James Beard Foundation & Wine Cruise: Windward Ways & Tobago Cays
 
Oranjestad to Bridgetown
Sat Mar 15, 2025 - Sat Mar 22, 2025,
 7 days
 on Star Pride
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Starting from $3,649 USD
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Oranjestad to Bridgetown
They say you can’t please everyone, but this cruise through the Windward and ABC islands may just prove them wrong.
 
Those who love snorkeling and diving will be on Cloud 9 as they swim with fish and sea turtles in Tobago Cays Marine Park, Bonaire National Marine Park, and the proposed Speyside Marine Protected Area. There’s also plenty for nature lovers on land. From Man-o-War Bay, swim in a picture-perfect waterfall pool surrounded by the oldest Forest Reserve in the Western Hemisphere. Take in the Bali-like beauty of the Pitons on St. Lucia, where rainforest meets some of the healthiest coral reefs in the Caribbean. And discover Bonaire, with its stunning desert-palette motifs like pink flamingos on white salt pans.
 
Those who are looking for the classic Caribbean will find it in Mayreau – just 1.5 square miles with fewer than 300 inhabitants, only reachable by boat. And those who love colonial harbors can enjoy British Bridgetown with its UNESCO garrison as well as the triple Dutch treat of Kralendijk, Willemstad, and Oranjestad.
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: 
Sat Mar 15
Oranjestad
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Sun Mar 16
Willemstad
Arrive:  9:00 AM
Depart:  10:00 PM
Watersports Platform: 
Mon Mar 17
Kralendijk
Arrive:  7:00 AM
Depart:  9:00 PM
Watersports Platform: 
Tue Mar 18
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Wed Mar 19
Soufriere
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Thu Mar 20
Mayreau
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Fri Mar 21
Scarborough, Tobago
Arrive:  7:00 AM
Depart:  4:30 PM
Watersports Platform: 
Sat Mar 22
Bridgetown
Arrive:  5:00 AM
Depart:  
Watersports Platform: 
This James Beard Foundation cruise includes:

• Chef-hosted dinner with wine pairing
• 2 cooking demonstrations on board - recipes included
• Market tour with the Chef
 
Meet The Chef – Chef Jamilka Borges
As the Executive Chef at Independent Hospitality Group, overseer of Lilith, Independent, Hidden Harbor and Lorelei kitchen in Pittsburgh, Jamilka was born and raised in San Juan, Puerto Rico where she developed an interest in art and food early in her life. In 2015 she was recognized by the James Beard Foundation as a Rising Star Chef Semifinalist and was honored as Best Chefs America’s Rising Star Chef. She is recognized for her commitment to her community, culinary skills, and volunteerism. Currently, she works with 412 Food Rescue, a non-profit organization looking to eliminate hunger while reducing food waste and is also a James Beard Boot Camp for Policy and Change alumna.
Winery Details:

J Vineyards is thrilled to collaborate with Chef Jamilka Borges on this voyage, pairing their exceptional wines with her innovative cuisine. This unique journey features two enriching seminars with wine tastings by J Vineyards and Winery, making it the perfect complement to your adventure. Experience the perfect pairing of award-winning wines and gourmet dishes as you sail from Oranjestad to Bridgetown. This collaboration aligns with J Vineyards' commitment to celebrating diversity, highlighted by their Shifting the Lens program. Launched in 2022, Shifting the Lens spotlights historically overlooked cuisines and perspectives, earning the Sonoma County Tourism Innovation Award for fostering inclusivity and diversity.

J Vineyards and Winery stands as the pinnacle of luxury wine and culinary excellence in Sonoma Wine Country. Known for its extraordinary single vineyard Pinot Noir, Chardonnay, and sparkling wines, J captivates visitors with exceptional experiences. Led by Winemaker Nicole Hitchcock, honored as Winemaker of the Year in 2022, J crafts world-class wines from the cool-climate fruit of the renowned Russian River Valley. This cruise includes two complimentary enriching seminars with tastings.
 
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.
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 $3,649 per guest
? All-inclusive price from $4,342 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
Sat, Mar 15 - Sat, Mar 22, 2025
STAR PRIDE
$4,342
$3,649
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SAILING