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Palm-fringed beach and turquoise waters in Punta Cana.

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

Regent Seven Seas

17-night Yucatán Gems and Serene Isles Cruise

Aboard

Seven Seas Grandeur

From

Miami, Florida

1 Sailing

Nov 24, 2025

1 Sailing

Nov 24, 2025

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.

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

Oceania Cruises

12-night Curated Caribbean Voyage

Aboard

Allura

From

Miami, Florida

1 Sailing

Nov 16, 2025

1 Sailing

Nov 16, 2025

Published prices from

$4,999

per person*

taxes & fees included

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

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

Regent Seven Seas

10-night Island Adventures Cruise

Bahamian Waters

St. Maarten (Philipsburg)

Aboard

Seven Seas Grandeur

From

Miami, Florida

1 Sailing

Dec 1, 2025

1 Sailing

Dec 1, 2025

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

Boats on a canal in Fort Lauderdale.

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

10-night Eastern Caribbean Cruise

St. John (U.S.V.I.)

Aboard

Silver Ray

From

Fort Lauderdale, Florida

3 Sailings

Dec 2, 2025 - Jan 27, 2026

3 Sailings

Dec 2, 2025 - Jan 27, 2026

Published prices from

$7,900

per person*

taxes & fees included

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

Cupecoy Beach with white resort buildings, St. Maarten.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

7-night Classic Caribbean Cruise

St. Maarten (Philipsburg)

Iles des Saintes

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

11 Sailings

Dec 7, 2025 - Mar 20, 2027

11 Sailings

Dec 7, 2025 - Mar 20, 2027

Rocky beach and palm trees in Barbados.

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

21-night Caribbean & South America Cruise

St. Thomas (Charlotte Amalie)

Aboard

Silver Shadow

From

Fort Lauderdale, Florida

1 Sailing

Nov 10, 2025

1 Sailing

Nov 10, 2025

Statue of Liberty and Manhattan skyline.

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

Regent Seven Seas

15-night Auburn Sunsets, Turquoise Seas Cruise

Royal Naval Dockyard

Bridgetown (Barbados)

Aboard

Seven Seas Splendor

From

New York, New York

1 Sailing

Nov 2, 2025

1 Sailing

Nov 2, 2025

Published prices from

$13,299

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.

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

7-night South Caribbean Cruise - Bridgetown To Bridgetown

Bridgetown (Barbados)

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Dec 8, 2025

1 Sailing

Dec 8, 2025

Published prices from

$5,800

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.

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

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

14-night Star Collector: Caribbean Explorations Cruise

St. Maarten (Philipsburg)

Iles des Saintes

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

19 Sailings

Dec 7, 2025 - Mar 13, 2027

19 Sailings

Dec 7, 2025 - Mar 13, 2027

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

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

7-night Eastern & Southern Caribbean Cruise

Bridgetown (Barbados)

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Dec 15, 2025

1 Sailing

Dec 15, 2025

Published prices from

$5,200

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 All-Inclusive Package Upgrade*+ 1 more offer

Windstar

19-night Star Collector: Hearty Ports & Rum Punches - A Trans-Atlantic Crossing Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Nov 18, 2025

1 Sailing

Nov 18, 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.

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

Oceania Cruises

10-night Caribbean Elegance Voyage

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Nautica

From

Miami, Florida

1 Sailing

Dec 17, 2025

1 Sailing

Dec 17, 2025

Published prices from

$2,999

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.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

6-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

4 Sailings

Dec 14, 2025 - Mar 28, 2026

4 Sailings

Dec 14, 2025 - Mar 28, 2026

A stunning aerial view of the turquoise waters and white-sand beaches around Paradise Island in Nassau, Bahamas, with the Atlantis resort visible in the distance.

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

Oceania Cruises

25-night Iberian & Island Dreams Voyage

Seville (Cadiz)

Aboard

Nautica

From

Barcelona, Spain

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

Published prices from

$6,699

per person*

taxes & fees included

A scenic Caribbean bay near Kingstown, Saint Vincent and the Grenadines, with small boats anchored in the turquoise water and lush green hillsides with colorful houses.

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

12-night Eastern & Southern Caribbean Cruise

St. Thomas (Charlotte Amalie)

Aboard

Silver Shadow

From

Fort Lauderdale, Florida

1 Sailing

Nov 10, 2025

1 Sailing

Nov 10, 2025

Published prices from

$7,800

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 All-Inclusive Package Upgrade*+ 1 more offer

Windstar

5-night Barefoot Break in the British Virgin Islands Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

A wide shot of the spectacular Petrohué Falls near Puerto Montt, Chile, with turquoise water cascading over volcanic rock, set against the backdrop of the snow-capped Osorno Volcano.

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

Oceania Cruises

77-night Spanning The Americas Voyage - 2026 World Voyage Segment

Puerto Vallarta

Aboard

Vista

From

Los Angeles, California

1 Sailing

Dec 20, 2025

1 Sailing

Dec 20, 2025

Published prices from

$23,599

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.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

7-night San Juan & The Virgin Islands Cruise

St. Maarten (Philipsburg)

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.

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

12-night Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean Cruise

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

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

FREE All-Inclusive Package Upgrade*+ 1 more offer

Windstar

14-night Star Collector: Lovely Leewards Cruise

St. Maarten (Philipsburg)

Aboard

Star Pride

From

San Juan, Puerto Rico

13 Sailings

Nov 2, 2025 - Jan 3, 2027

13 Sailings

Nov 2, 2025 - Jan 3, 2027

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*+ 2 more offers

11-night Eastern Caribbean Cruise

St. John (U.S.V.I.)

Aboard

Silver Ray

From

Fort Lauderdale, Florida

3 Sailings

Dec 12, 2025 - Feb 6, 2026

3 Sailings

Dec 12, 2025 - Feb 6, 2026

Published prices from

$8,400

per person*

taxes & fees included

A vibrant panoramic view of Castries, St. Lucia, with colorful buildings nestled along the harbor and lush green hills in the background under a blue sky with white clouds.

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

Oceania Cruises

19-night Caribbean Spectrum Voyage

Aboard

Allura

From

Miami, Florida

1 Sailing

Nov 16, 2025

1 Sailing

Nov 16, 2025

Published prices from

$6,499

per person*

taxes & fees included

A vibrant panoramic view of Castries, St. Lucia, with colorful buildings nestled along the harbor and lush green hills in the background under a blue sky with white clouds.

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

20-night Transatlantic Cruise

Funchal (Madeira)

Santa Cruz de La Palma

Sao Vicente (Mindelo)

Bridgetown (Barbados)

Aboard

Silver Spirit

From

Lisbon, Portugal

1 Sailing

Nov 25, 2025

1 Sailing

Nov 25, 2025