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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 Blissful Escapes & Shoreline Splendour From Miami, Florida

Miami
Providenciales
Puerto Plata
Casa de Campo
Jost Van Dyke
+7 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Nov 8, 2026

1 Sailing

Nov 8, 2026

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

5-night A Journey Through Tropical Shores And Ocean Days From St. John's, Antigua and Barbuda

St. John's
Road Bay
San Juan
Miami

Aboard

EXPLORA I

From

St. John's, Antigua and Barbuda

1 Sailing

Nov 12, 2026

1 Sailing

Nov 12, 2026

Published prices from

$4,200

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

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

$15,785

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 Blissful Escapes & Island Splendour From San Juan, Puerto Rico

San Juan
Road Bay
St. John's
St. Croix
Catalina Island/Casa de Campo
+3 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Nov 15, 2026

1 Sailing

Nov 15, 2026

Published prices from

$7,450

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 Road Bay, Anguilla, showing a pristine white sand beach, lush green vegetation, and the stunningly clear turquoise water of the Caribbean Sea.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

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

Lisbon
St. John's
St. Maarten (Philipsburg)
Falmouth Harbour
Gustavia
+5 more

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Dec 5, 2026

1 Sailing

Dec 5, 2026

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

$7,560

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 idyllic white-sand beach with turquoise water and palm trees on Jost Van Dyke, with a lush green hill in the background.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

15-night An Extended Journey Through Wild Beauty And Tropical Festivities From San Juan, Puerto Rico

San Juan
Road Bay
St. John's
Basseterre
Grand Turk
+7 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Dec 13, 2026

1 Sailing

Dec 13, 2026

Published prices from

$10,255

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 Caribbean Gems & Multi-Coloured Coasts From San Juan, Puerto Rico

San Juan
Road Bay
St. John's
Basseterre
Grand Turk
+2 more

Aboard

EXPLORA III

From

San Juan, Puerto Rico

1 Sailing

Dec 13, 2026

1 Sailing

Dec 13, 2026

Published prices from

$6,100

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
Windstar

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

St. Maarten (Philipsburg)
Falmouth Harbour
Gustavia
Road Bay
Sopers Hole
+7 more

Aboard

Wind Surf

From

Philipsburg, St. Maarten, The Netherlands

13 Sailings

Dec 19, 2026 - Mar 13, 2027

13 Sailings

Dec 19, 2026 - Mar 13, 2027

Published prices from

$5,280

per person*

taxes & fees included

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

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

St. Maarten (Philipsburg)
Falmouth Harbour
Gustavia
Road Bay
Sopers Hole
+2 more

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

$2,726

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

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

15-night An Extended Journey Into Island Bliss & Lively Celebrations From San Juan, Puerto Rico

San Juan
Basseterre
Roadtown
Gustavia
Road Bay
+7 more

Aboard

EXPLORA I

From

San Juan, Puerto Rico

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 2026

Published prices from

$12,365

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 Caribbean Celebrations & Island Wonders From San Juan, Puerto Rico

San Juan
Basseterre
Roadtown
Gustavia
Road Bay
+2 more

Aboard

EXPLORA I

From

San Juan, Puerto Rico

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 2026

Published prices from

$7,000

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

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

15-night An Extended Journey Through Caribbean Treasures & Peaceful Nature From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Road Bay
St. Pierre
Basseterre
+7 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Jan 21, 2027

1 Sailing

Jan 21, 2027

Published prices from

$9,635

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

8-night A Journey Of Sunny Shores & Caribbean Island Bliss From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Road Bay
St. Pierre
Basseterre
+3 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Jan 21, 2027

1 Sailing

Jan 21, 2027

Published prices from

$7,800

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

$15,260

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

19-night An Extended Journey Of Rainforest Wonders & Ocean Serenity From Manaus (Amazon River), Brazil

Manaus (Amazon River)
Parintins (Amazon River)
Alter Do Chão (Amazon River)
Macapa (Amazon River)
Devil's Island
+12 more

Aboard

EXPLORA I

From

Manaus (Amazon River), Brazil

1 Sailing

Feb 17, 2027

1 Sailing

Feb 17, 2027

Published prices from

$12,710

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

$15,035

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

9-night A Journey Through Caribbean Delights & Wildlife Wonders From Miami, Florida

Miami
Puerto Plata
Cayo Levantado
San Juan
Virgin Gorda
+2 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Feb 19, 2027

1 Sailing

Feb 19, 2027

Published prices from

$8,350

per person*

taxes & fees included

A sunny, tropical beach on Grand Turk Island with multiple hot air balloons flying over the turquoise water and shoreline.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

23-night A Grand Journey Into Island Whispers & Beauty-Rich Shores From San Juan, Puerto Rico

San Juan
St. John's
Road Bay
Virgin Gorda
Grand Turk
+7 more

Aboard

EXPLORA I

From

San Juan, Puerto Rico

1 Sailing

Mar 1, 2027

1 Sailing

Mar 1, 2027

Published prices from

$12,825

per person*

taxes & fees included

A snorkeler swims in the turquoise waters of the Baths National Park on Virgin Gorda, surrounded by massive granite boulders and palm trees.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

7-night A Journey From Exciting Escapades To Idyllic Tranquillity From San Juan, Puerto Rico

San Juan
St. John's
Road Bay
Virgin Gorda
Grand Turk
+2 more

Aboard

EXPLORA I

From

San Juan, Puerto Rico

1 Sailing

Mar 1, 2027

1 Sailing

Mar 1, 2027

Published prices from

$6,200

per person*

taxes & fees included

The picturesque fishing village of Deshaies, Guadeloupe, with its colorful waterfront and red-roofed church nestled on a tranquil bay.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

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

Lisbon
Funchal (Madeira)
Jost Van Dyke
St. Maarten (Philipsburg)
Gustavia
+6 more

Aboard

Wind Surf

From

Lisbon, Portugal

1 Sailing

Nov 5, 2027

1 Sailing

Nov 5, 2027

Published prices from

$4,813

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.