Windward Ways & Tobago Cays

 
Bridgetown to Oranjestad
Fri Dec 4, 2026 - Sat Dec 12, 2026,
 8 days
 on Star Legend
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Starting from $2,999 USD
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Bridgetown to Oranjestad
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: 
Fri Dec 4
Bridgetown
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Sat Dec 5
Rodney Bay
Arrive:  3:00 PM
Depart:  8:00 AM
Watersports Platform: 
Sat Dec 5
The Pitons
Arrive:  5:30 PM
Depart:  6:30 PM
Watersports Platform: 
Sun Dec 6
Scarborough, Tobago
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Mon Dec 7
Bequia
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Tue Dec 8
Mayreau
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Dec 9
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Thu Dec 10
Kralendijk
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Fri Dec 11
Willemstad
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Sat Dec 12
Oranjestad
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
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
Guaranteed Suite** (chosen by Windstar)
? 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
ALL DATES &
FARES
2026 & 2027 Early Booking Offer
Go All-Inclusive — On Us
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
$3,299
$3,299
Sun, Mar 15 - Sun, Mar 22, 2026
STAR PRIDE
$2,699
$2,699
Fri, Dec 4 - Sat, Dec 12, 2026
STAR LEGEND
$2,999
$2,999
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