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189 Results

Taxes and fees included in all prices shown

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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

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 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

$1,154

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

$1,412

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

18 nights South Caribbean From Genoa, Italy

Genoa
Rome (Civitavecchia)
Corsica (Ajaccio)
Provence (Marseille)
Barcelona (Tarragona)
+9 more

Aboard

MSC Seaview

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

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

$1,069

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

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

17 nights South Caribbean From Civitavecchia, Rome, Italy

Rome (Civitavecchia)
Corsica (Ajaccio)
Provence (Marseille)
Barcelona (Tarragona)
Puerto del Rosario
+8 more

Aboard

MSC Seaview

From

Civitavecchia, Rome, Italy

1 Sailing

Nov 15, 2026

1 Sailing

Nov 15, 2026

Published prices from

$1,209

per person*

taxes & fees included

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

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

$1,467

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*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

24 nights South Caribbean From Tarragona, Spain

Barcelona (Tarragona)
Puerto del Rosario
Santa Cruz de Tenerife
Philipsburg
Basseterre
+8 more

Aboard

MSC World Europa

From

Tarragona, Spain

1 Sailing

Nov 18, 2026

1 Sailing

Nov 18, 2026

An aerial view of the vibrant marina and coastline of Pointe-à-Pitre, Guadeloupe, showing numerous boats docked in the harbor, surrounded by lush green hills and the turquoise Caribbean Sea.
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
Las Palmas (Gran Canaria)
Santa Cruz de Tenerife
Philipsburg
+8 more

Aboard

MSC Seaview

From

Tarragona, Spain

1 Sailing

Nov 18, 2026

1 Sailing

Nov 18, 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

14 nights South Caribbean From Tarragona, Spain

Barcelona (Tarragona)
Puerto del Rosario
Las Palmas (Gran Canaria)
Santa Cruz de Tenerife
Philipsburg
+5 more

Aboard

MSC Seaview

From

Tarragona, Spain

1 Sailing

Nov 18, 2026

1 Sailing

Nov 18, 2026

Published prices from

$978

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

24 nights South Caribbean From Tarragona, Spain

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

Aboard

MSC Seaview

From

Tarragona, Spain

1 Sailing

Nov 18, 2026

1 Sailing

Nov 18, 2026

Colorful buildings in Las Palmas, Spain.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
MSC Cruises logo

17 nights South Caribbean From Tarragona, Spain

Barcelona (Tarragona)
Puerto del Rosario
Las Palmas (Gran Canaria)
Santa Cruz de Tenerife
Philipsburg
+7 more

Aboard

MSC Seaview

From

Tarragona, Spain

1 Sailing

Nov 18, 2026

1 Sailing

Nov 18, 2026

Published prices from

$1,132

per person*

taxes & fees included

A stunning panoramic view of Rodney Bay on the island of St. Lucia, showing a bustling harbor filled with sailboats, a colorful town, and lush green hills under a bright blue, cloudy sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

15-night Southern Caribbean In Depth Cruise From Miami, Florida

Miami
San Juan
Jost Van Dyke
Carambola Beach
Roseau
+8 more

Aboard

Seabourn Ovation

From

Miami, Florida

1 Sailing

Nov 20, 2026

1 Sailing

Nov 20, 2026

Published prices from

$7,399

per person*

taxes & fees included

    • Showing results 1 - 24 of 189

*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.