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
- Any Destination
Travel Dates
Narrow Date Range
Departure Port
- San Juan, Puerto Rico
Cruise Length
- All Durations
Cruise Line
- Windstar Cruises
Cruise Ships
- All Cruise Ships

Cruises from San Juan


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

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

$3,130

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

$3,162

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

$3,162

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

Nov 22, 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

$3,330

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

$3,330

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

Dec 20, 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

$3,330

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

$3,462

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

Jan 03, 2027

(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

$4,030

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

$4,062

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

Oct 28, 2026

(Wednesday)

11 Night Masterpieces at Sea Gems of the Leeward 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, Falmouth Harbour, Iles des Saintes...

11 Nights


Add to Favorites
Compare Favorites
from

$4,257

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

$4,262

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

Apr 06, 2026

(Monday)

7 Night New World Caribbean Trio Cruise

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

7 Nights


Add to Favorites
Compare Favorites
from

$4,426

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

Dec 06, 2026

(Sunday)

14 Night Star Collector Lovely Leewards 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, Cruz Bay...

14 Nights


Add to Favorites
Compare Favorites
from

$4,993

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

Nov 29, 2026

(Sunday)

14 Night Star Collector Lovely Leewards 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...

14 Nights


Add to Favorites
Compare Favorites
from

$4,993

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

Nov 22, 2026

(Sunday)

14 Night Star Collector Lovely Leewards 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, Cruz Bay...

14 Nights


Add to Favorites
Compare Favorites
from

$5,193

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

Dec 13, 2026

(Sunday)

14 Night Star Collector Lovely Leewards 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...

14 Nights


Add to Favorites
Compare Favorites
from

$5,193

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

Mar 13, 2026

(Friday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Seeker
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, Marigot, Iles des Saintes, Mayreau, Bequia, Pigeon Island, The Pitons, San Juan

7 Nights


Add to Favorites
Compare Favorites
from

$5,733

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

Nov 15, 2026

(Sunday)

14 Night Star Collector Lovely Leewards 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...

14 Nights


Add to Favorites
Compare Favorites
from

$5,793

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

Nov 08, 2026

(Sunday)

14 Night Star Collector Lovely Leewards 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, Cruz Bay, Basseterre...

14 Nights


Add to Favorites
Compare Favorites
from

$5,793

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

Feb 27, 2026

(Friday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Seeker
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, Philipsburg (St. Maarten), Iles des Saintes, Mayreau, Bequia, Soufriere , San Juan

7 Nights


Add to Favorites
Compare Favorites
from

$5,836

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

Feb 13, 2026

(Friday)

7 Night Windward Islands Surf and Sunsets Cruise

Star Seeker
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, Bequia, Mayreau, Soufriere , Iles des Saintes, Marigot, San Juan

7 Nights


Add to Favorites
Compare Favorites
from

$5,927

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

Mar 27, 2026

(Friday)

10 Night Gems of the Leeward Islands Cruise

Star Seeker
Windstar Cruises
Starts: San Juan, Puerto Rico
Ends: San Juan, Puerto Rico
Ports of Call:
San Juan, Cruz Bay, St John's, Iles des Saintes, Pigeon Island, St George's, Gustavia St. Barts...

10 Nights


Add to Favorites
Compare Favorites
from

$6,757

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

Dec 20, 2026

(Sunday)

14 Night Star Collector Lovely Leewards 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, Cruz Bay...

14 Nights


Add to Favorites
Compare Favorites
from

$6,793

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

Jan 03, 2027

(Sunday)

14 Night Star Collector Lovely Leewards 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, Cruz Bay, Basseterre...

14 Nights


Add to Favorites
Compare Favorites
from

$7,293

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

Dec 27, 2026

(Sunday)

14 Night Star Collector Lovely Leewards 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...

14 Nights


Add to Favorites
Compare Favorites
from

$7,393

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



Overlay Title