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*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.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

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

San Juan
Cruz Bay
Gustavia
Basseterre
St. Maarten (Philipsburg)
+7 more

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 30, 2025

1 Sailing

Nov 30, 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

San Juan
Cruz Bay
Gustavia
Basseterre
St. Maarten (Philipsburg)
+13 more

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

14-night Star Collector: Leeward & Windward Caribbean Havens Cruise

St. Maarten (Philipsburg)
Falmouth Harbour
Road Bay
Sopers Hole
Jost Van Dyke
+8 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

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

San Juan
Cruz Bay
Basseterre
Gustavia
St. Maarten (Philipsburg)
+2 more

Aboard

Star Seeker

From

San Juan, Puerto Rico

4 Sailings

Jan 23 - Mar 6, 2026

4 Sailings

Jan 23 - Mar 6, 2026

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

10-night Caribbean Cruise

Ft. Lauderdale
Virgin Gorda
St. John (U.S.V.I.)
St. John's
Deshaies
+5 more

Aboard

Silver Spirit

From

Fort Lauderdale, Florida

1 Sailing

Jan 16, 2026

1 Sailing

Jan 16, 2026

Published prices from

$7,300

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

7-night Southern Caribbean Voyage

San Juan
Virgin Gorda
St. John's
St. Pierre
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

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

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

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
Azamara logo

8-night Southern Caribbean Voyage

San Juan
St. Thomas (Charlotte Amalie)
Virgin Gorda
St. John's
St. Pierre
+4 more

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

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)
Sopers Hole
Jost Van Dyke
Virgin Gorda
Gustavia
+5 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 2, 2025

1 Sailing

Dec 2, 2025

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
TCW EXCLUSIVE
Silversea logo

14-night Eastern & Southern Caribbean Cruise

Ft. Lauderdale
San Juan
St. John (U.S.V.I.)
Basseterre
Deshaies
+5 more

Aboard

Silver Ray

From

Fort Lauderdale, Florida

1 Sailing

Dec 23, 2025

1 Sailing

Dec 23, 2025

Published prices from

$12,700

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

San Juan
Cruz Bay
Basseterre
Gustavia
St. Maarten (Philipsburg)
+2 more

Aboard

Star Pride

From

San Juan, Puerto Rico

10 Sailings

Nov 2, 2025 - Jan 10, 2027

10 Sailings

Nov 2, 2025 - Jan 10, 2027

A view of the stunning architecture of the Hassan II Mosque in Casablanca, Morocco, featuring a long series of ornate stone arches and a spacious courtyard.
FREE $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers
Azamara logo

25-night Transatlantic Cruise: Lisbon To Miami

Lisbon
Casablanca
Miami
San Juan
St. John (U.S.V.I.)
+6 more

Aboard

Azamara Onward

From

Lisbon, Portugal

1 Sailing

Nov 17, 2025

1 Sailing

Nov 17, 2025

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
Azamara logo

14-night Eastern Caribbean Voyage

San Juan
Virgin Gorda
St. John's
St. Pierre
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

$3,689

per person*

taxes & fees included

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

21-night Caribbean Cruise

Bridgetown (Barbados)
Bequia
Castries
Deshaies
Roseau
+9 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

2 Sailings

Jan 5 - Feb 2, 2026

2 Sailings

Jan 5 - Feb 2, 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.
FREE $200 Shipboard Credit & More with Azamara Circle*+ 2 more offers
Azamara logo

18-night Eastern Caribbean Voyage

San Juan
St. Thomas (Charlotte Amalie)
Virgin Gorda
St. John's
St. Pierre
+10 more

Aboard

Azamara Quest

From

San Juan, Puerto Rico

1 Sailing

Dec 19, 2025

1 Sailing

Dec 19, 2025

Published prices from

$4,449

per person*

taxes & fees included

An aerial view of Anse Mitan in Martinique, a beautiful Caribbean village with a bustling beach, sailboats moored in the bay, and lush green hills in the distance.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

21-night Star Collector: A Lesser Antilles Odyssey Cruise

St. Maarten (Philipsburg)
Falmouth Harbour
Road Bay
Sopers Hole
Jost Van Dyke
+13 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

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)
Sopers Hole
Jost Van Dyke
Virgin Gorda
Gustavia

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

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

St. Maarten (Philipsburg)
Falmouth Harbour
Road Bay
Sopers Hole
Jost Van Dyke
+2 more

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 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)
Charlestown
Roseau
Pigeon Island
Iles des Saintes
+7 more

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

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*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

12-night Eastern Caribbean Voyage

Miami
San Juan
St. John (U.S.V.I.)
St. Maarten (Philipsburg)
St. John's
+4 more

Aboard

Azamara Onward

From

Miami, Florida

1 Sailing

Nov 30, 2025

1 Sailing

Nov 30, 2025

A sunny view of the colorful waterfront of Willemstad, Curacao, with its iconic pastel-colored Dutch colonial buildings lining the Handelskade street and a ship docked in the port.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

28-night Star Collector: The Best Of The Windward & Leeward Isles Cruise

St. Maarten (Philipsburg)
Falmouth Harbour
Road Bay
Sopers Hole
Jost Van Dyke
+19 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

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

Lisbon
St. Maarten (Philipsburg)
Sopers Hole
Jost Van Dyke
Virgin Gorda
+2 more

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Nov 18, 2025

1 Sailing

Nov 18, 2025

A sunny view of the colorful waterfront of Willemstad, Curacao, with its iconic pastel-colored Dutch colonial buildings lining the Handelskade street and a ship docked in the port.
FREE All-Inclusive Package Upgrade*+ 1 more offer
Windstar

55-night Star Collector: A Grand Caribbean Adventure Cruise

St. Maarten (Philipsburg)
Falmouth Harbour
Road Bay
Sopers Hole
Jost Van Dyke
+33 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 4, 2026

1 Sailing

Jan 4, 2026

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

17-night Star Collector: Hidden Gems of the Caribbean Cruise

St. Maarten (Philipsburg)
Little Bay
Roseau
Castries
Mayreau
+10 more

Aboard

Wind Spirit

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Jan 14, 2026

1 Sailing

Jan 14, 2026

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night Star Seeker Christening: Dominican Republic and BVI Adventure Cruise

Miami
Puerto Plata
Bahia de Samana
Great Harbour
Virgin Gorda
+3 more

Aboard

Star Seeker

From

Miami, Florida

1 Sailing

Jan 15, 2026

1 Sailing

Jan 15, 2026