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14 Results

Taxes and fees included in all prices shown

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Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

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

Miami
Grand Turk
Basseterre
Oranjestad
Kralendijk
+4 more

Aboard

Silver Ray

From

Miami, Florida

1 Sailing

Dec 22, 2026

1 Sailing

Dec 22, 2026

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
Silversea logo

7-night Caribbean Cruise From Miami, Florida

Miami
Great Exuma
Grand Turk
Bimini
Key West

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

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Silversea logo

12-night Caribbean Cruise From Miami, Florida

Miami
Great Exuma
Samaná
San Juan
St. John (U.S.V.I.)
+4 more

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

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
Silversea logo

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

Miami
St. John (U.S.V.I.)
Gustavia
St. John's
Grand Turk

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

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.
Silversea logo

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

Miami
Key West
St. John (U.S.V.I.)
St. John's
Anguilla
+4 more

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

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.
Silversea logo

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

Ft. Lauderdale
Grand Turk
Anguilla
St. John's
Gustavia
+2 more

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.
Silversea logo

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

Miami
Bimini
Puerto Plata
Samaná
La Romana
+2 more

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

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.
Silversea logo

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

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.
Silversea logo

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

Miami
Grand Turk
St. John (U.S.V.I.)
Gustavia
Anguilla
+3 more

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

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.
Silversea logo

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

Miami
Puerto Plata
Samaná
San Juan
Grand Turk

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.
Silversea logo

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

Miami
Grand Turk
Gustavia
St. John's
Anguilla
+2 more

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

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.
Silversea logo

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

Miami
Grand Turk
Virgin Gorda
Gustavia
St. John's
+3 more

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

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

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

Miami
Grand Turk
Virgin Gorda
St. John's
Gustavia
+6 more

Aboard

Silver Ray

From

Miami, Florida

1 Sailing

Feb 25, 2029

1 Sailing

Feb 25, 2029

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.
Silversea logo

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

Miami
St. John (U.S.V.I.)
Gustavia
St. John's
Grand Turk
+5 more

Aboard

Silver Spirit

From

Miami, Florida

1 Sailing

Mar 4, 2029

1 Sailing

Mar 4, 2029

*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.