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23 Results

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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

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 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
Azamara logo

14-night Caribbean Voyage: San Juan, Antigua & Barbados 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 21, 2026

1 Sailing

Nov 21, 2026

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

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

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+9 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Nov 28, 2026

1 Sailing

Nov 28, 2026

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

13-night Caribbean Voyage: San Juan, Antigua & St. Lucia From San Juan, Puerto Rico

San Juan
Virgin Gorda
St. John's
St. Pierre
Port Elizabeth (Bequia)
+8 more

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 2026

Published prices from

$5,729

per person*

taxes & fees included

A high-angle view of the rugged, rocky coastline of St. John, US Virgin Islands, with the deep blue sea crashing against the cliffs and islands in the distance under a cloudy blue sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

34-night South America & Antarctica Voyage: Miami To Chile From Miami, Florida

Miami
St. John (U.S.V.I.)
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Charlestown
+18 more

Aboard

Azamara Journey

From

Miami, Florida

1 Sailing

Jan 14, 2027

1 Sailing

Jan 14, 2027

A view of the volcanic black sand beach and coastline of St. Pierre, Martinique, with colorful buildings and a lush, mountainous landscape under a beautiful sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

11-night Eastern Caribbean Voyage: St.Kitts, Antigua & Martinique From Miami, Florida

Miami
St. John (U.S.V.I.)
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Charlestown
+6 more

Aboard

Azamara Journey

From

Miami, Florida

1 Sailing

Jan 14, 2027

1 Sailing

Jan 14, 2027

Published prices from

$2,669

per person*

taxes & fees included

Modern Panama City skyline with skyscrapers.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

74-night Circle South America Grand Voyage From Miami, Florida

Miami
St. John (U.S.V.I.)
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Charlestown
+42 more

Aboard

Azamara Journey

From

Miami, Florida

1 Sailing

Jan 14, 2027

1 Sailing

Jan 14, 2027

A turquoise and white ferry boat cruises through the harbor in Hamilton, Bermuda, with a backdrop of pastel-colored buildings and houses along the waterfront.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Azamara logo

17-night Bermuda & Eastern Caribbean Cruise: Sint Maarten, Antigua & Tobago From New York City, New York

New York City
Hamilton
St. Maarten (Philipsburg)
Roadtown
San Juan
+9 more

Aboard

Azamara Quest

From

New York City, New York

1 Sailing

Oct 28, 2027

1 Sailing

Oct 28, 2027

Published prices from

$4,129

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
Azamara logo

24-night Bermuda & Eastern Caribbean Cruise: Tortola, Barbados & Saint Kitts From New York City, New York

New York City
Hamilton
St. Maarten (Philipsburg)
Roadtown
San Juan
+13 more

Aboard

Azamara Quest

From

New York City, New York

1 Sailing

Oct 28, 2027

1 Sailing

Oct 28, 2027

Published prices from

$6,129

per person*

taxes & fees included

A view of the volcanic black sand beach and coastline of St. Pierre, Martinique, with colorful buildings and a lush, mountainous landscape under a beautiful sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Azamara logo

8-night Southern Caribbean Cruise: Martinique, Grenada & U.S. Virgin Islands From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
Virgin Gorda
St. John's
St. Pierre
+4 more

Aboard

Azamara Quest

From

San Juan, Puerto Rico

2 Sailings

Nov 6 - Dec 19, 2027

2 Sailings

Nov 6 - Dec 19, 2027

Published prices from

$2,269

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
Azamara logo

15-night Eastern Caribbean Cruise: Antigua, Grenada & Saint Lucia From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
Virgin Gorda
St. John's
St. Pierre
+10 more

Aboard

Azamara Quest

From

San Juan, Puerto Rico

1 Sailing

Nov 6, 2027

1 Sailing

Nov 6, 2027

Published prices from

$4,319

per person*

taxes & fees included

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*+ 2 more offers
TCW EXCLUSIVE
Azamara logo

14-night Southern Caribbean Cruise: Dominica, Bequia & Grenada From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+9 more

Aboard

Azamara Quest

From

Bridgetown, Barbados

2 Sailings

Nov 14 - Nov 28, 2027

2 Sailings

Nov 14 - Nov 28, 2027

Published prices from

$3,199

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
Azamara logo

14-night Eastern Caribbean Cruise: Antigua, Grenada & Saint Lucia From San Juan, Puerto Rico

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

Aboard

Azamara Quest

From

San Juan, Puerto Rico

2 Sailings

Nov 21 - Dec 5, 2027

2 Sailings

Nov 21 - Dec 5, 2027

Published prices from

$3,329

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
Azamara logo

7-night Southern Caribbean Cruise: Antigua, Martinique & Bequia From San Juan, Puerto Rico

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

Aboard

Azamara Quest

From

San Juan, Puerto Rico

1 Sailing

Nov 21, 2027

1 Sailing

Nov 21, 2027

Published prices from

$1,699

per person*

taxes & fees included

A snorkeler swims in the turquoise waters of the Baths National Park on Virgin Gorda, surrounded by massive granite boulders and palm trees.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Azamara logo

7-night Southern Caribbean Cruise: Puerto Rico, British Virgin Islands & Grenada From San Juan, Puerto Rico

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

Aboard

Azamara Quest

From

San Juan, Puerto Rico

1 Sailing

Dec 5, 2027

1 Sailing

Dec 5, 2027

Published prices from

$1,789

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
Azamara logo

15-night Southern Caribbean Cruise: Dominica, Bequia & Grenada From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+10 more

Aboard

Azamara Quest

From

Bridgetown, Barbados

1 Sailing

Dec 12, 2027

1 Sailing

Dec 12, 2027

Published prices from

$4,089

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
Azamara logo

17-night Eastern & Southern Caribbean Cruise: Grenada, Barbados & Aruba From San Juan, Puerto Rico

San Juan
Virgin Gorda
St. John's
Portsmouth
Port Elizabeth (Bequia)
+10 more

Aboard

Azamara Quest

From

San Juan, Puerto Rico

1 Sailing

Dec 19, 2027

1 Sailing

Dec 19, 2027

Published prices from

$4,929

per person*

taxes & fees included

An aerial view of Bocas del Toro, a vibrant town on the Caribbean coast of Panama, featuring colorful houses built over clear blue water and numerous sailboats docked nearby.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

77-night Circle South America Grand Voyage From Miami, Florida

Miami
Cozumel
Belize City
Roatan Island
Puerto Limon
+45 more

Aboard

Azamara Quest

From

Miami, Florida

1 Sailing

Jan 5, 2028

1 Sailing

Jan 5, 2028

Published prices from

$28,869

per person*

taxes & fees included

A beautiful frontal shot of the Uruguayan Legislative Palace, or Palacio Legislativo, in Montevideo, with its grand neoclassical architecture, majestic columns, and wide stone staircase.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

58-night Valparaiso To Miami Grand Voyage From Valparaiso (Santiago), Chile

Santiago (Valparaiso)
Puerto Montt
Castro
Puerto Chacabuco
Chilean Fjords
+34 more

Aboard

Azamara Quest

From

Valparaiso (Santiago), Chile

1 Sailing

Jan 24, 2028

1 Sailing

Jan 24, 2028

Published prices from

$26,859

per person*

taxes & fees included

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*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

35-night Buenos Aires To Miami Grand Voyage From Buenos Aires, Argentina

Buenos Aires
Montevideo
Rio Grande
Porto Belo
Sao Francisco do Sul
+19 more

Aboard

Azamara Quest

From

Buenos Aires, Argentina

1 Sailing

Feb 16, 2028

1 Sailing

Feb 16, 2028

Published prices from

$14,819

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
Azamara logo

9-night Southern Caribbean Cruise: Grenada, Saint Lucia & Martinique From Bridgetown, Barbados

Bridgetown (Barbados)
St. George's
Castries
St. Pierre
Roseau
+4 more

Aboard

Azamara Quest

From

Bridgetown, Barbados

1 Sailing

Mar 13, 2028

1 Sailing

Mar 13, 2028

Published prices from

$2,999

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.