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?
* Pricing for Windstar Cruises is dynamic pricing and subject to availability. 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.
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
- Sail, swim, and kayak off the Watersports Platform
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
Pricing available on request
From $6,446*pp
2025 Departures: 14/28 Dec
2026 Departures: 4/24/31 Jan, 14/21 Feb, 7/14/28 Mar
2025 Departures: 26 Oct, 2/9/16/23/30 Nov
2026 Departures: 23 Jan, 6/20 Feb, 6 Mar, 15/29 Nov, 13/27 Dec
2027 Departures: 10 Jan
*Based on 23 Jan 26 departure onboard Star Seeker.
Pricing available on request
2025 Departures: 7/14/21 Dec
2026 Departures: 31 Jan, 7/28 Feb, 14/21 Mar
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7 NIGHTS - WINDWARD ISLANDS SURF AND SUNSETS
- San Juan to San Juan -
- Includes the All Inclusive Package – Wi-Fi, gratuities, and unlimited beer, wine and cocktails*
- Walk up Mount Pleasant with a spectacular view of Bequia's Admiral Bay
- Shop for spices, especially nutmeg and cinnamon in St. George’s local markets
- See San Juan’s UNESCO site El Morrow Fortress
- Discover the underwater world of Les Saintes
- Enjoy some of the best snorkeling around in the deep blue waters of Guadeloupe
- The UNESCO site Piton's two volcanic peaks, rising more than 2,400 feet, welcome you to St. Lucia
- Shop the 100% duty free island of two nations, St. Maarten and St. Martin
Pricing available on request
2026 Departures: 30 Jan, 13/27 Feb, 13 Mar
Alaska | Asia | Canada & New England | Caribbean | Greek Isles | Italy | Mediterranean | Mexico | Northern Europe | Panama & Costa Rica | South Pacific | Tahiti | Themed Cruises
Experience Your Next Getaway in Casual Elegance!
Call 1300 749 875 or talk to your Travel Agent to get onboard.
Subscribe to our newsletter
Alaska | Asia | Canada & New England | Caribbean | Greek Isles | Italy | Mediterranean | Mexico | Northern Europe | Panama & Costa Rica | South Pacific | Tahiti | Themed Cruises
7 NIGHTS - JEWELS OF THE WINDWARD ISLANDS
- Bridgetown to Bridgetown -
- Includes the All Inclusive Package – Wi-Fi, gratuities, and unlimited beer, wine and cocktails*
- Have extra time at St. Lucia to enjoy more of the beachside resorts and national park there
- Stand on deck for scenic cruising past the UNESCO World Heritage Site Pitons (volcanic spires) on St. Lucia
- Walk up Mount Pleasant and see the amazing view from Fort Hamilton on Bequia
- Make time for a visit to Grand Etang National Park on Grenada
- Savour the beauty of scenic cruising around St. Vincent & the Grenadines
- Indulge yourself at Windstar's Signature Beach Party with plenty of Caribbean flavors and spirit to savour and share
Pricing available on request
2026 Departures: 18 Jan, 7/21 Mar
10 or 11 NIGHTS - COLOMBIAN & SOUTHERN CARIBBEAN COASTLINES
- Bridgetown to Colon (or vice versa) -
- Includes the All Inclusive Package – Wi-Fi, gratuities, and unlimited beer, wine and cocktails*
- Dive and snorkel in Bonaire's plentiful marine sanctuary
- Tour Willemstad’s colonial town centre, a UNESCO World Heritage Site
- In Aruba take a stroll along L.G. Smith Boulevard with its boutiques and shopping malls.
- View the port and fortresses of Cartagena, a UNESCO World Heritage Site
- Observe the Hato Caves on Curaςao with their fancifully named stalactites and stalagmites
- Visit the Old Hegg Turtle Sanctuary in Bequia, where over 2,000 hawksbill turtles have been released over the past 12 years
Pricing available on request
2025 Departures: 18 Nov
14 NIGHTS - STAR COLLECTOR: LOVELY LEEWARDS
- San Juan to San Juan -
- Includes the All Inclusive Package – Wi-Fi, gratuities, and unlimited beer, wine and cocktails*
- Walk up Mount Pleasant with a spectacular view of Bequia's Admiral Bay
- Discover the imposing façade of El Morrow Fortress, a UNESCO site in San Juan
- Enjoy a relaxing beach day in St. Barts, long the haunt of the rich
- Visit the “Pompeii of the Caribbean” at Montserrat with its half-buried city
- Pick up tempting souvenirs at the pastel-coloured buildings and shops of duty-free Philipsburg
- Enjoy the spice market and some of the best snorkelling around on Grenada, the Spice Island
- The Piton's two volcanic peaks, rising more than 2,400, feet welcome you to St. Lucia
- Pack light with complimentary daily laundry service
Pricing available on request
2025 Departures: 2/9/16/23 Nov
2026 Departures: 23/30 Jan, 6/13/20/27 Feb, 6 Mar
7 NIGHTS - WINDWARD WAYS & TOBAGO CAYS
- Bridgetown to Oranjestad (or vice versa) -
- Includes the All Inclusive Package – Wi-Fi, gratuities, and unlimited beer, wine and cocktails*
- 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
- Snorkel the impressive coral reefs of Tobago Cay at the confluence of the Atlantic and Caribbean Sea
- Have your binoculars ready for birdwatching on Bonaire, home of flamingos, Amazon parrots, native parakeets and pink sea salt
- Visit Mayreau, the smallest island of the Grenadines and enjoy the exclusive Signature Beach Party
- Known for its brightly coloured architecture, Willemstad is a UNESCO site
Pricing available on request
2026 Departures: 25 Jan
7 NIGHTS - CLASSIC CARIBBEAN
- 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 twin Pitons, rising majestically from the turquoise sea
- Savour the distinctive French charm of enchanting Les Saintes
- Embrace the island life on St. Kitt’s one-of-a-kind Shipwreck Beach
- Let yourself go – at Windstar’s signature beach barbecue, the Caribbean’s best party
- Enjoy the unspoiled paradise of Barbuda, with its pink beaches and soaring frigate birds
Pricing available on request
2025 Departures: 7/21 Dec
2026 Departures: 7/28 Feb, 21 Mar
Looking for more Windstar deals?
7 NIGHTS - WINWARD ISLAND DELIGHTS
- Bridgetown to Bridgetown -
- Includes the All Inclusive Package – Wi-Fi, gratuities, and unlimited beer, wine and cocktails*
- Find the botanical gardens, the Old Bread Oven and excellent shopping of Anse Mitan
- Take a hike in Dominica’s Morne Trois Pitons National Park, a UNESCO site and see Trafalgar Waterfalls.
- Even novice snorkelers will delight in exploring the crystal-clear waters of Les Saintes.
- Visit the “Pompeii of the Caribbean” on Montserrat, half lush and green, half covered in ash.
- Have extra time at St. Lucia to enjoy more of the beachside resorts and national park there.
- The UNESCO-site Pitons stand majestically above the beautiful beach of Pigeon Island where you will feast on the Signature Beach Barbecue
Pricing available on request
2026 Departures: 14 Mar
8 NIGHTS - STAR SEEKER CHRISTENING SAILING
- Miami to San Juan -
- Includes the All Inclusive Package – Wi-Fi, gratuities, and unlimited beer, wine and cocktails*
- Take a swim in the Bubbly Pool on Jost Van Dyke, a natural rock formation where the ocean waves create a frothy, bubbling oasis, perfect for a unique and refreshing swim.
- In Puerto Plata, Dominican Republic, step back in time with a visit to Fort San Felipe, a historical 16th-century fortress overlooking the Atlantic Ocean.
- In the Dominican Republic’s Samana, visit Los Haitises National Park to discover its dramatic limestone karsts, mangrove forests, ancient Taino caves with petroglyphs, and abundant wildlife, including rare birds and manatees.
-Indulge yourself at Windstar's Signature Beach Party with plenty of Caribbean flavours and spirit to savour and share.
- Find your beautiful spot on the beach while you sample some of the most delicious rum punch and the softest sand found in the Caribbean.
- Stroll Pusser’s Landing, the charming boardwalk of Soper’s Hole, Tortola, BVIs on your way to a secluded beach.
From $8,023*pp
2026 Departures: 15 Jan
*Based on Category IN1 Infinity Suite on 15 Jan 26 departure onboard Star Seeker.
