Star Pride: 14-Night Caribbean
This 14-night Caribbean (Eastern) cruise aboard the Star Pride by Windstar Cruises departs San Juan on November 29, 2026, calling at St. John, St. Barthelemy, St. Kitts, and 9 more ports, and returns December 13, 2026. Cabin prices start from $5,422 per person.
How this date compares
1 of 6 dates
Star Pride sails round trip from San Juan to these 12 ports on 6 dates between November 2026 and January 2027. In the table below, December 13, 2026 and December 27, 2026 call at them in the same order.
Highest of 6
At $5,422 for a ocean view cabin, this date is the highest of the 6 dates from November 2026 to January 2027 in the table below. The lowest is $3,083 on Dec 13, 2026.
San Juan cruise port is one of the busiest in the Caribbean and one of the few that doubles as both a major embarkation point and a popular port of call. The port sits in Old San Juan, the historic colonial core of Puerto Rico's capital, founded by Spanish colonists in 1521.
Read more →Basseterre cruise port in St. Kitts uses the Port Zante terminal, a purpose-built cruise facility in the heart of Basseterre, the capital of St. Kitts and Nevis. Port Zante includes two dedicated cruise piers capable of berthing the largest modern ships plus a marina, restaurants, shops, and the Amina Craft Market.
Read more →St. Maarten cruise port is one of the busiest in the Caribbean, with ships docking at the A.C.
Read more →San Juan cruise port is one of the busiest in the Caribbean and one of the few that doubles as both a major embarkation point and a popular port of call. The port sits in Old San Juan, the historic colonial core of Puerto Rico's capital, founded by Spanish colonists in 1521.
Read more →Balcony cabin
New to these charts? How to read cruise price history
Star Pride to these 12 ports on other dates
| Departs | Port order | Ocean view from | vs Nov 29 |
|---|---|---|---|
| Nov 29, 2026 | St. John, St. Barthelemy, St. Kitts, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda, San Juan, St Georges, Bequia, Mayreau, Deshaies, Marigot | $5,422 | this sailing |
| Dec 6, 2026 | St Georges, Bequia, Mayreau, Deshaies, Marigot, San Juan, St. John, St. Barthelemy, St. Kitts, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda | $4,434 | −$988 |
| Dec 13, 2026 | St. John, St. Barthelemy, St. Kitts, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda, San Juan, St Georges, Bequia, Mayreau, Deshaies, Marigot | $3,083 | −$2,339 |
| Dec 20, 2026 | St Georges, Bequia, Mayreau, Deshaies, Marigot, San Juan, St. John, St. Barthelemy, St. Kitts, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda | $5,064 | −$358 |
| Dec 27, 2026 | St. John, St. Barthelemy, St. Kitts, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda, San Juan, St Georges, Bequia, Mayreau, Deshaies, Marigot | $4,784 | −$638 |
| Jan 3, 2027 | St Georges, Bequia, Mayreau, Deshaies, Marigot, San Juan, St. John, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda | $5,204 | −$218 |
Star Pride, round trip from San Juan, 14 nights. Ocean view cabin, per person, two sharing, taxes and port fees included. Prices checked as of Nov 11, 2026.
Other Caribbean (Eastern) departures
Questions about this sailing
How much does this cruise cost per night?
Ocean view cabins start at $5,422 per person for the 14 nights, about $387 a night, with taxes and port fees included. A balcony starts at $7,724, about $552 a night.
Is $5,422 a good price for this sailing?
It is $2,162 above the lowest ocean view price we have recorded for this sailing since March 9, 2026 ($3,260 on August 14, 2026). Among the 6 dates from November 2026 to January 2027 on this route shown above, the lowest is $3,083 on Dec 13, 2026.
Which ports does it visit?
It sails round trip from San Juan and calls at St. John, St. Barthelemy, St. Kitts, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda, San Juan, St Georges, Bequia, Mayreau, Deshaies and Marigot, with 1 day at sea.
Are there other dates with the same ports?
Yes. Star Pride sails this route on 6 dates between November 2026 and January 2027.
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