Star Collector: Lovely Leewards
 
San Juan to San Juan
Sun Nov 22, 2026 - Sun Dec 6, 2026,
 14 days
 on Star Pride
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Starting from $3,999 USD
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San Juan to San Juan
Whether you’re passionate about swimming among rarely seen undersea wildlife or the intricate cultures and intertwined European histories of the Windward Islands, this 2-week cruise offers the best combinations of charm, island heritage and natural beauty. Shop unique designer apparel in St. Barts, where you’ll discover a fashionable confluence of high-end brands normally associated with places like Madison Avenue, but displayed in an ambiance that’s anything but intimidating. Master the art of cooking with distinct spices like nutmeg, cloves, and allspice in authentic Caribbean cuisine while taking direction from a highly-skilled native chef in Philipsburg. This Caribbean getaway is the perfect duration for lovers of island life and those who want to spend more time exploring the Windward Islands overlooked by other cruise lines.
voyage map
Popular Highlights
Complimentary laundry
Pack light with complimentary daily laundry service
 
Montserrat
Visit the “Pompeii of the Caribbean” at Montserrat with its half-buried city
 
Philipsburg
Pick up tempting souvenirs at the pastel-colored buildings and shops of duty-free Philipsburg
 
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Sun Nov 22
San Juan
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Mon Nov 23
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Tue Nov 24
St. George's
Arrive:  9:00 AM
Depart:  10:00 PM
Watersports Platform: 
Wed Nov 25
Bequia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Thu Nov 26
Mayreau
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Fri Nov 27
Les Saintes
Arrive:  10:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Nov 28
Marigot, St. Martin
Arrive:  8:00 AM
Depart:  3:00 PM
Watersports Platform: 
Sun Nov 29
San Juan
Arrive:  7:00 AM
Depart:  7:00 PM
Watersports Platform: 
Mon Nov 30
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Dec 1
Gustavia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Wed Dec 2
Basseterre
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Thu Dec 3
Philipsburg, St. Maarten
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Dec 4
Jost Van Dyke, Great Harbour
Arrive:  9:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Dec 5
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sun Dec 6
San Juan
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
Accommodations & Pricing
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
? Call for Availability
The Windstar Life
The Windstar staff-to-guest ratio is 1:1.5, and it shows.The moment you board you’ll feel it: an ever-attentive crew at your service, providing you with what you want and need, when you want and need it.
Friendly and Relaxed Atmosphere
Signature Onboard Barbecue
Cooking Demonstrations
ALL DATES &
FARES
Holiday Sailings
Go All-Inclusive — On Us
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited select beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sun, Nov 2 - Sun, Nov 16, 2025
STAR PRIDE
$4,599
$4,599
Sun, Nov 9 - Sun, Nov 23, 2025
STAR PRIDE
$4,099
$4,099
Sun, Nov 16 - Sun, Nov 30, 2025
STAR PRIDE
$4,099
$4,099
Sun, Nov 23 - Sun, Dec 7, 2025
STAR PRIDE
$4,099
$4,099
Fri, Jan 23 - Fri, Feb 6, 2026
STAR SEEKER
$16,599
$16,599
Fri, Jan 30 - Fri, Feb 13, 2026
STAR SEEKER
$8,899
$8,899
Fri, Feb 6 - Fri, Feb 20, 2026
STAR SEEKER
$8,799
$8,799
Fri, Feb 13 - Fri, Feb 27, 2026
STAR SEEKER
$7,799
$7,799
Fri, Feb 20 - Fri, Mar 6, 2026
STAR SEEKER
$7,799
$7,799
Fri, Feb 27 - Fri, Mar 13, 2026
STAR SEEKER
Call For Availability
Fri, Mar 6 - Fri, Mar 20, 2026
STAR SEEKER
Call For Availability
Sun, Nov 8 - Sun, Nov 22, 2026
STAR PRIDE
$5,385
$3,999
Sun, Nov 15 - Sun, Nov 29, 2026
STAR PRIDE
$5,385
$3,999
Sun, Nov 22 - Sun, Dec 6, 2026
STAR PRIDE
$5,385
$3,999
THIS
SAILING
Sun, Nov 29 - Sun, Dec 13, 2026
STAR PRIDE
$5,385
$3,999
Sun, Dec 6 - Sun, Dec 20, 2026
STAR PRIDE
$5,385
$3,999
Sun, Dec 13 - Sun, Dec 27, 2026
STAR PRIDE
$5,485
$4,099
Sun, Dec 20 - Sun, Jan 3, 2027
STAR PRIDE
$5,785
$4,399
Sun, Dec 27 - Sun, Jan 10, 2027
STAR PRIDE
$5,885
$4,499
Sun, Jan 3 - Sun, Jan 17, 2027
STAR PRIDE
$5,685
$4,299
Star Collector: Lovely Leewards
Port to port
San Juan to San Juan
Duration
14 days
Day
Port
Day 1
San Juan
Day 2
AT SEA
Day 3
St. George's
Day 4
Bequia
Day 5
Mayreau
Day 6
Les Saintes
Day 7
Marigot, St. Martin
Day 8
San Juan
Day 9
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Day 10
Gustavia
Day 11
Basseterre
Day 12
Philipsburg, St. Maarten
Day 13
Jost Van Dyke, Great Harbour
Day 14
Virgin Gorda / Prickly Pear, British Virgin Islands
Day 15
San Juan
ALL DATES &
FARES
Holiday Sailings
Go All-Inclusive — On Us
Great cruise-only fares or make it an all-inclusive voyage with unlimited select beer, wine, and cocktails, Wi-Fi, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sun
Nov 2
2025
STAR PRIDE
$4,599
$4,599
Sun
Nov 9
2025
STAR PRIDE
$4,099
$4,099
Sun
Nov 16
2025
STAR PRIDE
$4,099
$4,099
Sun
Nov 23
2025
STAR PRIDE
$4,099
$4,099
Fri
Jan 23
2026
STAR SEEKER
$16,599
$16,599
Fri
Jan 30
2026
STAR SEEKER
$8,899
$8,899
Fri
Feb 6
2026
STAR SEEKER
$8,799
$8,799
Fri
Feb 13
2026
STAR SEEKER
$7,799
$7,799
Fri
Feb 20
2026
STAR SEEKER
$7,799
$7,799
Fri
Feb 27
2026
STAR SEEKER
Call For Availability
Fri
Mar 6
2026
STAR SEEKER
Call For Availability
Sun
Nov 8
2026
STAR PRIDE
$5,385
$3,999
Sun
Nov 15
2026
STAR PRIDE
$5,385
$3,999
Sun
Nov 22
2026
STAR PRIDE
$5,385
$3,999
Sun
Nov 29
2026
STAR PRIDE
$5,385
$3,999
Sun
Dec 6
2026
STAR PRIDE
$5,385
$3,999
Sun
Dec 13
2026
STAR PRIDE
$5,485
$4,099
Sun
Dec 20
2026
STAR PRIDE
$5,785
$4,399
Sun
Dec 27
2026
STAR PRIDE
$5,885
$4,499
Sun
Jan 3
2027
STAR PRIDE
$5,685
$4,299
Click on the date to view the map and itinerary by date