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98 Results

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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.
FREE Spa Treatment*+ 1 more offer
Royal Caribbean logo

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

San Juan
St. Croix
St. Maarten (Philipsburg)
St. John's
Fort de France
+2 more

Aboard

Rhapsody of the Seas

From

San Juan, Puerto Rico

37 Sailings

Oct 31, 2026 - Apr 15, 2028

37 Sailings

Oct 31, 2026 - Apr 15, 2028

Published prices from

$530

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
TCW EXCLUSIVE
Royal Caribbean logo

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

San Juan
Roadtown
St. John's
Fort de France
St. Vincent (Kingstown)
+2 more

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

$521

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
Viking

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

San Juan
Roadtown
Basseterre
Castries
Bridgetown (Barbados)
+4 more

Aboard

Viking Sea

From

San Juan, Puerto Rico

25 Sailings

Nov 5, 2026 - Jan 29, 2029

25 Sailings

Nov 5, 2026 - Jan 29, 2029

Published prices from

$3,599

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
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

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

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

San Juan
St. George's
Bequia
Mayreau
Iles des Saintes
+2 more

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

$2,442

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*+ 2 more offers
TCW EXCLUSIVE
Windstar

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

San Juan
Cruz Bay
Basseterre
Gustavia
St. Maarten (Philipsburg)
+8 more

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

$4,108

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*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

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

San Juan
St. Maarten (Philipsburg)
Basseterre
Bridgetown (Barbados)
Castries
+2 more

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

$709

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
TCW EXCLUSIVE
Celebrity Cruise Line logo

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

San Juan
Roadtown
St. John's
Castries
St. George's
+5 more

Aboard

Celebrity Constellation

From

San Juan, Puerto Rico

1 Sailing

Nov 17, 2026

1 Sailing

Nov 17, 2026

Published prices from

$1,542

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
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*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

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

San Juan
Roadtown
Basseterre
Bridgetown (Barbados)
Castries
+2 more

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

$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*+ 4 more offers
TCW EXCLUSIVE
Celebrity Cruise Line logo

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

San Juan
St. Thomas (Charlotte Amalie)
St. John's
Roseau
Castries
+2 more

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

$559

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
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 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*+ 2 more offers
TCW EXCLUSIVE
Viking

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

San Juan
Bridgetown (Barbados)
Iles du Salut
Amazon River
Santarem
+8 more

Aboard

Viking Sea

From

San Juan, Puerto Rico

3 Sailings

Dec 15, 2026 - Feb 8, 2029

3 Sailings

Dec 15, 2026 - Feb 8, 2029

Published prices from

$12,499

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
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 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*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

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

San Juan
Oranjestad
St. Maarten (Philipsburg)
St. Thomas (Charlotte Amalie)
Roadtown

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

$939

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
TCW EXCLUSIVE
Royal Caribbean logo

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

San Juan
Roadtown
St. John's
Roseau
St. Croix
+2 more

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

$1,235

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
TCW EXCLUSIVE
Silversea logo

14-night Caribbean Cruise From San Juan, Puerto Rico

San Juan
Jost Van Dyke
Little Bay
Castries
Canouan Island
+7 more

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
TCW EXCLUSIVE
Silversea logo

7-night Caribbean Cruise From San Juan, Puerto Rico

San Juan
Jost Van Dyke
Little Bay
Castries
Canouan Island
+2 more

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

$4,900

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*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

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

San Juan
St. Maarten (Philipsburg)
Basseterre
Bridgetown (Barbados)
Castries
+2 more

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

$1,009

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Princess Cruises logo

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

San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
St. John's
Castries
+5 more

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
TCW EXCLUSIVE
Princess Cruises logo

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

San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
St. John's
Castries
+2 more

Aboard

Crown Princess

From

San Juan, Puerto Rico

13 Sailings

Dec 27, 2026 - Mar 21, 2027

13 Sailings

Dec 27, 2026 - Mar 21, 2027

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
TCW EXCLUSIVE
Silversea logo

8-night Caribbean Cruise From San Juan, Puerto Rico

San Juan
St. John (U.S.V.I.)
Charlestown
Roseau
St. John's
+3 more

Aboard

Silver Nova

From

San Juan, Puerto Rico

1 Sailing

Dec 29, 2026

1 Sailing

Dec 29, 2026

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*+ 5 more offers
TCW EXCLUSIVE
Norwegian Cruise Line logo.

7-night Caribbean Round-Trip San Juan Cruise: Curacao & Aruba From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
Roadtown
Oranjestad
Willemstad

Aboard

Norwegian Prima

From

San Juan, Puerto Rico

3 Sailings

Jan 3 - Mar 14, 2027

3 Sailings

Jan 3 - Mar 14, 2027

Published prices from

$889

per person*

taxes & fees included

    • Showing results 1 - 24 of 98

*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.