Windward Ways & Tobago Cays
 
Oranjestad to Bridgetown
Sun Mar 15, 2026 - Sun Mar 22, 2026,
 7 days
 on Star Pride
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Starting from $2,599 USD
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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
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.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports 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.
Accommodations & Pricing
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 $2,599 per guest
? All-inclusive price from $3,292 per guest
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
ALL DATES &
FARES
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
Sun, Jan 25 - Sun, Feb 1, 2026
WIND SURF
$3,692
$2,999
Sun, Mar 15 - Sun, Mar 22, 2026
STAR PRIDE
$3,292
$2,599
THIS
SAILING