Get FREE Price Alerts

Subscribe to our weekly cruise deals email and enjoy FREE price change alerts and updates for this cruise and others like it.

We promise to protect your privacy and personal data. You can review our privacy policy here.

Modify Your Choices
Vacation Type


Filters
Destination
- Caribbean
Travel Dates
Narrow Date Range
Departure Port
- All Departure Ports
Cruise Length
- All Durations
Cruise Line
- Windstar Cruises
Cruise Ships
- All Cruise Ships

Search Results


Sailings per page
152 Matched Sailings
Departing
Itinerary and Ship
Length
Save to
Favorites
Priced from

Dec 07, 2025

(Sunday)

6 Night The Spanish Main Rise of the New World Cruise

Star Pride
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: Colon, Panama
Ports of Call:
San Juan, Santo Domingo, Cartagena, San Blas Islands, Colon

6 Nights


Add to Favorites
Compare Favorites
from

$1,854

per person
(double occupancy)
Includes taxes & fees
Learn More

Dec 07, 2025

(Sunday)

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


Add to Favorites
Compare Favorites
from

$2,051

per person
(double occupancy)
Includes taxes & fees
Learn More

Dec 13, 2025

(Saturday)

7 Night Enchanting Colombia and Panamanian Islands Cruise

Wind Spirit
Windstar Cruises
Starts: Colon, Panama
Ends: Oranjestad, Aruba
Ports of Call:
Colon, San Blas Islands, Cartagena, Oranjestad

7 Nights


Add to Favorites
Compare Favorites
from

$2,174

per person
(double occupancy)
Includes taxes & fees
Learn More

Feb 01, 2026

(Sunday)

8 Night In the Wake of the Spanish Armadas Cruise

Wind Surf
Windstar Cruises
Starts: Oranjestad, Aruba
Ends: Colon, Panama
Ports of Call:
Oranjestad, Cartagena, San Blas Islands, Bocas Del Toro, Colon

8 Nights


Add to Favorites
Compare Favorites
from

$2,420

per person
(double occupancy)
Includes taxes & fees
Learn More

Oct 20, 2026

(Tuesday)

8 Night Mind Body and Spirit Collection Bermuda Bliss Cruise

Star Pride
Windstar Cruises
Starts: Boston, Massachusetts
Ends: San Juan, Puerto Rico
Ports of Call:
Boston, Hamilton, St George, San Juan

8 Nights


Add to Favorites
Compare Favorites
from

$2,426

per person
(double occupancy)
Includes taxes & fees
Learn More

Mar 09, 2026

(Monday)

6 Night Panamas Pristine Caribbean Cruise

Star Pride
Windstar Cruises
Starts: Colon, Panama
Ends: Oranjestad, Aruba
Ports of Call:
Colon, Bocas Del Toro, San Blas Islands, Cartagena, Oranjestad

6 Nights


Add to Favorites
Compare Favorites
from

$2,519

per person
(double occupancy)
Includes taxes & fees
Learn More

Dec 05, 2026

(Saturday)

14 Night Ocean Crossing Cruise

Wind Surf
Windstar Cruises
Starts: Lisbon, Portugal
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Lisbon, St John's, Philipsburg (St. Maarten)

14 Nights


Add to Favorites
Compare Favorites
from

$2,529

per person
(double occupancy)
Includes taxes & fees
Learn More

Jan 02, 2027

(Saturday)

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


Add to Favorites
Compare Favorites
from

$2,567

per person
(double occupancy)
Includes taxes & fees
Learn More

Jan 11, 2026

(Sunday)

6 Night Panama Canal Cartagena San Blas Islands and More Cruise

Star Pride
Windstar Cruises
Starts: Balboa, Panama
Ends: Oranjestad, Aruba
Ports of Call:
Balboa, Cruising the Panama Canal, Bocas Del Toro, San Blas Islands, Cartagena, Oranjestad

6 Nights


Add to Favorites
Compare Favorites
from

$2,574

per person
(double occupancy)
Includes taxes & fees
Learn More

Apr 04, 2026

(Saturday)

14 Night Knot Your Average Crossing Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Lisbon, Portugal
Ports of Call:
Philipsburg (St. Maarten), Ponta Delgada, Lisbon

14 Nights


Add to Favorites
Compare Favorites
from

$2,626

per person
(double occupancy)
Includes taxes & fees
Learn More

Jan 23, 2027

(Saturday)

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


Add to Favorites
Compare Favorites
from

$2,651

per person
(double occupancy)
Includes taxes & fees
Learn More

Feb 06, 2027

(Saturday)

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


Add to Favorites
Compare Favorites
from

$2,651

per person
(double occupancy)
Includes taxes & fees
Learn More

Feb 20, 2027

(Saturday)

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


Add to Favorites
Compare Favorites
from

$2,651

per person
(double occupancy)
Includes taxes & fees
Learn More

Mar 06, 2027

(Saturday)

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


Add to Favorites
Compare Favorites
from

$2,651

per person
(double occupancy)
Includes taxes & fees
Learn More

Mar 20, 2027

(Saturday)

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


Add to Favorites
Compare Favorites
from

$2,651

per person
(double occupancy)
Includes taxes & fees
Learn More

Feb 16, 2027

(Tuesday)

6 Night Panama Canal Cartagena San Blas Islands and More Cruise

Star Legend
Windstar Cruises
Starts: Fuerte Amador, Panama
Ends: Oranjestad, Aruba
Ports of Call:
Fuerte Amador, Cruising the Panama Canal, Bocas Del Toro, San Blas Islands, Cartagena, Oranjestad

6 Nights


Add to Favorites
Compare Favorites
from

$2,665

per person
(double occupancy)
Includes taxes & fees
Learn More

Jan 30, 2027

(Saturday)

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), Road Bay, Sopers Hole, Great Harbour...

7 Nights


Add to Favorites
Compare Favorites
from

$2,667

per person
(double occupancy)
Includes taxes & fees
Learn More

Mar 13, 2027

(Saturday)

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


Add to Favorites
Compare Favorites
from

$2,667

per person
(double occupancy)
Includes taxes & fees
Learn More

Jan 11, 2026

(Sunday)

7 Night Lush and Lovely Islands of the Lesser Antilles Cruise

Wind Surf
Windstar Cruises
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Bridgetown, Barbados
Ports of Call:
Philipsburg (St. Maarten), Basseterre, Gustavia St. Barts, St John's, Iles des Saintes, Roseau...

7 Nights


Add to Favorites
Compare Favorites
from

$2,676

per person
(double occupancy)
Includes taxes & fees
Learn More

Nov 08, 2026

(Sunday)

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


Add to Favorites
Compare Favorites
from

$2,730

per person
(double occupancy)
Includes taxes & fees
Learn More

Dec 06, 2026

(Sunday)

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


Add to Favorites
Compare Favorites
from

$2,730

per person
(double occupancy)
Includes taxes & fees
Learn More

Nov 27, 2026

(Friday)

7 Night Jewels of the Windward Islands Cruise

Star Legend
Windstar Cruises
Starts: Bridgetown, Barbados
Ends: Bridgetown, Barbados
Ports of Call:
Bridgetown, Anse Mitan, Pigeon Island, Castries, The Pitons, Mayreau, St George's, Bequia...

7 Nights


Add to Favorites
Compare Favorites
from

$2,738

per person
(double occupancy)
Includes taxes & fees
Learn More

Dec 26, 2026

(Saturday)

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


Add to Favorites
Compare Favorites
from

$2,751

per person
(double occupancy)
Includes taxes & fees
Learn More

Dec 13, 2026

(Sunday)

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, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Great Harbour...

7 Nights


Add to Favorites
Compare Favorites
from

$2,762

per person
(double occupancy)
Includes taxes & fees
Learn More

Nov 29, 2026

(Sunday)

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, Gustavia St. Barts, Basseterre, Philipsburg (St. Maarten), Great Harbour...

7 Nights


Add to Favorites
Compare Favorites
from

$2,762

per person
(double occupancy)
Includes taxes & fees
Learn More



Overlay Title