New York City

Windward Islands Surf & Sunsets

Register TODAY at (330) 940-4321 or fill out your email for more information about available packages!

All Suite Ship

Starting 07/06/2021

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All Suite Ship

✔ Starting 07/06/2021, this all-suite ship will complete renovation as part of the $250 Million Star Plus Initiative to provide more of what our guests love. New public areas, including a two new dining venues, a new spa, infinity pool, and fitness area. The ship also boasts all new bathrooms in every suite and a new category of Star suites, featuring a new layout. With ocean-views and over 277 square feet of comfort, Star Pride is the perfect ship to watch glaciers and fjords drift by from the serenity of your suite.

✔ 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!

✔ Call (330) 940-4321 or fill out the form for a complete itinerary and to get your questions answered!

Image by Zidhan Ibrahim

This is the kind of tropical itinerary that people dream of, suffused by an unspoiled sleepy charm which once-upon-a-time was typical in the Caribbean but today has all but disappeared.

The Story

  • One of the most sought-after yachting destinations in the Caribbean, the Windward Islands give you a glimpse of what the West Indies looked like in days of old. Technicolor travel posters come to life in its lush green mountains, shimmering blue waters, swaying palm trees and uncrowded beaches. Colorful fishing boats bob in the harbor next to private yachts, and resorts give way to charming boutique hotels and B&Bs.

  • Pastel Georgian buildings, crumbling forts, and rusting canons recall the days when pirates roamed the seas and Britain and France fought over who would rule these islands. And while each island has its unique charms, the pace of life is almost universally slow, with time to absorb the copious amounts of natural beauty and chat with people who are genuinely welcoming.

  • Sip a local Carib beer in the shade of sea grape trees. Dive off the Watersports Platform and snorkel above coral gardens entirely undisturbed by your passage. Stand on the ramparts of forts that have seen centuries come and go staring out at a view that never grows old. Discover islands that perfectly match your dreams.

The last day to register is May 31st 2021!

Call (330) 940-4321 or fill out the form above for more information!

San Juan to San Juan

Revel in seven days of surf, sand and sunsets during this leisurely cruise up and down the Caribbean’s Windward Islands. It’s a perfect vacation getaway for anyone craving a quick escape from life’s everyday obligations. Swim among sea turtles and glide above dazzling coral reefs with a highly skilled diving guide off the coast of Les Saintes’ volcanic shoreline. Stroll the weather-beaten parapets of the citadel of El Morro near San Juan, Puerto Rico and run your fingers along the stone scars left by Dutch invasions and American bombardments. Then clip into a zip line and hang on as moss-covered limbs and colorful wild birds rush by your head as you glide through St. Lucia’s rainforest canopy. Vacation time is always well spent among the Windward Islands, but nothing makes it more perfect than the personalized attention and unique excursion opportunities offered by Windstar.

Insider Tips:

  • An island’s windward side faces the trade winds, which come from across the Atlantic. On the leeward side, the Caribbean Sea is calmer. As a result, you’ll usually find the best beaches on the west side of each island.

  • Check out the nutmeg ice cream on Grenada, the Spice Island. It’s like a summer version of eggnog.

  • In tiny Bequia, an island of just 7 square miles, all beaches are public. They’re also clean and uncrowded, so take your pick.

  • The incredibly beautiful twin pitons on Saint Lucia are a UNESCO World Heritage Site. You can climb Gros Piton (with a guide), but it’s an exhausting climb and you’ll need good hiking shoes and plenty of water.

  • The people you meet in Les Saintes are descended from Breton corsairs (pirates), and they’re skilled sailors. Their distinctive shallow white hats are called salacos. If you would like to take a photo, be sure to ask first.

The World's Best Small Ship Cruise Line

Signature Expeditions

Introducing the Windstar Signature Expeditions program. Helmed by a team of onboard expedition experts who sail with the cruise the entire time, they'll provide more insight, understanding, and commentary to show you an Alaska you've never seen before.

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.

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.


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, sail-boarding, even water skiing. And it’s all complimentary, of course. Sun yourself on deck, take a dip in the whirlpool, then catch up on email ororder 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.


Other cruise lines have bingo and trivia nights. Windstsar has a Watersports Platform that opens directly from the back of our ships and includes complimentary kayaks, paddleboards, water trampolines, and water skis. Spend time in the Lounge regaling your fellow guests about the bears you saw catching fish from the river or simply relax in the Library with an intriguing book. Take some "you" time in the tranquil World Spa by Windstar...enjoy a dip in the off that decadent dessert in the Fitness Center...and, of course, you are always welcome to visit the Bridge to examine navigation charts with the Captain.

Relax by The Pool or Hot Tub

The last day to register is May 31st 2021!

Call (330) 940-4321 or fill out the form above for more information!

Image by Saud Edum
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