Windward Ways & Tobago Cays
 
Oranjestad to Bridgetown
Sat Feb 15, 2025 - Sat Feb 22, 2025,
 7 days
 on Star Pride
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Oranjestad to Bridgetown
Those who love watersports, snorkeling and diving will be on Cloud 9 on this cruise through the Windward and ABC islands. Swim with vibrant fish and friendly sea turtles as you visit ports in Tobago Cays Marine Park, in Bonaire National Marine Park, and in the proposed Speyside Marine Protected Area. Paddleboard right from the Watersports Platform as we visit smaller ports and less-visited bays away from the crowds. And when you’ve had your fill of ocean action (if you ever do), head to shore and explore colorful Dutch colonial harbors, sugar-white beaches and mouthwatering island cuisines.
voyage map
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Day 1: Oranjestad
Known for having some of the best beaches in the Caribbean, this Dutch port makes it easy to just … take it easy. Walk through town to choose your favorite carved wooden door, or spend the day like the Arubans do playing dominos at a beachside table.
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Day 2: Willemstad
Savor the pastel colors of the historic UNESCO site Old Town and the way the elaborate Dutch gables cut baroque curlicues from the sky. It’s the perfect appetizer for a day of watersports or an adventure below ground at the magical Hato Caves—filled with eerie limestone formations and ancient petroglyphs.
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Day 3: Kralendijk
The ice cream colors of the stucco houses will draw your lens, as will the pink flamingos on the salt pans. But you’ll need a waterproof camera to complete the portrait since more than 400 fish species and 50 types of coral wait beneath the surface
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Day 5: 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 6: 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 7: Man-O-War Bay
Listen for the sound of a conch announcing the return of the fishing boats. Bobbing next to us are flotillas of pelicans – hinting at the excellent snorkeling waiting for you here and in neighboring Pirate’s Bay.
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Day 8: Bridgetown
Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you’ll find historic sugar plantations and the fairyland magic of Harrison’s Cave.
Popular Highlights
Bonaire Bird
Have your binoculars ready for birdwatching on Bonaire, home of flamingos, Amazon parrots, native parakeets and pink sea salt.
Colonial Town
 Four magical colonial towns (including two that are UNESCO-listed) contrast with tiny out-of-the-way ports and bays on this week-long adventure.
Mayreau
Visit Mayreau, the smallest island of the Grenadines and enjoy the exclusive Signature Beach Party.
Tobago Cay
 Snorkel the impressive coral reefs of Tobago Cay at the confluence of the Atlantic and Caribbean Sea.
Willemstad
Known for its brightly colored architecture, Willemstad is a UNESCO site.
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Sat Feb 15
Oranjestad
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Sun Feb 16
Willemstad
Arrive:  9:00 AM
Depart:  10:00 PM
Watersports Platform: 
Mon Feb 17
Kralendijk
Arrive:  7:00 AM
Depart:  9:00 PM
Watersports Platform: 
Tue Feb 18
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Wed Feb 19
Soufriere
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Thu Feb 20
Mayreau
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Fri Feb 21
Man-O-War Bay
Arrive:  7:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Feb 22
Bridgetown
Arrive:  5:00 AM
Depart:  
Watersports Platform: 
 
Insider Tips
  • You’ll find some of the best beaches in the Caribbean on Aruba. Aside from the beach resorts, every stretch of sand on the island is open to all, and easily accessible by public transportation.
  • Mayreau is about as uncrowded as you can get. But if even that’s too much for you, head to Mopian. Surrounded by reef, the tiny dollop of sand has room for just one thatch umbrella.
  • Bonaire’s arid climate contributes to its exceptionally clear waters, a quality that has helped make it the #1-rated dive destination in the Caribbean.
  • If you plan to snorkel or dive, bring an underwater camera. Colorful fish like blue tangs and damsel fish are everywhere. And with luck, you may spot a hawksbill, a green turtle, or maybe even a seahorse.
  • For a taste of authentic Curacao cuisine, cross Willemstad’s Queens Emma Bridge (the “Swinging Old Lady”) to Plasa Bieu. The pitched-roof food court offers many island favorites, plus the chance to mingle with hungry locals.
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.
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
Last Minute Cruise Deals
Pick Your Perk
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sat, Dec 14 - Sat, Dec 21, 2024
STAR PRIDE
$2,691
$1,998
Sat, Jan 4 - Sat, Jan 11, 2025
STAR PRIDE
$3,369
$2,676
Sat, Jan 11 - Sat, Jan 18, 2025
STAR PRIDE
$6,092
$5,399
Sat, Feb 15 - Sat, Feb 22, 2025
STAR PRIDE
Call For Availability
THIS
SAILING
Sat, Feb 22 - Sat, Mar 1, 2025
STAR PRIDE
$4,342
$3,649
Sun, Jan 25 - Sun, Feb 1, 2026
WIND SURF
$3,492
$2,799
Sun, Mar 15 - Sun, Mar 22, 2026
STAR PRIDE
$3,292
$2,599