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37 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

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 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
Seabourn logo

7-night Caribbean Gems Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Carambola Beach
Terre-de-Haut
St. Pierre
Roseau
+2 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

2 Sailings

Dec 12, 2026 - Feb 6, 2027

2 Sailings

Dec 12, 2026 - Feb 6, 2027

Published prices from

$3,599

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 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.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

16-night An Extended Journey Of Island Energy & Ocean Tranquillity From San Juan, Puerto Rico

San Juan
St. Maarten (Philipsburg)
Terre-de-Haut
St. George's
Castries
+7 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Jan 13, 2027

1 Sailing

Jan 13, 2027

Published prices from

$11,600

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

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.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

15-night An Extended Journey Through Caribbean Treasures & Peaceful Nature From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Road Bay
St. Pierre
Basseterre
+7 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Jan 21, 2027

1 Sailing

Jan 21, 2027

Published prices from

$9,635

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

8-night A Journey Of Sunny Shores & Caribbean Island Bliss From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Road Bay
St. Pierre
Basseterre
+3 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Jan 21, 2027

1 Sailing

Jan 21, 2027

Published prices from

$7,800

per person*

taxes & fees included

A classic, two-story colonial building, the Abbey of Our Lady of Exile, with a red roof, a clock tower, and arches in Port of Spain, Trinidad and Tobago, under a cloudy blue sky.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

19-night An Extended Journey Of Caribbean Charms & Amazonian Wonders From Miami, Florida

Miami
Puerto Plata
St. Maarten (Philipsburg)
Terre-de-Haut
Basseterre
+10 more

Aboard

EXPLORA I

From

Miami, Florida

1 Sailing

Jan 29, 2027

1 Sailing

Jan 29, 2027

Published prices from

$11,735

per person*

taxes & fees included

A scenic landscape view of Admiralty Bay in Bequia, St. Vincent and the Grenadines, with dozens of sailboats moored on the vibrant turquoise water, surrounded by lush green hills.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

24-night An Extended Journey Into Island Elegance & Mysteries Of The Amazon From San Juan, Puerto Rico

San Juan
Gustavia
St. Pierre
Bridgetown (Barbados)
Port of Spain
+11 more

Aboard

EXPLORA I

From

San Juan, Puerto Rico

1 Sailing

Feb 5, 2027

1 Sailing

Feb 5, 2027

Published prices from

$17,510

per person*

taxes & fees included

A classic, two-story colonial building, the Abbey of Our Lady of Exile, with a red roof, a clock tower, and arches in Port of Spain, Trinidad and Tobago, under a cloudy blue sky.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

12-night A Journey Of Amazon Exploration & Cultural Discovery From San Juan, Puerto Rico

San Juan
Gustavia
St. Pierre
Bridgetown (Barbados)
Port of Spain
+5 more

Aboard

EXPLORA I

From

San Juan, Puerto Rico

1 Sailing

Feb 5, 2027

1 Sailing

Feb 5, 2027

Published prices from

$9,600

per person*

taxes & fees included

Historic Halifax waterfront buildings.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

25-night Star Collector: Autumn In Newfoundland And New England Cruise From Boston, Massachusetts

Boston
Portland
Bar Harbor
Halifax (Nova Scotia)
Charlottetown
+13 more

Aboard

Star Pride

From

Boston, Massachusetts

2 Sailings

Sep 16, 2027 - Sep 14, 2028

2 Sailings

Sep 16, 2027 - Sep 14, 2028

Published prices from

$11,582

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

    • Showing results 1 - 24 of 37

*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.