San Juan, Puerto Rico Cruise Deals

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

Upcoming San Juan, Puerto Rico Cruise Deals

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Start your journey in paradise with San Juan cruise deals. Find the best prices on tropical departures from this vibrant island port.

Showing results 1 - 24 of 86

*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.

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

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

14-night Southern Caribbean Adventurer Cruise

St. Maarten (Philipsburg)

Bridgetown (Barbados)

Aboard

Grand Princess

From

San Juan, Puerto Rico

20 Sailings

Nov 9, 2025 - Mar 22, 2026

20 Sailings

Nov 9, 2025 - Mar 22, 2026

Published prices from

$2,329

per person*

taxes & fees included

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

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

13-night Star Collector: Beaches & Bastions Of The BVI And Spanish Caribbean Cruise

St. Maarten (Philipsburg)

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 30, 2025

1 Sailing

Nov 30, 2025

Colorful colonial balconies in Cartagena.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

6-night The Spanish Main: Rise Of The New World Cruise

Cartagena (Colombia)

San Blas Islands

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Dec 7, 2025

1 Sailing

Dec 7, 2025

Immaculate Conception Cathedral in Colon.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

20-night Star Collector: Central America & The Caribbean: Cloudforest Coastlines, Canal Locks & Calypso Concerts Cruise

St. Maarten (Philipsburg)

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 30, 2025

1 Sailing

Nov 30, 2025

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

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

7-night Caribbean Cruise: Barbados, Antigua & St. Lucia

Bridgetown (Barbados)

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

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

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

Viking

10-night West Indies Explorer Cruise

Bridgetown (Barbados)

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

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

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

7-night San Juan & The Virgin Islands Cruise

St. Maarten (Philipsburg)

Aboard

Star Seeker

From

San Juan, Puerto Rico

4 Sailings

Jan 23 - Mar 6, 2026

4 Sailings

Jan 23 - Mar 6, 2026

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

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

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

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

FREE Dining, Onboard Activities & More*

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

$1,391

per person*

taxes & fees included

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

FREE Dining, Onboard Activities & More*

7-night Southern Caribbean Cruise

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

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

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 FREE $2,000 Onboard Credit*

8-night Yachtsman's Caribbean Cruise

Carambola Beach

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

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.

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

14-night Eastern Caribbean Voyage

Port Elizabeth (Bequia)

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

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.

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

13-night Eastern Caribbean Voyage

St. Thomas (Charlotte Amalie)

Port Elizabeth (Bequia)

Aboard

Azamara Quest

From

San Juan, Puerto Rico

1 Sailing

Dec 6, 2025

1 Sailing

Dec 6, 2025

A tranquil beach on Isla Parida, with gentle waves lapping against the sandy shore and a lush green rainforest lining the coast.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

13-night Star Collector: Coffee, Canal & Callaloo: Central America, Colombia & The Caribbean Cruise

Cartagena (Colombia)

San Blas Islands

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Dec 7, 2025

1 Sailing

Dec 7, 2025

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

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

7-night Southern Caribbean Voyage

Port Elizabeth (Bequia)

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 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 FREE $2,000 Onboard Credit*

20-night Holiday Caribbean Enchantment Cruise

Carambola Beach

Aboard

Seabourn Ovation

From

San Juan, Puerto Rico

1 Sailing

Dec 14, 2025

1 Sailing

Dec 14, 2025

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.

FREE Dining, Onboard Activities & More*

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

$652

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.

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

8-night Southern Caribbean Voyage

St. Thomas (Charlotte Amalie)

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

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

St. Maarten (Philipsburg)

Bridgetown (Barbados)

Aboard

Grand Princess

From

San Juan, Puerto Rico

21 Sailings

Nov 9, 2025 - Mar 29, 2026

21 Sailings

Nov 9, 2025 - Mar 29, 2026

Published prices from

$1,154

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 FREE $2,000 Onboard Credit*

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

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.

Up to FREE $2,000 Onboard Credit*

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 high-angle view of the bustling harbor of Marigot, St. Martin, with boats and yachts docked along the coast and colorful buildings nestled against the green hills.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

14-night Star Collector: Lovely Leewards Cruise

Iles des Saintes

Aboard

Star Pride

From

San Juan, Puerto Rico

12 Sailings

Nov 9, 2025 - Jan 3, 2027

12 Sailings

Nov 9, 2025 - Jan 3, 2027

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.

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

18-night Eastern Caribbean Voyage

St. Thomas (Charlotte Amalie)

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 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.

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

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 high-angle view of the bustling harbor of Marigot, St. Martin, with boats and yachts docked along the coast and colorful buildings nestled against the green hills.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

7-night San Juan & The Virgin Islands Cruise

Iles des Saintes

Aboard

Star Pride

From

San Juan, Puerto Rico

9 Sailings

Nov 9, 2025 - Jan 10, 2027

9 Sailings

Nov 9, 2025 - Jan 10, 2027