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175 Results

Taxes and fees included in all prices shown

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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

25-night Canada & Caribbean Cruise From Montreal, Quebec

Montreal
Quebec City
Charlottetown
Halifax (Nova Scotia)
Boston
+11 more

Aboard

Silver Shadow

From

Montreal, Quebec

1 Sailing

Oct 24, 2026

1 Sailing

Oct 24, 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*+ 2 more offers
Explora Journeys Logo

14-night An Extended Journey Of Maritime Soul & Island Zest 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

Oct 25, 2026

1 Sailing

Oct 25, 2026

Published prices from

$12,280

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*+ 2 more offers
TCW EXCLUSIVE
Windstar

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

San Juan
Cruz Bay
Gustavia
Basseterre
Falmouth Harbour
+6 more

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Oct 28, 2026

1 Sailing

Oct 28, 2026

Published prices from

$4,296

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
Explora Journeys Logo

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

San Juan
Roadtown
Basseterre
Gustavia
Road Bay
+6 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Nov 1, 2026

1 Sailing

Nov 1, 2026

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Beverages, Gratuities, Wi-Fi & More*+ 2 more offers
Explora Journeys Logo

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

San Juan
Roadtown
Basseterre
Gustavia
Road Bay
+2 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Nov 1, 2026

1 Sailing

Nov 1, 2026

Published prices from

$5,120

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*+ 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

Published prices from

$6,300

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
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

Published prices from

$9,185

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*+ 2 more offers
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

Published prices from

$5,400

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

$4,014

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

$6,249

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*+ 2 more offers
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

$10,835

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

Published prices from

$3,579

per person*

taxes & fees included

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*+ 2 more offers
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

$10,835

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
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

$6,410

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

$4,849

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*+ 2 more offers
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

$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
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

$6,410

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

    • Showing results 1 - 24 of 175

*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.