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92 Results

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A scenic view of the white sand beach and lush palm trees of Mystery Island, Aneityum, with calm, turquoise water under a clear blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

23-night Star Collector Cruise: Spanish Mystery & Atlantic Crossing From Barcelona, Spain

Barcelona
Mystery Island (Aneityum)
Malaga
Tangier
Casablanca
+3 more

Aboard

Star Legend

From

Barcelona, Spain

1 Sailing

Nov 4, 2026

1 Sailing

Nov 4, 2026

Published prices from

$7,587

per person*

taxes & fees included

A scenic view of Forte de São João Baptista, a fortress built on a rocky islet in the Berlengas Archipelago, connected by a stone causeway over turquoise water.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night 2026 Spanish Mystery Cruise From Barcelona, Spain

Barcelona
Mystery Port
Malaga

Aboard

Star Legend

From

Barcelona, Spain

1 Sailing

Nov 4, 2026

1 Sailing

Nov 4, 2026

Published prices from

$2,982

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

22-night Star Collector Cruise: Caribbean Beats & Transatlantic Treats From Malaga, Spain

Malaga
Tangier
Casablanca
Funchal (Madeira)
Bridgetown (Barbados)
+8 more

Aboard

Star Legend

From

Malaga, Spain

1 Sailing

Nov 12, 2026

1 Sailing

Nov 12, 2026

Published prices from

$7,458

per person*

taxes & fees included

A picturesque view of the historic Cape Spartel Lighthouse on a cliff overlooking the Atlantic Ocean near Tangier, Morocco.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

13-night Ocean Crossings Cruise From Malaga, Spain

Malaga
Tangier
Casablanca
Funchal (Madeira)
Bridgetown (Barbados)

Aboard

Star Legend

From

Malaga, Spain

1 Sailing

Nov 12, 2026

1 Sailing

Nov 12, 2026

Published prices from

$5,785

per person*

taxes & fees included

A view of Pigeon Island National Landmark, St. Lucia, showing a lush, green peninsula jutting out into the ocean with waves crashing on the rocks.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

15-night Star Collector: Captivating Caribbean Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Anse Mitan
Pigeon Island
Castries
The Pitons
+9 more

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Nov 27, 2026

1 Sailing

Nov 27, 2026

Published prices from

$4,768

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

7-night Jewels Of The Windward Islands Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Anse Mitan
Pigeon Island
Castries
The Pitons
+3 more

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Nov 27, 2026

1 Sailing

Nov 27, 2026

Published prices from

$2,458

per person*

taxes & fees included

A breathtaking aerial view of the iconic Pitons, two majestic volcanic peaks, rising from the turquoise waters of the Caribbean Sea on the island of St. Lucia, with a small bay and sailboats.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

16-night Star Collector: Windward Islands & Spanish New World Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Rodney Bay
The Pitons
Scarborough
Bequia
+10 more

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Dec 4, 2026

1 Sailing

Dec 4, 2026

Published prices from

$5,244

per person*

taxes & fees included

A breathtaking tropical beach on Mayreau Island, Grenadines, with white sand, tall palm trees, and turquoise water under a perfectly blue sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night Windward Ways & Tobago Cays Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Rodney Bay
The Pitons
Scarborough
Bequia
+5 more

Aboard

Star Legend

From

Bridgetown, Barbados

1 Sailing

Dec 4, 2026

1 Sailing

Dec 4, 2026

Published prices from

$2,760

per person*

taxes & fees included

An aerial view of Bocas del Toro, a vibrant town on the Caribbean coast of Panama, featuring colorful houses built over clear blue water and numerous sailboats docked nearby.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night Panama Canal, Cartagena, San Blas Islands & More Cruise From Oranjestad, Aruba, Caribbean

Oranjestad
Cartagena (Colombia)
Bocas del Toro
San Blas Islands
Panama Canal
+2 more

Aboard

Star Legend

From

Oranjestad, Aruba, Caribbean

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$3,612

per person*

taxes & fees included

Lush rainforest and beach in Costa Rica.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

16-night Star Collector: Latin America Explorer Cruise From Oranjestad, Aruba, Caribbean

Oranjestad
Cartagena (Colombia)
Bocas del Toro
San Blas Islands
Panama Canal
+9 more

Aboard

Star Legend

From

Oranjestad, Aruba, Caribbean

1 Sailing

Dec 12, 2026

1 Sailing

Dec 12, 2026

Published prices from

$6,056

per person*

taxes & fees included

Lush rainforest and beach in Costa Rica.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night Naturally Costa Rica Cruise From Balboa, Panama

Balboa
Isla Parida
Golfo Dulce (Puerto Jimenez)
Quepos
Punta Leona
+4 more

Aboard

Star Legend

From

Balboa, Panama

1 Sailing

Dec 20, 2026

1 Sailing

Dec 20, 2026

Published prices from

$3,004

per person*

taxes & fees included

An aerial view of the bustling city of Balboa, Panama, with a scenic coastal road alongside a marina and tall modern skyscrapers in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

12-night Monteverde Cloud Forest & Arenal Volcano Cruise/Land Package From Quepos, Costa Rica

Quepos
Punta Leona
Curu (Reserve)
Playa Flamingo
Puerto Caldera (Puntarenas)
+6 more

Aboard

Star Legend

From

Quepos, Costa Rica

1 Sailing

Dec 24, 2026

1 Sailing

Dec 24, 2026

Modern Panama City skyline with skyscrapers.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

13-night Costa Rica, Panama Canal & Machu Picchu Cruise/Land Package From Puerto Caldera, Costa Rica

Puerto Caldera (Puntarenas)
Punta Leona
Quepos
Golfo Dulce (Puerto Jimenez)
Isla Parida
+9 more

Aboard

Star Legend

From

Puerto Caldera, Costa Rica

1 Sailing

Dec 28, 2026

1 Sailing

Dec 28, 2026

An aerial view of the bustling city of Balboa, Panama, with a scenic coastal road alongside a marina and tall modern skyscrapers in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night Costa Rica & Panama Canal Cruise From Puerto Caldera, Costa Rica

Puerto Caldera (Puntarenas)
Punta Leona
Quepos
Golfo Dulce (Puerto Jimenez)
Isla Parida
+4 more

Aboard

Star Legend

From

Puerto Caldera, Costa Rica

1 Sailing

Dec 28, 2026

1 Sailing

Dec 28, 2026

Published prices from

$3,596

per person*

taxes & fees included

A close-up of a small, adorable squirrel monkey with a black cap and a light brown body, perched on a tree branch surrounded by lush, yellow-green leaves.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

12-night Costa Rica, Panama Canal & Machu Picchu Cruise/Land Package From Lima, Peru

Lima
Cuzco
Sacred Valley
Machu Picchu
Panama City
+8 more

Aboard

Star Legend

From

Lima, Peru

3 Sailings

Dec 31, 2026 - Jan 28, 2027

3 Sailings

Dec 31, 2026 - Jan 28, 2027

National Theatre of Costa Rica in San José.
FREE All-Inclusive Upgrade + up to $400 Onboard Credit*
Windstar

10-night Monteverde Cloud Forest & Arenal Volcano Cruise/Land Package From Colon, Panama

Colon (Panama)
Panama Canal
Balboa
Isla Parida
Golfo Dulce (Puerto Jimenez)
+6 more

Aboard

Star Legend

From

Colon, Panama

3 Sailings

Jan 5 - Feb 2, 2027

3 Sailings

Jan 5 - Feb 2, 2027

A dreamy long-exposure shot of the coastline in Manuel Antonio National Park near Quepos, Costa Rica, with a tranquil, misty ocean flowing between large, jagged rocks and a lush green headland in the distance at sunset.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

7-night Costa Rica & Panama Canal Cruise From Colon, Panama

Colon (Panama)
Panama Canal
Balboa
Isla Parida
Golfo Dulce (Puerto Jimenez)
+3 more

Aboard

Star Legend

From

Colon, Panama

3 Sailings

Jan 5 - Feb 2, 2027

3 Sailings

Jan 5 - Feb 2, 2027

Published prices from

$3,236

per person*

taxes & fees included

A dramatic sunset over Lake Arenal in Costa Rica, with a majestic, conical Arenal Volcano emitting a plume of smoke and fiery clouds into the orange sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

11-night Monteverde Cloud Forest & Arenal Volcano Cruise/Land Package From San Jose, Costa Rica

San Jose (C.R.)
Arenal
Monteverde
Puerto Caldera (Puntarenas)
Quepos
+6 more

Aboard

Star Legend

From

San Jose, Costa Rica

2 Sailings

Jan 8 - Jan 22, 2027

2 Sailings

Jan 8 - Jan 22, 2027

An aerial view of the bustling city of Balboa, Panama, with a scenic coastal road alongside a marina and tall modern skyscrapers in the background.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

7-night Costa Rica & Panama Canal Cruise From Puerto Caldera, Costa Rica

Puerto Caldera (Puntarenas)
Quepos
Golfo Dulce (Puerto Jimenez)
Isla Parida
Balboa
+3 more

Aboard

Star Legend

From

Puerto Caldera, Costa Rica

2 Sailings

Jan 12 - Jan 26, 2027

2 Sailings

Jan 12 - Jan 26, 2027

Published prices from

$3,236

per person*

taxes & fees included

A breathtaking panoramic view of the ancient Inca citadel of Machu Picchu, a UNESCO World Heritage site, showcasing its stone structures and terraced fields amid the Andes Mountains in Peru.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

12-night Costa Rica, Panama Canal & Machu Picchu Cruise/Land Package From Puerto Caldera, Costa Rica

Puerto Caldera (Puntarenas)
Quepos
Golfo Dulce (Puerto Jimenez)
Isla Parida
Balboa
+7 more

Aboard

Star Legend

From

Puerto Caldera, Costa Rica

2 Sailings

Jan 12 - Jan 26, 2027

2 Sailings

Jan 12 - Jan 26, 2027

A scenic view of a pristine beach on the San Blas Islands, Panama, with a line of tall palm trees casting shadows on the white sand and clear turquoise water.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

13-night Latin America Explorer Cruise From Puerto Caldera, Costa Rica

Puerto Caldera (Puntarenas)
Playa Flamingo
Punta Leona
Quepos
Golfo Dulce (Puerto Jimenez)
+8 more

Aboard

Star Legend

From

Puerto Caldera, Costa Rica

1 Sailing

Feb 9, 2027

1 Sailing

Feb 9, 2027

Published prices from

$8,656

per person*

taxes & fees included

A close-up of a small, adorable squirrel monkey with a black cap and a light brown body, perched on a tree branch surrounded by lush, yellow-green leaves.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

7-night Naturally Costa Rica Cruise From Puerto Caldera, Costa Rica

Puerto Caldera (Puntarenas)
Playa Flamingo
Punta Leona
Quepos
Golfo Dulce (Puerto Jimenez)
+3 more

Aboard

Star Legend

From

Puerto Caldera, Costa Rica

1 Sailing

Feb 9, 2027

1 Sailing

Feb 9, 2027

Published prices from

$3,764

per person*

taxes & fees included

Colorful colonial balconies in Cartagena.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

6-night Panama Canal, Cartagena, San Blas Islands & More Cruise From Fuerte Amador, Panama

Fuerte Amador (Panama City)
Panama Canal
Bocas del Toro
San Blas Islands
Cartagena (Colombia)
+2 more

Aboard

Star Legend

From

Fuerte Amador, Panama

1 Sailing

Feb 16, 2027

1 Sailing

Feb 16, 2027

Published prices from

$5,292

per person*

taxes & fees included

A breathtaking aerial view of the iconic Pitons, two majestic volcanic peaks, rising from the turquoise waters of the Caribbean Sea on the island of St. Lucia, with a small bay and sailboats.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

14-night Star Collector: Windward Islands & Spanish New World Cruise From Fuerte Amador, Panama

Fuerte Amador (Panama City)
Panama Canal
Bocas del Toro
San Blas Islands
Cartagena (Colombia)
+10 more

Aboard

Star Legend

From

Fuerte Amador, Panama

1 Sailing

Feb 16, 2027

1 Sailing

Feb 16, 2027

Published prices from

$9,662

per person*

taxes & fees included

A stunning panoramic view of Rodney Bay on the island of St. Lucia, showing a bustling harbor filled with sailboats, a colorful town, and lush green hills under a bright blue, cloudy sky.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Windstar

8-night Windward Ways & Tobago Cays Cruise From Oranjestad, Aruba, Caribbean

Oranjestad
Willemstad
Kralendijk
St. Georges
Rodney Bay
+5 more

Aboard

Star Legend

From

Oranjestad, Aruba, Caribbean

1 Sailing

Feb 22, 2027

1 Sailing

Feb 22, 2027

Published prices from

$4,840

per person*

taxes & fees included

    • Showing results 1 - 24 of 92

*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.