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21 Results

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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

25-night Star Collector: Southern Caribbean Thanksgiving Jubilee Cruise From Lisbon, Portugal

Lisbon
Bridgetown (Barbados)
Bequia
St. George's
Kralendijk
+6 more

Aboard

Wind Star

From

Lisbon, Portugal

1 Sailing

Nov 10, 2026

1 Sailing

Nov 10, 2026

Published prices from

$7,989

per person*

taxes & fees included

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

18-night Star Collector: Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica Via The Panama Canal Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Bequia
St. George's
Kralendijk
Willemstad
+11 more

Aboard

Wind Star

From

Bridgetown, Barbados

1 Sailing

Nov 24, 2026

1 Sailing

Nov 24, 2026

Published prices from

$8,272

per person*

taxes & fees included

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

11-night Colombian & Southern Caribbean Coastlines Cruise From Bridgetown, Barbados

Bridgetown (Barbados)
Bequia
St. George's
Kralendijk
Willemstad
+5 more

Aboard

Wind Star

From

Bridgetown, Barbados

1 Sailing

Nov 24, 2026

1 Sailing

Nov 24, 2026

Published prices from

$4,792

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

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

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 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

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

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

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

$7,990

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

$4,264

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

$5,828

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

$2,452

per person*

taxes & fees included

A close-up shot of two cougars, or pumas, resting on a rocky ledge. The cougar in the foreground looks directly at the camera, its tawny-colored face and alert eyes focused, while the other cougar is curled up and resting behind it.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

21-night Star Collector Cruise: Costa Rica, Panama & Aruba From Puerto Caldera, Costa Rica

Puerto Caldera (Puntarenas)
Playa Flamingo
Punta Leona
Quepos
Golfo Dulce (Puerto Jimenez)
+14 more

Aboard

Star Pride

From

Puerto Caldera, Costa Rica

1 Sailing

Feb 21, 2028

1 Sailing

Feb 21, 2028

Published prices from

$9,584

per person*

taxes & fees included

A close-up shot of two cougars, or pumas, resting on a rocky ledge. The cougar in the foreground looks directly at the camera, its tawny-colored face and alert eyes focused, while the other cougar is curled up and resting behind it.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

14-night Star Collector Cruise: Latin America Explorer From Puerto Caldera, Costa Rica

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

Aboard

Star Pride

From

Puerto Caldera, Costa Rica

1 Sailing

Feb 21, 2028

1 Sailing

Feb 21, 2028

Published prices from

$7,436

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*+ 1 more offer
TCW EXCLUSIVE
Windstar

14-night Star Collector Cruise: Panama, Aruba & The British Virgin Islands From Balboa, Panama

Balboa
Panama Canal
Bocas del Toro
San Blas Islands
Cartagena (Colombia)
+8 more

Aboard

Star Pride

From

Balboa, Panama

1 Sailing

Feb 28, 2028

1 Sailing

Feb 28, 2028

Published prices from

$6,520

per person*

taxes & fees included

A cruise ship navigating through the Gatun Locks of the Panama Canal, an important navigational route and popular tourist destination.
Up to $500 FREE Onboard Credit*+ 1 more offer
TCW EXCLUSIVE
Windstar

7-night Panama Canal, Cartagena, San Blas Islands & More Cruise From Balboa, Panama

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

Aboard

Star Pride

From

Balboa, Panama

1 Sailing

Feb 28, 2028

1 Sailing

Feb 28, 2028

Published prices from

$4,932

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.