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211 Results

Taxes and fees included in all prices shown

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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
Azamara logo

7-night Southern Caribbean Voyage: Antigua, Grenada & Barbados From San Juan, Puerto Rico

San Juan
Virgin Gorda
St. John's
St. Pierre
Port Elizabeth (Bequia)
+3 more

Aboard

Azamara Journey

From

San Juan, Puerto Rico

3 Sailings

Nov 7 - Dec 5, 2026

3 Sailings

Nov 7 - Dec 5, 2026

Published prices from

$839

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

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

$869

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
Windstar

7-night Windward Islands Surf & Sunsets Cruise From San Juan, Puerto Rico

San Juan
St. George's
Bequia
Mayreau
Iles des Saintes
+2 more

Aboard

Star Pride

From

San Juan, Puerto Rico

9 Sailings

Nov 8, 2026 - Mar 27, 2028

9 Sailings

Nov 8, 2026 - Mar 27, 2028

Published prices from

$2,442

per person*

taxes & fees included

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

14-night Star Collector: Lovely Leewards Cruise From San Juan, Puerto Rico

San Juan
Cruz Bay
Basseterre
Gustavia
St. Maarten (Philipsburg)
+8 more

Aboard

Star Pride

From

San Juan, Puerto Rico

14 Sailings

Nov 8, 2026 - Mar 20, 2028

14 Sailings

Nov 8, 2026 - Mar 20, 2028

Published prices from

$4,108

per person*

taxes & fees included

An aerial view of the vast Amazon River in Peru, meandering through a dense, green rainforest with a small floating lodge anchored along its banks.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

22-night Secrets Of The Amazon Cruise From Miami, Florida

Miami
Bridgetown (Barbados)
Port of Spain
Amazon River
Santarem
+7 more

Aboard

Seven Seas Mariner

From

Miami, Florida

1 Sailing

Nov 9, 2026

1 Sailing

Nov 9, 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*+ 2 more offers
TCW EXCLUSIVE
Windstar

25-night Star Collector: Southern Caribbean Thanksgiving Jubilee Cruise From Lisbon, Portugal

Lisbon
Bridgetown (Barbados)
Bequia
St. George's
Kralendijk
+6 more

Aboard

Wind Star

From

Lisbon, Portugal

1 Sailing

Nov 10, 2026

1 Sailing

Nov 10, 2026

Published prices from

$7,989

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

$7,458

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

$1,472

per person*

taxes & fees included

Roman Amphitheatre of Tarragona by the sea.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

22 nights South Caribbean From Genoa, Italy

Genoa
Rome (Civitavecchia)
Corsica (Ajaccio)
Provence (Marseille)
Barcelona (Tarragona)
+10 more

Aboard

MSC Seaview

From

Genoa, Italy

1 Sailing

Nov 14, 2026

1 Sailing

Nov 14, 2026

Published prices from

$1,369

per person*

taxes & fees included

A panoramic aerial shot of the arid landscape of Fuerteventura, Spain, with the town of Antigua visible in the foreground and the Atlantic Ocean in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

21 nights South Caribbean From Genoa, Italy

Genoa
Rome (Civitavecchia)
La Spezia
Provence (Marseille)
Barcelona (Tarragona)
+9 more

Aboard

MSC World Europa

From

Genoa, Italy

1 Sailing

Nov 14, 2026

1 Sailing

Nov 14, 2026

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
MSC Cruises logo

28 nights South Caribbean From Genoa, Italy

Genoa
Rome (Civitavecchia)
La Spezia
Provence (Marseille)
Barcelona (Tarragona)
+12 more

Aboard

MSC World Europa

From

Genoa, Italy

1 Sailing

Nov 14, 2026

1 Sailing

Nov 14, 2026

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

28 nights South Caribbean From Genoa, Italy

Genoa
Rome (Civitavecchia)
Corsica (Ajaccio)
Provence (Marseille)
Barcelona (Tarragona)
+13 more

Aboard

MSC Seaview

From

Genoa, Italy

1 Sailing

Nov 14, 2026

1 Sailing

Nov 14, 2026

Published prices from

$1,985

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*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

21 nights South Caribbean From Genoa, Italy

Genoa
Rome (Civitavecchia)
Corsica (Ajaccio)
Provence (Marseille)
Barcelona (Tarragona)
+11 more

Aboard

MSC Seaview

From

Genoa, Italy

1 Sailing

Nov 14, 2026

1 Sailing

Nov 14, 2026

Published prices from

$1,411

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

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

20 nights South Caribbean From Civitavecchia, Rome, Italy

Rome (Civitavecchia)
La Spezia
Provence (Marseille)
Barcelona (Tarragona)
Puerto del Rosario
+8 more

Aboard

MSC World Europa

From

Civitavecchia, Rome, Italy

1 Sailing

Nov 15, 2026

1 Sailing

Nov 15, 2026

Published prices from

$1,130

per person*

taxes & fees included

A stunning view of the Old Port of Marseille, Provence, featuring the basilica of Notre-Dame de la Garde perched on a hill overlooking the harbor filled with many yachts.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

21 nights South Caribbean From Civitavecchia, Rome, Italy

Rome (Civitavecchia)
Corsica (Ajaccio)
Provence (Marseille)
Barcelona (Tarragona)
Puerto del Rosario
+11 more

Aboard

MSC Seaview

From

Civitavecchia, Rome, Italy

1 Sailing

Nov 15, 2026

1 Sailing

Nov 15, 2026

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

20 nights South Caribbean From Civitavecchia, Rome, Italy

Rome (Civitavecchia)
Corsica (Ajaccio)
Provence (Marseille)
Barcelona (Tarragona)
Puerto del Rosario
+10 more

Aboard

MSC Seaview

From

Civitavecchia, Rome, Italy

1 Sailing

Nov 15, 2026

1 Sailing

Nov 15, 2026

Published prices from

$1,414

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

19 nights South Caribbean From Marseille, Provence, France

Provence (Marseille)
Barcelona (Tarragona)
Puerto del Rosario
Santa Cruz de Tenerife
Philipsburg
+7 more

Aboard

MSC World Europa

From

Marseille, Provence, France

1 Sailing

Nov 17, 2026

1 Sailing

Nov 17, 2026

Published prices from

$1,221

per person*

taxes & fees included

A panoramic aerial shot of the arid landscape of Fuerteventura, Spain, with the town of Antigua visible in the foreground and the Atlantic Ocean in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

18 nights South Caribbean From Marseille, Provence, France

Provence (Marseille)
Barcelona (Tarragona)
Puerto del Rosario
Santa Cruz de Tenerife
Philipsburg
+6 more

Aboard

MSC World Europa

From

Marseille, Provence, France

1 Sailing

Nov 17, 2026

1 Sailing

Nov 17, 2026

Published prices from

$1,317

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*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

18 nights South Caribbean From Marseille, Provence, France

Provence (Marseille)
Barcelona (Tarragona)
Puerto del Rosario
Las Palmas (Gran Canaria)
Santa Cruz de Tenerife
+8 more

Aboard

MSC Seaview

From

Marseille, Provence, France

1 Sailing

Nov 17, 2026

1 Sailing

Nov 17, 2026

Published prices from

$1,153

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

19 nights South Caribbean From Marseille, Provence, France

Provence (Marseille)
Barcelona (Tarragona)
Puerto del Rosario
Las Palmas (Gran Canaria)
Santa Cruz de Tenerife
+9 more

Aboard

MSC Seaview

From

Marseille, Provence, France

1 Sailing

Nov 17, 2026

1 Sailing

Nov 17, 2026

Published prices from

$1,209

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

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

18 nights South Caribbean From Tarragona, Spain

Barcelona (Tarragona)
Puerto del Rosario
Santa Cruz de Tenerife
Philipsburg
Basseterre
+6 more

Aboard

MSC World Europa

From

Tarragona, Spain

1 Sailing

Nov 18, 2026

1 Sailing

Nov 18, 2026

Published prices from

$953

per person*

taxes & fees included

    • Showing results 1 - 24 of 211

*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.