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295 Results

Taxes and fees included in all prices shown

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Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Cunard

21-night Caribbean Cruise From Miami, Florida

Miami
San Juan
St. John's
Castries
Bridgetown (Barbados)
+7 more

Aboard

Queen Elizabeth

From

Miami, Florida

5 Sailings

Oct 15 - Nov 26, 2026

5 Sailings

Oct 15 - Nov 26, 2026

Published prices from

$1,818

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*+ 3 more offers
TCW EXCLUSIVE
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

3 Sailings

Oct 15 - Nov 26, 2026

3 Sailings

Oct 15 - Nov 26, 2026

Published prices from

$1,039

per person*

taxes & fees included

A beautiful autumn landscape in Saguenay with a river flowing under a bridge, surrounded by hillsides adorned with houses and vibrant yellow, orange, and red fall foliage.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

25-night Canada & Caribbean Isles Voyage From Montreal, Quebec

Montreal
Quebec City
Saguenay
Baie-Comeau (Comeau Bay)
Sept-Iles
+16 more

Aboard

Vista

From

Montreal, Quebec

1 Sailing

Oct 17, 2026

1 Sailing

Oct 17, 2026

Published prices from

$11,949

per person*

taxes & fees included

The iconic Library of Celsus in the ancient city of Ephesus, Turkey, with its magnificent, two-story facade and marble columns standing against a backdrop of cypress trees and green hills.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

70-night Star Collector: Grand Mediterranean And Latin America Adventure Cruise From Istanbul, Turkey

Istanbul
Myrina
Mykonos
Kusadasi (Ephesus)
Bodrum
+43 more

Aboard

Star Legend

From

Istanbul, Turkey

1 Sailing

Oct 19, 2026

1 Sailing

Oct 19, 2026

Published prices from

$25,588

per person*

taxes & fees included

An aerial view of a sandbar in Alter do Chão, Brazil, with a few small huts and boats, surrounded by the clear, calm waters of the Tapajós River.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

57-night Old & New World Discovery Voyage From Fusina, Venice, Italy

Venice (Fusina)
Rijeka
Split
Kotor
Igoumenitsa (Meteora)
+33 more

Aboard

Insignia

From

Fusina, Venice, Italy

1 Sailing

Oct 23, 2026

1 Sailing

Oct 23, 2026

Published prices from

$35,549

per person*

taxes & fees included

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

14-night Caribbean Enchantment Voyage From New York City, New York

New York City
St. Thomas (Charlotte Amalie)
Roadtown
St. John's
Basseterre
+6 more

Aboard

Vista

From

New York City, New York

1 Sailing

Oct 28, 2026

1 Sailing

Oct 28, 2026

Published prices from

$5,599

per person*

taxes & fees included

A secluded cove with white sand and turquoise water on Half Moon Cay, Bahamas, surrounded by jagged, rocky cliffs and a serene blue ocean under a partly cloudy sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

21-night Western & Eastern Caribbean Cruise: Mexico & Leeward Islands From Fort Lauderdale, Florida

Ft. Lauderdale
Half Moon Cay
Falmouth (Jamaica)
Grand Cayman (George Town)
Mahogany Bay
+9 more

Aboard

Rotterdam

From

Fort Lauderdale, Florida

6 Sailings

Oct 31, 2026 - Mar 6, 2027

6 Sailings

Oct 31, 2026 - Mar 6, 2027

Published prices from

$1,694

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

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

12-night Southern Caribbean Islander Cruise From New York City, New York

New York City
St. Maarten (Philipsburg)
Basseterre
Castries
Curacao
+3 more

Aboard

Majestic Princess

From

New York City, New York

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 2026

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

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

14-night Caribbean: Aruba & Curacao Cruise From Boston, Massachusetts

Boston
St. Thomas (Charlotte Amalie)
Castries
St. George's
Willemstad
+4 more

Aboard

Norwegian Breakaway

From

Boston, Massachusetts

1 Sailing

Nov 8, 2026

1 Sailing

Nov 8, 2026

Published prices from

$1,069

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

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
Holland America logo

21-night Eastern & Western Caribbean Cruise: Leeward Islands & Mexico From Fort Lauderdale, Florida

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

Aboard

Rotterdam

From

Fort Lauderdale, Florida

5 Sailings

Nov 10, 2026 - Feb 23, 2027

5 Sailings

Nov 10, 2026 - Feb 23, 2027

Published prices from

$1,749

per person*

taxes & fees included

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 $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Holland America logo

11-night Eastern Caribbean Cruise: Windward & Leeward Islands From Fort Lauderdale, Florida

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

Aboard

Rotterdam

From

Fort Lauderdale, Florida

6 Sailings

Nov 10, 2026 - Mar 16, 2027

6 Sailings

Nov 10, 2026 - Mar 16, 2027

Published prices from

$1,104

per person*

taxes & fees included

A scenic shot of the stunning Seven Mile Beach in Grand Cayman, with a wide, sandy beach, calm turquoise water, and resorts with palm trees under a beautiful blue sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

14-night Dutchman's Caribbean Voyage From Miami, Florida

Miami
Grand Cayman (George Town)
Falmouth (Jamaica)
Oranjestad
Willemstad
+5 more

Aboard

Vista

From

Miami, Florida

1 Sailing

Nov 11, 2026

1 Sailing

Nov 11, 2026

Published prices from

$6,499

per person*

taxes & fees included

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

22-night Star Collector Cruise: Caribbean Beats & Transatlantic Treats From Malaga, Spain

Malaga
Tangier
Casablanca
Funchal (Madeira)
Bridgetown (Barbados)
+8 more

Aboard

Star Legend

From

Malaga, Spain

1 Sailing

Nov 12, 2026

1 Sailing

Nov 12, 2026

Published prices from

$5,368

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*+ 4 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

10-night Ultimate Southern Caribbean Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
St. Maarten (Philipsburg)
Castries
St. George's
Roseau
+2 more

Aboard

Celebrity Ascent

From

Fort Lauderdale, Florida

15 Sailings

Nov 13, 2026 - Apr 7, 2028

15 Sailings

Nov 13, 2026 - Apr 7, 2028

Published prices from

$1,362

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

Published prices from

$4,289

per person*

taxes & fees included

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

$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*+ 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

$819

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

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

18-night Brazilian Adventure Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
St. Maarten (Philipsburg)
Castries
Bridgetown (Barbados)
Fortaleza
+4 more

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 19, 2026

1 Sailing

Nov 19, 2026

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

33-night Brazilian & Cape Horn Grand Adventure Cruise From Fort Lauderdale, Florida

Ft. Lauderdale
St. Maarten (Philipsburg)
Castries
Bridgetown (Barbados)
Fortaleza
+12 more

Aboard

Majestic Princess

From

Fort Lauderdale, Florida

1 Sailing

Nov 19, 2026

1 Sailing

Nov 19, 2026

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

21-night Southern & Eastern Caribbean Cruise: Abc Islands From Fort Lauderdale, Florida

Ft. Lauderdale
Kralendijk
Willemstad
Half Moon Cay
St. Maarten (Philipsburg)
+7 more

Aboard

Nieuw Amsterdam

From

Fort Lauderdale, Florida

1 Sailing

Nov 20, 2026

1 Sailing

Nov 20, 2026

Published prices from

$1,734

per person*

taxes & fees included

    • Showing results 1 - 24 of 295

*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.