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191 Results

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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

11-night Eastern Caribbean Cruise From Miami, Florida

Miami
San Juan
St. John (U.S.V.I.)
Gustavia
Basseterre
+3 more

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 2026

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*+ 1 more offer
Explora Journeys Logo

14-night An Extended Journey Of Blissful Escapes & Shoreline Splendour From Miami, Florida

Miami
Providenciales
Puerto Plata
Casa de Campo
Jost Van Dyke
+7 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Nov 8, 2026

1 Sailing

Nov 8, 2026

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 Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

7-night A Journey Through Beguiling Caribbean Coastlines & Lush Landscapes From Miami, Florida

Miami
Providenciales
Puerto Plata
Casa de Campo
Jost Van Dyke
+3 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Nov 8, 2026

1 Sailing

Nov 8, 2026

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

$4,014

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
Windstar

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

San Juan
Cruz Bay
Basseterre
Gustavia
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

A high-angle view of the rugged, rocky coastline of St. John, US Virgin Islands, with the deep blue sea crashing against the cliffs and islands in the distance under a cloudy blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

11-night Eastern Caribbean Cruise From Miami, Florida

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

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 18, 2026

1 Sailing

Nov 18, 2026

Published prices from

$7,800

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

Published prices from

$4,889

per person*

taxes & fees included

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 Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

14-night An Extended Journey Of Sunlit Horizons & Sapphire Bays From Miami, Florida

Miami
Cruz Bay
St. John's
Terre-de-Haut
St. Maarten (Philipsburg)
+6 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Nov 22, 2026

1 Sailing

Nov 22, 2026

Published prices from

$7,995

per person*

taxes & fees included

An aerial view of the vibrant marina and coastline of Pointe-à-Pitre, Guadeloupe, showing numerous boats docked in the harbor, surrounded by lush green hills and the turquoise Caribbean Sea.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

12-night Antillean Island Sojourn Voyage From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Gustavia
Fort de France
+4 more

Aboard

Vista

From

Miami, Florida

1 Sailing

Nov 25, 2026

1 Sailing

Nov 25, 2026

Published prices from

$5,199

per person*

taxes & fees included

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

14-night Caribbean Voyage: Barbados, St. Lucia & St. Maarten From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+9 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Nov 28, 2026

1 Sailing

Nov 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*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

10-night Riviera Chic & Caribbean Cool Cruise From Miami, Florida

Miami
San Juan
Gustavia
St. Maarten (Philipsburg)
Frederiksted
+3 more

Aboard

Seven Seas Grandeur

From

Miami, Florida

1 Sailing

Nov 29, 2026

1 Sailing

Nov 29, 2026

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

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

San Juan
Roadtown
Basseterre
Gustavia
Grand Turk
+5 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Nov 29, 2026

1 Sailing

Nov 29, 2026

Published prices from

$8,220

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

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

San Juan
Roadtown
Basseterre
Gustavia
Grand Turk
+2 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Nov 29, 2026

1 Sailing

Nov 29, 2026

Published prices from

$6,100

per person*

taxes & fees included

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

11-night Eastern Caribbean Cruise From Miami, Florida

Miami
San Juan
St. John (U.S.V.I.)
Gustavia
Basseterre
+2 more

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 30, 2026

1 Sailing

Nov 30, 2026

Published prices from

$5,500

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*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

10-night Tropical Island Havens Voyage From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Gustavia
St. Maarten (Philipsburg)
Frederiksted
+2 more

Aboard

Allura

From

Miami, Florida

4 Sailings

Dec 2, 2026 - Mar 21, 2027

4 Sailings

Dec 2, 2026 - Mar 21, 2027

Published prices from

$4,799

per person*

taxes & fees included

An aerial view of Road Bay, Anguilla, showing a pristine white sand beach, lush green vegetation, and the stunningly clear turquoise water of the Caribbean Sea.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

21-night Star Collector: Hearty Ports & Rum Punches - A Transatlantic Crossing Cruise From Lisbon, Portugal

Lisbon
St. John's
St. Maarten (Philipsburg)
Falmouth Harbour
Gustavia
+5 more

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 2026

A panoramic view of Fort-de-France, Martinique, showing a bustling bay filled with boats and yachts, with colorful houses nestled on the surrounding green hillsides and the deep blue Caribbean Sea beyond.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

7-night Southern Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Bequia
Fort de France
Deshaies
Gustavia
+2 more

Aboard

Silver Spirit

From

Bridgetown, Barbados

2 Sailings

Dec 5, 2026 - Feb 28, 2027

2 Sailings

Dec 5, 2026 - Feb 28, 2027

Published prices from

$3,950

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*+ 1 more offer
Explora Journeys Logo

14-night An Extended Journey Through Islands Of Scenic Wonder & Coastal History From Miami, Florida

Miami
Cruz Bay
St. John's
Terre-de-Haut
Gustavia
+5 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Dec 6, 2026

1 Sailing

Dec 6, 2026

Published prices from

$7,560

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*+ 1 more offer
Explora Journeys Logo

7-night A Journey Of Colourful Treasures & Idyllic Island Scenery From Miami, Florida

Miami
Cruz Bay
St. John's
Terre-de-Haut
Gustavia
+2 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Dec 6, 2026

1 Sailing

Dec 6, 2026

Published prices from

$6,100

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

12-night Collector's Caribbean Voyage From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Gustavia
St. John's
Fort de France
+4 more

Aboard

Marina

From

Miami, Florida

1 Sailing

Dec 10, 2026

1 Sailing

Dec 10, 2026

Published prices from

$4,399

per person*

taxes & fees included

A scenic beach in Montego Bay, Jamaica, with a long line of palm trees and resort hotels along the white sand, and a large school of fish visible in the clear blue water.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

17-night Tropical Sparkle & Holiday Cheer Cruise From Galveston, Texas

Galveston
Montego Bay
Ocho Rios
Punta Cana
San Juan
+6 more

Aboard

Seven Seas Splendor

From

Galveston, Texas

1 Sailing

Dec 11, 2026

1 Sailing

Dec 11, 2026

Published prices from

$11,999

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
TCW EXCLUSIVE
Silversea logo

11-night Eastern Caribbean Cruise From Miami, Florida

Miami
San Juan
St. John (U.S.V.I.)
Basseterre
Gustavia
+3 more

Aboard

Silver Ray

From

Miami, Florida

4 Sailings

Dec 11, 2026 - Jan 27, 2027

4 Sailings

Dec 11, 2026 - Jan 27, 2027

Published prices from

$8,350

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

9-night Sunlit Caribbean Gems Voyage From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Gustavia
St. Maarten (Philipsburg)
Roadtown

Aboard

Allura

From

Miami, Florida

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$3,949

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*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

16-night Caribbean Christmas Voyage: Barbados, St. Lucia & St. Thomas From Bridgetown, Barbados

Bridgetown (Barbados)
Castries
Roseau
Basseterre
Charlestown
+11 more

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$3,749

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*+ 1 more offer
Explora Journeys Logo

14-night An Extended Journey Of Island Calm & Coastal Retreats From Miami, Florida

Miami
Cruz Bay
St. John's
Terre-de-Haut
St. Maarten (Philipsburg)
+6 more

Aboard

EXPLORA I

From

Miami, Florida

1 Sailing

Dec 13, 2026

1 Sailing

Dec 13, 2026

Published prices from

$8,090

per person*

taxes & fees included

    • Showing results 1 - 24 of 191

*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.