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45 Results

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

14-night An Extended Journey Of Tropical Harmony & Natural Wonders From San Juan, Puerto Rico

San Juan
Road Bay
St. John's
St. Croix
Catalina Island/Casa de Campo
+6 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Nov 15, 2026

1 Sailing

Nov 15, 2026

Published prices from

$10,115

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
Seabourn logo

14-night Leeward Island Jewels Cruise From Miami, Florida

Miami
San Juan
Road Bay
Carambola Beach
Roseau
+6 more

Aboard

Seabourn Quest

From

Miami, Florida

2 Sailings

Nov 22 - Dec 6, 2026

2 Sailings

Nov 22 - Dec 6, 2026

Published prices from

$6,999

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.
Up to 40% Off + up to $1,300 Onboard Credit*
Explora Journeys Logo

7-night A Journey Of Caribbean Adventure & Shimmering Tropical Harmony From Miami, Florida

Miami
Cruz Bay
St. John's
Terre-de-Haut
St. Maarten (Philipsburg)
+2 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Nov 22, 2026

1 Sailing

Nov 22, 2026

Published prices from

$6,400

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

14-night An Extended Journey Of Sunlit Horizons & Sapphire Bays From Miami, Florida

Miami
Cruz Bay
St. John's
Terre-de-Haut
St. Maarten (Philipsburg)
+6 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Nov 22, 2026

1 Sailing

Nov 22, 2026

Published prices from

$9,650

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

14-night An Extended Journey Through Golden Shores & Island Grace From San Juan, Puerto Rico

San Juan
Roadtown
Basseterre
Gustavia
Grand Turk
+5 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Nov 29, 2026

1 Sailing

Nov 29, 2026

Published prices from

$8,220

per person*

taxes & fees included

A close-up of vibrant, traditional Mayan textiles from Santo Tomás de Castilla, Guatemala, featuring intricate, colorful hand-embroidered floral patterns on a dark fabric.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

15-night An Extended Journey Of Cultural Treasures & Seaside Harmony From Miami, Florida

Miami
Cozumel
Costa Maya
Santo Tomas de Castilla
Belize City
+7 more

Aboard

EXPLORA I

From

Miami, Florida

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 2026

Published prices from

$7,115

per person*

taxes & fees included

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.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

14-night Yachtsman's Caribbean In Depth Cruise From Philipsburg, St. Maarten, The Netherlands

St. Maarten (Philipsburg)
Sopers Hole
Carambola Beach
Trois Isles
Port Elizabeth (Bequia)
+7 more

Aboard

Seabourn Ovation

From

Philipsburg, St. Maarten, The Netherlands

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 2026

Published prices from

$5,899

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

14-night An Extended Journey Through Islands Of Scenic Wonder & Coastal History From Miami, Florida

Miami
Cruz Bay
St. John's
Terre-de-Haut
Gustavia
+5 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Dec 6, 2026

1 Sailing

Dec 6, 2026

Published prices from

$8,330

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 Colourful Treasures & Idyllic Island Scenery From Miami, Florida

Miami
Cruz Bay
St. John's
Terre-de-Haut
Gustavia
+2 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Dec 6, 2026

1 Sailing

Dec 6, 2026

Published prices from

$6,400

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.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

7-night Caribbean Gems Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Carambola Beach
Terre-de-Haut
St. Pierre
Roseau
+2 more

Aboard

Seabourn Ovation

From

Bridgetown, Barbados

2 Sailings

Dec 12, 2026 - Feb 6, 2027

2 Sailings

Dec 12, 2026 - Feb 6, 2027

Published prices from

$3,599

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

14-night An Extended Journey Of Island Calm & Coastal Retreats From Miami, Florida

Miami
Cruz Bay
St. John's
Terre-de-Haut
St. Maarten (Philipsburg)
+6 more

Aboard

EXPLORA I

From

Miami, Florida

1 Sailing

Dec 13, 2026

1 Sailing

Dec 13, 2026

Published prices from

$8,090

per person*

taxes & fees included

An aerial view of the vibrant red-roofed houses of Terre-de-Haut in Guadeloupe, with sailboats anchored in the turquoise bay and a small island nearby.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

7-night A Journey Of Caribbean Adventure & Shimmering Tropical Harmony From Miami, Florida

Miami
Cruz Bay
St. John's
Terre-de-Haut
St. Maarten (Philipsburg)
+2 more

Aboard

EXPLORA I

From

Miami, Florida

1 Sailing

Dec 13, 2026

1 Sailing

Dec 13, 2026

Published prices from

$5,850

per person*

taxes & fees included

An aerial view of Carambola Beach Resort in St. Croix, with red-roofed buildings nestled among lush green tropical trees along the turquoise Caribbean Sea.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Seabourn logo

16-night Leeward Island Holiday Cruise From Miami, Florida

Miami
San Juan
Road Bay
Carambola Beach
Marigot
+8 more

Aboard

Seabourn Quest

From

Miami, Florida

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 2026

Published prices from

$10,999

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

16-night An Extended Journey Through Enchanting Islands & Lush Landscapes From Miami, Florida

Miami
Cruz Bay
Gustavia
St. John's
Roadtown
+8 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Jan 5, 2027

1 Sailing

Jan 5, 2027

Published prices from

$12,960

per person*

taxes & fees included

A view of the volcanic black sand beach and coastline of St. Pierre, Martinique, with colorful buildings and a lush, mountainous landscape under a beautiful sky.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

16-night An Extended Journey Of Island Energy & Ocean Tranquillity From San Juan, Puerto Rico

San Juan
St. Maarten (Philipsburg)
Terre-de-Haut
St. George's
Castries
+7 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Jan 13, 2027

1 Sailing

Jan 13, 2027

Published prices from

$11,600

per person*

taxes & fees included

A vibrant panoramic view of Castries, St. Lucia, with colorful buildings nestled along the harbor and lush green hills in the background under a blue sky with white clouds.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

8-night A Journey Of Lively Caribbean Culture & Stunning Beaches From San Juan, Puerto Rico

San Juan
St. Maarten (Philipsburg)
Terre-de-Haut
St. George's
Castries
+3 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Jan 13, 2027

1 Sailing

Jan 13, 2027

Published prices from

$7,400

per person*

taxes & fees included

Cupecoy Beach with white resort buildings, St. Maarten.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

16-night An Extended Journey Through Ancient Marvels & Glittering Shores From Miami, Florida

Miami
Ocho Rios
Santo Tomas de Castilla
Roatan Island
Belize City
+7 more

Aboard

EXPLORA I

From

Miami, Florida

1 Sailing

Jan 20, 2027

1 Sailing

Jan 20, 2027

Published prices from

$9,000

per person*

taxes & fees included

A classic, two-story colonial building, the Abbey of Our Lady of Exile, with a red roof, a clock tower, and arches in Port of Spain, Trinidad and Tobago, under a cloudy blue sky.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

19-night An Extended Journey Of Caribbean Charms & Amazonian Wonders From Miami, Florida

Miami
Puerto Plata
St. Maarten (Philipsburg)
Terre-de-Haut
Basseterre
+10 more

Aboard

EXPLORA I

From

Miami, Florida

1 Sailing

Jan 29, 2027

1 Sailing

Jan 29, 2027

Published prices from

$11,735

per person*

taxes & fees included

An aerial view of the vibrant red-roofed houses of Terre-de-Haut in Guadeloupe, with sailboats anchored in the turquoise bay and a small island nearby.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

7-night A Journey Through Stunning Scenery & Charming Caribbean Culture From Miami, Florida

Miami
Puerto Plata
St. Maarten (Philipsburg)
Terre-de-Haut
Basseterre
+2 more

Aboard

EXPLORA I

From

Miami, Florida

1 Sailing

Jan 29, 2027

1 Sailing

Jan 29, 2027

Published prices from

$6,700

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

14-night An Extended Journey Of Natural Allure & Captivating Culture From Miami, Florida

Miami
St. Maarten (Philipsburg)
Gustavia
Basseterre
Cruz Bay
+6 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Feb 5, 2027

1 Sailing

Feb 5, 2027

Published prices from

$12,720

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

16-night An Extended Journey Of Relaxing Waters & Blissful Shores From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
St. John's
Terre-de-Haut
Puerto Plata
+5 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Feb 12, 2027

1 Sailing

Feb 12, 2027

Published prices from

$12,560

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

7-night A Journey Through Captivating Caribbean Culture & Sunlit Shores From San Juan, Puerto Rico

San Juan
St. Thomas (Charlotte Amalie)
St. John's
Terre-de-Haut
Puerto Plata
+2 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Feb 12, 2027

1 Sailing

Feb 12, 2027

Published prices from

$7,550

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

16-night An Extended Journey Of Pearl-Blue Horizons & Maritime Grace From Miami, Florida

Miami
Puerto Plata
Cayo Levantado
San Juan
Virgin Gorda
+6 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Feb 19, 2027

1 Sailing

Feb 19, 2027

Published prices from

$12,375

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

14-night An Extended Journey Through Azure Horizons & Elegant Isles From Miami, Florida

Miami
Cruz Bay
St. John's
Terre-de-Haut
St. Thomas (Charlotte Amalie)
+6 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Feb 28, 2027

1 Sailing

Feb 28, 2027

Published prices from

$10,725

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

7-night A Journey From Glorious Shorelines To Nature's Allure From Miami, Florida

Miami
Cruz Bay
St. John's
Terre-de-Haut
St. Thomas (Charlotte Amalie)
+2 more

Aboard

EXPLORA III

From

Miami, Florida

2 Sailings

Feb 28 - Mar 29, 2027

2 Sailings

Feb 28 - Mar 29, 2027

Published prices from

$6,800

per person*

taxes & fees included

    • Showing results 1 - 24 of 45

*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.