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 - Eastern
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
113 Matched Sailings
Departing
Itinerary and Ship
Length
Save to
Favorites
Priced from

Oct 20, 2026

(Tuesday)

8 Night 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

Nov 10, 2026

(Tuesday)

14 Night Ocean Crossing Cruise

Wind Star
Windstar Cruises
4.2 based on 5 ratings
Starts: Lisbon, Portugal
Ends: Bridgetown, Barbados
Ports of Call:
Lisbon, Bridgetown

14 Nights


Add to Favorites
Compare Favorites
from

$2,525

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

$2,562

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

Nov 15, 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, Basseterre, Gustavia St. Barts, Philipsburg (St. Maarten), Great Harbour...

7 Nights


Add to Favorites
Compare Favorites
from

$2,562

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

$2,562

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

Jan 10, 2027

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

7 Nights


Add to Favorites
Compare Favorites
from

$2,562

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

Dec 02, 2025

(Tuesday)

5 Night Barefoot Break in the British Virgin Islands Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Sopers Hole, Great Harbour, Prickly Pear British Virgin Islands...
Special Promotions

5 Nights


Add to Favorites
Compare Favorites
from

$2,645

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

Dec 27, 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

Mar 21, 2026

(Saturday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
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...
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$3,044

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

Dec 07, 2025

(Sunday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
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...
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$3,044

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

Oct 19, 2025

(Sunday)

7 Night Mind Body and Spirit Collection Bermuda Bliss Cruise

Star Pride
Windstar Cruises
Starts: New York, New York
Ends: San Juan, Puerto Rico
Ports of Call:
New York, St George, San Juan
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$3,119

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

Dec 14, 2025

(Sunday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
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...
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$3,160

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

Mar 28, 2026

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
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


Add to Favorites
Compare Favorites
from

$3,160

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

Mar 08, 2025

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
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

$3,174

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

Feb 28, 2026

(Saturday)

7 Night Lush and Lovely Islands of the Lesser Antilles Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
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...
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$3,213

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

Feb 28, 2026

(Saturday)

7 Night Classic Caribbean Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Charlestown, Roseau, Pigeon Island, Deshaies, Basseterre...
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$3,244

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

Jan 31, 2026

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
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...
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$3,253

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

Jan 04, 2026

(Sunday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Surf
Windstar Cruises
4.3 based on 8 ratings
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...
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$3,303

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

Feb 07, 2026

(Saturday)

7 Night Classic Caribbean Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), Charlestown, Roseau, Mayreau, Anse Mitan, Basseterre...
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$3,310

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
4.3 based on 8 ratings
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...
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$3,329

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

Feb 14, 2026

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
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...
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$3,353

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

Jan 24, 2026

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), St John's, Road Bay, Prickly Pear British Virgin Islands, Sopers Hole...
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$3,353

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

Feb 21, 2026

(Saturday)

7 Night Beach Fun and Sun A Remote Caribbean Getaway Cruise

Wind Spirit
Windstar Cruises
4.3 based on 6 ratings
Starts: Philipsburg (St. Maarten), Netherlands Antilles
Ends: Philipsburg (St. Maarten), Netherlands Antilles
Ports of Call:
Philipsburg (St. Maarten), St John's, Road Bay, Prickly Pear British Virgin Islands, Sopers Hole...
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$3,353

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

Nov 30, 2025

(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...
Special Promotions

7 Nights


Add to Favorites
Compare Favorites
from

$3,355

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

Oct 26, 2025

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

7 Nights


Add to Favorites
Compare Favorites
from

$3,355

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



Overlay Title