Small Ship CARIBBEAN CRUISES

 
Windstar Knows the Way to the Caribbean

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
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
WINDSTAR VOYAGES TO THE CARIBBEAN
SPECIAL AVAILABLE Beach Fun & Sun: A Remote Caribbean Getaway

Beach Fun & Sun: A Remote Caribbean Getaway

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
7 Days
All-Inclusive From?
$3,072
Cruise Only From?
$2,379
SPECIAL AVAILABLE Classic Caribbean

Classic Caribbean

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
7 Days
All-Inclusive From?
$2,992
Cruise Only From?
$2,299
SPECIAL AVAILABLE Windward Islands Surf & Sunsets

Windward Islands Surf & Sunsets

Port to port
San Juan to San Juan
Duration
7 Days
All-Inclusive From?
$3,692
Cruise Only From?
$2,999
SPECIAL AVAILABLE Mind, Body and Spirit Collection: Bermuda Bliss

Mind, Body and Spirit Collection: Bermuda Bliss

Port to port
New York City to San Juan
Duration
7 Days
All-Inclusive From?
$2,852
Cruise Only From?
$2,159
SPECIAL AVAILABLE Star Collector: Hidden Gems of the Caribbean

Star Collector: Hidden Gems of the Caribbean

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
17 Days
All-Inclusive From?
$6,782
Cruise Only From?
$5,099
SPECIAL AVAILABLE Windward Island Delights

Windward Island Delights

Port to port
Bridgetown to Bridgetown
Duration
7 Days
All-Inclusive From?
$3,592
Cruise Only From?
$2,899
SPECIAL AVAILABLE Blue Waters of the Leeward Islands

Blue Waters of the Leeward Islands

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
10 Days
All-Inclusive From?
$4,789
Cruise Only From?
$3,799
SPECIAL AVAILABLE The Spanish Main: Rise of the New World

The Spanish Main: Rise of the New World

Port to port
San Juan to Colón
Duration
6 Days
All-Inclusive From?
$3,393
Cruise Only From?
$2,799
SPECIAL AVAILABLE Windward Ways & Tobago Cays

Windward Ways & Tobago Cays

Port to port
Oranjestad to Bridgetown
Duration
7 Days
All-Inclusive From?
$3,247
Cruise Only From?
$2,554
SPECIAL AVAILABLE Stars of the Greater Antilles

Stars of the Greater Antilles

Port to port
Cozumel to Philipsburg, St. Maarten
Duration
11 Days
All-Inclusive From?
$5,088
Cruise Only From?
$3,999
SPECIAL AVAILABLE An ABC Christmas

An ABC Christmas

Port to port
Oranjestad to Bridgetown
Duration
8 Days
All-Inclusive From?
$3,400
Cruise Only From?
$2,608
SPECIAL AVAILABLE Barefoot Break in the British Virgin Islands

Barefoot Break in the British Virgin Islands

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
5 Days
All-Inclusive From?
$2,594
Cruise Only From?
$2,099
SPECIAL AVAILABLE Colombian & Southern Caribbean Coastlines

Colombian & Southern Caribbean Coastlines

Port to port
Colón to Bridgetown
Duration
11 Days
All-Inclusive From?
$5,088
Cruise Only From?
$3,999
SPECIAL AVAILABLE Gems of the Leeward Islands

Gems of the Leeward Islands

Port to port
San Juan to San Juan
Duration
10 Days
All-Inclusive From?
$4,989
Cruise Only From?
$3,999
SPECIAL AVAILABLE In the Wake of the Spanish Armadas

In the Wake of the Spanish Armadas

Port to port
Oranjestad to Colón
Duration
8 Days
All-Inclusive From?
$3,991
Cruise Only From?
$3,199
SPECIAL AVAILABLE James Beard Foundation & Wine Cruise: Windward Ways & Tobago Cays

James Beard Foundation & Wine Cruise: Windward Ways & Tobago Cays

Port to port
Oranjestad to Bridgetown
Duration
7 Days
All-Inclusive From?
$3,892
Cruise Only From?
$3,199
SPECIAL AVAILABLE Jewels of the Windward Islands

Jewels of the Windward Islands

Port to port
Bridgetown to Bridgetown
Duration
7 Days
All-Inclusive From?
$3,091
Cruise Only From?
$2,398
SPECIAL AVAILABLE Lush & Lovely Islands of the Lesser Antilles

Lush & Lovely Islands of the Lesser Antilles

Port to port
Philipsburg, St. Maarten to Bridgetown
Duration
7 Days
All-Inclusive From?
$3,192
Cruise Only From?
$2,499
SPECIAL AVAILABLE New World Caribbean Trio

New World Caribbean Trio

Port to port
San Juan to Colón
Duration
7 Days
All-Inclusive From?
$3,892
Cruise Only From?
$3,199
SPECIAL AVAILABLE Panama’s Pristine Caribbean

Panama’s Pristine Caribbean

Port to port
Colón to Oranjestad
Duration
6 Days
All-Inclusive From?
$2,993
Cruise Only From?
$2,399
SPECIAL AVAILABLE San Juan & the Virgin Islands

San Juan & the Virgin Islands

Port to port
San Juan to San Juan
Duration
7 Days
All-Inclusive From?
$3,292
Cruise Only From?
$2,599
SPECIAL AVAILABLE Star Collector: A Lesser Antilles Odyssey

Star Collector: A Lesser Antilles Odyssey

Port to port
Philipsburg, St. Maarten to Bridgetown
Duration
22 Days
All-Inclusive From?
$8,378
Cruise Only From?
$6,299
SPECIAL AVAILABLE Star Collector: Antilles Adventures

Star Collector: Antilles Adventures

Port to port
Philipsburg, St. Maarten to Bridgetown
Duration
15 Days
All-Inclusive From?
$5,585
Cruise Only From?
$4,199
SPECIAL AVAILABLE Star Collector: Blue Seas of the Windward Islands

Star Collector: Blue Seas of the Windward Islands

Port to port
Bridgetown to Bridgetown
Duration
14 Days
All-Inclusive From?
$5,485
Cruise Only From?
$4,099
SPECIAL AVAILABLE Star Collector: Captivating Caribbean

Star Collector: Captivating Caribbean

Port to port
Bridgetown to Oranjestad
Duration
14 Days
All-Inclusive From?
$5,985
Cruise Only From?
$4,599
SPECIAL AVAILABLE Star Collector: Caribbean Beats & Transatlantic Treats

Star Collector: Caribbean Beats & Transatlantic Treats

Port to port
Bridgetown to Lisbon
Duration
22 Days
All-Inclusive From?
$6,277
Cruise Only From?
$4,099
SPECIAL AVAILABLE Star Collector: Caribbean Cultures: Latin America & the Greater Antilles

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

Port to port
Colón to Philipsburg, St. Maarten
Duration
19 Days
All-Inclusive From?
$7,980
Cruise Only From?
$6,099
SPECIAL AVAILABLE Star Collector: Caribbean Explorations

Star Collector: Caribbean Explorations

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
14 Days
All-Inclusive From?
$5,085
Cruise Only From?
$3,699
SPECIAL AVAILABLE Star Collector: Central American Explorations via the Panama Canal

Star Collector: Central American Explorations via the Panama Canal

Port to port
San Juan to Puerto Vallarta
Duration
22 Days
All-Inclusive From?
$10,677
Cruise Only From?
$8,499
SPECIAL AVAILABLE Star Collector: Deep Dive into the Blue: Underwater Worlds of the Caribbean

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?
$7,181
Cruise Only From?
$5,399
SPECIAL AVAILABLE Star Collector: Grand Caribbean & Americas Explorer

Star Collector: Grand Caribbean & Americas Explorer

Port to port
San Juan to Juneau
Duration
49 Days
All-Inclusive From?
$22,150
Cruise Only From?
$17,299
SPECIAL AVAILABLE Star Collector: Grand Caribbean Adventure

Star Collector: Grand Caribbean Adventure

Port to port
Philipsburg, St. Maarten to Philipsburg, St. Maarten
Duration
55 Days
All-Inclusive From?
$23,344
Cruise Only From?
$17,899
SPECIAL AVAILABLE Star Collector: Historic Caribbean: Legendary Islands, Colombia and Panama

Star Collector: Historic Caribbean: Legendary Islands, Colombia and Panama

Port to port
San Juan to Puerto Caldera
Duration
24 Days
All-Inclusive From?
$10,475
Cruise Only From?
$8,099
SPECIAL AVAILABLE Star Collector: Ivory Beaches & Sapphire Seas of the Caribbean

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?
$4,587
Cruise Only From?
$3,399
SPECIAL AVAILABLE Star Collector: Leeward & Windward Caribbean Havens

Star Collector: Leeward & Windward Caribbean Havens

Port to port
Philipsburg, St. Maarten to Bridgetown
Duration
14 Days
All-Inclusive From?
$5,485
Cruise Only From?
$4,099
SPECIAL AVAILABLE Star Collector: Lovely Leewards

Star Collector: Lovely Leewards

Port to port
San Juan to San Juan
Duration
14 Days
All-Inclusive From?
$5,485
Cruise Only From?
$4,099
SPECIAL AVAILABLE Star Collector: Natural History Meets Ancient Mystery: Latin America & Beyond

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

Port to port
Oranjestad to Cozumel
Duration
16 Days
All-Inclusive From?
$6,783
Cruise Only From?
$5,199
SPECIAL AVAILABLE Star Collector: Reefs & Rainforests: The Caribbean, Colombia, Panama & Costa Rica via the Panama Canal

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?
$9,281
Cruise Only From?
$7,499
SPECIAL AVAILABLE Star Collector: Seeking the Antilles

Star Collector: Seeking the Antilles

Port to port
San Juan to Colón
Duration
17 Days
All-Inclusive From?
$7,282
Cruise Only From?
$5,599
SPECIAL AVAILABLE Star Collector: Spectacular Transatlantic Journey: Caribbean to the Azores

Star Collector: Spectacular Transatlantic Journey: Caribbean to the Azores

Port to port
Philipsburg, St. Maarten to Lisbon
Duration
21 Days
All-Inclusive From?
$6,078
Cruise Only From?
$3,999
SPECIAL AVAILABLE Star Collector: The Best of the Windward & Leeward Isles

Star Collector: The Best of the Windward & Leeward Isles

Port to port
Philipsburg, St. Maarten to Oranjestad
Duration
28 Days
All-Inclusive From?
$11,171
Cruise Only From?
$8,399
SPECIAL AVAILABLE Star Collector: Windward Islands & Spanish New World

Star Collector: Windward Islands & Spanish New World

Port to port
Balboa / Fuerte Amador to Bridgetown
Duration
14 Days
All-Inclusive From?
$6,484
Cruise Only From?
$4,999
SPECIAL AVAILABLE Star Collector: Windward Treasures: An Antilles Odyssey

Star Collector: Windward Treasures: An Antilles Odyssey

Port to port
Bridgetown to Bridgetown
Duration
14 Days
All-Inclusive From?
$12,285
Cruise Only From?
$10,899

Star Seeker Christening Sailing

Port to port
Miami to San Juan
Duration
8 Days
All-Inclusive From?
$6,191
Cruise Only From?
$5,399
SPECIAL AVAILABLE Sublime Southern Caribbean

Sublime Southern Caribbean

Port to port
Bridgetown to Philipsburg, St. Maarten
Duration
10 Days
All-Inclusive From?
$4,389
Cruise Only From?
$3,399
Mind, Body and Spirit Collection: Bermuda Bliss
Port to port
New York City to San Juan
Duration
7 days
Day
Port
Day 1
New York City
Day 2
AT SEA
Day 3
AT SEA
Day 4
St. George's
Day 5
St. George's
Day 6
AT SEA
Day 7
AT SEA
Day 8
San Juan
ALL DATES &
FARES
7-for-7
Great cruise-only fares or make it an all-inclusive voyage with unlimited beer, wine, and cocktails, Wi-Fi, and gratuities. From $89 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Sun
Oct 19
2025
STAR PRIDE
$2,852
$2,159
Click on the date to view the map and itinerary by date