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14 Results

Taxes and fees included in all prices shown

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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

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

$11,149

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
Regent Seven Seas Cruises.

10-night Caribbean Mystique Cruise From San Juan, Puerto Rico

San Juan
Roadtown
Basseterre
St. John's
Gustavia
+6 more

Aboard

Seven Seas Prestige

From

San Juan, Puerto Rico

1 Sailing

Mar 30, 2027

1 Sailing

Mar 30, 2027

Published prices from

$6,849

per person*

taxes & fees included

A picturesque view of Avalon Harbor on Catalina Island, California, with sailboats and yachts moored in the bay in front of a hillside village.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

7-night A Journey Across the Caribbean's Colourful Heart From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
Catalina Island/Casa de Campo
Puerto Plata
Key West
+3 more

Aboard

EXPLORA IV

From

San Juan, Puerto Rico

1 Sailing

Nov 13, 2027

1 Sailing

Nov 13, 2027

Published prices from

$4,200

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

7-night A Journey Through Shimmering Island History & Mesmerisingly Cultures From San Juan, Puerto Rico

San Juan
Gustavia
Virgin Gorda
St. Thomas (Charlotte Amalie)
Cayo Levantado
+3 more

Aboard

EXPLORA IV

From

San Juan, Puerto Rico

1 Sailing

Nov 27, 2027

1 Sailing

Nov 27, 2027

Published prices from

$4,200

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Azamara logo

17-night Eastern & Southern Caribbean Cruise: Grenada, Barbados & Aruba From San Juan, Puerto Rico

San Juan
Virgin Gorda
St. John's
Portsmouth
Port Elizabeth (Bequia)
+10 more

Aboard

Azamara Quest

From

San Juan, Puerto Rico

1 Sailing

Dec 19, 2027

1 Sailing

Dec 19, 2027

Published prices from

$5,729

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

7-night A Journey of Salsa Beats, Spectacular Fireworks & Dominican Charm From San Juan, Puerto Rico

San Juan
Cruz Bay
Cayo Levantado
Puerto Plata
Ocean Cay
+2 more

Aboard

EXPLORA IV

From

San Juan, Puerto Rico

1 Sailing

Dec 30, 2027

1 Sailing

Dec 30, 2027

Published prices from

$5,160

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

7-night A Journey to Island Rhythms & Tranquil Bahamian Bliss From San Juan, Puerto Rico

San Juan
Roadtown
Pointe A Pitre
Gustavia
Ocean Cay
+2 more

Aboard

EXPLORA II

From

San Juan, Puerto Rico

2 Sailings

Jan 2 - Jan 23, 2028

2 Sailings

Jan 2 - Jan 23, 2028

Published prices from

$4,020

per person*

taxes & fees included

An idyllic, wide-angle photo of a beautiful white sand beach at Ocean Cay MSC Marine Reserve in The Bahamas. The foreground features soft, white sand leading to shallow turquoise water. Several upright palm trees are visible on the left, casting shadows, and the background shows the vast, clear blue ocean meeting a horizon under a sky with scattered white clouds.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

7-night A Journey Through the Caribbean's Elegant Charm & Vibrant Soul From San Juan, Puerto Rico

San Juan
Gustavia
St. Thomas (Charlotte Amalie)
Cayo Levantado
Puerto Plata
+3 more

Aboard

EXPLORA IV

From

San Juan, Puerto Rico

1 Sailing

Jan 22, 2028

1 Sailing

Jan 22, 2028

Published prices from

$4,020

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

7-night A Journey Of Intimate Island Bliss & Caribbean Breeze From San Juan, Puerto Rico

San Juan
Gustavia
St. Thomas (Charlotte Amalie)
Virgin Gorda
Ocean Cay
+2 more

Aboard

EXPLORA IV

From

San Juan, Puerto Rico

1 Sailing

Feb 5, 2028

1 Sailing

Feb 5, 2028

Published prices from

$4,020

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

7-night A Journey Across Turquoise Seas And Timeless Streets From San Juan, Puerto Rico

San Juan
St. Maarten (Philipsburg)
Terre-de-Haut
Road Bay
Ocean Cay
+2 more

Aboard

EXPLORA IV

From

San Juan, Puerto Rico

1 Sailing

Feb 19, 2028

1 Sailing

Feb 19, 2028

Published prices from

$4,200

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

A Journey Through The Caribbean's Rich History & Palm-Shaded Paradise From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
Cayo Levantado
Puerto Plata
Key West
+3 more

Aboard

EXPLORA IV

From

San Juan, Puerto Rico

1 Sailing

Mar 4, 2028

1 Sailing

Mar 4, 2028

Published prices from

$4,020

per person*

taxes & fees included

A stunning panoramic view of Road Town on Tortola, British Virgin Islands, showing the harbor filled with boats and a small town surrounded by lush green hills overlooking the Caribbean Sea.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

7-night A Journey Through Tropical Utopia & Rhythmic Streets From San Juan, Puerto Rico

San Juan
Roadtown
Gustavia
St. Croix
Ocean Cay
+2 more

Aboard

EXPLORA II

From

San Juan, Puerto Rico

1 Sailing

Mar 12, 2028

1 Sailing

Mar 12, 2028

Published prices from

$4,020

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.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

7-night A Journey Through Historical Gems & Idyllic Coastlines From San Juan, Puerto Rico

San Juan
Cruz Bay
Pointe A Pitre
Marigot
Ocean Cay
+2 more

Aboard

EXPLORA IV

From

San Juan, Puerto Rico

3 Sailings

Mar 18 - Apr 29, 2028

3 Sailings

Mar 18 - Apr 29, 2028

Published prices from

$3,755

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.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

7-night A Journey Through The Caribbean's Rich History & Palm-Shaded Paradise From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
Cayo Levantado
Puerto Plata
Key West
+3 more

Aboard

EXPLORA IV

From

San Juan, Puerto Rico

1 Sailing

Apr 1, 2028

1 Sailing

Apr 1, 2028

Published prices from

$4,020

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.