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Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.

25-night Canada & Caribbean Cruise From Montreal, Quebec

Halifax (Nova Scotia)

Aboard

Silver Shadow

From

Montreal, Quebec

1 Sailing

Oct 24, 2026

1 Sailing

Oct 24, 2026

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.

Windstar

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

Falmouth Harbour

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Oct 28, 2026

1 Sailing

Oct 28, 2026

Published prices from

$4,568

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.

11-night Eastern Caribbean Cruise From Miami, Florida

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

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 7, 2026

1 Sailing

Nov 7, 2026

Published prices from

$7,400

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.

Windstar

14-night Star Collector: Lovely Leewards Cruise From San Juan, Puerto Rico

St. Maarten (Philipsburg)

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

$4,070

per person*

taxes & fees included

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

Windstar

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

St. Maarten (Philipsburg)

Aboard

Star Pride

From

San Juan, Puerto Rico

9 Sailings

Nov 15, 2026 - Mar 20, 2028

9 Sailings

Nov 15, 2026 - Mar 20, 2028

Published prices from

$2,548

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.

11-night Eastern Caribbean Cruise From Miami, Florida

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

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 18, 2026

1 Sailing

Nov 18, 2026

Published prices from

$8,000

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.

14-night Caribbean Voyage: San Juan, Antigua & Barbados From San Juan, Puerto Rico

Port Elizabeth (Bequia)

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Nov 21, 2026

1 Sailing

Nov 21, 2026

Published prices from

$3,999

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.

Oceania Cruises

12-night Antillean Island Sojourn Voyage From Miami, Florida

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Vista

From

Miami, Florida

1 Sailing

Nov 25, 2026

1 Sailing

Nov 25, 2026

Published prices from

$4,462

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.

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

Bridgetown (Barbados)

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Nov 28, 2026

1 Sailing

Nov 28, 2026

Published prices from

$4,009

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.

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

St. Maarten (Philipsburg)

Aboard

Seven Seas Grandeur

From

Miami, Florida

1 Sailing

Nov 29, 2026

1 Sailing

Nov 29, 2026

Published prices from

$6,949

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.

11-night Eastern Caribbean Cruise From Miami, Florida

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

Aboard

Silver Shadow

From

Miami, Florida

1 Sailing

Nov 30, 2026

1 Sailing

Nov 30, 2026

Published prices from

$7,500

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.

Oceania Cruises

10-night Tropical Island Havens Voyage From Miami, Florida

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Allura

From

Miami, Florida

4 Sailings

Dec 2, 2026 - Mar 21, 2027

4 Sailings

Dec 2, 2026 - Mar 21, 2027

Published prices from

$3,899

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.

Windstar

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

St. Maarten (Philipsburg)

Falmouth Harbour

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.

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

$6,000

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

Oceania Cruises

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

St. Thomas (Charlotte Amalie)

Aboard

Marina

From

Miami, Florida

1 Sailing

Dec 10, 2026

1 Sailing

Dec 10, 2026

Published prices from

$3,400

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.

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

Aboard

Seven Seas Splendor

From

Galveston, Texas

1 Sailing

Dec 11, 2026

1 Sailing

Dec 11, 2026

Published prices from

$10,999

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.

11-night Eastern Caribbean Cruise From Miami, Florida

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

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

$8,300

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.

Oceania Cruises

9-night Sunlit Caribbean Gems Voyage From Miami, Florida

St. Thomas (Charlotte Amalie)

St. Maarten (Philipsburg)

Aboard

Allura

From

Miami, Florida

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$3,549

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.

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

Bridgetown (Barbados)

Aboard

Azamara Journey

From

Bridgetown, Barbados

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$4,399

per person*

taxes & fees included

A wide-angle view of the bustling harbor of Charlotte Amalie, St. Thomas, with many sailboats and yachts docked in the tranquil blue water, and the town's buildings climbing the lush green hills.

18-night Caribbean Holiday Voyage: San Juan, St. Barts & Curacao From San Juan, Puerto Rico

St. Thomas (Charlotte Amalie)

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Dec 18, 2026

1 Sailing

Dec 18, 2026

Published prices from

$5,529

per person*

taxes & fees included

A stunning view of Port Elizabeth in Bequia, St. Vincent and the Grenadines, with a sandy beach lined with palm trees and a building on the shore, and numerous sailboats anchored in the calm turquoise bay.

10-night Southern Caribbean Voyage: Antigua, St.Barts & Martinique From San Juan, Puerto Rico

St. Thomas (Charlotte Amalie)

Aboard

Azamara Journey

From

San Juan, Puerto Rico

1 Sailing

Dec 18, 2026

1 Sailing

Dec 18, 2026

Published prices from

$2,209

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.

Windstar

7-night Beach Fun & Sun: A Remote Caribbean Getaway Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

7 Sailings

Dec 19, 2026 - Mar 13, 2027

7 Sailings

Dec 19, 2026 - Mar 13, 2027

Published prices from

$2,623

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.

Windstar

14-night Star Collector: Caribbean Explorations Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Falmouth Harbour

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

14 Sailings

Dec 19, 2026 - Jan 23, 2028

14 Sailings

Dec 19, 2026 - Jan 23, 2028

Published prices from

$4,208

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.

Oceania Cruises

17-night Tropical Serenade Voyage From Miami, Florida

Aboard

Allura

From

Miami, Florida

1 Sailing

Dec 21, 2026

1 Sailing

Dec 21, 2026

Published prices from

$10,399

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.

Windstar

7-night Classic Caribbean Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

8 Sailings

Dec 26, 2026 - Nov 28, 2027

8 Sailings

Dec 26, 2026 - Nov 28, 2027

Published prices from

$2,432

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.