Windward Islands Surf & Sunsets
 
San Juan to San Juan
Fri Feb 27, 2026 - Fri Mar 6, 2026,
 7 days
 on Star Seeker
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San Juan to San Juan
Revel in seven days of surf, sand and sunsets during this leisurely cruise up and down the Caribbean’s Windward Islands. It’s a perfect vacation getaway for anyone craving a quick escape from life’s everyday obligations. Clip into a zipline and hang on as moss-covered limbs and colorful wild birds rush by your head as you glide through St. Lucia’s rainforest canopy. Vacation time is always well spent among the Windward Islands, but nothing makes it more perfect than the personalized attention and unique excursion opportunities offered by Windstar.

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: 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 3: 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 4: 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 5: 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 6: 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 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.
Popular Highlights
St. Barts
Tour St. Barts to find a chic collection of designer boutiques, stunning beaches, and delightful restaurants
Bequia
Beautiful Bequia’s Admiralty Bay is only for small yachts and ships like ours and the island is famous for its model miniature boat builders.
Pigeon Island
Pigeon Island National Park features splendid beaches,  relics of Arawak Indians and English fort ruins
Les Saintes
Discover the underwater world of Les Saintes and enjoy some of the best snorkeling around in the deep blue waters of Guadeloupe
St. Georges
Shop for spices, especially nutmeg and cinnamon in St. George’s local markets.
St. Lucia Pitons
The UNESCO site Piton's two volcanic peaks, rising more than 2,400 feet, welcome you to St. Lucia.
St. Maarten
Shop the 100% duty free island of two nations, St. Maarten and St. Martin.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Fri Feb 27
San Juan
Arrive:  
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:  3:00 PM
Watersports Platform: 
Mon Mar 2
Mayreau
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Tue Mar 3
Bequia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Wed Mar 4
Soufriere
Arrive:  9:00 AM
Depart:  6:00 PM
Watersports Platform: 
Thu Mar 5
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Mar 6
San Juan
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
“This is the kind of tropical itinerary that people dream of, suffused by an unspoiled sleepy charm which once-upon-a-time was typical in the Caribbean but today has all but disappeared.”
The Story
One of the most sought-after yachting destinations in the Caribbean, the Windward Islands give you a glimpse of what the West Indies looked like in days of old. Technicolor travel posters come to life in its lush green mountains, shimmering blue waters, swaying palm trees and uncrowded beaches. Colorful fishing boats bob in the harbor next to private yachts, and resorts give way to charming boutique hotels and B&Bs.

Pastel Georgian buildings, crumbling forts, and rusting canons recall the days when pirates roamed the seas and Britain and France fought over who would rule these islands. And while each island has its unique charms, the pace of life is almost universally slow, with time to absorb the copious amounts of natural beauty and chat with people who are genuinely welcoming.

Sip a local Carib beer in the shade of sea grape trees. Dive off the Watersports Platform and snorkel above coral gardens entirely undisturbed by your passage. Stand on the ramparts of forts that have seen centuries come and go staring out at a view that never grows old. Discover islands that perfectly match your dreams.
Insider Tips:
  • An island’s windward side faces the trade winds, which come from across the Atlantic. On the leeward side, the Caribbean Sea is calmer. As a result, you’ll usually find the best beaches on the west side of each island.
  • Check out the nutmeg ice cream on Grenada, the Spice Island. It’s like a summer version of eggnog.
  • In tiny Bequia, an island of just 7 square miles, all beaches are public. They’re also clean and uncrowded, so take your pick.
  • The incredibly beautiful twin pitons on Saint Lucia are a UNESCO World Heritage Site. You can climb Gros Piton (with a guide), but it’s an exhausting climb and you’ll need good hiking shoes and plenty of water.
  • The people you meet in Les Saintes are descended from Breton corsairs (pirates), and they’re skilled sailors. Their distinctive shallow white hats are called salacos. If you would like to take a photo, be sure to ask first.
Accommodations & Pricing
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
Marina
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Early Booking Offer 2026 & 2027
Holiday Sailings
Pick Your Perk
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
Fri, Jan 30 - Fri, Feb 6, 2026
STAR SEEKER
$4,192
$3,499
Fri, Feb 13 - Fri, Feb 20, 2026
STAR SEEKER
$4,092
$3,399
Fri, Feb 27 - Fri, Mar 6, 2026
STAR SEEKER
Call For Availability
THIS
SAILING
Fri, Mar 13 - Fri, Mar 20, 2026
STAR SEEKER
$3,692
$2,999
Sun, Nov 8 - Sun, Nov 15, 2026
STAR PRIDE
$2,499
$2,499
Sun, Nov 22 - Sun, Nov 29, 2026
STAR PRIDE
$2,499
$2,499
Sun, Dec 6 - Sun, Dec 13, 2026
STAR PRIDE
$2,499
$2,499
Sun, Dec 20 - Sun, Dec 27, 2026
STAR PRIDE
$2,699
$2,699
Sun, Jan 3 - Sun, Jan 10, 2027
STAR PRIDE
$2,599
$2,599