from

$1,199

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
Azamara logo

14-night Caribbean Voyage: San Juan, St. Lucia & St. Kitts From San Juan, Puerto Rico

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

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 2026

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
Up to $500 FREE Onboard Credit*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

7-night Caribbean Cruise: Great Stirrup Cay & Dominican Republic From Miami, Florida

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

Aboard

Norwegian Aqua

From

Miami, Florida

21 Sailings

Nov 8, 2026 - Mar 28, 2027

21 Sailings

Nov 8, 2026 - Mar 28, 2027

Published prices from

$439

per person*

taxes & fees included

Statue of Liberty and Manhattan skyline.
Up to $500 FREE Onboard Credit*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

12-night Caribbean Cruise: Dominican Republic & St. Thomas From New York City, New York

New York City
Puerto Plata
San Juan
Basseterre
Roadtown
+3 more

Aboard

Norwegian Bliss

From

New York City, New York

7 Sailings

Nov 9, 2026 - Mar 1, 2027

7 Sailings

Nov 9, 2026 - Mar 1, 2027

Published prices from

$1,119

per person*

taxes & fees included

A beautiful view from Fort King George in Scarborough, Tobago, with historic cannons overlooking the Caribbean Sea and the town below, framed by lush tropical trees.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

40-night Amazon & Tropical Isles Voyage From Lisbon, Portugal

Lisbon
Arrecife
Las Palmas (Gran Canaria)
Santa Cruz de La Palma
San Juan
+17 more

Aboard

Insignia

From

Lisbon, Portugal

1 Sailing

Nov 9, 2026

1 Sailing

Nov 9, 2026

Published prices from

$23,299

per person*

taxes & fees included

Statue of Liberty and Manhattan skyline.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Cunard

25-night Transatlantic Crossing and Eastern Caribbean Cruise From Southampton (London), England

London (Southampton)
New York City
St. Thomas (Charlotte Amalie)
Roadtown
Basseterre
+2 more

Aboard

Queen Mary 2

From

Southampton (London), England

1 Sailing

Nov 10, 2026

1 Sailing

Nov 10, 2026

Published prices from

$2,839

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
Cunard

18-night Transatlantic Crossing and Eastern Caribbean Cruise From Southampton (London), England

London (Southampton)
New York City
St. Thomas (Charlotte Amalie)
Roadtown
Basseterre
+2 more

Aboard

Queen Mary 2

From

Southampton (London), England

1 Sailing

Nov 10, 2026

1 Sailing

Nov 10, 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.
Up to $500 FREE Onboard Credit*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

7-night Caribbean Cruise: Great Stirrup Cay & Dominican Republic From Port Canaveral, Florida

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

Aboard

Norwegian Escape

From

Port Canaveral, Florida

18 Sailings

Nov 13, 2026 - Mar 26, 2027

18 Sailings

Nov 13, 2026 - Mar 26, 2027

Published prices from

$399

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
Azamara logo

14-night Caribbean Voyage: Barbados, St. Lucia & St. Kitts From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+9 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Nov 14, 2026

1 Sailing

Nov 14, 2026

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

7-night Eastern Caribbean Voyage: St.Lucia, Dominica & St.Kitts From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+3 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

2 Sailings

Nov 14 - Nov 28, 2026

2 Sailings

Nov 14 - Nov 28, 2026

Published prices from

$929

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*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

7-night Caribbean Round-trip San Juan Cruise: St. Thomas & Tortola From San Juan, Puerto Rico

San Juan
St. Maarten (Philipsburg)
Basseterre
Bridgetown (Barbados)
Castries
+2 more

Aboard

Norwegian Prima

From

San Juan, Puerto Rico

10 Sailings

Nov 15, 2026 - Mar 18, 2028

10 Sailings

Nov 15, 2026 - Mar 18, 2028

Published prices from

$709

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
Cunard

18-night Transatlantic Crossing and Eastern Caribbean Cruise From New York City, New York

New York City
St. Thomas (Charlotte Amalie)
Roadtown
Basseterre
St. Maarten (Philipsburg)
+2 more

Aboard

Queen Mary 2

From

New York City, New York

1 Sailing

Nov 17, 2026

1 Sailing

Nov 17, 2026

Published prices from

$1,798

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Cunard

11-night Eastern Caribbean Cruise From New York City, New York

New York City
St. Thomas (Charlotte Amalie)
Roadtown
Basseterre
St. Maarten (Philipsburg)

Aboard

Queen Mary 2

From

New York City, New York

1 Sailing

Nov 17, 2026

1 Sailing

Nov 17, 2026

Published prices from

$1,199

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*+ 4 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

11-night Southern Caribbean Intensive Cruise From San Juan, Puerto Rico

San Juan
Roadtown
St. John's
Castries
St. George's
+5 more

Aboard

Celebrity Constellation

From

San Juan, Puerto Rico

1 Sailing

Nov 17, 2026

1 Sailing

Nov 17, 2026

Published prices from

$1,542

per person*

taxes & fees included

A scenic view of Catalina Island, Dominican Republic, with a pristine sandy beach lined with palm trees and the calm turquoise waters of the Caribbean Sea in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

14 nights Dominican Republic From Bridgetown, Barbados

Bridgetown (Barbados)
Fort de France
Pointe A Pitre
Roadtown
La Romana
+5 more

Aboard

MSC Opera

From

Bridgetown, Barbados

23 Sailings

Nov 19, 2026 - Oct 28, 2027

23 Sailings

Nov 19, 2026 - Oct 28, 2027

Published prices from

$1,345

per person*

taxes & fees included

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

14 nights Dominican Republic From Fort de France, Martinique

Fort de France
St. John's
Roadtown
La Romana
Bahia de Samana
+6 more

Aboard

MSC Opera

From

Fort de France, Martinique

8 Sailings

Nov 20, 2026 - Feb 26, 2027

8 Sailings

Nov 20, 2026 - Feb 26, 2027

Published prices from

$1,464

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

7-night Caribbean Round-Trip San Juan Cruise: Barbados & St. Thomas From San Juan, Puerto Rico

San Juan
Roadtown
Basseterre
Bridgetown (Barbados)
Castries
+2 more

Aboard

Norwegian Prima

From

San Juan, Puerto Rico

17 Sailings

Nov 22, 2026 - Apr 15, 2028

17 Sailings

Nov 22, 2026 - Apr 15, 2028

Published prices from

$899

per person*

taxes & fees included

    • Showing results 1 - 24 of 263

*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.