Tropical Adventure in Private Yacht Style

180 degrees from ordinary


Get closer to the world aboard a small ship


This year, treat yourself to a tropical adventure you’ll never forget. Explore the gorgeous islands of Tahiti—blissful Bora Bora, shimmering Moorea, sparkling Maroe Bay in Huahine. Or, immerse yourself in the verdant natural wonders of Costa Rica, home to storied animal and plant life, before visiting the historic Panama Canal. Or, sojourn to the Caribbean and its legendary locales like the Windward Islands, San Juan, and St. Maarten, while enjoying swimming, sailing, and jet skiing from our Watersports Platform. Each night, you’ll return to a welcoming crew devoted to the best in pampered service, dine on world-class cuisine paired with local flavors, and dance under the stars until you retire to your well-appointed suite or stateroom.

When you choose to cruise the Windstar way, you’ll delight in your freedom to choose the way you spend your time—onboard and ashore. Docking in exotic ports that only a small ship can reach and travelling with a small number of like-minded fellow passengers assures an elegant, relaxing and memorable getaway. Take advantage of fantastic seasonal values this year, and bring the whole family on a magical journey they’ll never forget.

Bridgetown to Oranjestad - 7 Days

This is the Caribbean for those with a taste for something a bit more exotic. Colonial influences are still going strong here, from the “Little England” island of Barbados to still-very-Dutch Aruba, Bonaire, and Curaçao. Days ashore promise unexpected discoveries – a donkey sanctuary on Bonaire, underground rivers and caves in Barbados, a chocolate factory on Grenada, an artist colony on Curaçao. Beaches seem to shrug off the challenge of more northerly islands as they establish a standard of beauty all their own, swept by steady gust-free trade winds that make learning to windsurf a breeze. And between each eventful island, there is time to savor your surroundings – both on shore and on the decks of your elegant yacht.

Complimentary Destination Discovery Event • Mayreau: Island Experience

$5,999
per person
sale price
$1,779
Per Person

Bridgetown to San Juan - 7 Days

Spend pampered days and nights in the secret hideaways of the Caribbean, kayaking off the Watersports Platform, walking on uncrowded beaches, and admiring sunsets reserved just for you. Linger on smaller islands where sea turtles nest and smiles are genuine. Learn how to say “amazing place” in Creole. Let nature and the Windstar staff fulfill every dream you’ve ever had about paradise.

Complimentary Destination Discovery Event • St. Lucia: Island Experience

$5,499
per person
sale price
$1,879
Per Person

Philipsburg to Philipsburg - 7 Days

From the stunning drama of the Pitons to the captivating charm of Les Saintes. From hidden coves and secret beaches to exotic markets and lively cafés. Here’s the best of the Caribbean in one single voyage. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.

Complimentary Destination Discovery Event • St. Lucia: Island Experience

$4,999
per person
sale price
$1,679
Per Person

Puerto Caldera to Colón - 7 Days

Come find the natural and man-made wonders combined on this exotic voyage full of bucket list places and activities.  Learn about the area from a local Naturalist on board, then take a Zodiac ashore and find rare experiences for yourself. Hike through Manuel Antonio National Park in search of its lovely beaches and abundant animal life. Soar high above the Quepos jungle floor as you zipline searching for such wildlife residents as monkeys, sloths, and toucans, then explore Golfo Dulce with some of the most intense rainforest landscapes in the world. Take a daylight transit the massive Panama Canal, one of the world's most stunning feats of engineering on a yacht that lets you see it all.

Complimentary Destination Discovery Event • Panama Canal: Deck Side Festival

$6,199
per person
sale price
$1,779
Per Person

Papeete to Papeete - 7 Days

A graceful sailing yacht is the perfect way to experience the true wonder of Tahiti. We’ll let the trade winds fill our sails as we visit one legendary island after another, staying overnight in most to give you time to swim and snorkel in crystal-clear lagoons, meander through lush rainforests, and experience the fascinating Polynesian culture from tikis to tiare flowers.

Complimentary Destination Discovery Event • Bora Bora: Celebration Festival

$6,899
per person
sale price
$1,979
Per Person

Bridgetown to Bridgetown - 7 Days

This is the Caribbean of days gone by – deep blue waters, quiet coves, and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the rugged natural beauty of St. Lucia to little-known isles that are off the tourist radar. From colorful Bequia and Mayreau in St. Vincent & the Grenadines to the open-air markets of exotic St. George’s, you’ll discover a part of the Caribbean that remains authentic and unspoiled. This is everything that makes the Caribbean synonymous with paradise.

Complimentary Destination Discovery Event • Mayreau: Island Experience

$4,999
per person
sale price
$1,479
Per Person

Puerto Caldera to Puerto Caldera - 7 Days

Lush, full of life, kissed by the sun and blessed with a breathtaking shoreline, Costa Rica beckons you to discover this unique country.  Board a Zodiac and head ashore to explore the Curú National Wildlife Refuge, hike the tropical rainforest, float the rivers along Drake Bay, swim and snorkel off Tortuga Island’s palm-fringed beaches and listen for the calls of capuchin monkeys. Zipline through the rainforest canopy in Playas del Coco, visit Quepos in search of wildlife or try surfing at Manuel Antonio, the jewel of Costa Rica. Adventure-filled days happily ended as the refreshing comforts of your graceful Windstar yacht await you.

Complimentary Destination Discovery Event • Tortuga: Island Experience

$5,399
per person
sale price
$1,279
Per Person

San Juan to San Juan - 7 Days

Begin and end your journey where Old World meets New, in historic San Juan, littered with more than 400 restored Spanish colonial buildings. Then explore Puerto Rico’s best-kept secret: the island of Culebra. It’s a natural paradise, home to one of the oldest bird sanctuaries in the United States and to Playa Flamenco, rated the third-best beach in the world. As you continue on this bewitching cruise through the Virgin Islands, no two days are alike. One day, you’re shopping chic French boutiques for the latest fashions from Paris. On another, snorkeling a secluded cove known only to lucky yachtsmen – like you. Skip more common and commercial ports like St. Thomas and Philipsburg in favor of less-visited destinations like Marigot and Montserrat. Bypass the major cruise terminals in favor of exclusive marinas and anchorages. And as guests on larger cruise ships take an excursion from Tortola to reach tiny Jost Van Dyke, your elegant yacht is already there.   

Complimentary Destination Discovery Event • Prickly Pear Beach: Island Experience

$5,499
per person
sale price
$1,779
Per Person

Colón to Oranjestad - 7 Days

Discover the “deep south” of the Caribbean, beyond the mainstream cruises. The Dutch ABC islands acclaimed for their crystalline waters and world-class beaches, diving, and snorkeling. Seldom-visited mainland ports with a lively Caribbean vibe. And towns founded on Spanish gold that retain their colonial charm all these centuries later. It’s a voyage of discovery you won’t want to miss.

Complimentary Destination Discovery Event • Curacao: An Antillean Experience

$5,599
per person
sale price
$1,279
Per Person

Papeete to Papeete - 10 Days

The trade winds of French Polynesia have enticed sailors for centuries – and now those same beautiful breezes fill the sails of Wind Spirit as we sail through the windward and leeward Society Islands to the serene natural beauty of the Tuamotu Islands, where pristine atolls and crystal lagoons welcome you to a hidden paradise. Visit Fakarava where rare species are found nowhere else on earth.

Complimentary Destination Discovery Event • Bora Bora: Celebration Festival

$8,599
per person
sale price
$2,979
Per Person

Philipsburg to Philipsburg - 7 Days

Let us take you into hidden coves and tiny harbors no one else can reach as you fully experience the Caribbean’s private yachting scene. Explore the quaint island charm of Soper’s Hole and the inviting beaches of Jost Van Dyke as you overnight in the harbor. Sail to Virgin Gorda, with its assembly of house-sized rocks called The Baths. Savor the high life on St. Barts.

Complimentary Destination Discovery Event • Prickly Pear Beach: Island Experience

$4,999
per person
sale price
$1,279
Per Person

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