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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

11-night Gems Of The Leeward Islands Cruise From San Juan, Puerto Rico

San Juan
Cruz Bay
Gustavia
Basseterre
Falmouth Harbour
+6 more

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Oct 28, 2026

1 Sailing

Oct 28, 2026

Published prices from

$4,241

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

7-night Windward Islands Surf & Sunsets Cruise From San Juan, Puerto Rico

San Juan
St. George's
Bequia
Mayreau
Iles des Saintes
+2 more

Aboard

Star Pride

From

San Juan, Puerto Rico

9 Sailings

Nov 8, 2026 - Mar 27, 2028

9 Sailings

Nov 8, 2026 - Mar 27, 2028

Published prices from

$2,411

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.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

14-night Star Collector: Lovely Leewards Cruise From San Juan, Puerto Rico

San Juan
Cruz Bay
Basseterre
Gustavia
St. Maarten (Philipsburg)
+8 more

Aboard

Star Pride

From

San Juan, Puerto Rico

14 Sailings

Nov 8, 2026 - Mar 20, 2028

14 Sailings

Nov 8, 2026 - Mar 20, 2028

Published prices from

$4,014

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

7-night San Juan & The Virgin Islands Cruise From San Juan, Puerto Rico

San Juan
Cruz Bay
Basseterre
Gustavia
St. Maarten (Philipsburg)
+2 more

Aboard

Star Pride

From

San Juan, Puerto Rico

8 Sailings

Nov 15, 2026 - Mar 20, 2028

8 Sailings

Nov 15, 2026 - Mar 20, 2028

Published prices from

$2,443

per person*

taxes & fees included

Tulip fields with traditional windmills, showcasing the beauty of the Netherlands in springtime.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

16-night Ocean Crossings Cruise From San Juan, Puerto Rico

San Juan
Lisbon
Brest
Amsterdam

Aboard

Star Pride

From

San Juan, Puerto Rico

2 Sailings

Mar 30, 2027 - Apr 3, 2028

2 Sailings

Mar 30, 2027 - Apr 3, 2028

Published prices from

$2,760

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*+ 1 more offer
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*+ 1 more offer
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

$4,057

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 1 more offer
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

$4,874

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*+ 1 more offer
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

A snorkeler swims in the turquoise waters of the Baths National Park on Virgin Gorda, surrounded by massive granite boulders and palm trees.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

7-night San Juan & The Virgin Islands Cruise From San Juan, Puerto Rico

San Juan
Cruz Bay
Gustavia
St. Maarten (Philipsburg)
Basseterre
+2 more

Aboard

Star Legend

From

San Juan, Puerto Rico

5 Sailings

Dec 20, 2027 - Feb 14, 2028

5 Sailings

Dec 20, 2027 - Feb 14, 2028

Published prices from

$2,443

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.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

14-night Star Collector Cruise: Lovely Leewards From San Juan, Puerto Rico

San Juan
St. George's
Bequia
Mayreau
Iles des Saintes
+8 more

Aboard

Star Legend

From

San Juan, Puerto Rico

9 Sailings

Dec 20, 2027 - Feb 14, 2028

9 Sailings

Dec 20, 2027 - Feb 14, 2028

Published prices from

$4,014

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*+ 1 more offer
TCW EXCLUSIVE
Windstar

7-night Windward Islands Surf & Sunsets Cruise From San Juan, Puerto Rico

San Juan
St. George's
Bequia
Mayreau
Iles des Saintes
+2 more

Aboard

Star Legend

From

San Juan, Puerto Rico

5 Sailings

Dec 27, 2027 - Feb 21, 2028

5 Sailings

Dec 27, 2027 - Feb 21, 2028

Published prices from

$2,411

per person*

taxes & fees included

A picturesque view of a small town nestled at the base of a lush, green mountain on Iles des Saintes, Guadeloupe, with boats moored in the deep blue water and fluffy clouds in the sky.
Windstar

22-night Star Collector Cruise: Caribbean Charms To Iberian Shores From San Juan, Puerto Rico

San Juan
St. George's
Bequia
Mayreau
Iles des Saintes
+5 more

Aboard

Star Legend

From

San Juan, Puerto Rico

1 Sailing

Feb 21, 2028

1 Sailing

Feb 21, 2028

Published prices from

$4,271

per person*

taxes & fees included

An aerial view of Agadir, Morocco, showcasing the city's long sandy beach and curving coastline, with a busy marina and port in the foreground.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

15-night Ocean Crossings Cruise From San Juan, Puerto Rico

San Juan
Agadir
Casablanca
Lisbon

Aboard

Star Legend

From

San Juan, Puerto Rico

1 Sailing

Feb 28, 2028

1 Sailing

Feb 28, 2028

A scenic landscape view of Admiralty Bay in Bequia, St. Vincent and the Grenadines, with dozens of sailboats moored on the vibrant turquoise water, surrounded by lush green hills.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

23-night Star Collector Cruise: Tropical Horizons To Historic Amsterdam From San Juan, Puerto Rico

San Juan
St. George's
Bequia
Mayreau
Iles des Saintes
+5 more

Aboard

Star Pride

From

San Juan, Puerto Rico

1 Sailing

Mar 27, 2028

1 Sailing

Mar 27, 2028

Published prices from

$4,211

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.