Windward Islands Surf & Sunsets
 
San Juan to San Juan
Sat Nov 23, 2024 - Sat Nov 30, 2024,
 7 days
 on Star Pride
?All-inclusive from
$2,621
?Cruise Only From
$1,998
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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 3: St. George's
Inhale the intoxicating aroma of the “Isle of Spice” as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.
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Day 4: 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 5: Pigeon Island
The UNESCO site Pitons’ with their two majestic volcanic peaks and 24 miles of vibrant coral reef welcome you to St. Lucia. Nearby Pigeon Island National Park features impressive ruins of English forts, archaeological relics of Arawak Indians, and splendid beaches.
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Day 6: 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 7: 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 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
Watersports
PlatformWatersports Platform: 
Sat Nov 23
San Juan
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Nov 24
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Mon Nov 25
St. George's
Arrive:  9:00 AM
Depart:  10:00 PM
Watersports Platform: 
Tue Nov 26
Bequia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Wed Nov 27
Pigeon Island
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Thu Nov 28
Les Saintes
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Fri Nov 29
Philipsburg, St. Maarten
Arrive:  8:00 AM
Depart:  2:00 PM
Watersports Platform: 
Sat Nov 30
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.
Star Pride
Carrying only 312 guests, Star Pride still tucks into small ports like Le Lavandou and Wrangell or narrow waterways like the Corinth and Keil Canal. We can’t wait to welcome you onboard for your next 180 degree from ordinary adventure! Learn more about the newly renovated ship and the $250 Million Star Plus Initiative.
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Accommodations & Pricing
This all-suite ship completed renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love.
Star Porthole Suite
Star Porthole Suite
These rooms represent a nod to the sailing tradition of porthole windows. And while sailors might have had cramped quarters, your 277 square foot stateroom is wonderfully spacious and furnished with all the modern amenities and comforts of home.
? Cruise only from $1,998 per guest
? All-inclusive price from $2,621 per guest
Ocean View Suite
Ocean View Suite
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, and savor a treat from the fresh fruit bowl.
? Cruise only from $2,078 per guest
? All-inclusive price from $2,701 per guest
Ocean View Suite 1
Ocean View Suite 1
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $2,198 per guest
? All-inclusive price from $2,821 per guest
Ocean View Suite 2
Ocean View Suite 2
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $2,899 per guest
? All-inclusive price from $2,899 per guest
Balcony Suite
Balcony Suite
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $3,699 per guest
? All-inclusive price from $3,699 per guest
Balcony Suite 1
Balcony Suite 1
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $3,999 per guest
? All-inclusive price from $3,999 per guest
Star Balcony Suite 1
Star Balcony Suite 1
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $4,099 per guest
? All-inclusive price from $4,099 per guest
Star Ocean View Suite 1
Star Ocean View Suite 1
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Call for Availability
Ocean View Suite 3
Ocean View Suite 3
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Call for Availability
Star Balcony Suite
Star Balcony Suite
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Call for Availability
Deluxe Suite
Deluxe Suite
Brand new Deluxe Suites welcome you with 468 square feet of casually elegant living space and an ocean viewing French balcony. All these suites feature 3rd berths, and a sleep-inducing queen bed easily converted to twins.
? Call for Availability
Classic Suite
Classic Suite
Relax in 400 to 530 spacious square feet. Your living area offers beautiful views from the forward-facing window and French doors onto your private veranda. Two spacious closets give you plenty of room to unpack.
? Call for Availability
Owner's Suite
Owner's Suite
With 575 square feet, your Owner’s Suite offers separate living room and dining areas. A veranda, Interactive TVs and a full master bath and separate powder room indulge you in spacious comfort. 
? 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
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
Sat, Nov 9 - Sat, Nov 16, 2024
STAR PRIDE
$4,799
$4,799
Sat, Nov 23 - Sat, Nov 30, 2024
STAR PRIDE
$2,621
$1,998
THIS
SAILING
Fri, Jan 30 - Fri, Feb 6, 2026
STAR SEEKER
$3,299
$3,299
Fri, Feb 13 - Fri, Feb 20, 2026
STAR SEEKER
$3,299
$3,299
Fri, Feb 27 - Fri, Mar 6, 2026
STAR SEEKER
$2,999
$2,999
Fri, Mar 13 - Fri, Mar 20, 2026
STAR SEEKER
$2,999
$2,999