Windstar Cruises Cruises to Caribbean - Southern 80 cruises on Windstar Cruises found

Your search Clear selections

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

Close

80 cruises found

Sort by

Filter by

More

Ports

  • San Juan, Puerto Rico
  • Bequia, Grenadines
  • Mayreau, Grenadines
  • Soufriere, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Marigot, Saint Martin
  • Cruz Bay, St. John, U.S.V.I.
  • Basseterre, St. Kitts
  • Philipsburg, St. Maarten
  • Gustavia, St. Barthelemy
  • Jost Van Dyke, B.V.I.
  • Prickly Pear Island, B.V.I.
View more ports

Ports

San Juan, Puerto Rico - Bequia, Grenadines - Mayreau, Grenadines - Soufriere, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Marigot, Saint Martin - Cruz Bay, St. John, U.S.V.I. - Basseterre, St. Kitts - Philipsburg, St. Maarten - Gustavia, St. Barthelemy - Jost Van Dyke, B.V.I. - Prickly Pear Island, B.V.I. - View more ports

Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

N/A

N/A

$5490*

 

N/A

N/A

N/A

$5490*

 

N/A

N/A

N/A

$5490*

Ports

  • San Juan, Puerto Rico
  • Cruz Bay, St. John, U.S.V.I.
  • Basseterre, St. Kitts
  • Philipsburg, St. Maarten
  • Gustavia, St. Barthelemy
  • Jost Van Dyke, B.V.I.
  • Prickly Pear Island, B.V.I.
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Soufriere, St. Lucia
  • Bequia, Grenadines
  • Mayreau, Grenadines
View more ports

Ports

San Juan, Puerto Rico - Cruz Bay, St. John, U.S.V.I. - Basseterre, St. Kitts - Philipsburg, St. Maarten - Gustavia, St. Barthelemy - Jost Van Dyke, B.V.I. - Prickly Pear Island, B.V.I. - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Soufriere, St. Lucia - Bequia, Grenadines - Mayreau, Grenadines - View more ports

Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

N/A

N/A

$5299*

 

N/A

N/A

N/A

$5299*

 

N/A

N/A

N/A

$5299*

Ports

  • San Juan, Puerto Rico
  • Cruz Bay, St. John, U.S.V.I.
  • Basseterre, St. Kitts
  • Philipsburg, St. Maarten
  • Gustavia, St. Barthelemy
  • Jost Van Dyke, B.V.I.
  • Prickly Pear Island, B.V.I.
View more ports

Ports

San Juan, Puerto Rico - Cruz Bay, St. John, U.S.V.I. - Basseterre, St. Kitts - Philipsburg, St. Maarten - Gustavia, St. Barthelemy - Jost Van Dyke, B.V.I. - Prickly Pear Island, B.V.I. - View more ports

Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

N/A

N/A

$3162*

 

N/A

N/A

N/A

$3199*

 

N/A

N/A

N/A

$3199*

Ports

  • Philipsburg, St. Maarten
  • Soper's Hole, Tortola, B.V.I.
  • Jost Van Dyke, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
  • Gustavia, St. Barthelemy
  • ROAD BAY, ANGUILLA
  • Falmouth Harbour,Antigua
  • Basseterre, St. Kitts
  • Little Bay, Montserrat
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Bridgetown, Barbados
  • Anse Mitan, Martinique
View more ports

Ports

Philipsburg, St. Maarten - Soper's Hole, Tortola, B.V.I. - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - Gustavia, St. Barthelemy - ROAD BAY, ANGUILLA - Falmouth Harbour,Antigua - Basseterre, St. Kitts - Little Bay, Montserrat - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Roseau, Dominica - Pigeon Island, St. Lucia - Bridgetown, Barbados - Anse Mitan, Martinique - View more ports

Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$6298*

N/A

$16198*

 

N/A

$6298*

N/A

$16198*

 

N/A

$6298*

N/A

$16198*

Ports

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

Ports

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

Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$2660*

N/A

$6160*

 

N/A

$2698*

N/A

$6198*

 

N/A

$2698*

N/A

$6198*

Ports

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

N/A

$4181*

N/A

$11081*

 

N/A

$4198*

N/A

$11098*

 

N/A

$4198*

N/A

$11098*

Ports

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Soufriere, St. Lucia
  • Bequia, Grenadines
  • Mayreau, Grenadines
  • Cruz Bay, St. John, U.S.V.I.
  • Basseterre, St. Kitts
  • Gustavia, St. Barthelemy
  • Jost Van Dyke, B.V.I.
  • Prickly Pear Island, B.V.I.
View more ports

Ports

San Juan, Puerto Rico - Philipsburg, St. Maarten - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Soufriere, St. Lucia - Bequia, Grenadines - Mayreau, Grenadines - Cruz Bay, St. John, U.S.V.I. - Basseterre, St. Kitts - Gustavia, St. Barthelemy - Jost Van Dyke, B.V.I. - Prickly Pear Island, B.V.I. - View more ports

Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

N/A

N/A

$6199*

 

N/A

N/A

N/A

$7399*

 

N/A

N/A

N/A

$7399*

Ports

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Soufriere, St. Lucia
  • Bequia, Grenadines
  • Mayreau, Grenadines
View more ports

Ports

San Juan, Puerto Rico - Philipsburg, St. Maarten - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Soufriere, St. Lucia - Bequia, Grenadines - Mayreau, Grenadines - View more ports

Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

N/A

N/A

$3136*

 

N/A

N/A

N/A

$3199*

 

N/A

N/A

N/A

$3199*

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
 

N/A

$2520*

N/A

$6020*

 

N/A

$2537*

N/A

$6037*

 

N/A

$2537*

N/A

$6037*

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
  • Anse Mitan, Martinique
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 - Anse Mitan, Martinique - View more ports

Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$4037*

N/A

$10437*

 

N/A

$4037*

N/A

$10437*

 

N/A

$4037*

N/A

$10437*

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