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37 Results

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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.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

14-night Dutchman's Caribbean Voyage From Miami, Florida

Miami
Grand Cayman (George Town)
Falmouth (Jamaica)
Oranjestad
Willemstad
+5 more

Aboard

Vista

From

Miami, Florida

1 Sailing

Nov 11, 2026

1 Sailing

Nov 11, 2026

Published prices from

$5,649

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

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

17-night Tropical Serenade Voyage From Miami, Florida

Miami
Costa Maya
Roatan Island
Harvest Caye
Cozumel
+6 more

Aboard

Allura

From

Miami, Florida

1 Sailing

Dec 21, 2026

1 Sailing

Dec 21, 2026

Published prices from

$11,399

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.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

14-night Caribbean Celebration Voyage From Miami, Florida

Miami
Grand Cayman (George Town)
Montego Bay
Oranjestad
Willemstad
+5 more

Aboard

Marina

From

Miami, Florida

1 Sailing

Dec 22, 2026

1 Sailing

Dec 22, 2026

Published prices from

$4,699

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

9-night Alluring Antilles Voyage From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Basseterre
Roadtown

Aboard

Allura

From

Miami, Florida

1 Sailing

Jan 27, 2027

1 Sailing

Jan 27, 2027

Published prices from

$5,799

per person*

taxes & fees included

Oranjestad, Aruba harbor with boats and colorful Dutch architecture.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

12-night Exotic Caribbean Escape Voyage From Miami, Florida

Miami
Oranjestad
Willemstad
St. Vincent (Kingstown)
Castries
+4 more

Aboard

Marina

From

Miami, Florida

1 Sailing

Feb 1, 2027

1 Sailing

Feb 1, 2027

Published prices from

$3,949

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
Oceania Cruises

7-night Yachtsman's Harbors Voyage From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
St. John's
Basseterre
+2 more

Aboard

Allura

From

Miami, Florida

1 Sailing

Feb 5, 2027

1 Sailing

Feb 5, 2027

Published prices from

$4,149

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

20-night Sju to Mia Voyage From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Basseterre
St. John's
+10 more

Aboard

Allura

From

San Juan, Puerto Rico

1 Sailing

Feb 19, 2027

1 Sailing

Feb 19, 2027

Published prices from

$11,349

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

8-night Caribbean Essence Voyage From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Basseterre
St. John's
+3 more

Aboard

Allura

From

San Juan, Puerto Rico

1 Sailing

Feb 19, 2027

1 Sailing

Feb 19, 2027

Published prices from

$4,299

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

10-night Golden Caribbean Strands Voyage From Miami, Florida

Miami
San Juan
Basseterre
St. Maarten (Philipsburg)
Roadtown
+3 more

Aboard

Marina

From

Miami, Florida

1 Sailing

Feb 23, 2027

1 Sailing

Feb 23, 2027

Published prices from

$4,149

per person*

taxes & fees included

A vibrant orange and red sunset over the tranquil harbor in Sydney, Nova Scotia, with the setting sun reflecting on the water.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

27-night East Coast Escapade Voyage From Montreal, Quebec

Montreal
Quebec City
Saguenay
Baie-Comeau (Comeau Bay)
Havre-Saint-Pierre
+16 more

Aboard

Sirena

From

Montreal, Quebec

1 Sailing

Oct 25, 2027

1 Sailing

Oct 25, 2027

Published prices from

$8,899

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
Oceania Cruises

15-night Broadway To The Abc Islands Voyage From New York City, New York

New York City
Roadtown
St. John's
Basseterre
Kralendijk
+6 more

Aboard

Sirena

From

New York City, New York

1 Sailing

Nov 6, 2027

1 Sailing

Nov 6, 2027

Published prices from

$4,149

per person*

taxes & fees included

The ancient stone ruins of a majestic Mayan temple or pyramid, featuring historic architecture at an archaeological site in Mexico's Costa Maya region.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

31-night Loving The Island Life Voyage From Miami, Florida

Miami
Cozumel
Roatan Island
Harvest Caye
Costa Maya
+16 more

Aboard

Sirena

From

Miami, Florida

1 Sailing

Nov 21, 2027

1 Sailing

Nov 21, 2027

Published prices from

$8,649

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.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

12-night Beach-Blessed Isles Voyage From Miami, Florida

Miami
Nassau
Puerto Plata
San Juan
St. Thomas (Charlotte Amalie)
+5 more

Aboard

Sirena

From

Miami, Florida

1 Sailing

Dec 10, 2027

1 Sailing

Dec 10, 2027

Published prices from

$3,499

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
Oceania Cruises

21-night Holiday Horizons Voyage From Miami, Florida

Miami
Costa Maya
Belize City
Roatan Island
Cozumel
+8 more

Aboard

Marina

From

Miami, Florida

1 Sailing

Dec 20, 2027

1 Sailing

Dec 20, 2027

Published prices from

$5,499

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.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

10-night Fantasy Islands Voyage From Miami, Florida

Miami
Nassau
San Juan
Roadtown
Basseterre
+4 more

Aboard

Marina

From

Miami, Florida

1 Sailing

Dec 27, 2027

1 Sailing

Dec 27, 2027

Published prices from

$3,499

per person*

taxes & fees included

Hollywood sign on hills of Los Angeles.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Oceania Cruises

44-night Sun, Sand & Seas of Stars Voyage From Los Angeles, California

Los Angeles
Ensenada
Cabo San Lucas
Acapulco
Puerto Quetzal
+21 more

Aboard

Oceania Sonata

From

Los Angeles, California

1 Sailing

Jan 6, 2028

1 Sailing

Jan 6, 2028

Published prices from

$22,449

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
Oceania Cruises

10-night Caribbean Splendor Voyage From Miami, Florida

Miami
San Juan
St. Thomas (Charlotte Amalie)
Basseterre
Pointe A Pitre
+2 more

Aboard

Oceania Sonata

From

Miami, Florida

1 Sailing

Feb 2, 2028

1 Sailing

Feb 2, 2028

Published prices from

$4,799

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Oceania Cruises

10-night Paradise at Sea Voyage From Miami, Florida

Miami
Nassau
San Juan
Basseterre
St. John's
+4 more

Aboard

Marina

From

Miami, Florida

1 Sailing

Feb 7, 2028

1 Sailing

Feb 7, 2028

Published prices from

$3,599

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Oceania Cruises

17-night Caribbean Carried Away Voyage From Miami, Florida

Miami
Puerto Plata
San Juan
Frederiksted
Basseterre
+7 more

Aboard

Marina

From

Miami, Florida

1 Sailing

Feb 17, 2028

1 Sailing

Feb 17, 2028

Published prices from

$5,449

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
Oceania Cruises

10-night Splendid Sunsets Voyage From Miami, Florida

Miami
Puerto Plata
San Juan
Frederiksted
Basseterre
+3 more

Aboard

Marina

From

Miami, Florida

1 Sailing

Feb 17, 2028

1 Sailing

Feb 17, 2028

Published prices from

$3,449

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
Oceania Cruises

11-night Caribbean Island Tapestry Voyage From Miami, Florida

Miami
Puerto Plata
San Juan
St. Thomas (Charlotte Amalie)
Basseterre
+4 more

Aboard

Oceania Sonata

From

Miami, Florida

1 Sailing

Feb 19, 2028

1 Sailing

Feb 19, 2028

Published prices from

$5,299

per person*

taxes & fees included

A breathtaking underwater view of a coral reef with multiple schools of fish swimming over the colorful and diverse marine ecosystem near Roatan Island, Honduras.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Oceania Cruises

17-night Tropical Triumph Voyage From Miami, Florida

Miami
Puerto Plata
San Juan
St. Thomas (Charlotte Amalie)
Basseterre
+7 more

Aboard

Oceania Sonata

From

Miami, Florida

1 Sailing

Mar 1, 2028

1 Sailing

Mar 1, 2028

Published prices from

$7,799

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Oceania Cruises

10-night Tropical Coves Voyage From Miami, Florida

Miami
Puerto Plata
San Juan
St. Thomas (Charlotte Amalie)
Basseterre
+3 more

Aboard

Oceania Sonata

From

Miami, Florida

1 Sailing

Mar 1, 2028

1 Sailing

Mar 1, 2028

Published prices from

$4,799

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
Oceania Cruises

12-night Caribbean Breezes Voyage From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Roadtown
St. Maarten (Philipsburg)
Gustavia
+7 more

Aboard

Oceania Aurelia

From

Miami, Florida

1 Sailing

Oct 27, 2028

1 Sailing

Oct 27, 2028

Published prices from

$5,749

per person*

taxes & fees included

    • Showing results 1 - 24 of 37

*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.