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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*+ 2 more offers

TCW EXCLUSIVE

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

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Oct 28, 2026

1 Sailing

Oct 28, 2026

Published prices from

$3,966

per person*

taxes & fees included

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

FREE Beverages, Gratuities, Wi-Fi & More*+ 2 more offers

14-night An Extended Journey Into Island Delights, Hidden Coves & Chic Coastlines From San Juan, Puerto Rico

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Nov 1, 2026

1 Sailing

Nov 1, 2026

Published prices from

$16,640

per person*

taxes & fees included

FREE Beverages, Gratuities, Wi-Fi & More*+ 2 more offers

7-night A Journey Into Caribbean Exploration & Island Delights From San Juan, Puerto Rico

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Nov 1, 2026

1 Sailing

Nov 1, 2026

Published prices from

$4,480

per person*

taxes & fees included

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

TCW EXCLUSIVE

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

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

$529

per person*

taxes & fees included

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

TCW EXCLUSIVE

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

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

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

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

$1,189

per person*

taxes & fees included

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

TCW EXCLUSIVE

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

Port Elizabeth (Bequia)

+9 more

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 2026

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

TCW EXCLUSIVE

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

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

$2,411

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

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

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

$4,014

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

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

$849

per person*

taxes & fees included

An aerial view of a luxurious resort and pristine sandy beach on the coast of Puerto Plata, Dominican Republic, with turquoise waters, lush green hills, and a cityscape in the background.

FREE Beverages, Gratuities, Wi-Fi & More*+ 2 more offers

14-night An Extended Journey Of Tropical Harmony & Natural Wonders From San Juan, Puerto Rico

Catalina Island/Casa de Campo

+6 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Nov 15, 2026

1 Sailing

Nov 15, 2026

Published prices from

$10,200

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.

FREE Beverages, Gratuities, Wi-Fi & More*+ 2 more offers

7-night A Journey Of Blissful Escapes & Island Splendour From San Juan, Puerto Rico

Catalina Island/Casa de Campo

+3 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Nov 15, 2026

1 Sailing

Nov 15, 2026

Published prices from

$4,200

per person*

taxes & fees included

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

TCW EXCLUSIVE

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

St. Maarten (Philipsburg)

+2 more

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

TCW EXCLUSIVE

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

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

TCW EXCLUSIVE

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

Port Elizabeth (Bequia)

+9 more

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Nov 21, 2026

1 Sailing

Nov 21, 2026

Published prices from

$4,799

per person*

taxes & fees included

Up to $500 FREE Onboard Credit*+ 5 more offers

TCW EXCLUSIVE

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

$949

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

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

San Juan

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

$662

per person*

taxes & fees included

FREE Beverages, Gratuities, Wi-Fi & More*+ 2 more offers

14-night An Extended Journey Through Golden Shores & Island Grace From San Juan, Puerto Rico

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Nov 29, 2026

1 Sailing

Nov 29, 2026

Published prices from

$10,835

per person*

taxes & fees included

FREE Beverages, Gratuities, Wi-Fi & More*+ 2 more offers

7-night A Journey Through A Caribbean Tapestry Of Serenity & Splendour From San Juan, Puerto Rico

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Nov 29, 2026

1 Sailing

Nov 29, 2026

Published prices from

$5,325

per person*

taxes & fees included

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

TCW EXCLUSIVE

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

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

$7,849

per person*

taxes & fees included

FREE Beverages, Gratuities, Wi-Fi & More*+ 2 more offers

15-night An Extended Journey Through Wild Beauty And Tropical Festivities From San Juan, Puerto Rico

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Dec 13, 2026

1 Sailing

Dec 13, 2026

Published prices from

$10,985

per person*

taxes & fees included

FREE Beverages, Gratuities, Wi-Fi & More*+ 2 more offers

7-night A Journey Through Caribbean Gems & Multi-Coloured Coasts From San Juan, Puerto Rico

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Dec 13, 2026

1 Sailing

Dec 13, 2026

Published prices from

$4,200

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

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

San Juan

Bridgetown (Barbados)

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

$11,999

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

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

San Juan

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

$1,679

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

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

San Juan

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

$5,819

per person*

taxes & fees included

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

$3,966

14-night An Extended Journey Into Island Delights, Hidden Coves & Chic Coastlines From San Juan, Puerto Rico

$16,640

7-night A Journey Into Caribbean Exploration & Island Delights From San Juan, Puerto Rico

$4,480

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

$529

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

$3,599

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

$1,189

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

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

$2,411

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

$4,014

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

$849

14-night An Extended Journey Of Tropical Harmony & Natural Wonders From San Juan, Puerto Rico

$10,200

7-night A Journey Of Blissful Escapes & Island Splendour From San Juan, Puerto Rico

$4,200

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

$2,443

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

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

$4,799

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

$949

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

$662

14-night An Extended Journey Through Golden Shores & Island Grace From San Juan, Puerto Rico

$10,835

7-night A Journey Through A Caribbean Tapestry Of Serenity & Splendour From San Juan, Puerto Rico

$5,325

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

$7,849

15-night An Extended Journey Through Wild Beauty And Tropical Festivities From San Juan, Puerto Rico

$10,985

7-night A Journey Through Caribbean Gems & Multi-Coloured Coasts From San Juan, Puerto Rico

$4,200

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

$11,999

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

$1,679

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

$5,819

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

$3,966

14-night An Extended Journey Into Island Delights, Hidden Coves & Chic Coastlines From San Juan, Puerto Rico

$16,640

7-night A Journey Into Caribbean Exploration & Island Delights From San Juan, Puerto Rico

$4,480

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

$529

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

$3,599

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

$1,189

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

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

$2,411

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

$4,014

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

$849

14-night An Extended Journey Of Tropical Harmony & Natural Wonders From San Juan, Puerto Rico

$10,200

7-night A Journey Of Blissful Escapes & Island Splendour From San Juan, Puerto Rico

$4,200

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

$2,443

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