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A stunning panoramic view of Road Town on Tortola, British Virgin Islands, showing the harbor filled with boats and a small town surrounded by lush green hills overlooking the Caribbean Sea.

Up to $500 FREE Onboard Credit*+ 3 more offers

26-night Canada & Caribbean Voyage: Montreal, Quebec & Barbados From Montreal, Quebec

Aboard

Azamara Journey

From

Montreal, Quebec

1 Sailing

Oct 19, 2026

1 Sailing

Oct 19, 2026

Published prices from

$7,859

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*+ 1 more offer

Windstar

11-night Gems Of The Leeward Islands Cruise From San Juan, Puerto Rico

Falmouth Harbour

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Oct 28, 2026

1 Sailing

Oct 28, 2026

Published prices from

$4,348

per person*

taxes & fees included

Statue of Liberty and Manhattan skyline.

Up to $500 FREE Onboard Credit*+ 3 more offers

16-night Caribbean Voyage: New York, Bermuda & Barbados From New York City, New York

St. Maarten (Philipsburg)

Aboard

Azamara Journey

From

New York City, New York

1 Sailing

Oct 29, 2026

1 Sailing

Oct 29, 2026

Published prices from

$4,669

per person*

taxes & fees included

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

7-night Southern Caribbean Voyage: Antigua, Grenada & Barbados From San Juan, Puerto Rico

Port Elizabeth (Bequia)

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

$1,429

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

14-night Caribbean Voyage: San Juan, St. Lucia & St. Kitts From San Juan, Puerto Rico

Port Elizabeth (Bequia)

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 2026

Published prices from

$4,789

per person*

taxes & fees included

An idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

14-night Star Collector: Lovely Leewards Cruise From San Juan, Puerto Rico

St. Maarten (Philipsburg)

Aboard

Star Pride

From

San Juan, Puerto Rico

14 Sailings

Nov 8, 2026 - Mar 20, 2028

14 Sailings

Nov 8, 2026 - Mar 20, 2028

Published prices from

$3,902

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

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

Bridgetown (Barbados)

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

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

7-night San Juan & The Virgin Islands Cruise From San Juan, Puerto Rico

St. Maarten (Philipsburg)

Aboard

Star Pride

From

San Juan, Puerto Rico

8 Sailings

Nov 15, 2026 - Mar 20, 2028

8 Sailings

Nov 15, 2026 - Mar 20, 2028

Published prices from

$2,443

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*+ 2 more offers

7 nights Dominican Republic From La Romana, Dominican Republic

Catalina Island

Aboard

MSC Opera

From

La Romana, Dominican Republic

73 Sailings

Nov 16, 2026 - Apr 3, 2028

73 Sailings

Nov 16, 2026 - Apr 3, 2028

Published prices from

$456

per person*

taxes & fees included

A scenic view of Catalina Island, Dominican Republic, with a pristine sandy beach lined with palm trees and the calm turquoise waters of the Caribbean Sea in the background.

Up to $500 FREE Onboard Credit*+ 2 more offers

14 nights Dominican Republic From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

MSC Opera

From

Bridgetown, Barbados

23 Sailings

Nov 19, 2026 - Oct 28, 2027

23 Sailings

Nov 19, 2026 - Oct 28, 2027

Published prices from

$1,404

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*+ 2 more offers

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

Carambola Beach

Aboard

Seabourn Ovation

From

Miami, Florida

1 Sailing

Nov 20, 2026

1 Sailing

Nov 20, 2026

Published prices from

$7,198

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.

Up to $500 FREE Onboard Credit*+ 2 more offers

14 nights Dominican Republic From Fort de France, Martinique

Bahia de Samana

Aboard

MSC Opera

From

Fort de France, Martinique

8 Sailings

Nov 20, 2026 - Feb 26, 2027

8 Sailings

Nov 20, 2026 - Feb 26, 2027

Published prices from

$1,468

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

14-night Caribbean Voyage: San Juan, Antigua & Barbados From San Juan, Puerto Rico

Port Elizabeth (Bequia)

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Nov 21, 2026

1 Sailing

Nov 21, 2026

Published prices from

$4,369

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

14-night Leeward Island Jewels Cruise From Miami, Florida

Carambola Beach

Aboard

Seabourn Quest

From

Miami, Florida

2 Sailings

Nov 22 - Dec 6, 2026

2 Sailings

Nov 22 - Dec 6, 2026

Published prices from

$7,498

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.

Up to $500 FREE Onboard Credit*+ 3 more offers

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

Bridgetown (Barbados)

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Nov 28, 2026

1 Sailing

Nov 28, 2026

Published prices from

$4,009

per person*

taxes & fees included

An aerial view of Road Bay, Anguilla, showing a pristine white sand beach, lush green vegetation, and the stunningly clear turquoise water of the Caribbean Sea.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

21-night Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing Cruise From Lisbon, Portugal

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 2026

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.

Up to $500 FREE Onboard Credit*+ 3 more offers

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

Port Elizabeth (Bequia)

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 2026

Published prices from

$5,689

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

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

Bridgetown (Barbados)

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$4,399

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

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

St. Thomas (Charlotte Amalie)

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Dec 18, 2026

1 Sailing

Dec 18, 2026

Published prices from

$1,979

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

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

St. Thomas (Charlotte Amalie)

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Dec 18, 2026

1 Sailing

Dec 18, 2026

Published prices from

$5,239

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*+ 1 more offer

Windstar

14-night Star Collector: Caribbean Explorations Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

13 Sailings

Dec 19, 2026 - Mar 13, 2027

13 Sailings

Dec 19, 2026 - Mar 13, 2027

Published prices from

$4,880

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

7-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

7 Sailings

Dec 19, 2026 - Mar 13, 2027

7 Sailings

Dec 19, 2026 - Mar 13, 2027

Published prices from

$2,658

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.

Up to $500 FREE Onboard Credit*+ 3 more offers

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

Bridgetown (Barbados)

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Dec 28, 2026

1 Sailing

Dec 28, 2026

Published prices from

$6,059

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

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

St. Maarten (Philipsburg)

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Jan 5, 2027

1 Sailing

Jan 5, 2027

Published prices from

$2,549

per person*

taxes & fees included

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*+ 2 more offers

14 nights Dominican Republic From La Romana, Dominican Republic

Catalina Island

Aboard

MSC Opera

From

La Romana, Dominican Republic

52 Sailings

Apr 5, 2027 - Mar 27, 2028

52 Sailings

Apr 5, 2027 - Mar 27, 2028

Published prices from

$1,270

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.