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18 Results

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

12-night Antillean Island Sojourn Voyage From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
Gustavia
Fort de France
+4 more

Aboard

Vista

From

Miami, Florida

1 Sailing

Nov 25, 2026

1 Sailing

Nov 25, 2026

Published prices from

$5,199

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

10-night Tropical Island Havens Voyage From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Gustavia
St. Maarten (Philipsburg)
Frederiksted
+2 more

Aboard

Allura

From

Miami, Florida

4 Sailings

Dec 2, 2026 - Mar 21, 2027

4 Sailings

Dec 2, 2026 - Mar 21, 2027

Published prices from

$4,849

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

Cupecoy Beach with white resort buildings, St. Maarten.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Oceania Cruises

9-night Sunlit Caribbean Gems Voyage From Miami, Florida

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

Aboard

Allura

From

Miami, Florida

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$3,949

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

$11,349

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

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

$3,399

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

A unique architectural close-up of Casapueblo, a white plaster Mediterranean-style villa and museum built by Carlos Páez Vilaró on the cliffs of Punta del Este, Uruguay, against a clear blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Oceania Cruises

71-night Grand South America Adventure Voyage From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Roadtown
St. Maarten (Philipsburg)
Gustavia
+40 more

Aboard

Oceania Aurelia

From

Miami, Florida

1 Sailing

Oct 27, 2028

1 Sailing

Oct 27, 2028

Published prices from

$37,399

per person*

taxes & fees included

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
Oceania Cruises

22-night Connoisseur's Caribbean Voyage From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Gustavia
St. John's
Fort de France
+9 more

Aboard

Vista

From

Miami, Florida

1 Sailing

Nov 13, 2028

1 Sailing

Nov 13, 2028

Published prices from

$8,699

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
Oceania Cruises

12-night Leeward Jewels & Legends Voyage From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Gustavia
St. John's
Fort de France
+4 more

Aboard

Vista

From

Miami, Florida

1 Sailing

Nov 13, 2028

1 Sailing

Nov 13, 2028

Published prices from

$4,899

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
Oceania Cruises

12-night Lush Peaks & Coral Sands Voyage From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Gustavia
St. John's
Fort de France
+4 more

Aboard

Vista

From

Miami, Florida

1 Sailing

Dec 16, 2028

1 Sailing

Dec 16, 2028

Published prices from

$5,499

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
Oceania Cruises

22-night Caribbean Holiday Tapestry Voyage From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Gustavia
St. John's
Fort de France
+9 more

Aboard

Vista

From

Miami, Florida

1 Sailing

Dec 16, 2028

1 Sailing

Dec 16, 2028

Published prices from

$10,149

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
TCW EXCLUSIVE
Oceania Cruises

9-night Sunlit Caribbean Gems Voyage From Miami, Florida

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

Aboard

Vista

From

Miami, Florida

1 Sailing

Feb 7, 2029

1 Sailing

Feb 7, 2029

Published prices from

$4,299

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.