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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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

11-night Eastern Caribbean Cruise From Miami, Florida

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 18, 2026

1 Sailing

Nov 18, 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.

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

TCW EXCLUSIVE

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

$6,600

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

$4,600

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

TCW EXCLUSIVE

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

$6,200

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

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

$8,100

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

$5,400

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

TCW EXCLUSIVE

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

$5,900

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

$5,800

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

Published prices from

$7,500

per person*

taxes & fees included

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

$13,300

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

$6,500

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

$7,000

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

$10,100

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

$7,100

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

$6,900

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

$7,600

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

Published prices from

$7,200

per person*

taxes & fees included

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

Published prices from

$7,900

per person*

taxes & fees included

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

Published prices from

$11,400

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*+ 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

$8,000

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

Published prices from

$11,300

per person*

taxes & fees included

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

*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.

Silversea Cruises to Eastern Caribbean

Upcoming Silversea Cruises to Eastern Caribbean

11-night Eastern Caribbean Cruise From Miami, Florida

11-night Eastern Caribbean Cruise From Miami, Florida

$6,600

7-night Southern Caribbean Cruise From Bridgetown, Barbados

$4,600

10-night Caribbean Cruise From Miami, Florida

$6,200

11-night Eastern Caribbean Cruise From Miami, Florida

$8,100

10-night Southern Caribbean Cruise From Bridgetown, Barbados

$5,400

8-night Caribbean Cruise From Bridgetown, Barbados

$5,900

14-night Caribbean Cruise From San Juan, Puerto Rico

7-night Caribbean Cruise From San Juan, Puerto Rico

$5,800

8-night Caribbean Cruise From Bridgetown, Barbados

$7,500

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

$13,300

8-night Caribbean Cruise From San Juan, Puerto Rico

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

$6,500

11-night Caribbean Cruise From Bridgetown, Barbados

$7,000

76-night Grand Voyage From Miami, Florida

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

$10,100

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

$7,100

10-night Southern Caribbean Cruise From Bridgetown, Barbados

$6,900

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

$7,600

12-night Southern Caribbean Cruise From Bridgetown, Barbados

$7,200

12-night Southern Caribbean Cruise From Miami, Florida

$7,900

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

$11,400

10-night Caribbean Cruise From Bridgetown, Barbados

$8,000

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

$11,300

23-night Transatlantic Cruise From San Juan, Puerto Rico

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