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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*+ 4 more offers

7-night Southern Caribbean Cruise From San Juan, Puerto Rico

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Rhapsody of the Seas

From

San Juan, Puerto Rico

53 Sailings

Jul 11, 2026 - Apr 15, 2028

53 Sailings

Jul 11, 2026 - Apr 15, 2028

Published prices from

$548

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

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

Up to $500 FREE Onboard Credit*+ 4 more offers

7-night Southern Caribbean Cruise From San Juan, Puerto Rico

St. Vincent (Kingstown)

Aboard

Vision of the Seas

From

San Juan, Puerto Rico

42 Sailings

Nov 1, 2026 - Apr 16, 2028

42 Sailings

Nov 1, 2026 - Apr 16, 2028

Published prices from

$533

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

Viking

10-night West Indies Explorer Cruise From San Juan, Puerto Rico

Bridgetown (Barbados)

Aboard

Viking Sea

From

San Juan, Puerto Rico

17 Sailings

Nov 5, 2026 - Feb 16, 2028

17 Sailings

Nov 5, 2026 - Feb 16, 2028

Published prices from

$3,799

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

$4,289

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 Windward Islands Surf & Sunsets Cruise From San Juan, Puerto Rico

Iles des Saintes

Aboard

Star Pride

From

San Juan, Puerto Rico

9 Sailings

Nov 8, 2026 - Mar 27, 2028

9 Sailings

Nov 8, 2026 - Mar 27, 2028

Published prices from

$1,934

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 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*+ 6 more offers

7-night Caribbean Round-trip San Juan Cruise: St. Thomas & Tortola From San Juan, Puerto Rico

St. Maarten (Philipsburg)

Bridgetown (Barbados)

Aboard

Norwegian Prima

From

San Juan, Puerto Rico

10 Sailings

Nov 15, 2026 - Mar 18, 2028

10 Sailings

Nov 15, 2026 - Mar 18, 2028

Published prices from

$1,239

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*+ 4 more offers

11-night Southern Caribbean Intensive Cruise From San Juan, Puerto Rico

Aboard

Celebrity Constellation

From

San Juan, Puerto Rico

1 Sailing

Nov 17, 2026

1 Sailing

Nov 17, 2026

Published prices from

$1,389

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

$4,179

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.

Up to $500 FREE Onboard Credit*+ 6 more offers

7-night Caribbean Round-Trip San Juan Cruise: Barbados & St. Thomas From San Juan, Puerto Rico

Bridgetown (Barbados)

Aboard

Norwegian Prima

From

San Juan, Puerto Rico

17 Sailings

Nov 22, 2026 - Apr 15, 2028

17 Sailings

Nov 22, 2026 - Apr 15, 2028

Published prices from

$1,259

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*+ 4 more offers

7-night Southern Caribbean Cruise From San Juan, Puerto Rico

St. Thomas (Charlotte Amalie)

Aboard

Celebrity Constellation

From

San Juan, Puerto Rico

18 Sailings

Nov 28, 2026 - Mar 27, 2027

18 Sailings

Nov 28, 2026 - Mar 27, 2027

Published prices from

$766

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

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

An aerial view of the vast Amazon River in Peru, meandering through a dense, green rainforest with a small floating lodge anchored along its banks.

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

Viking

21-night From The Caribbean To The Amazon Cruise From San Juan, Puerto Rico

Bridgetown (Barbados)

Aboard

Viking Sea

From

San Juan, Puerto Rico

2 Sailings

Dec 15, 2026 - Jan 6, 2028

2 Sailings

Dec 15, 2026 - Jan 6, 2028

Published prices from

$11,499

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

$5,529

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*+ 6 more offers

7-night Caribbean Round-Trip San Juan Cruise: St. Thomas & Tortola From San Juan, Puerto Rico

St. Thomas (Charlotte Amalie)

Aboard

Norwegian Prima

From

San Juan, Puerto Rico

2 Sailings

Dec 20, 2026 - Mar 28, 2027

2 Sailings

Dec 20, 2026 - Mar 28, 2027

Published prices from

$1,409

per person*

taxes & fees included

A panoramic view of a long, gray pier extending into the calm turquoise waters of St. Croix, US Virgin Islands, with the town and a lush green mountain in the background.

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

7-night Southern Caribbean Holiday Cruise From San Juan, Puerto Rico

Aboard

Vision of the Seas

From

San Juan, Puerto Rico

2 Sailings

Dec 20 - Dec 27, 2026

2 Sailings

Dec 20 - Dec 27, 2026

Published prices from

$657

per person*

taxes & fees included

A stunning image of Little Bay in Anguilla, a secluded, beautiful beach with turquoise water surrounded by towering rocky cliffs and lush green vegetation.

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

14-night Caribbean Cruise From San Juan, Puerto Rico

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 2026

A stunning image of Little Bay in Anguilla, a secluded, beautiful beach with turquoise water surrounded by towering rocky cliffs and lush green vegetation.

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

7-night Caribbean Cruise From San Juan, Puerto Rico

Aboard

Silver Shadow

From

San Juan, Puerto Rico

3 Sailings

Dec 20, 2026 - Feb 26, 2027

3 Sailings

Dec 20, 2026 - Feb 26, 2027

Published prices from

$4,500

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*+ 6 more offers

7-night Caribbean Round-trip San Juan Cruise: Barbados & St. Thomas From San Juan, Puerto Rico

St. Maarten (Philipsburg)

Bridgetown (Barbados)

Aboard

Norwegian Prima

From

San Juan, Puerto Rico

3 Sailings

Dec 27, 2026 - Feb 14, 2027

3 Sailings

Dec 27, 2026 - Feb 14, 2027

Published prices from

$1,419

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.

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

14-night Southern Caribbean Adventurer Cruise From San Juan, Puerto Rico

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Crown Princess

From

San Juan, Puerto Rico

12 Sailings

Dec 27, 2026 - Mar 14, 2027

12 Sailings

Dec 27, 2026 - Mar 14, 2027

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

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

7-night Southern Caribbean Cruise With Barbados From San Juan, Puerto Rico

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Crown Princess

From

San Juan, Puerto Rico

13 Sailings

Dec 27, 2026 - Mar 21, 2027

13 Sailings

Dec 27, 2026 - Mar 21, 2027

Published prices from

$667

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.