Hold times may be longer than usual: We're currently undergoing a reservation system upgrade and are still fixing some issues. Please contact us if you have any questions.
Windward Ways & Tobago Cays
 
Oranjestad to Bridgetown
Sun Mar 15, 2026 - Sun Mar 22, 2026,
 7 days
 on Star Pride
Call For Availability
VIEW ALL SAILING
DATES & FARES
ADD TO
WISH LIST
REMOVE
FROM
WISH LIST
VIEW THE JOURNEY
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
VIEW THE JOURNEY
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.
VIEW THE JOURNEY
Day 2: 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
VIEW THE JOURNEY
Day 4: 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.
VIEW THE JOURNEY
Day 4: The Pitons
Located near the town of Soufriere, St. Lucia the Pitons are a UNESCO World Heritage Site and a spectacular landmark. Gros Piton is 2,619 feet high (798 meters) and Petit Piton is 2,438 feet high (743 meters). Gros Piton is home to at least 148 plant species and 27 bird species (5 of them endemic) and Petit Piton has 97 plant species with 8 rare tree species.
VIEW THE JOURNEY
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.
VIEW THE JOURNEY
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.
VIEW THE JOURNEY
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.
VIEW THE JOURNEY
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: 
Sun Mar 15
Oranjestad
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Mon Mar 16
Kralendijk
Arrive:  8:00 AM
Depart:  9:00 PM
Watersports Platform: 
Tue Mar 17
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Wed Mar 18
Pigeon Island
Arrive:  8:00 AM
Depart:  2:30 PM
Watersports Platform: 
Wed Mar 18
The Pitons
Arrive:  5:30 PM
Depart:  6:30 PM
Watersports Platform: 
Thu Mar 19
Bequia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Mar 20
Mayreau
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Sat Mar 21
Man-O-War Bay
Arrive:  7:00 AM
Depart:  4:00 PM
Watersports Platform: 
Sun Mar 22
Bridgetown
Arrive:  6:00 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.
LEARN MORE →
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
Complimentary All-Inclusive Upgrade
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, Dec 14 - Sat, Dec 21, 2024
STAR PRIDE
$2,499
$2,499
Sat, Jan 4 - Sat, Jan 11, 2025
STAR PRIDE
$2,899
$2,899
Sat, Jan 11 - Sat, Jan 18, 2025
STAR PRIDE
$3,499
$3,499
Sat, Feb 15 - Sat, Feb 22, 2025
STAR PRIDE
Call For Availability
Sat, Feb 22 - Sat, Mar 1, 2025
STAR PRIDE
$3,199
$3,199
Sun, Jan 25 - Sun, Feb 1, 2026
WIND SURF
$3,322
$2,699
Sun, Mar 15 - Sun, Mar 22, 2026
STAR PRIDE
Call For Availability
THIS
SAILING