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Small Ship CARIBBEAN CRUISES

 

Windstar Knows the Way to the Caribbean

IF YOU COULD DESIGN THE PERFECT ISLAND itinerary it would look a lot like these. Ports of call would include tiny towns and hidden harbors known only to private yachts and small ships like ours. Schedules would allow for dropping the Watersports Platform in turquoise bays and raising sails on the way to your next island rendezvous. And the laid-back island vibe would continue on board with a mouthwatering Signature Onboard Barbecue by the pool. Best of all, on every cruise there would be one day that was even more special than the rest, when you land on a secluded beach for Windstar’s Signature Beach Party, elaborate buffet and watersports included.

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 Secrets
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

Beach Fun & Sun: A Remote Caribbean Getaway

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
7 Days
All-Inclusive From?
$2,799
Cruise Only From?
$2,399
SPECIAL AVAILABLE

Classic Caribbean

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
7 Days
All-Inclusive From?
$2,922
Cruise Only From?
$2,299
SPECIAL AVAILABLE

Windward Islands Surf & Sunsets

Port to port
San Juan to San Juan
Duration
7 Days
All-Inclusive From?
$2,499
Cruise Only From?
$2,499
SPECIAL AVAILABLE

Hidden Treasures of the Lesser Antilles

Port to port
Bridgetown to Bridgetown
Duration
10 Days
All-Inclusive From?
$3,699
Cruise Only From?
$3,699

Star Collector: Hidden Gems of the Caribbean

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
17 Days
All-Inclusive From?
$6,312
Cruise Only From?
$4,799
SPECIAL AVAILABLE

Windward Island Delights

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

Blue Waters of the Leeward Islands

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
10 Days
All-Inclusive From?
$4,389
Cruise Only From?
$3,499

The Spanish Main: Rise of the New World

Port to port
San Juan to Colón
Duration
6 Days
All-Inclusive From?
$3,333
Cruise Only From?
$2,799
SPECIAL AVAILABLE

Windward Ways & Tobago Cays

Port to port
Bridgetown to Oranjestad
Duration
7 Days
All-Inclusive From?
$2,871
Cruise Only From?
$2,248

Stars of the Greater Antilles

Port to port
Cozumel to Philipsburg, St. Maarten
Duration
11 Days
All-Inclusive From?
$4,778
Cruise Only From?
$3,799
SPECIAL AVAILABLE

Winter Antilles Escape

Port to port
San Juan to Bridgetown
Duration
7 Days
All-Inclusive From?
$2,499
Cruise Only From?
$2,499

Barefoot Break in the British Virgin Islands

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
5 Days
All-Inclusive From?
$2,444
Cruise Only From?
$1,999
SPECIAL AVAILABLE

Bermuda Bliss

Port to port
New York City to San Juan
Duration
7 Days
All-Inclusive From?
$2,962
Cruise Only From?
$2,339
SPECIAL AVAILABLE

Boston Sights, Warm Caribbean Nights

Port to port
Boston to San Juan
Duration
11 Days
All-Inclusive From?
$2,799
Cruise Only From?
$2,799
SPECIAL AVAILABLE

Colombian & Southern Caribbean Coastlines

Port to port
Colón to Bridgetown
Duration
11 Days
All-Inclusive From?
$3,599
Cruise Only From?
$3,599

In the Wake of the Spanish Armadas

Port to port
Oranjestad to Colón
Duration
8 Days
All-Inclusive From?
$3,911
Cruise Only From?
$3,199
SPECIAL AVAILABLE

James Beard Foundation: Windward Ways & Tobago Cays

Port to port
Oranjestad to Bridgetown
Duration
7 Days
All-Inclusive From?
$2,999
Cruise Only From?
$2,999
SPECIAL AVAILABLE

Jewels of the Windward Islands

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

Lush & Lovely Islands of the Lesser Antilles

Port to port
Philipsburg, St. Maarten to Bridgetown
Duration
7 Days
All-Inclusive From?
$3,022
Cruise Only From?
$2,399
SPECIAL AVAILABLE

San Juan & the Virgin Islands

Port to port
San Juan to San Juan
Duration
6 Days
All-Inclusive From?
$2,499
Cruise Only From?
$2,499

Star Collector: A Lesser Antilles Odyssey

Port to port
Philipsburg, St. Maarten to Bridgetown
Duration
21 Days
All-Inclusive From?
$7,968
Cruise Only From?
$6,099

Star Collector: Antilles Adventures

Port to port
Philipsburg, St. Maarten to Bridgetown
Duration
14 Days
All-Inclusive From?
$5,245
Cruise Only From?
$3,999

Star Collector: Blue Seas of the Windward Islands

Port to port
Bridgetown to Bridgetown
Duration
14 Days
All-Inclusive From?
$5,345
Cruise Only From?
$4,099

Star Collector: Captivating Caribbean

Port to port
Bridgetown to Oranjestad
Duration
14 Days
All-Inclusive From?
$5,545
Cruise Only From?
$4,299

Star Collector: Caribbean Cultures: Latin America & the Greater Antilles

Port to port
Colón to Philipsburg, St. Maarten
Duration
19 Days
All-Inclusive From?
$7,290
Cruise Only From?
$5,599
SPECIAL AVAILABLE

Star Collector: Caribbean Explorations

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
14 Days
All-Inclusive From?
$4,945
Cruise Only From?
$3,699

Star Collector: Deep Dive into the Blue: Underwater Worlds of the Caribbean

Port to port
Cozumel to Philipsburg, St. Maarten
Duration
18 Days
All-Inclusive From?
$6,401
Cruise Only From?
$4,799
SPECIAL AVAILABLE

Star Collector: Fall Leaves & Caribbean Breezes

Port to port
Montreal to San Juan
Duration
22 Days
All-Inclusive From?
$7,199
Cruise Only From?
$7,199

Star Collector: Grand Caribbean Adventure

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
55 Days
All-Inclusive From?
$21,594
Cruise Only From?
$16,699

Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
12 Days
All-Inclusive From?
$4,467
Cruise Only From?
$3,399

Star Collector: Leeward & Windward Caribbean Havens

Port to port
Philipsburg, St. Maarten to Bridgetown
Duration
14 Days
All-Inclusive From?
$5,245
Cruise Only From?
$3,999
SPECIAL AVAILABLE

Star Collector: Lovely Leewards

Port to port
San Juan to San Juan
Duration
14 Days
All-Inclusive From?
$3,999
Cruise Only From?
$3,999

Star Collector: Natural History Meets Ancient Mystery: Latin America & Beyond

Port to port
Oranjestad to Cozumel
Duration
16 Days
All-Inclusive From?
$6,523
Cruise Only From?
$5,099
SPECIAL AVAILABLE

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

Port to port
Bridgetown to Puerto Caldera
Duration
18 Days
All-Inclusive From?
$7,101
Cruise Only From?
$5,499

Star Collector: The Best of the Windward & Leeward Isles

Port to port
Philipsburg, St. Maarten to Oranjestad
Duration
28 Days
All-Inclusive From?
$10,891
Cruise Only From?
$8,399
SPECIAL AVAILABLE

Star Collector: White Sands of the Windwards

Port to port
San Juan to Oranjestad
Duration
14 Days
All-Inclusive From?
$3,999
Cruise Only From?
$3,999
SPECIAL AVAILABLE

Star Collector: Windward Islands & Spanish New World

Port to port
Bridgetown to Balboa / Fuerte Amador
Duration
14 Days
All-Inclusive From?
$4,399
Cruise Only From?
$4,399
SPECIAL AVAILABLE

Star Collector: Windward Treasures: An Antilles Odyssey

Port to port
Bridgetown to Bridgetown
Duration
14 Days
All-Inclusive From?
$4,399
Cruise Only From?
$4,399