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22 Results

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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

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

$1,069

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
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

Published prices from

$6,249

per person*

taxes & fees included

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

Published prices from

$3,579

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
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

$7,849

per person*

taxes & fees included

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

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

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+2 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$1,129

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
Azamara logo

16-night Caribbean Christmas Voyage: Barbados, St. Lucia & St. Thomas From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+11 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

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
Azamara logo

18-night Caribbean Holiday Voyage: San Juan, St. Barts & Curacao From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
Virgin Gorda
St. John's
Gustavia
+11 more

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Dec 18, 2026

1 Sailing

Dec 18, 2026

A sunny view of the colorful waterfront of Willemstad, Curacao, with its iconic pastel-colored Dutch colonial buildings lining the Handelskade street and a ship docked in the port.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

8-night Caribbean Voyage: Curacao, Aruba & St.Lucia From Bridgetown, Barbados

Bridgetown (Barbados)
Oranjestad
Willemstad
Castries
Charlestown
+3 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Dec 28, 2026

1 Sailing

Dec 28, 2026

Published prices from

$2,189

per person*

taxes & fees included

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

17-night Caribbean New Year Voyage: Barbados, Aruba & St. Barts From Bridgetown, Barbados

Bridgetown (Barbados)
Oranjestad
Willemstad
Castries
Charlestown
+10 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Dec 28, 2026

1 Sailing

Dec 28, 2026

Published prices from

$5,419

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

Published prices from

$9,699

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*+ 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

$2,839

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

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

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

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

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

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 Cruise: Saint Lucia, Sint Maarten & British Virgin Islands From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+3 more

Aboard

Azamara Quest

From

Bridgetown, Barbados

1 Sailing

Nov 14, 2027

1 Sailing

Nov 14, 2027

Published prices from

$1,939

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

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

$3,699

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
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

$3,849

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
Azamara logo

7-night Eastern Caribbean Cruise: Sint Maarten, Saint Kitts & Nevis From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+3 more

Aboard

Azamara Quest

From

Bridgetown, Barbados

1 Sailing

Nov 28, 2027

1 Sailing

Nov 28, 2027

Published prices from

$1,949

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
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

$4,749

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 Cruise: Saint Lucia, Dominica & Sint Maarten From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+3 more

Aboard

Azamara Quest

From

Bridgetown, Barbados

1 Sailing

Dec 12, 2027

1 Sailing

Dec 12, 2027

Published prices from

$1,949

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.