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
?All-inclusive from
$3,199
?Cruise Only From
$3,199
VIEW ALL SAILING
DATES & FARES
ADD TO
WISH LIST
REMOVE
FROM
WISH LIST
VIEW THE JOURNEY
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
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: 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.
VIEW THE JOURNEY
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
VIEW THE JOURNEY
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.
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: 
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
Man-O-War Bay
Arrive:  7:00 AM
Depart:  5:00 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.
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.
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 $3,199 per guest
? All-inclusive price from $3,199 per guest
Ocean View Suite
Ocean View Suite
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, and savor a treat from the fresh fruit bowl.
? Cruise only from $3,299 per guest
? All-inclusive price from $3,299 per guest
Ocean View Suite 1
Ocean View Suite 1
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 $3,549 per guest
? All-inclusive price from $3,549 per guest
Star Ocean View Suite 1
Star Ocean View Suite 1
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $3,599 per guest
? All-inclusive price from $3,599 per guest
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 $3,649 per guest
Ocean View Suite 3
Ocean View Suite 3
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 $3,799 per guest
? All-inclusive price from $3,799 per guest
Balcony Suite
Balcony Suite
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 $4,599 per guest
? All-inclusive price from $4,599 per guest
Star Balcony Suite
Star Balcony Suite
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $4,649 per guest
? All-inclusive price from $4,649 per guest
Balcony Suite 1
Balcony Suite 1
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 $4,699 per guest
? All-inclusive price from $4,699 per guest
Star Balcony Suite 1
Star Balcony Suite 1
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $4,799 per guest
? All-inclusive price from $4,799 per guest
Deluxe Suite
Deluxe Suite
Brand new Deluxe Suites welcome you with 468 square feet of casually elegant living space and an ocean viewing French balcony. All these suites feature 3rd berths, and a sleep-inducing queen bed easily converted to twins.
? Cruise only from $5,699 per guest
? All-inclusive price from $5,699 per guest
Classic Suite
Classic Suite
Relax in 400 to 530 spacious square feet. Your living area offers beautiful views from the forward-facing window and French doors onto your private veranda. Two spacious closets give you plenty of room to unpack.
? Cruise only from $6,599 per guest
? All-inclusive price from $6,599 per guest
Owner's Suite
Owner's Suite
With 575 square feet, your Owner’s Suite offers separate living room and dining areas. A veranda, Interactive TVs and a full master bath and separate powder room indulge you in spacious comfort. 
? 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
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, Mar 15 - Sat, Mar 22, 2025
STAR PRIDE
$3,199
$3,199
THIS
SAILING