Windstar Caribbean Itineraries

Experience Caribbean Aboard

What Feels Like Your Own Yacht

Small Enchanting Ports. Small Ship Cruising. See More of Caribbean with Windstar.

This is your invitation to experience Caribbean

Candy-coloured cocktails sipped in seaside watering holes. Carefree days followed by calypso-flavoured nights. These are the siren songs that lure anyone with a small ship and a yearning to escape to the incomparable Caribbean Islands. Whether you’re cruising through turquoise waters or lazing on powdery white beaches, the glamorous harbours and unknown coves of this area remain a hidden treasure.

Which voyage will you embark on first?

* Prices and availability correct as at 11 Aug 23. Check with consultant for pricing, availability and full terms and conditions.
All Inclusive Package: Beverages - Includes all domestic and imported beer and 33 varieties of wine or sparkling wine by the glass plus cordials, liqueurs, aperitifs, cocktails, and mini-bar items. Cocktails are based on house and select brands, and guests may choose from more than 40 liquors such as Grey Goose, Hendricks, Johnny Walker Black, Ketel One, Glenfiddich, Hennessy, and more (brands rotate and are subject to availability.) Wi-Fi - Wi-Fi allows guests to keep in touch depending on course and position of the ship. Wi-Fi access is possible in most public areas, staterooms, and suites. Service Charges - All hotel and beverage service fees are included. If you purchased beverages a la carte there is a 18% (subject to change) gratuity added to purchases.

- Visit magical countries and delightful cities as you travel through the most fascinating cultures and breathtaking scenery.

- Your small ship docks close to the centre of most ports placing you steps away from major sights, while overnight stays in ports gives you time to savour more of the destination's wonders.

- Enjoy the delicious contrast of your glistening white ship parting the bright aqua waters of the Caribbean.

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7 NIGHTS - BEACH FUN AND SUN: A REMOTE CARIBBEAN GETAWAY

- St Maarten to St Maarten -

- Includes the All Inclusive Package – Wi-Fi, gratuities, and unlimited beer, wine and cocktails*

- Let yourself go – at Windstar’s Signature Beach Party, where the Caribbean spirit is in full swing

- Let the Bubbly Pool on Jost Van Dyke wash your cares away

- Relax on the sands of Norman Island, inspiration for Robert Louis Stevenson’s Treasure Island

- Soak in the natural bathing pools of "The Baths" at Virgin Gorda

- Stroll Pusser’s Landing, the charming boardwalk of Soper’s Hole on your way to a secluded beach

- Find your beautiful spot on the beach while you sample some of the most delicious rum punch found in the Caribbean at Road Bay

Experience Your Next Getaway in Casual Elegance!

7 NIGHTS - SAN JUAN & THE VIRGIN ISLANDS

- San Juan to San Juan -

- Includes the All Inclusive Package – Wi-Fi, gratuities, and unlimited beer, wine and cocktails*

- Admire the incredible views from El Morro’s 16th-century ramparts, a UNESCO World Heritage Site, in San Juan

- Learn all about the pirates’ favourite grog at San Juan’s famous Bacardi Rum Distillery

- Take a horse-drawn carriage ride through the streets of Old San Juan

- Go for a hike in Puerto Rico’s El Yunque National Rainforest

- Snorkel with sea turtles on Isla Culebra

- Mingle with the glitterati in St. Barts

- Discover a town swallowed by a volcano during a rare visit to Montserrat

- Sail, swim, and kayak off the Watersports Platform

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Star Collector Voyages combine some of our most popular itineraries for a more in-depth exploration of each region. Featuring longer voyages of 14+ days and few repeated ports, take advantage of your time here and unpack only once. Travel the world spending more time sampling exotic cuisines, immersing yourself in new cultures, and discovering perspectives that open your heart and return home with a soul fulfilled.

All Star Collector Voyages feature FREE daily laundry, so you can travel light and come home with a well-travelled suitcase and one less chore.

See Even More of the world aboard a Casually Elegant Private Small Ship Cruise

13 or 14 NIGHTS - STAR COLLECTOR: CARIBBEAN EXPLORATIONS

- St. Maarten to St. Maarten-

- Includes the All Inclusive Package – Wi-Fi, gratuities, and unlimited beer, wine and cocktails*

- Anchor alongside the pristine beaches of Pigeon Island's 40-acre National Park and explore at your leisure

- Discover St. Lucia's UNESCO Site when you see the twin Pitons, rising majestically from the turquoise sea

- Embrace the island life on St. Kitt's one-of-a-kind Shipwreck Beach

- Soak in the natural bathing pools of "The Baths" at Virgin Gorga

- Overnight in Jost Van Dyke and Virgin Gorda for more in-depth exploration

- Enjoy Windstar's exclusive Signature Beach Barbecue at Prickly Pear Beach