Windstar Cruises Cruises to Caribbean - Southern 42 Cruises on Windstar Cruises Found

Your Search Clear Selections

Any Destination
All Sail Months
Any Length
Any Port
Windstar Cruises
Any Ship

Close

42 Cruises Found

Sort By

Filter By

More

Ports

  • Philipsburg, St. Maarten
  • ROAD BAY, ANGUILLA
  • Soper's Hole, Tortola, B.V.I.
  • Jost Van Dyke, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
  • Gustavia, St. Barthelemy
  • Falmouth Harbour,Antigua
View More Ports

Ports

Philipsburg, St. Maarten - ROAD BAY, ANGUILLA - Soper's Hole, Tortola, B.V.I. - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - Gustavia, St. Barthelemy - Falmouth Harbour,Antigua - View More Ports

Loading itinerary...
Loading reviews...

Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$2399*

N/A

$4299*

See Offers

N/A

$2499*

N/A

$4399*

Ports

  • San Juan, Puerto Rico
  • VIEQUES, PUERTO RICO
  • Gustavia, St. Barthelemy
  • Little Bay, Montserrat
  • Philipsburg, St. Maarten
  • Jost Van Dyke, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
View More Ports

Ports

San Juan, Puerto Rico - VIEQUES, PUERTO RICO - Gustavia, St. Barthelemy - Little Bay, Montserrat - Philipsburg, St. Maarten - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - View More Ports

Loading itinerary...
Loading reviews...

Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

N/A

N/A

$1799*

See Offers

N/A

N/A

N/A

$1599*

See Offers

N/A

N/A

N/A

$2299*

See Offers

N/A

$3099*

$3999*

$5799*

See Offers

N/A

N/A

N/A

$2599*

See Offers

N/A

$2599*

$3499*

$5299*

See Offers

N/A

$2599*

$3499*

$5299*

See Offers

N/A

$2399*

$3299*

$5099*

See Offers

N/A

$2399*

$3299*

$5099*

Ports

  • San Juan, Puerto Rico
  • VIEQUES, PUERTO RICO
  • Philipsburg, St. Maarten
  • Little Bay, Montserrat
  • Gustavia, St. Barthelemy
  • Jost Van Dyke, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Pigeon Island, St. Lucia
  • St. George's, Grenada
  • Bequia, Grenadines
View More Ports

Ports

San Juan, Puerto Rico - VIEQUES, PUERTO RICO - Philipsburg, St. Maarten - Little Bay, Montserrat - Gustavia, St. Barthelemy - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Pigeon Island, St. Lucia - St. George's, Grenada - Bequia, Grenadines - View More Ports

Loading itinerary...
Loading reviews...

Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

N/A

N/A

$2499*

See Offers

N/A

N/A

N/A

$3699*

See Offers

N/A

N/A

N/A

$3799*

See Offers

N/A

N/A

N/A

$2899*

Ports

  • Bridgetown, Barbados
  • ANSE MATIN, MARTINIQUE
  • Pigeon Island, St. Lucia
  • Castries, St. Lucia
  • St. George's, Grenada
  • Mayreau, Grenadines
  • Bequia, Grenadines
View More Ports

Ports

Bridgetown, Barbados - ANSE MATIN, MARTINIQUE - Pigeon Island, St. Lucia - Castries, St. Lucia - St. George's, Grenada - Mayreau, Grenadines - Bequia, Grenadines - View More Ports

Loading itinerary...
Loading reviews...

Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$2299*

N/A

$4899*

See Offers

N/A

$2499*

N/A

$4399*

See Offers

N/A

$2499*

N/A

$4399*

See Offers

N/A

$2399*

N/A

$4299*

See Offers

N/A

$2399*

N/A

$4299*

Ports

  • Miami, Florida
  • Key West, Florida
  • Costa Maya (Mahahual), Mexico
  • Coxen Hole, Roatan, Bay Islands, Honduras
  • Belize City, Belize
  • Cozumel, Mexico
View More Ports

Ports

Miami, Florida - Key West, Florida - Costa Maya (Mahahual), Mexico - Coxen Hole, Roatan, Bay Islands, Honduras - Belize City, Belize - Cozumel, Mexico - View More Ports

Loading itinerary...
Loading reviews...

Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$3099*

$3999*

$5799*

Ports

  • Miami, Florida
  • Key West, Florida
  • Costa Maya (Mahahual), Mexico
  • Coxen Hole, Roatan, Bay Islands, Honduras
  • Belize City, Belize
  • Cozumel, Mexico
View More Ports

Ports

Miami, Florida - Key West, Florida - Costa Maya (Mahahual), Mexico - Coxen Hole, Roatan, Bay Islands, Honduras - Belize City, Belize - Cozumel, Mexico - View More Ports

Loading itinerary...
Loading reviews...

Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$4099*

$4999*

$6799*

Ports

  • Bridgetown, Barbados
  • Roseau, Dominica
  • Little Bay, Montserrat
  • Gustavia, St. Barthelemy
  • Falmouth Harbour,Antigua
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Pigeon Island, St. Lucia
  • Castries, St. Lucia
  • Fort-De-France, Martinique
  • Mayreau, Grenadines
  • St. George's, Grenada
  • Bequia, Grenadines
View More Ports

Ports

Bridgetown, Barbados - Roseau, Dominica - Little Bay, Montserrat - Gustavia, St. Barthelemy - Falmouth Harbour,Antigua - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Pigeon Island, St. Lucia - Castries, St. Lucia - Fort-De-France, Martinique - Mayreau, Grenadines - St. George's, Grenada - Bequia, Grenadines - View More Ports

Loading itinerary...
Loading reviews...

Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$3499*

N/A

$6599*

Ports

  • Bridgetown, Barbados
  • Roseau, Dominica
  • Little Bay, Montserrat
  • Gustavia, St. Barthelemy
  • Falmouth Harbour,Antigua
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Pigeon Island, St. Lucia
View More Ports

Ports

Bridgetown, Barbados - Roseau, Dominica - Little Bay, Montserrat - Gustavia, St. Barthelemy - Falmouth Harbour,Antigua - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Pigeon Island, St. Lucia - View More Ports

Loading itinerary...
Loading reviews...

Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$2499*

N/A

$4399*

See Offers

N/A

$1999*

N/A

$4299*

Ports

  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts
  • Gustavia, St. Barthelemy
  • Little Bay, Montserrat
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Bridgetown, Barbados
View More Ports

Ports

Philipsburg, St. Maarten - Basseterre, St. Kitts - Gustavia, St. Barthelemy - Little Bay, Montserrat - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Roseau, Dominica - Pigeon Island, St. Lucia - Bridgetown, Barbados - View More Ports

Loading itinerary...
Loading reviews...

Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$2199*

N/A

$4099*

Ports

  • Miami, Florida
  • Key West, Florida
  • Cozumel, Mexico
  • Belize City, Belize
  • Trujillo, Honduras
  • San Antonio, Chile
  • Puerto Limon, Costa Rica
  • Bocas Del Toro, Panama
  • Colon, Panama
View More Ports

Ports

Miami, Florida - Key West, Florida - Cozumel, Mexico - Belize City, Belize - Trujillo, Honduras - San Antonio, Chile - Puerto Limon, Costa Rica - Bocas Del Toro, Panama - Colon, Panama - View More Ports

Loading itinerary...
Loading reviews...

Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

N/A

N/A

$2599*

All prices are per person based on double occupancy and do not include port / government fees and gratuities.