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Roadtown

St. John's

Castries

Aboard

Norwegian Epic

From

San Juan, Puerto Rico

19 Sailings

Nov 23, 2025 - Apr 5, 2026

19 Sailings

Nov 23, 2025 - Apr 5, 2026

Published prices from

$750

per person*

taxes & fees included

7-night Southern Caribbean Cruise

St. Croix

Fort de France

FREE Wi-Fi, Dining, Spa Access & More*+ 1 more offer

Aboard

Jewel of the Seas

From

San Juan, Puerto Rico

24 Sailings

Nov 8, 2025 - Apr 18, 2026

24 Sailings

Nov 8, 2025 - Apr 18, 2026

Published prices from

$692

per person*

taxes & fees included

10-night West Indies Explorer Cruise

+4 more

Aboard

Viking Sea

From

San Juan, Puerto Rico

27 Sailings

Dec 19, 2025 - Feb 16, 2028

27 Sailings

Dec 19, 2025 - Feb 16, 2028

Published prices from

$3,599

per person*

taxes & fees included

7-night Windward Islands Surf & Sunsets Cruise

Aboard

Star Seeker

From

San Juan, Puerto Rico

4 Sailings

Jan 30 - Mar 13, 2026

4 Sailings

Jan 30 - Mar 13, 2026

7-night Southern Caribbean Holiday Cruise

Aboard

Brilliance of the Seas

From

San Juan, Puerto Rico

1 Sailing

Dec 21, 2025

1 Sailing

Dec 21, 2025

Published prices from

$1,575

per person*

taxes & fees included

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.

Buy One, Get One FREE Airfare*+ 5 more offers

10-night Southern Caribbean Cruise

Aboard

Brilliance of the Seas

From

San Juan, Puerto Rico

1 Sailing

Feb 1, 2026

1 Sailing

Feb 1, 2026

Published prices from

$1,593

per person*

taxes & fees included

7-night Caribbean Cruise: Curacao, Aruba & Bonaire

Aboard

Norwegian Epic

From

San Juan, Puerto Rico

2 Sailings

Dec 14, 2025 - Apr 12, 2026

2 Sailings

Dec 14, 2025 - Apr 12, 2026

Published prices from

$799

per person*

taxes & fees included

Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers

14-night Southern Caribbean Adventurer Cruise

Dominica

St. John's

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

+4 more

Aboard

Grand Princess

From

San Juan, Puerto Rico

21 Sailings

Nov 2, 2025 - Mar 22, 2026

21 Sailings

Nov 2, 2025 - Mar 22, 2026

Published prices from

$2,329

per person*

taxes & fees included

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.

7-night Caribbean Cruise

Aboard

Silver Spirit

From

San Juan, Puerto Rico

1 Sailing

Dec 29, 2025

1 Sailing

Dec 29, 2025

Published prices from

$9,200

per person*

taxes & fees included

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.

14-night Star Collector: Lovely Leewards Cruise

FREE $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers

+5 more

Aboard

Star Seeker

From

San Juan, Puerto Rico

7 Sailings

Jan 23 - Mar 6, 2026

7 Sailings

Jan 23 - Mar 6, 2026

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.

18-night Eastern Caribbean Voyage

Aboard

Azamara Quest

From

San Juan, Puerto Rico

1 Sailing

Dec 19, 2025

1 Sailing

Dec 19, 2025

Published prices from

$4,549

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.

FREE Butler Service, Gourmet Dining & More*+ 1 more offer

8-night Yachtsman's Caribbean Cruise

Aboard

Seabourn Ovation

From

San Juan, Puerto Rico

1 Sailing

Dec 14, 2025

1 Sailing

Dec 14, 2025

Published prices from

$3,999

per person*

taxes & fees included

28-night Transatlantic Cruise

Aboard

Silver Ray

From

San Juan, Puerto Rico

1 Sailing

Feb 24, 2026

1 Sailing

Feb 24, 2026

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.

20-night Southern Caribbean Discovery Cruise

Aboard

Seabourn Ovation

From

San Juan, Puerto Rico

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

Published prices from

$11,499

per person*

taxes & fees included

A snorkeler swims in the turquoise waters of the Baths National Park on Virgin Gorda, surrounded by massive granite boulders and palm trees.

7-night San Juan & The Virgin Islands Cruise

Aboard

Star Pride

From

San Juan, Puerto Rico

10 Sailings

Nov 2, 2025 - Jan 10, 2027

10 Sailings

Nov 2, 2025 - Jan 10, 2027

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

14-night Star Collector: Lovely Leewards Cruise

FREE $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers

+8 more

Aboard

Star Pride

From

San Juan, Puerto Rico

13 Sailings

Nov 2, 2025 - Jan 3, 2027

13 Sailings

Nov 2, 2025 - Jan 3, 2027

7-night Southern Caribbean Voyage

Port Elizabeth (Bequia)

+3 more

Aboard

Azamara Quest

From

San Juan, Puerto Rico

3 Sailings

Nov 8 - Dec 6, 2025

3 Sailings

Nov 8 - Dec 6, 2025

Published prices from

$609

per person*

taxes & fees included

A panoramic view of the coastal city of Roseau in Dominica, with its colorful buildings nestled between the Caribbean Sea and lush, mountainous terrain under a beautiful sky.

Exclusive Events, Experiences & More with Captain's Circle*+ 2 more offers

7-night Southern Caribbean with Barbados Cruise

Dominica

St. George's

Aboard

Grand Princess

From

San Juan, Puerto Rico

22 Sailings

Nov 2, 2025 - Mar 29, 2026

22 Sailings

Nov 2, 2025 - Mar 29, 2026

Published prices from

$1,154

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.

7-night Southern Caribbean Cruise

St. Vincent (Kingstown)

Aboard

Brilliance of the Seas

From

San Juan, Puerto Rico

18 Sailings

Nov 9, 2025 - Apr 12, 2026

18 Sailings

Nov 9, 2025 - Apr 12, 2026

Published prices from

$655

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.

9-night Southern Caribbean Cruise

Aboard

Brilliance of the Seas

From

San Juan, Puerto Rico

1 Sailing

Feb 20, 2026

1 Sailing

Feb 20, 2026

Published prices from

$1,091

per person*

taxes & fees included

An aerial view of the Kralendijk waterfront in Bonaire, showcasing the contrast between the deep blue ocean and the shallow turquoise water near the shore, with sailboats anchored offshore.

12-night Treasures Of Aruba, Bonaire & Curacao Cruise

Aboard

Seabourn Ovation

From

San Juan, Puerto Rico

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

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

FREE $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers

20-night Holiday Caribbean Enchantment Cruise

Aboard

Seabourn Ovation

From

San Juan, Puerto Rico

1 Sailing

Dec 14, 2025

1 Sailing

Dec 14, 2025

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.

8-night Southern Caribbean Voyage

FREE $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers

Aboard

Azamara Quest

From

San Juan, Puerto Rico

1 Sailing

Dec 19, 2025

1 Sailing

Dec 19, 2025

Published prices from

$1,479

per person*

taxes & fees included

14-night Eastern Caribbean Voyage

Port Elizabeth (Bequia)

+9 more

Aboard

Azamara Quest

From

San Juan, Puerto Rico

2 Sailings

Nov 8 - Nov 22, 2025

2 Sailings

Nov 8 - Nov 22, 2025

Published prices from

$3,889

per person*

taxes & fees included

FREE $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers

13-night Eastern Caribbean Voyage