Caribbean
 

Hidden Harbors. Private Beaches.
Island-Hopping in Windstar Style.

Candy-colored cocktails sipped in seaside watering holes. Carefree days followed by calypso-flavored nights. These are the siren songs that lure anyone with a yacht 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 harbors and unknown coves of this area remain a hidden treasure.
 

Authentic Caribbean
Let Your Soul Dance
SHH. THERE ARE STILL SECRET PLACES HERE that the big ships pass by. Places where there’s only one beach bar in sight, closed if the proprietor decides to go spear fishing. Your Windstar yacht has an uncanny ability to find places like this. Places where your day’s activities are timed by the rumble of your stomach, the drowsiness following a good swim, an iridescent sunset that heralds “sailor’s delight” on the morrow. But then, one glance at your itinerary already told you that.
Find Your Perfect Island
Choose from 24 unique Caribbean itineraries ranging from Puerto Rico to Antigua, Cartagena to Barbados. Or, see it all on our 35-day Grand Caribbean & Panamanian Adventure itinerary
Yachtsman's Secret
Visit ports reserved for small ships and private yachts like Mayreau, Bequia, Jost Van Dyke, and Virgin Gorda
Our Specialties
Enjoy Windstar’s Signature Beach Party and a Signature Onboard Barbecue on every itinerary - events that are a highlight for our guests. Kayak, paddleboard or enjoy other water toys directly off the complimentary Watersports Platform located at the back of the yacht and your own set of personalized snorkel gear to use throughout your cruise.
Featured Port: Road Bay/Anguilla
With its protected shoreline, calm surf, spectacular coral reefs and sugar-soft beaches, Road Bay has become a destination for boaters, with its delightful restaurants, bars, and shops. Anguilla has some of the most beautiful sunsets and delicious rum punch to be found in the Caribbean. It is also home to Cuban tree frogs, red-footed tortoise, green iguanas and five species of bats. Worth checking out is Wallblake House, a heritage plantation house and museum said to be the oldest building on the island and located nearby.
Shore Excursion Must-Do: Cooking Caribbean Flavors & Lifestyles (Roseau, Dominica)
Today is your opportunity to learn about Dominican cuisine, traditions, and lifestyles at a private home nestled in Roseau’s tropical rainforest. Your hostess will introduce you to the herbs and fresh ingredients on the day’s menu. Then, you can either choose to help prepare a local delicacy, spend your time viewing the mountains or the Caribbean Sea, or stroll the property learning about fruits and spices. End the day by feasting on traditional Caribbean dishes and fruit cocktail blends.
WINDSTAR VOYAGES TO THE CARIBBEAN
SPECIAL AVAILABLE

San Juan & the Virgin Islands

Port to port
San Juan to San Juan
Duration
7 Days
All-Inclusive From?
$2,822
Cruise Only From?
$2,199
SPECIAL AVAILABLE

Windward Islands Surf & Sunsets

Port to port
San Juan to San Juan
Duration
7 Days
All-Inclusive From?
$2,822
Cruise Only From?
$2,199
SPECIAL AVAILABLE

Blue Waters of the Leeward Islands

Port to port
St. Maarten to St. Maarten
Duration
10 Days
All-Inclusive From?
$2,889
Cruise Only From?
$2,099

Boston Sights, Warm Caribbean Nights

Port to port
Boston to St. Maarten
Duration
9 Days
All-Inclusive From?
$3,300
Cruise Only From?
$2,499
SPECIAL AVAILABLE

Caribbean Pleasures

Port to port
St. Maarten to St. Maarten
Duration
11 Days
All-Inclusive From?
$3,168
Cruise Only From?
$2,299
SPECIAL AVAILABLE

Central America Revealed

Port to port
Miami to Balboa / Fuerte Amador
Duration
11 Days
All-Inclusive From?
$3,768
Cruise Only From?
$2,899
SPECIAL AVAILABLE

Classic Caribbean

Port to port
St. Maarten to St. Maarten
Duration
7 Days
All-Inclusive From?
$2,452
Cruise Only From?
$1,899

Colombian & Southern Caribbean Coastlines

Port to port
Colón to Bridgetown
Duration
11 Days
All-Inclusive From?
$3,978
Cruise Only From?
$2,999
SPECIAL AVAILABLE

Gems of the Leeward Islands

Port to port
San Juan to San Juan
Duration
10 Days
All-Inclusive From?
$2,989
Cruise Only From?
$2,199

Jewels of the Windward Islands

Port to port
Bridgetown to Bridgetown
Duration
7 Days
All-Inclusive From?
$3,222
Cruise Only From?
$2,599
SPECIAL AVAILABLE

Jungles & Jewels of the Central American Coast

Port to port
Miami to Miami
Duration
10 Days
All-Inclusive From?
$4,089
Cruise Only From?
$3,299
SPECIAL AVAILABLE

Lush & Lovely Islands of the Lesser Antilles

Port to port
St. Maarten to Bridgetown
Duration
7 Days
All-Inclusive From?
$2,522
Cruise Only From?
$1,899
SPECIAL AVAILABLE

Star Collector: A Leeward Island Loop

Port to port
St. Maarten to St. Maarten
Duration
17 Days
All-Inclusive From?
$5,442
Cruise Only From?
$4,099

Star Collector: A Lesser Antilles Odyssey

Port to port
St. Maarten to Bridgetown
Duration
21 Days
All-Inclusive From?
$9,568
Cruise Only From?
$7,699
SPECIAL AVAILABLE

Star Collector: Antilles Adventures

Port to port
St. Maarten to Bridgetown
Duration
14 Days
All-Inclusive From?
$4,545
Cruise Only From?
$3,299

Star Collector: Captivating Caribbean

Port to port
Bridgetown to Oranjestad
Duration
14 Days
All-Inclusive From?
$5,745
Cruise Only From?
$4,499
SPECIAL AVAILABLE

Star Collector: Caribbean Explorations

Port to port
St. Maarten to St. Maarten
Duration
14 Days
All-Inclusive From?
$5,445
Cruise Only From?
$4,199
SPECIAL AVAILABLE

Star Collector: Caribbean Icons

Port to port
St. Maarten to St. Maarten
Duration
18 Days
All-Inclusive From?
$4,821
Cruise Only From?
$3,399

Star Collector: Grand Caribbean Adventure

Port to port
St. Maarten to Balboa / Fuerte Amador
Duration
35 Days
All-Inclusive From?
$13,814
Cruise Only From?
$10,699
SPECIAL AVAILABLE

Star Collector: Leeward & Windward Caribbean Havens

Port to port
Bridgetown to St. Maarten
Duration
14 Days
All-Inclusive From?
$4,545
Cruise Only From?
$3,299
SPECIAL AVAILABLE

Star Collector: Lovely Leewards

Port to port
San Juan to San Juan
Duration
14 Days
All-Inclusive From?
$4,745
Cruise Only From?
$3,499

Star Collector: Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica via the Panama Canal

Port to port
Puerto Caldera to Bridgetown
Duration
18 Days
All-Inclusive From?
$6,301
Cruise Only From?
$4,699
SPECIAL AVAILABLE

Star Collector: Windward Islands & Spanish New World

Port to port
Bridgetown to Balboa / Fuerte Amador
Duration
14 Days
All-Inclusive From?
$4,845
Cruise Only From?
$3,599
SPECIAL AVAILABLE

Windward Ways & Tobago Cays

Port to port
Oranjestad to Bridgetown
Duration
7 Days
All-Inclusive From?
$2,822
Cruise Only From?
$2,199
SPECIAL AVAILABLE

Yachtsman's Caribbean

Port to port
St. Maarten to St. Maarten
Duration
7 Days
All-Inclusive From?
$3,422
Cruise Only From?
$2,799