Silversea Cruises to Eastern Caribbean

An underwater view of a sea turtle swimming in the clear blue waters of Barbados in the Eastern Caribbean, a popular excursion on a Silversea cruise.

Overview

A Silversea cruise to the Eastern Caribbean is a journey of sophisticated exploration, blending ultra-luxury with authentic island experiences. Onboard, guests enjoy an all-inclusive lifestyle with personalized service and gourmet dining. The smaller, more agile Silversea ships are perfectly suited for navigating the intimate coves and harbors of the Eastern Caribbean, offering a more secluded and in-depth view of the islands.

The itineraries are carefully crafted to showcase the region's most captivating destinations, from the chic shores of St. Barts to the volcanic peaks of St. Lucia. Guests can discover hidden beaches, vibrant local cultures, and breathtaking natural wonders. The focus on destination immersion ensures that every port of call becomes a truly memorable experience, allowing travelers to connect with the local life, culture, and cuisine of the islands.

Upcoming Silversea Cruises to Eastern Caribbean

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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

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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

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

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11-night Eastern Caribbean Cruise From Miami, Florida

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 2026

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

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11-night Eastern Caribbean Cruise From Miami, Florida

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 18, 2026

1 Sailing

Nov 18, 2026

Published prices from

$6,500

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

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11-night Eastern Caribbean Cruise From Miami, Florida

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 30, 2026

1 Sailing

Nov 30, 2026

Published prices from

$5,700

per person*

taxes & fees included

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

7-night Southern Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

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

A stunning image of Little Bay in Anguilla, a secluded, beautiful beach with turquoise water surrounded by towering rocky cliffs and lush green vegetation.

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

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10-night Caribbean Cruise From Miami, Florida

Miami

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

St. Maarten (Philipsburg)

Basseterre

Iles des Saintes

+5 more

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Dec 10, 2026

1 Sailing

Dec 10, 2026

Published prices from

$5,200

per person*

taxes & fees included

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

TCW EXCLUSIVE

11-night Eastern Caribbean Cruise From Miami, Florida

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

The picturesque fishing village of Deshaies, Guadeloupe, with its colorful waterfront and red-roofed church nestled on a tranquil bay.

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

TCW EXCLUSIVE

10-night Southern Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$3,950

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

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8-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Silver Spirit

From

Bridgetown, Barbados

2 Sailings

Dec 19 - Dec 27, 2026

2 Sailings

Dec 19 - Dec 27, 2026

Published prices from

$5,050

per person*

taxes & fees included

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

TCW EXCLUSIVE

14-night Caribbean Cruise From San Juan, Puerto Rico

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 2026

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

TCW EXCLUSIVE

7-night Caribbean Cruise From San Juan, Puerto Rico

Aboard

Silver Shadow

From

San Juan, Puerto Rico

3 Sailings

Dec 20, 2026 - Feb 26, 2027

3 Sailings

Dec 20, 2026 - Feb 26, 2027

Published prices from

$4,900

per person*

taxes & fees included

A scenic landscape view of Admiralty Bay in Bequia, St. Vincent and the Grenadines, with dozens of sailboats moored on the vibrant turquoise water, surrounded by lush green hills.

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

TCW EXCLUSIVE

8-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Silver Nova

From

Bridgetown, Barbados

1 Sailing

Dec 21, 2026

1 Sailing

Dec 21, 2026

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.

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

TCW EXCLUSIVE

14-night Eastern & Southern Caribbean Cruise From Miami, Florida

Aboard

Silver Ray

From

Miami, Florida

1 Sailing

Dec 22, 2026

1 Sailing

Dec 22, 2026

Published prices from

$11,050

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*+ 2 more offers

TCW EXCLUSIVE

8-night Caribbean Cruise From San Juan, Puerto Rico

Aboard

Silver Nova

From

San Juan, Puerto Rico

1 Sailing

Dec 29, 2026

1 Sailing

Dec 29, 2026

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

TCW EXCLUSIVE

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

Aboard

Silver Shadow

From

San Juan, Puerto Rico

2 Sailings

Jan 3 - Jan 30, 2027

2 Sailings

Jan 3 - Jan 30, 2027

Published prices from

$5,500

per person*

taxes & fees included

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

TCW EXCLUSIVE

11-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Silver Spirit

From

Bridgetown, Barbados

3 Sailings

Jan 4, 2027 - Feb 29, 2028

3 Sailings

Jan 4, 2027 - Feb 29, 2028

Published prices from

$5,100

per person*

taxes & fees included

A wide-angle view of a serene rainforest stream with moss-covered rocks and lush green vegetation near Macapa, Brazil, at the mouth of the Amazon River.

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

TCW EXCLUSIVE

76-night Grand Voyage From Miami, Florida

Aboard

Silver Nova

From

Miami, Florida

1 Sailing

Jan 6, 2027

1 Sailing

Jan 6, 2027

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

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

TCW EXCLUSIVE

12-night Eastern & Southern Caribbean Cruise From Miami, Florida

Aboard

Silver Nova

From

Miami, Florida

1 Sailing

Jan 6, 2027

1 Sailing

Jan 6, 2027

Published prices from

$7,600

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

10-night Eastern & Southern Caribbean Cruise From San Juan, Puerto Rico

Aboard

Silver Shadow

From

San Juan, Puerto Rico

2 Sailings

Jan 10 - Feb 6, 2027

2 Sailings

Jan 10 - Feb 6, 2027

Published prices from

$5,300

per person*

taxes & fees included

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

TCW EXCLUSIVE

10-night Southern Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Silver Spirit

From

Bridgetown, Barbados

2 Sailings

Jan 15 - Feb 18, 2027

2 Sailings

Jan 15 - Feb 18, 2027

Published prices from

$5,900

per person*

taxes & fees included

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

TCW EXCLUSIVE

10-night Eastern & Southern Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Silver Shadow

From

Bridgetown, Barbados

1 Sailing

Jan 20, 2027

1 Sailing

Jan 20, 2027

Published prices from

$6,500

per person*

taxes & fees included

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

TCW EXCLUSIVE

12-night Southern Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Silver Spirit

From

Bridgetown, Barbados

2 Sailings

Jan 25 - Mar 7, 2027

2 Sailings

Jan 25 - Mar 7, 2027

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

TCW EXCLUSIVE

12-night Southern Caribbean Cruise From Miami, Florida

Aboard

Silver Spirit

From

Miami, Florida

2 Sailings

Feb 6 - Mar 19, 2027

2 Sailings

Feb 6 - Mar 19, 2027

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

TCW EXCLUSIVE

12-night Eastern & Southern Caribbean Cruise From Miami, Florida

Aboard

Silver Ray

From

Miami, Florida

1 Sailing

Feb 7, 2027

1 Sailing

Feb 7, 2027

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*+ 2 more offers

TCW EXCLUSIVE

10-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Silver Shadow

From

Bridgetown, Barbados

1 Sailing

Feb 16, 2027

1 Sailing

Feb 16, 2027

Published prices from

$6,800

per person*

taxes & fees included

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

TCW EXCLUSIVE

12-night Eastern & Southern Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Silver Ray

From

Bridgetown, Barbados

1 Sailing

Feb 26, 2027

1 Sailing

Feb 26, 2027

A scenic view of the iconic Plaza de España in Seville, Spain, featuring its grand arcade of arches and columns, a main building with a clock tower, and a bright blue sky.

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

TCW EXCLUSIVE

23-night Transatlantic Cruise From San Juan, Puerto Rico

San Juan

Jost Van Dyke

St. John's

Santa Cruz de La Palma

Santa Cruz de Tenerife

+8 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Mar 9, 2027

1 Sailing

Mar 9, 2027

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

TCW EXCLUSIVE

14-night Transatlantic Cruise From San Juan, Puerto Rico

San Juan

Jost Van Dyke

St. John's

Santa Cruz de La Palma

Santa Cruz de Tenerife

+2 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Mar 9, 2027

1 Sailing

Mar 9, 2027

A breathtaking panoramic aerial view of the city of Mindelo on the island of São Vicente, Cape Verde, with its bustling harbor and town surrounded by rugged, volcanic hills.

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

TCW EXCLUSIVE

25-night Trans-Atlantic Cruise From Miami, Florida

Aboard

Silver Spirit

From

Miami, Florida

1 Sailing

Mar 19, 2027

1 Sailing

Mar 19, 2027

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

TCW EXCLUSIVE

26-night Mediterranean & Transatlantic Cruise From Monte Carlo, Monaco

Aboard

Silver Dawn

From

Monte Carlo, Monaco

1 Sailing

Nov 15, 2027

1 Sailing

Nov 15, 2027

A panoramic sunset shot of the beautiful harbor in Palma de Mallorca, Spain, with a marina full of boats and buildings on the surrounding hills.

Up to $5,000 Off + up to $600 Onboard Credit*

27-night Transatlantic Crossing Featuring Spain & the Caribbean Cruise From Civitavecchia, Rome, Italy

Rome (Civitavecchia)

Florence/Pisa (Livorno)

Aboard

Silver Nova

From

Civitavecchia, Rome, Italy

1 Sailing

Nov 21, 2027

1 Sailing

Nov 21, 2027

A panoramic shot of the colorful waterfront houses and palm trees of Key West, Florida, reflecting on the calm, turquoise water under a clear blue sky.

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

TCW EXCLUSIVE

7-night Caribbean Cruise From Miami, Florida

Aboard

Silver Shadow

From

Miami, Florida

4 Sailings

Nov 26 - Dec 17, 2027

4 Sailings

Nov 26 - Dec 17, 2027

Published prices from

$5,000

per person*

taxes & fees included

A stunning view of Santa Cruz de la Palma's black sand beach, with gentle waves from the Atlantic Ocean, a colorful town, and green, volcanic mountains in the background.

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

TCW EXCLUSIVE

14-night Transatlantic Cruise From Lisbon, Portugal

Lisbon

Funchal (Madeira)

Santa Cruz de La Palma

Santa Cruz de Tenerife

Sao Vicente (Mindelo)

+3 more

Aboard

Silver Dawn

From

Lisbon, Portugal

1 Sailing

Nov 27, 2027

1 Sailing

Nov 27, 2027

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

TCW EXCLUSIVE

26-night Transatlantic Cruise From Lisbon, Portugal

Lisbon

Gibraltar

St. Maarten (Philipsburg)

San Juan

Miami

+6 more

Aboard

Silver Nova

From

Lisbon, Portugal

1 Sailing

Dec 3, 2027

1 Sailing

Dec 3, 2027

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

TCW EXCLUSIVE

15-night Transatlantic Cruise From Lisbon, Portugal

Lisbon

Gibraltar

St. Maarten (Philipsburg)

San Juan

Miami

Aboard

Silver Nova

From

Lisbon, Portugal

1 Sailing

Dec 3, 2027

1 Sailing

Dec 3, 2027

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

TCW EXCLUSIVE

10-night Eastern Caribbean Cruise From San Juan, Puerto Rico

Aboard

Silver Dawn

From

San Juan, Puerto Rico

2 Sailings

Dec 11, 2027 - Jan 15, 2028

2 Sailings

Dec 11, 2027 - Jan 15, 2028

Published prices from

$5,100

per person*

taxes & fees included

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

TCW EXCLUSIVE

11-night Caribbean Cruise From Miami, Florida

Aboard

Silver Nova

From

Miami, Florida

7 Sailings

Dec 18, 2027 - Feb 22, 2028

7 Sailings

Dec 18, 2027 - Feb 22, 2028

Published prices from

$6,650

per person*

taxes & fees included

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

TCW EXCLUSIVE

8-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Silver Ray

From

Bridgetown, Barbados

1 Sailing

Dec 18, 2027

1 Sailing

Dec 18, 2027

Published prices from

$5,200

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

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

Aboard

Silver Dawn

From

San Juan, Puerto Rico

2 Sailings

Dec 21 - Dec 28, 2027

2 Sailings

Dec 21 - Dec 28, 2027

Published prices from

$4,100

per person*

taxes & fees included

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

TCW EXCLUSIVE

12-night Caribbean Cruise From Miami, Florida

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Dec 24, 2027

1 Sailing

Dec 24, 2027

Published prices from

$6,050

per person*

taxes & fees included

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

TCW EXCLUSIVE

8-night Caribbean Cruise From San Juan, Puerto Rico

Aboard

Silver Ray

From

San Juan, Puerto Rico

1 Sailing

Dec 26, 2027

1 Sailing

Dec 26, 2027

Published prices from

$5,800

per person*

taxes & fees included

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

TCW EXCLUSIVE

13-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Dec 28, 2027

1 Sailing

Dec 28, 2027

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

TCW EXCLUSIVE

12-night Caribbean Cruise From Miami, Florida

Aboard

Silver Ray

From

Miami, Florida

1 Sailing

Jan 3, 2028

1 Sailing

Jan 3, 2028

Published prices from

$6,800

per person*

taxes & fees included

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

TCW EXCLUSIVE

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

Aboard

Silver Dawn

From

San Juan, Puerto Rico

1 Sailing

Jan 4, 2028

1 Sailing

Jan 4, 2028

Published prices from

$5,200

per person*

taxes & fees included

A close-up view of the colorful stilt houses, known as palafitos, lining the waterfront of Castro, Chiloé Island, Chile, with their reflections visible in the calm water.

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

TCW EXCLUSIVE

41-night 2028 World Cruise Segment: Chapter 1, 2 & 3 From Miami, Florida

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Jan 5, 2028

1 Sailing

Jan 5, 2028

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

TCW EXCLUSIVE

10-night 2028 World Cruise Segment: Chapter 1 - Anthem of the Tropics From Miami, Florida

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Jan 5, 2028

1 Sailing

Jan 5, 2028

Published prices from

$6,300

per person*

taxes & fees included

Abu Dhabi skyline featuring modern skyscrapers.

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

TCW EXCLUSIVE

132-night 2028 World Cruise: An Ode to the Moment From Miami, Florida

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Jan 5, 2028

1 Sailing

Jan 5, 2028

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

TCW EXCLUSIVE

12-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Silver Spirit

From

Bridgetown, Barbados

3 Sailings

Jan 10 - Feb 17, 2028

3 Sailings

Jan 10 - Feb 17, 2028

Published prices from

$5,600

per person*

taxes & fees included

An aerial shot of the port city of Ushuaia, Argentina, at dusk, showing city lights along the Beagle Channel with the snow-capped Andes Mountains in the background.

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

TCW EXCLUSIVE

77-night Grand Voyage Cruise From Miami, Florida

Aboard

Silver Ray

From

Miami, Florida

1 Sailing

Jan 15, 2028

1 Sailing

Jan 15, 2028

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

TCW EXCLUSIVE

21-night Eastern & Southern Caribbean Cruise From San Juan, Puerto Rico

Aboard

Silver Dawn

From

San Juan, Puerto Rico

1 Sailing

Jan 15, 2028

1 Sailing

Jan 15, 2028

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

TCW EXCLUSIVE

7-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Silver Spirit

From

Bridgetown, Barbados

3 Sailings

Jan 22 - Mar 11, 2028

3 Sailings

Jan 22 - Mar 11, 2028

Published prices from

$4,100

per person*

taxes & fees included

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.

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

TCW EXCLUSIVE

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

Aboard

Silver Dawn

From

San Juan, Puerto Rico

1 Sailing

Jan 25, 2028

1 Sailing

Jan 25, 2028

Published prices from

$5,200

per person*

taxes & fees included

Up to $5,000 Off + up to $600 Onboard Credit*

9-night Southern Caribbean Featuring Anguilla & St. Kitts Cruise From San Juan, Puerto Rico

Aboard

Silver Dawn

From

San Juan, Puerto Rico

1 Sailing

Feb 10, 2028

1 Sailing

Feb 10, 2028

Published prices from

$4,900

per person*

taxes & fees included

Up to $5,000 Off + up to $600 Onboard Credit*

25-night Transatlantic Cruise From Miami, Florida

Aboard

Silver Nova

From

Miami, Florida

1 Sailing

Feb 22, 2028

1 Sailing

Feb 22, 2028

Up to $5,000 Off + up to $600 Onboard Credit*

8-night Southern Caribbean Featuring Anguilla & St. Kitts Cruise From San Juan, Puerto Rico

Aboard

Silver Dawn

From

San Juan, Puerto Rico

1 Sailing

Feb 24, 2028

1 Sailing

Feb 24, 2028

Published prices from

$4,900

per person*

taxes & fees included

A picturesque view of a small town nestled at the base of a lush, green mountain on Iles des Saintes, Guadeloupe, with boats moored in the deep blue water and fluffy clouds in the sky.

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

TCW EXCLUSIVE

18-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Silver Spirit

From

Bridgetown, Barbados

1 Sailing

Feb 29, 2028

1 Sailing

Feb 29, 2028

Up to $5,000 Off + up to $600 Onboard Credit*

11-night Eastern Caribbean Cruise From Miami, Florida

Aboard

Silver Dawn

From

Miami, Florida

1 Sailing

Mar 3, 2028

1 Sailing

Mar 3, 2028

Published prices from

$5,300

per person*

taxes & fees included

Up to $5,000 Off + up to $600 Onboard Credit*

10-night Eastern Caribbean Featuring St. Barts & Antugua Cruise From Miami, Florida

Aboard

Silver Dawn

From

Miami, Florida

1 Sailing

Mar 14, 2028

1 Sailing

Mar 14, 2028

Published prices from

$5,300

per person*

taxes & fees included

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

TCW EXCLUSIVE

26-night Transatlantic Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Silver Ray

From

Bridgetown, Barbados

1 Sailing

Mar 20, 2028

1 Sailing

Mar 20, 2028

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

TCW EXCLUSIVE

12-night Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)

Aboard

Silver Ray

From

Bridgetown, Barbados

1 Sailing

Mar 20, 2028

1 Sailing

Mar 20, 2028

Published prices from

$7,450

per person*

taxes & fees included

13-night Southern Caribbean Featuring St. Barts & Aruba Cruise From New York City, New York

Aboard

Silver Spirit

From

New York City, New York

1 Sailing

Oct 21, 2028

1 Sailing

Oct 21, 2028

Published prices from

$6,250

per person*

taxes & fees included

9-night Eastern Caribbean Featuring St. Barts & Antigua Cruise From Miami, Florida

Aboard

Silver Spirit

From

Miami, Florida

4 Sailings

Nov 3, 2028 - Mar 4, 2029

4 Sailings

Nov 3, 2028 - Mar 4, 2029

Published prices from

$4,150

per person*

taxes & fees included

12-night Eastern Caribbean Featuring St. Barts & St. Kitts Cruise From Miami, Florida

Aboard

Silver Spirit

From

Miami, Florida

3 Sailings

Nov 12, 2028 - Feb 20, 2029

3 Sailings

Nov 12, 2028 - Feb 20, 2029

Published prices from

$5,600

per person*

taxes & fees included

A scenic view of the twin lakes, Lagoa das Sete Cidades, on São Miguel Island in the Azores, with vibrant green vegetation and hydrangeas in the foreground and a small village and bridge in the distance.

13-night Transatlantic Crossing Featuring Portugal & the Caribbean Cruise From Lisbon, Portugal

Lisbon

Ponta Delgada (Azores)

Gustavia

Jost Van Dyke

San Juan

Aboard

Silver Shadow

From

Lisbon, Portugal

1 Sailing

Nov 24, 2028

1 Sailing

Nov 24, 2028

Published prices from

$4,200

per person*

taxes & fees included

12-night Eastern Caribbean Featuring Key West & Anguilla Cruise From Miami, Florida

Aboard

Silver Ray

From

Miami, Florida

1 Sailing

Dec 7, 2028

1 Sailing

Dec 7, 2028

Published prices from

$6,850

per person*

taxes & fees included

16-night Eastern Caribbean Featuring Les Saintes & St. Barts Cruise From San Juan, Puerto Rico

San Juan

Charlestown

St. Maarten (Philipsburg)

Iles des Saintes

Roseau

+5 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Dec 7, 2028

1 Sailing

Dec 7, 2028

9-night Eastern Caribbean Featuring Les Saintes & St. Barts Cruise From San Juan, Puerto Rico

San Juan

Charlestown

St. Maarten (Philipsburg)

Iles des Saintes

Roseau

+4 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Dec 7, 2028

1 Sailing

Dec 7, 2028

Published prices from

$5,300

per person*

taxes & fees included

10-night Eastern Caribbean Featuring St. Barts & Anguilla Cruise From Fort Lauderdale, Florida

Aboard

Silver Nova

From

Fort Lauderdale, Florida

2 Sailings

Dec 11, 2028 - Jan 3, 2029

2 Sailings

Dec 11, 2028 - Jan 3, 2029

Published prices from

$6,150

per person*

taxes & fees included

A secluded beach with bright turquoise water, palm trees, and a towering, dark limestone cliff on the coast of Samaná.

9-night Eastern Caribbean Featuring Dominican Republic & Grand Turk Cruise From Miami, Florida

Aboard

Silver Spirit

From

Miami, Florida

2 Sailings

Dec 13, 2028 - Feb 11, 2029

2 Sailings

Dec 13, 2028 - Feb 11, 2029

Published prices from

$4,300

per person*

taxes & fees included

7-night Eastern Caribbean Featuring Les Saintes & St. Barts Cruise From San Juan, Puerto Rico

St. Maarten (Philipsburg)

+2 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

5 Sailings

Dec 16, 2028 - Feb 10, 2029

5 Sailings

Dec 16, 2028 - Feb 10, 2029

Published prices from

$4,150

per person*

taxes & fees included

A scenic shot of the stunning Seven Mile Beach in Grand Cayman, with a wide, sandy beach, calm turquoise water, and resorts with palm trees under a beautiful blue sky.

16-night Eastern & Western Caribbean Featuring Key West Cruise From Miami, Florida

Miami

Cozumel

Grand Cayman (George Town)

Key West

Puerto Plata

+4 more

Aboard

Silver Ray

From

Miami, Florida

1 Sailing

Dec 19, 2028

1 Sailing

Dec 19, 2028

13-night Southern Caribbean Featuring Aruba & St. Barts Cruise From Fort Lauderdale, Florida

Aboard

Silver Nova

From

Fort Lauderdale, Florida

1 Sailing

Dec 21, 2028

1 Sailing

Dec 21, 2028

Published prices from

$9,250

per person*

taxes & fees included

A breathtaking panoramic view of Charlotte Amalie harbor in St. Thomas, with a cruise ship anchored in the bay, surrounded by rolling green hills and a colorful sunset.

11-night Eastern Caribbean Featuring Puerto Rico & St. Barts Cruise From Miami, Florida

Aboard

Silver Spirit

From

Miami, Florida

1 Sailing

Dec 22, 2028

1 Sailing

Dec 22, 2028

Published prices from

$5,750

per person*

taxes & fees included

14-night Eastern Caribbean Featuring Les Saintes & St. Barts Cruise From San Juan, Puerto Rico

St. Maarten (Philipsburg)

+6 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

2 Sailings

Dec 23, 2028 - Jan 27, 2029

2 Sailings

Dec 23, 2028 - Jan 27, 2029

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.

8-night Eastern Caribbean Featuring Puerto Rico & Dominican Republic Cruise From Miami, Florida

Aboard

Silver Ray

From

Miami, Florida

1 Sailing

Dec 27, 2028

1 Sailing

Dec 27, 2028

Published prices from

$5,600

per person*

taxes & fees included

A sunny, tropical beach on Grand Turk Island with multiple hot air balloons flying over the turquoise water and shoreline.

10-night Eastern Caribbean Featuring St. Barts & Anguilla Cruise From Miami, Florida

Aboard

Silver Ray

From

Miami, Florida

3 Sailings

Jan 4 - Feb 15, 2029

3 Sailings

Jan 4 - Feb 15, 2029

Published prices from

$6,100

per person*

taxes & fees included

10-night Southern Caribbean Featuring St. Kitts & Canouan Cruise From San Juan, Puerto Rico

San Juan

Rodney Bay

Bridgetown (Barbados)

St. George's

Canouan Island

+5 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

3 Sailings

Jan 6 - Mar 10, 2029

3 Sailings

Jan 6 - Mar 10, 2029

Published prices from

$5,850

per person*

taxes & fees included

10-night Eastern Caribbean Featuring St. Barts & Antigua Cruise From Miami, Florida

Aboard

Silver Spirit

From

Miami, Florida

1 Sailing

Jan 11, 2029

1 Sailing

Jan 11, 2029

Published prices from

$4,850

per person*

taxes & fees included

Colorful colonial balconies in Cartagena.

75-night Grand South America Cruise From Fort Lauderdale, Florida

Aboard

Silver Nova

From

Fort Lauderdale, Florida

1 Sailing

Jan 13, 2029

1 Sailing

Jan 13, 2029

9-night Southern Caribbean Featuring St. Barts & St. Lucia Cruise From Fort Lauderdale, Florida

Aboard

Silver Nova

From

Fort Lauderdale, Florida

1 Sailing

Jan 13, 2029

1 Sailing

Jan 13, 2029

Published prices from

$5,050

per person*

taxes & fees included

11-night Eastern Caribbean Featuring St. Barts & Anguilla Cruise From Miami, Florida

Aboard

Silver Ray

From

Miami, Florida

2 Sailings

Jan 14 - Feb 25, 2029

2 Sailings

Jan 14 - Feb 25, 2029

Published prices from

$6,700

per person*

taxes & fees included

11-night Southern Caribbean Featuring Aruba & Canouan Cruise From San Juan, Puerto Rico

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Jan 16, 2029

1 Sailing

Jan 16, 2029

Published prices from

$6,450

per person*

taxes & fees included

7-night Eastern Caribbean Featuring St. Barts & St. Kitts Cruise From San Juan, Puerto Rico

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Feb 3, 2029

1 Sailing

Feb 3, 2029

Published prices from

$4,350

per person*

taxes & fees included

11-night Eastern Caribbean Featuring Key West & St. Barts Cruise From Miami, Florida

Aboard

Silver Ray

From

Miami, Florida

1 Sailing

Feb 4, 2029

1 Sailing

Feb 4, 2029

Published prices from

$6,700

per person*

taxes & fees included

17-night Southern Caribbean Featuring Les Saintes & Canouan Juan Cruise From San Juan, Puerto Rico

St. Maarten (Philipsburg)

+11 more

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Feb 10, 2029

1 Sailing

Feb 10, 2029

25-night Transatlantic Crossing Featuring the Caribbean & Bermuda Cruise From Miami, Florida

Aboard

Silver Ray

From

Miami, Florida

1 Sailing

Feb 25, 2029

1 Sailing

Feb 25, 2029

11-night Southern Caribbean Featuring Aruba & Canouan Cruise From San Juan, Puerto Rico

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Feb 27, 2029

1 Sailing

Feb 27, 2029

Published prices from

$6,450

per person*

taxes & fees included

23-night Transatlantic Crossing Featuring the Caribbean & Spain Cruise From Miami, Florida

Aboard

Silver Spirit

From

Miami, Florida

1 Sailing

Mar 4, 2029

1 Sailing

Mar 4, 2029

Colorful houses on a hillside in Valparaíso, Chile.

32-night Transatlantic Crossing Featuring the Panama Canal & Bermuda Cruise From Valparaiso (Santiago), Chile

Santiago (Valparaiso)

Arica

Lima (Callao)

Fuerte Amador (Panama City)

Panama Canal

+7 more

Aboard

Silver Nova

From

Valparaiso (Santiago), Chile

1 Sailing

Mar 11, 2029

1 Sailing

Mar 11, 2029

A sunny, palm tree-lined park in Arica, Chile, with historic buildings and the prominent El Morro de Arica hill visible in the background.

18-night Central America Featuring the Panama Canal & Lima Cruise From Valparaiso (Santiago), Chile

Santiago (Valparaiso)

Arica

Lima (Callao)

Fuerte Amador (Panama City)

Panama Canal

+4 more

Aboard

Silver Nova

From

Valparaiso (Santiago), Chile

1 Sailing

Mar 11, 2029

1 Sailing

Mar 11, 2029

Published prices from

$13,500

per person*

taxes & fees included

14-night Transatlantic Crossing Featuring the Caribbean & Spain Cruise From San Juan, Puerto Rico

San Juan

Jost Van Dyke

St. John's

Santa Cruz de La Palma

Barcelona

Aboard

Silver Shadow

From

San Juan, Puerto Rico

1 Sailing

Mar 20, 2029

1 Sailing

Mar 20, 2029

Published prices from

$4,200

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.