Windward Islands Surf & Sunsets
 
San Juan to San Juan
Sat Mar 4, 2023 - Sat Mar 11, 2023,
 7 days
 on Star Pride
?All-inclusive from
$2,122
?Cruise Only From
$1,499
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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:
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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: 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
El Morro
See San Juan’s UNESCO site El Morro Fortress
Guadeloupe
Enjoy some of the best snorkeling around in the deep blue waters of Guadeloupe.
Les Saintes
Discover the underwater world of Les Saintes.
Mount Pleasant
Walk up Mount Pleasant with a spectacular view of Bequia's Admiral Bay.
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 Mar 4
San Juan
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Mar 5
AT SEA
Arrive:   N/A
Depart:   N/A
Watersports Platform: 
Mon Mar 6
St. George's
Arrive:  9:00 AM
Depart:  10:00 PM
Watersports Platform: 
Tue Mar 7
Bequia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Wed Mar 8
Pigeon Island
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Thu Mar 9
Les Saintes
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Fri Mar 10
St. Maarten
Arrive:  8:00 AM
Depart:  2:00 PM
Watersports Platform: 
Sat Mar 11
San Juan
Arrive:  7:00 AM
Depart:  
Watersports Platform: 
WINDSTAR SIGNATURE
A Complimentary Windstar Destination Discovery Event

Bora Bora is surrounded by a number of tiny islets called "motu" - small, pristine, secluded paradises that offer privacy, beauty, and relaxing ambiance. You will spend the evening on one of these perfect Polynesian oases accompanied only by other Windstar guests. As has long been the tradition in Tahiti, you will be welcomed to the motu with a fragrant flower lei.

Your private feast on the beach promises to be extraordinary. The menu has been carefully selected by Windstar's executive chef and is sure to please and tantalize your palate.

When your meal is complete and the stars begin to shine, the highlight of this enchanted evening will begin. Fire dancing has long been deeply embedded in the Polynesian culture as a way to send messages to the gods. Your fire dancing experts will be wearing traditional loincloths and will dazzle you with high-speed acrobatic moves, throwing flames so hot you'll feel the warmth 10 feet away.

Please note: This DestinationDiscovery Event has been scheduled in a way that will allow you to book and experience another shore excursion on the same day and you will not miss anything.

Bora Bora is surrounded by a number of tiny islets called "motu" - small, pristine, secluded paradises that offer privacy, beauty, and relaxing ambiance. You will spend the evening on one of these perfect Polynesian oases accompanied only by other Windstar guests. As has long been the tradition in Tahiti, you will be welcomed to the motu with a fragrant flower lei.

Bora Bora is surrounded by a number of tiny islets called "motu" - small, pristine, secluded paradises that offer privacy, beauty, and relaxing ambiance. You will spend the evening on one of these perfect Polynesian oases accompanied only by other Windstar guests. As has long been the tradition in Tahiti, you will be welcomed to the motu with a fragrant flower lei.

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.
LEARN MORE →
Accommodations & Pricing
This all-suite ship will complete 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 $1,499 per guest
? All-inclusive price from $2,122 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, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $1,599 per guest
? All-inclusive price from $2,222 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 $1,599 per guest
? All-inclusive price from $2,222 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.
? Cruise only from $1,699 per guest
? All-inclusive price from $2,322 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 $1,699 per guest
? All-inclusive price from $2,322 per guest
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.
? Cruise only from $1,799 per guest
? All-inclusive price from $2,422 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 $2,099 per guest
? All-inclusive price from $2,722 per guest
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.
? Cruise only from $2,099 per guest
? All-inclusive price from $2,722 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 $2,199 per guest
? All-inclusive price from $2,822 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 $2,299 per guest
? All-inclusive price from $2,922 per guest
Deluxe Suite
Deluxe 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.
? Cruise only from $4,599 per guest
? All-inclusive price from $5,222 per guest
Owner's Suite
Owner's Suite
With 575 square feet, your Owner’s Suite offers separate living room and dining areas. A veranda, two flat-screen TVs and DVD players, and a full master bath and separate powder room indulge you in spacious comfort. 
? Cruise only from $6,399 per guest
? All-inclusive price from $7,022 per guest
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
? Call for Availability
Guaranteed Balcony Suite** (chosen by Windstar)
Guaranteed Balcony Suite** (chosen by Windstar)
Guaranteed Balcony Suite** (chosen by Windstar)
? 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
ALL DATES &
FARES
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, Feb 4 - Sat, Feb 11, 2023
STAR PRIDE
$2,522
$1,899
Sat, Feb 18 - Sat, Feb 25, 2023
STAR PRIDE
$2,122
$1,499
Sat, Mar 4 - Sat, Mar 11, 2023
STAR PRIDE
$2,122
$1,499
THIS
SAILING
! ITINERARY CHANGE San Juan TO San Juan 7 days on Star Pride X
Please note: The ports in this itinerary have been updated as of XX/XX/XXXX
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Sat Mar 4
San Juan
Arrive:  
Depart:  7:00 PM
Watersports Platform: 
Sun Mar 5
AT SEA
Arrive:   N/A
Depart:   N/A
Watersports Platform: 
Mon Mar 6
St. George's
Arrive:  9:00 AM
Depart:  10:00 PM
Watersports Platform: 
Tue Mar 7
Bequia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Wed Mar 8
Pigeon Island
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Thu Mar 9
Les Saintes
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Fri Mar 10
St. Maarten
Arrive:  8:00 AM
Depart:  2:00 PM
Watersports Platform: 
Sat Mar 11
San Juan
Arrive:  7:00 AM
Depart:  
Watersports Platform: