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18 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 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

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

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

16-night An Extended Journey Of Sparkling Skies & Dramatic Natural Beauty From Miami, Florida

Miami
Ocho Rios
Catalina Island/Casa de Campo
Jost Van Dyke
St. Maarten (Philipsburg)
+8 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 2026

An elevated panoramic shot of the beautiful Ocho Rios Bay in Jamaica, showing a large cruise ship docked at the pier, a sandy beach, and luxury resorts under a blue sky.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

8-night A Journey Of Tropical Festivities & Dazzling Island Beauty From Miami, Florida

Miami
Ocho Rios
Catalina Island/Casa de Campo
Jost Van Dyke
St. Maarten (Philipsburg)
+3 more

Aboard

EXPLORA III

From

Miami, Florida

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 2026

Published prices from

$7,550

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

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 Through Island Joys & Volcanic Majesty From Miami, Florida

Miami
Puerto Plata
Catalina Island/Casa de Campo
Cruz Bay
San Juan
+8 more

Aboard

EXPLORA I

From

Miami, Florida

1 Sailing

Dec 27, 2026

1 Sailing

Dec 27, 2026

Published prices from

$12,320

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

8-night A Journey Of Sparkling Skies & Bright Beginnings From Miami, Florida

Miami
Puerto Plata
Catalina Island/Casa de Campo
Cruz Bay
San Juan
+4 more

Aboard

EXPLORA I

From

Miami, Florida

1 Sailing

Dec 27, 2026

1 Sailing

Dec 27, 2026

Published prices from

$8,350

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

$5,900

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*+ 2 more offers
TCW EXCLUSIVE
Windstar

21-night Star Collector Cruise: Windward Islands, Spanish Cities & Costa Rica From San Juan, Puerto Rico

San Juan
St. George's
Bequia
Mayreau
Iles des Saintes
+13 more

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 22, 2027

1 Sailing

Nov 22, 2027

Published prices from

$7,460

per person*

taxes & fees included

A high-angle view of the bustling harbor of Marigot, St. Martin, with boats and yachts docked along the coast and colorful buildings nestled against the green hills.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

14-night Star Collector Cruise: Caribbean Islands & Colombian Coast Discovery From San Juan, Puerto Rico

San Juan
St. George's
Bequia
Mayreau
Iles des Saintes
+7 more

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 22, 2027

1 Sailing

Nov 22, 2027

Published prices from

$4,197

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
Windstar

14-night Star Collector: Coffee, Canal & Callaloo: Central America, Colombia & The Caribbean Cruise From San Juan, Puerto Rico

San Juan
Catalina Island/Casa de Campo
Santo Domingo
Cartagena (Colombia)
San Blas Islands
+8 more

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 29, 2027

1 Sailing

Nov 29, 2027

Published prices from

$5,434

per person*

taxes & fees included

This is a scenic image of a tropical beach in Santo Domingo, with multiple colorful fishing boats resting on the sandy shore, tall palm trees, and the calm turquoise sea under a bright, clear sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

7-night The Spanish Main: Rise Of The New World Cruise From San Juan, Puerto Rico

San Juan
Catalina Island/Casa de Campo
Santo Domingo
Cartagena (Colombia)
San Blas Islands
+2 more

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Nov 29, 2027

1 Sailing

Nov 29, 2027

Published prices from

$2,416

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 Into Timeless Marvels & Historial Tales of the West Indies From Miami, Florida

Miami
Puerto Plata
Catalina Island/Casa de Campo
St. Thomas (Charlotte Amalie)
St. John's
+3 more

Aboard

EXPLORA II

From

Miami, Florida

1 Sailing

Dec 12, 2027

1 Sailing

Dec 12, 2027

Published prices from

$5,500

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 of Underwater Jewels & Captivating New Year's Eve Celebration From Miami, Florida

Miami
Puerto Plata
Catalina Island/Casa de Campo
St. Croix
St. Thomas (Charlotte Amalie)
+3 more

Aboard

EXPLORA II

From

Miami, Florida

1 Sailing

Dec 26, 2027

1 Sailing

Dec 26, 2027

Published prices from

$7,850

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 From Dominican Rhythms & Tranquil Bahamian Bliss From Miami, Florida

Miami
Puerto Plata
Catalina Island/Casa de Campo
St. Thomas (Charlotte Amalie)
Marigot
+3 more

Aboard

EXPLORA II

From

Miami, Florida

1 Sailing

Jan 9, 2028

1 Sailing

Jan 9, 2028

Published prices from

$3,655

per person*

taxes & fees included

A breathtaking panoramic view of Cruz Bay, St. John, showcasing a vibrant coastal town with white-sand beaches, clear turquoise waters, and numerous boats in the harbor.
FREE Beverages, Gratuities, Wi-Fi & More*+ 1 more offer
Explora Journeys Logo

7-night A Journey Into Dominican Rhythms & Caribbean Splendour From Miami, Florida

Miami
Puerto Plata
Catalina Island/Casa de Campo
St. Thomas (Charlotte Amalie)
Road Bay
+3 more

Aboard

EXPLORA II

From

Miami, Florida

1 Sailing

Jan 30, 2028

1 Sailing

Jan 30, 2028

Published prices from

$3,655

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.