Windward Ways & Tobago Cays
 
Oranjestad to Bridgetown
Sun Mar 15, 2026 - Sun Mar 22, 2026,
 7 days
 on Star Pride
?All-inclusive from
$3,822
?Cruise Only From
$3,199
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Life Onboard

A day on board your Windstar ship is a day of choices, all of them good. Perhaps you’ll begin with a relaxing massage in World Spa by Windstar. Or maybe an invigorating workout in the Fitness Center. Even better, why not both? After a sumptuous lunch in Veranda, make a splash from the Watersports Platform off the ship’s stern. Everything you can think of for fun in the water is there — swimming, kayaking, and stand-up paddleboarding. And it’s all complimentary, of course. Sun yourself on deck, take a dip in the whirlpool, then catch up on email or order a cheese plate for your stateroom or suite. After dinner, dance to live music in the Lounge. This is your yacht, so of course you’re welcome on the Bridge, where the Captain and officers are delighted to share charts, routes, and vistas with you.

As you prepare for another amazing Windstar day, enjoy a nightcap anywhere you like — on deck, in the Lounge, or why not let us bring it to your suite or stateroom? Your day ends just as it began, blissfully.

What's Included on Windstar

We strive to provide you the best experience at sea. Our attentive staff will take care of everything you need and anticipate anything you dream.

The best Watersports Platform*
Complimentary kayaks, stand-up paddle boards, and floating islands
*select voyages
Signature Onboard Barbecue
It’s more than just a barbecue, it’s a feast, complete with carving stations, dessert bar, and line dancing with the crew!
Meals in our venues
Try it all! Coursed meals in Amphora, buffet and a la carte in Veranda, and even reservations only restaurants.
24-hour Room Service
stay in tonight and even order from the main Amphora dining menu
Specialty Restaurants
Try Cuadro 44*, Candles, or Stella Bistro**
*Star Plus Class only
**Wind Surf only
Market tours with the Chef*
Come with our Chef to learn how to select some of the ingredients that will be featured in your dishes.
*select voyages
Cooking demonstrations
Take recipes and dishes as a souvenir of your journey
Sodas and bottled water
A little fizz and a bottle for your travels
Specialty tea and coffee
Wake up with a cappuccino or English breakfast tea
Locally inspired dishes
You didn’t come all this way for just a burger
Navigation Lessons
Come by the Open Bridge and say ‘hi’! We’re excited to meet you!
Windstar’s Crew Talent show
You don’t want to miss this! Our crew shows off their hidden talents beyond their day job.
Signature Sail Away event
It’s off to our next destination! Come to the deck as we bid the port farewell to the strains of Vangelis’ 1492.
Onboard lecturers*
Get a better understanding of history, culture, wildlife, and more
*select voyages
Local performances on board*
Brought to you by the locals who are eager to share their culture
*select voyages
Live music
Listen to the band in our lounges
Engaging entertainment
Trivia nights, themed shows, and so much fun!
Nightly port talks
Learn more about the adventures you’ll have tomorrow
Champagne welcome reception
Toast to a bon voyage!
Complimentary shoe polishing services
Get ready to shine
Complimentary gym use
Keep up with your fitness routine
Spa Amenities
Complimentary use of the sauna, steam room, Experience Shower*, and Thermal Suite* will help you relax
*Star Plus Class only
Complimentary Yoga classes
Stretch and set your intentions for the day
Star Boutique
Duty-free, tax-free luxury shopping
Complimentary digital newsstand
Catch up on today’s news or read your favorite magazines
Complimentary movies on demand
Romance? Action? Drama? Documentary? So many choices!
In-Room Filtered Water
Stay hydrated
In-Room Robes and Slippers
Snuggle up for extra comfort
All the essentials
Complimentary Safe, In Room Refrigerator, Hair Dryer
Custom fitted snorkel gear*
No need to pack snorkel, masks, and fins
*select voyages
World Class Dining Experience
We've upped the onboard dining game with our culinary program, featuring an array of fresh, seasonal ingredients sourced from each port along the journey. Each nightly menu is crafted to highlight the spectacular flavors of the regional cuisine.
Amphora
Here, the dining room manager seats you, but where is your decision. There are no pre-assigned tables or first or second seatings. When you dine and with whom are entirely up to you. Seating usually begins at 6:30 p.m. and will be printed in the ship's daily program. Each delightful dish is prepared exactly to your liking – an exquisite dinner served course-by-course with a fine selection of vintage wines.
Candles
Here’s the perfect place for a romantic tête-a-tête under the stars in Candles, Windstar’s signature outdoor restaurant transformed by night into a dreamlike paradise. Delectable cuisine, memorable surroundings, inspired wine pairings.
Cuadro 44 by Anthony Sasso
Savor flavors of Spanish local culture as you dine in intimate surroundings that encourage sharing and camaraderie by ten-time Michelin-starred Chef Anthony Sasso. With seating for 36 including a chef’s counter and communal table, it’s an inventive take on modern Spanish cuisine. (Coming Soon, Star Plus Class ships only).
Signature Onboard Barbecue
One of the highlights of your cruise will be the spectacular onboard barbecue. Your attentive crew will serve an amazing meal of international cuisines accompanied by their own special brand of entertainment for an evening of entertainment under the stars.
Star Grill by Steven Raichlen
You’ll find all your traditional grilled and barbecued favorites (and discover new dishes from around the world) in our new casual outdoor restaurant brought to you in partnership with global grilling authority, Steven Raichlen.
Veranda
It's breakfast alfresco, full service or buffet-style, anytime till 9:30 a.m. No need to hurry. Again, the choices are many in Veranda. Choose the sumptuous, seemingly endless buffet. Or, order from the lunch menu between noon and 2:30 p.m.
Activities
See, hear, smell, taste, and feel what it's like to sail on a small ship. No two days are the same. Be as active or as laid back as you want. After all, this is your yacht.
Meet The Captain On The Bridge
Local and Regional Dining
Live Music Duet
Relax By The Pool or Hot Tub
Room Service
Signature Sail Away
Take in The Sun
Enjoy Our Crew Talent Show
Tastings
Enjoy Fun In The Sun With Our Watersports Platform
Enjoy Our Yacht Club
Yoga Al Fresco
Live Entertainment

After a long day at port or sea, relax in the lounge and enjoy a drink while being entertained by our onboard band or by our talented crew members. Each cruise, our crew demonstrates their hidden abilities, whether dancing, singing, magic, or comedy. Our team will continue to delight you through the night during the crew talent show, and who knows, perhaps you'll find a hidden talent of your own.

Guest Lecturers

Have you ever wanted to learn about rowing across the Atlantic or the inner workings of the Monte Carlo Grand Prix? On select Windstar voyages, satisfy your curiosity and enhance your understanding of the local culture by listening to our onboard lecturers. We’ve curated a group of speakers designed to bring you an insider’s perspective on a multitude of intriguing topics. Listen raptly as your voyage becomes more than just a vacation – and a thought-provoking exploration of enchanting lands.