Departing | Itinerary and Ship | Length | Save to Favorites | Priced from |
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| 7 Night Jewels of the Windward Islands Cruise Star Legend Windstar Cruises Starts: Bridgetown, Barbados Ends: Bridgetown, Barbados Ports of Call: Bridgetown, Anse Mitan, Rodney Bay, Castries, The Pitons, Mayreau, St George's, Bequia, Bridgetown | 7 Nights | |
from
$1,942per person (double occupancy) Includes taxes & fees Learn More |
| 6 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Philipsburg (St. Maarten), Netherlands Antilles Ports of Call: Philipsburg (St. Maarten), Road Bay, Gustavia St. Barts, Great Harbour... | 6 Nights | |
from
$2,168per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Philipsburg (St. Maarten), Netherlands Antilles Ports of Call: Philipsburg (St. Maarten), St John's, Road Bay, Sopers Hole, Great Harbour... | 7 Nights | |
from
$2,273per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Philipsburg (St. Maarten), Netherlands Antilles Ports of Call: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour... | 7 Nights | |
from
$2,273per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Philipsburg (St. Maarten), Netherlands Antilles Ports of Call: Philipsburg (St. Maarten), St John's, Road Bay, Sopers Hole, Great Harbour... | 7 Nights | |
from
$2,273per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Philipsburg (St. Maarten), Netherlands Antilles Ports of Call: Philipsburg (St. Maarten), Falmouth Harbour, Road Bay, Sopers Hole, Great Harbour... | 7 Nights | |
from
$2,273per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Philipsburg (St. Maarten), Netherlands Antilles Ports of Call: Philipsburg (St. Maarten), St John's, Road Bay, Sopers Hole, Great Harbour... | 7 Nights | |
from
$2,273per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night Classic Caribbean Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Philipsburg (St. Maarten), Netherlands Antilles Ports of Call: Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre... | 7 Nights | |
from
$2,362per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night Classic Caribbean Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Philipsburg (St. Maarten), Netherlands Antilles Ports of Call: Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre... | 7 Nights | |
from
$2,362per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night Classic Caribbean Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Philipsburg (St. Maarten), Netherlands Antilles Ports of Call: Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre... | 7 Nights | |
from
$2,362per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night Classic Caribbean Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Philipsburg (St. Maarten), Netherlands Antilles Ports of Call: Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre... | 7 Nights | |
from
$2,362per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night Classic Caribbean Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Philipsburg (St. Maarten), Netherlands Antilles Ports of Call: Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre... | 7 Nights | |
from
$2,432per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night Classic Caribbean Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Philipsburg (St. Maarten), Netherlands Antilles Ports of Call: Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre... | 7 Nights | |
from
$2,432per person (double occupancy) Includes taxes & fees Learn More |
| 22 Night Star Collector Caribbean Charms to Iberian Shores Cruise Star Legend Windstar Cruises Starts: San Juan, Puerto Rico Ends: Lisbon, Portugal Ports of Call: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan, Agadir, Casablanca... | 22 Nights | |
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$2,451per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night Windward Islands Surf and Sunsets Cruise Star Pride Windstar Cruises Starts: San Juan, Puerto Rico Ends: San Juan, Puerto Rico Ports of Call: San Juan, St George's, Bequia, Mayreau, Deshaies, Marigot, San Juan | 7 Nights | |
from
$2,516per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night Windward Islands Surf and Sunsets Cruise Star Pride Windstar Cruises Starts: San Juan, Puerto Rico Ends: San Juan, Puerto Rico Ports of Call: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan | 7 Nights | |
from
$2,516per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night Classic Caribbean Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Philipsburg (St. Maarten), Netherlands Antilles Ports of Call: Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre... | 7 Nights | |
from
$2,537per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night San Juan and the Virgin Islands Cruise Star Pride Windstar Cruises Starts: San Juan, Puerto Rico Ends: San Juan, Puerto Rico Ports of Call: San Juan, Cruz Bay, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Great Harbour... | 7 Nights | |
from
$2,548per person (double occupancy) Includes taxes & fees Learn More |
| 15 Night Ocean Crossing Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Lisbon, Portugal Ports of Call: Philipsburg (St. Maarten), Horta, Ponta Delgada, Lisbon | 15 Nights | |
from
$2,580per person (double occupancy) Includes taxes & fees Learn More |
| 15 Night Ocean Crossing Cruise Wind Surf Windstar Cruises Starts: Lisbon, Portugal Ends: Philipsburg (St. Maarten), Netherlands Antilles Ports of Call: Lisbon, Madeira, Great Harbour, Philipsburg (St. Maarten) | 15 Nights | |
from
$2,580per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night Classic Caribbean Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Philipsburg (St. Maarten), Netherlands Antilles Ports of Call: Philipsburg (St. Maarten), Gustavia St. Barts, Charlestown, Roseau, Mayreau, Iles des Saintes... | 7 Nights | |
from
$2,607per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night Classic Caribbean Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Philipsburg (St. Maarten), Netherlands Antilles Ports of Call: Philipsburg (St. Maarten), Charlestown, Iles des Saintes, Mayreau, Roseau, Basseterre... | 7 Nights | |
from
$2,607per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night Classic Caribbean Cruise Wind Surf Windstar Cruises Starts: Philipsburg (St. Maarten), Netherlands Antilles Ends: Philipsburg (St. Maarten), Netherlands Antilles Ports of Call: Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Iles des Saintes, Basseterre... | 7 Nights | |
from
$2,607per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night Windward Islands Surf and Sunsets Cruise Star Pride Windstar Cruises Starts: San Juan, Puerto Rico Ends: San Juan, Puerto Rico Ports of Call: San Juan, St George's, Bequia, Mayreau, Iles des Saintes, Marigot, San Juan | 7 Nights | |
from
$2,621per person (double occupancy) Includes taxes & fees Learn More |
| 7 Night Windward Islands Surf and Sunsets Cruise Star Pride Windstar Cruises Starts: San Juan, Puerto Rico Ends: San Juan, Puerto Rico Ports of Call: San Juan, St George's, Bequia, Mayreau, Deshaies, Marigot, San Juan | 7 Nights | |
from
$2,621per person (double occupancy) Includes taxes & fees Learn More |