Name: 14-Night Caribbean Cruise
Brand: Windstar Cruises
Price: 5193 USD
Availability: InStock
Rating: 4.52 (95 reviews)

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14-Night Caribbean Cruise

Departs San Juan, Puerto Rico

Sailing Nov 22 - Dec 6, 2026

Windstar Cruises - Star Pride

4.595 Reviews

Dates & Pricing

Sail Date

Oceanview

Balcony

Suite

Currently Viewing

Sail DateNov 22 - Dec 06, `26

Oceanview

$5,193

Balcony

$7,613

Suite

$10,093

Sail Date

Oceanview

Balcony

Suite

Sail DateDec 06 - 20, `26

Oceanview

$4,993

Balcony

$7,413

Suite

$9,893

Sail DateDec 20, `26 - Jan 03, `27

Oceanview

$6,793

Balcony

$9,213

Suite

$11,693

Similar Sailings

Cruise Itinerary

Departs San Juan, Puerto Rico

Sailing Nov 22 - Dec 6, 2026

Day 1

Nov 22

San Juan

Puerto Rico, United States

Departs 7:00pm

Day 2

Nov 23

At Sea

Day 3

Nov 24

Saint George's

Grenada

Arrives 9:00am | Departs 10:00pm

Day 4

Nov 25

Bequia

Saint Vincent And The Grenadines

Arrives 8:00am | Departs 10:00pm

Day 5

Nov 26

Mayreau

Saint Vincent And The Grenadines

Arrives 8:00am | Departs 5:00pm

Day 6

Nov 27

îLes Des Saintes

Guadeloupe, France

Arrives 10:00am | Departs 5:00pm

Day 7

Nov 28

Marigot

St. Martin, France

Arrives 8:00am | Departs 3:00pm

Day 8

Nov 29

San Juan

Puerto Rico, United States

Arrives 7:00am | Departs 7:00pm

Day 9

Nov 30

Cruz Bay

St. John, United States Virgin Islands

Arrives 8:00am | Departs 6:00pm

Day 10

Dec 1

Gustavia

Saint Barthélemy, France

Arrives 8:00am | Departs 10:00pm

Day 11

Dec 2

Basseterre

St. Kitts, St. Kitts And Nevis

Arrives 8:00am | Departs 5:00pm

Day 12

Dec 3

Philipsburg

Sint Maarten

Arrives 8:00am | Departs 10:00pm

Day 13

Dec 4

Great Harbour

Jost Van Dyke, British Virgin Islands

Arrives 9:00am | Departs 10:00pm

Day 14

Dec 5

Prickly Pear

British Virgin Islands

Arrives 8:00am | Departs 5:00pm

Day 15

Dec 6

San Juan

Puerto Rico, United States

Arrives 7:00am

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