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52 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

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

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
Seabourn logo

8-night Southern Caribbean Gems Cruise From Miami, Florida

Miami
San Juan
Jost Van Dyke
Carambola Beach
Roseau
+3 more

Aboard

Seabourn Ovation

From

Miami, Florida

1 Sailing

Nov 20, 2026

1 Sailing

Nov 20, 2026

Published prices from

$4,299

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

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

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
Seabourn logo

14-night Exotic Caribbean In Depth Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Little Bay
St. John's
Carambola Beach
+7 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

7 Sailings

Nov 28, 2026 - Mar 13, 2027

7 Sailings

Nov 28, 2026 - Mar 13, 2027

Published prices from

$6,199

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

$5,729

per person*

taxes & fees included

An aerial view of Carambola Beach Resort in St. Croix, with red-roofed buildings nestled among lush green tropical trees along the turquoise Caribbean Sea.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

7-night Yachtsman's Caribbean Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Sopers Hole
Carambola Beach
Trois Isles
Port Elizabeth (Bequia)
+3 more

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

13 Sailings

Dec 5, 2026 - Mar 18, 2028

13 Sailings

Dec 5, 2026 - Mar 18, 2028

Published prices from

$3,299

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
Seabourn logo

14-night Yachtsman's Caribbean In Depth Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Sopers Hole
Carambola Beach
Trois Isles
Port Elizabeth (Bequia)
+7 more

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 2026

Published prices from

$5,899

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

Published prices from

$3,979

per person*

taxes & fees included

A stunning view of Port Elizabeth in Bequia, St. Vincent and the Grenadines, with a sandy beach lined with palm trees and a building on the shore, and numerous sailboats anchored in the calm turquoise bay.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

10-night Southern Caribbean Voyage: Antigua, St.Barts & Martinique From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
Virgin Gorda
St. John's
Gustavia
+6 more

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Dec 18, 2026

1 Sailing

Dec 18, 2026

Published prices from

$1,549

per person*

taxes & fees included

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 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 captivating half-underwater, half-above-water shot of a person snorkeling in the vibrant turquoise waters of the British Virgin Islands with stunning rock formations and palm trees visible above the waterline.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

14-night Caribbean Gems In Depth Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Sopers Hole
Carambola Beach
Trois Isles
Port Elizabeth (Bequia)
+7 more

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

3 Sailings

Jan 16 - Mar 6, 2027

3 Sailings

Jan 16 - Mar 6, 2027

Published prices from

$9,899

per person*

taxes & fees included

A long, green steel-arched bridge with multiple supports, the Laviolette Bridge, spanning the wide St. Lawrence River near Trois-Rivières, with a grassy riverbank in the foreground.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Seabourn logo

19-night Yachtsman's Caribbean & Atlantic Passage Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Sopers Hole
Carambola Beach
Trois Isles
Port Elizabeth (Bequia)
+7 more

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Mar 20, 2027

1 Sailing

Mar 20, 2027

Published prices from

$11,199

per person*

taxes & fees included

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

    • Showing results 1 - 24 of 52

*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.