Star Collector: Lovely Leewards
 
San Juan to San Juan
Fri Feb 20, 2026 - Fri Mar 6, 2026,
 14 days
 on Star Seeker
?All-inclusive from
$5,199
?Cruise Only From
$5,199
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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
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Day 1: San Juan
The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.
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Day 2: CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
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Day 3: Basseterre
With Georgian architecture situated against an irresistible backdrop of emerald green hills, Basseterre is one of the loveliest of the Caribbean’s small capitals. Beyond town, more than a quarter of St. Kitts has been set aside as Brimstone Hill Fortress national Park, a UNESCO World Heritage Site.
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Day 4: Philipsburg, St. Maarten
Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
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Day 5: Gustavia
Affectionately known as St. Barts, the Caribbean’s most chic island adds a French flair to Riviera-like beaches and duty-free boutiques. Walk past gingerbread cottages in search of celebrities, shop for designer fashions, or sip the island’s signature ti punch as kite surfers fly by.
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Day 6: Jost Van Dyke, Great Harbour
For an island comprised of a mere eight square miles, it’s amazing how much there is to do on Jost Van Dyke. Visit the national park on nearby Diamond Cay, snorkel among swaying sponges and angelfish at Sandy Spit, or pilot your own boat around Sir Francis  Drake Waterway. After all that, you’ll be ready for an evening drink on the beach — where you can admire your Windstar ship aglow in the harbor.
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Day 7: Virgin Gorda / Prickly Pear, British Virgin Islands
The  beautiful Bank Barrier coral reef wavers just beneath you as your ship makes the break to the bird sanctuary of Prickly Pear Island, so named because it is dotted with prickly pear cacti. Althought uninhabited, it does have a beach bar and water sports facilities. Not far away lies the curious assembly of house-sized boulders called “The Baths,” which form huge underground pools and caverns
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Day 8: San Juan
The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.
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Day 9: Philipsburg, St. Maarten
Pastel-colored buildings and shops filled with tempting souvenirs herald your arrival to bustling Philipsburg. Situated near the harbor on the Dutch side of St. Maarten, Philipsburg owes its discovery to Christopher Columbus in 1493. Today, celebrated Front Street is home to a number of local Creole restaurants as well as jewelry stores, stylish boutiques, and lively casinos for visitors seeking an upbeat island experience.
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Day 10: Les Saintes
This is the Caribbean as you’ve always imagined it, with yacht-filled harbors set against volcanic mountains and endless stretches of palm-fringed beach. The underwater world here attracted the likes of Jacques Cousteau, but even novice snorkelers will enjoy exploring these impossibly blue waters.
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Day 11: Soufriere
Nestled in the shadows of the UNESCO Pitons, Soufriere represents the heart and soul of St. Lucia. The tiny town center is full of street vendors and stores and some of the best resorts on the island can be found here. Nearby are secluded waterfalls and the waters here boast some of the best diving around. Sights to see include the Edmund Rainforest Trail, fond Doux Holiday plantation, Robot Estate and the Gros Piton Nature Trail.
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Day 12: Bequia
The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia’s whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island’s famed model boat builders at work on their miniature masterpieces.
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Day 13: Mayreau
With fewer than 300 inhabitants and miles of secluded beaches, it's easy to feel as if you're on your own private island. Saline Bay is a delightful anchorage that separates the Caribbean from the Atlantic - and a perfect place to play with some of the toys from the Watersports Platform.
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Day 15: San Juan
The imposing façade of El Morro fortress is just one of the many UNESCO World Heritage Sites in San Juan. Admire the colorful colonial buildings from your casually elegant ship, docked right in the heart of Old San Juan.
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
 
San Juan
Discover the imposing façade of El Morro Fortress, a UNESCO site in San Juan
 
St. Barts
Enjoy a relaxing beach day in St. Barts, long the haunt of the rich
 
St. George's
Enjoy the spice market and some of the best snorkeling around on Grenada, the Spice Island
 
St. Lucia
The Piton's two volcanic peaks, rising more than 2,400, feet welcome you to St. Lucia
 
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Fri Feb 20
San Juan
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sat Feb 21
CRUZ BAY, ST. JOHN, Virgin Islands (U.S.)
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sun Feb 22
Basseterre
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Mon Feb 23
Philipsburg, St. Maarten
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Tue Feb 24
Gustavia
Arrive:  7:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Feb 25
Jost Van Dyke, Great Harbour
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Thu Feb 26
Virgin Gorda / Prickly Pear, British Virgin Islands
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Fri Feb 27
San Juan
Arrive:  7:00 AM
Depart:  7:00 PM
Watersports Platform: 
Sat Feb 28
Philipsburg, St. Maarten
Arrive:  12:00 PM
Depart:  6:30 PM
Watersports Platform: 
Sun Mar 1
Les Saintes
Arrive:  9:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Mar 2
Soufriere
Arrive:  9:00 AM
Depart:  9:00 PM
Watersports Platform: 
Tue Mar 3
Bequia
Arrive:  9:00 AM
Depart:  10:00 PM
Watersports Platform: 
Wed Mar 4
Mayreau
Arrive:  8:00 AM
Depart:  4:30 PM
Watersports Platform: 
Thu Mar 5
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Mar 6
San Juan
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
Star Seeker
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Accommodations & Pricing
Oceanview Suite
Oceanview Suite
Experience the perfect blend of style and functionality in this thoughtfully designed 203-square-foot suite. The well-planned layout creates an ideal retreat with plenty of natural light, a view of the sea, a walk-in mosaic glass shower and an inviting queen bed (convertible into two twins if desired), perfect for unwinding after a day of fun and exploration.
? Cruise only from $5,199 per guest
? All-inclusive price from $5,199 per guest
Infinity Suite
Infinity Suite
This 280-square-foot suite features a wide floor-to-ceiling infinity window that allows for stunning ocean views. You can even open the top half to enjoy the cool ocean breeze. Your suite features an inviting queen bed (convertible into two twin beds if desired), a walk-in mosaic glass shower and a comfortable living area where you can lounge and enjoy the view.
? Cruise only from $5,699 per guest
? All-inclusive price from $5,699 per guest
Vista Infinity Suite
Vista Infinity Suite
Located on deck 7, this 280-square-foot suite features a wide floor-to-ceiling infinity window that allows for stunning ocean views. You can even open the top half to enjoy the cool ocean breeze. Your suite features an inviting queen bed (convertible into two twin beds if desired), a walk-in mosaic glass shower and a comfortable living area where you can lounge and enjoy the view.
? Cruise only from $6,099 per guest
? All-inclusive price from $6,099 per guest
Veranda Suite
Veranda Suite
Stylish comfort and ocean views welcome you to this 225-square-foot suite. Relax on your queen bed (convertible into two twin beds if desired) or lounge in the nearby living area. The outdoor space adds another 55 square feet, enough to sit outside comfortably and enjoy the breeze. In the bathroom, you’ll find a luxurious walk-in mosaic glass shower with rain head and body jets.
? Cruise only from $6,899 per guest
? All-inclusive price from $6,899 per guest
Premier Veranda Suite
Premier Veranda Suite
 Located at the middle of the ship, these 225-square-foot suites welcome you with stylish comfort and beautiful ocean views. Relax on your queen bed (convertible into two twin beds if desired) or lounge in the nearby living area. The outdoor space adds another 55 square feet, enough to sit outside comfortably and enjoy the breeze. In the bathroom, you’ll find a luxurious walk-in mosaic glass shower with rain head and body jets.
? Cruise only from $7,599 per guest
? All-inclusive price from $7,599 per guest
Triple Premier Veranda Suite
Triple Premier Veranda Suite
Located on deck 6, this 246-square-foot suite welcomes you with stylish comfort and stunning ocean views. Featuring an inviting queen bed (convertible into two twin beds if desired) and a pull-out sofa in the living area, the suite allows for triple occupancy. The outdoor space adds another 55 square feet, enough to sit outside comfortably and enjoy the breeze. In the bathroom, you’ll find a luxurious walk-in mosaic glass shower with rain head and body jets.
? Cruise only from $7,899 per guest
? All-inclusive price from $7,899 per guest
Triple Infinity Suite
Triple Infinity Suite
This roomy 301-square-foot suite features a wide floor-to-ceiling infinity window in the bedroom, allowing for stunning ocean views. You can even open the top half to enjoy the cool ocean breeze. This suite also features an inviting queen bed (convertible into two twin beds if desired) and a pull-out sofa in the separate living area, allowing for triple occupancy. In the bathroom, you’ll find a luxurious walk-in mosaic glass shower with rain head and body jets.
? Cruise only from $7,899 per guest
? All-inclusive price from $7,899 per guest
Vista Veranda Suite
Vista Veranda Suite
Located on deck 7, this 268-square-foot suite welcomes you with stylish comfort and stunning ocean views. Relax on your queen bed (convertible into two twin beds if desired) or lounge in the nearby living area. The outdoor space adds another 55 square feet, enough to sit outside comfortably and enjoy the breeze. In the bathroom, you’ll find a luxurious walk-in mosaic glass shower with rain head and body jets.
? Cruise only from $8,099 per guest
? All-inclusive price from $8,099 per guest
Deluxe Suite
Deluxe Suite
This 288-square-foot suite welcomes you with spectacular views, courtesy of the sliding glass doors that lead out to your private balcony. The outdoor space adds another 110 square feet, enough to sit outside comfortably and enjoy the breeze. The bedroom features an inviting queen bed (convertible into two twin beds if desired) and its own sliding glass door with balcony access, while the bathroom includes a luxurious walk-in mosaic glass shower with rain head and body jets.
? Cruise only from $10,299 per guest
? All-inclusive price from $10,299 per guest
Classic Suite
Classic Suite
Step into a stylish and bright open living area with a spacious adjacent bedroom. This 353-square-foot suite welcomes you with spectacular views, courtesy of the sliding glass doors that lead out to your private balcony. The outdoor space adds another 110 square feet, enough to sit outside comfortably and enjoy the breeze. The bedroom features an inviting queen bed that can be converted into two twins if desired, while the bathroom includes a luxurious walk-in mosaic glass shower with rain head and body jets.
? Cruise only from $12,099 per guest
? All-inclusive price from $12,099 per guest
Star Suite
Star Suite
Step into a stylish and bright open living area with a spacious adjacent bedroom. This 380-square-foot suite welcomes you with spectacular views, courtesy of the sliding glass doors that lead out to your private balcony. The outdoor space adds another 110 square feet, enough to sit outside comfortably and enjoy the breeze. The bedroom features an inviting queen bed (convertible into two twin beds if desired) and its own sliding glass door with balcony access, while the bathroom includes a bathtub and walk-in mosaic glass shower with rain head and body jets.
? Cruise only from $12,899 per guest
? All-inclusive price from $12,899 per guest
Horizon Owner’s Suite
Horizon Owner’s Suite
This luxurious 548-square-foot suite combines floor-to-ceiling windows and a wrap-around balcony for an unparalleled cruising experience. Perfect for evening cocktails or a private dinner, the wrap-around balcony adds 248 square feet of space and offers unobstructed views of the sea. The suite boasts a separate entryway — as well as separate dining and living areas — and a guest powder room. The bedroom includes an inviting king bed (convertible into two XL twin beds if desired), and the bathroom features a luxurious double walk-in mosaic glass shower with rain head and body jets. For family bookings, the adjacent suite can be combined to provide extra bedrooms and space for entertaining.
? Cruise only from $15,099 per guest
? All-inclusive price from $15,099 per guest
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
Genuine and Thoughtful Crew
Crew Talent Show
Open Bridge
Local and Live Performances
Relax at the Pool or Hot Tub
Complimentary 24 Hour Room Service
Signature Sail Away
Shopping With The Chef
Take In The Sun
Watersports Platform
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Complimentary All-Inclusive Upgrade
Early Booking Offer 2026
Holiday Sailings
Last Minute Cruise Deals
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited beer, wine, and cocktails, and gratuities. From $89 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sun, Nov 3 - Sat, Nov 16, 2024
STAR PRIDE
$7,399
$7,399
Sat, Nov 9 - Sat, Nov 23, 2024
STAR PRIDE
$5,399
$5,399
Sat, Nov 16 - Sat, Nov 30, 2024
STAR PRIDE
$6,299
$6,299
Sat, Nov 23 - Sat, Dec 7, 2024
STAR PRIDE
$6,299
$6,299
Sun, Nov 2 - Sun, Nov 16, 2025
STAR PRIDE
$5,845
$4,599
Sun, Nov 9 - Sun, Nov 23, 2025
STAR PRIDE
$5,345
$4,099
Sun, Nov 16 - Sun, Nov 30, 2025
STAR PRIDE
$5,345
$4,099
Sun, Nov 23 - Sun, Dec 7, 2025
STAR PRIDE
$5,345
$4,099
Fri, Jan 23 - Fri, Feb 6, 2026
STAR SEEKER
$5,599
$5,599
Fri, Jan 30 - Fri, Feb 13, 2026
STAR SEEKER
$5,299
$5,299
Fri, Feb 6 - Fri, Feb 20, 2026
STAR SEEKER
$5,299
$5,299
Fri, Feb 13 - Fri, Feb 27, 2026
STAR SEEKER
$5,399
$5,399
Fri, Feb 20 - Fri, Mar 6, 2026
STAR SEEKER
$5,199
$5,199
THIS
SAILING
Fri, Feb 27 - Fri, Mar 13, 2026
STAR SEEKER
$4,899
$4,899
Fri, Mar 6 - Fri, Mar 20, 2026
STAR SEEKER
$4,899
$4,899