Star Pride: 14-Night Caribbean
This 14-night Caribbean (Eastern) cruise aboard the Star Pride by Windstar Cruises departs San Juan on November 22, 2026, calling at St Georges, Bequia, Mayreau, and 9 more ports, and returns December 6, 2026. Cabin prices start from $5,204 per person.
How this date compares
1 of 7 dates
Star Pride sails round trip from San Juan to these 12 ports on 7 dates between November 2026 and March 2028.
Highest of 4
At $5,204 for a ocean view cabin, this date is the highest of the 4 dates from November 2026 to November 2027 in the table below. The lowest is $4,364 on Nov 8, 2027.
Star Legend
Star Legend also sails round trip from San Juan to these 12 ports in 14 nights, on 9 dates between December 2027 and February 2028.
- Dec 20, 2027 · Star Legend · No current price
- Dec 27, 2027 · Star Legend · No current price
- Jan 3, 2028 · Star Legend · No current price
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 →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 →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 22 |
|---|---|---|---|
| Nov 15, 2026 | St. John, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda, San Juan, St Georges, Bequia, Mayreau, Les Saintes, Marigot | $4,644 | −$560 |
| Nov 22, 2026 | St Georges, Bequia, Mayreau, Les Saintes, Marigot, San Juan, St. John, St. Barthelemy, St. Kitts, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda | $5,204 | this sailing |
| Nov 1, 2027 | St. John, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda, San Juan, St Georges, Bequia, Mayreau, Les Saintes, Marigot | $4,574 | −$630 |
| Nov 8, 2027 | St Georges, Bequia, Mayreau, Les Saintes, Marigot, San Juan, St. John, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda | $4,364 | −$840 |
| Nov 15, 2027 | St. John, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda, San Juan, St Georges, Bequia, Mayreau, Les Saintes, Marigot | Sold out | |
| Mar 13, 2028 | St Georges, Bequia, Mayreau, Les Saintes, Marigot, San Juan, St. John, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda | No current price | |
| Mar 20, 2028 | St. John, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda, San Juan, St Georges, Bequia, Mayreau, Les Saintes, Marigot | No current price |
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 $5,204 per person for the 14 nights, about $372 a night, with taxes and port fees included. A balcony starts at $6,744, about $482 a night.
Is $5,204 a good price for this sailing?
It is $2,098 above the lowest ocean view price we have recorded for this sailing since March 9, 2026 ($3,106 on August 24, 2026). Among the 4 dates from November 2026 to November 2027 on this route shown above, the lowest is $4,364 on Nov 8, 2027.
Which ports does it visit?
It sails round trip from San Juan and calls at St Georges, Bequia, Mayreau, Les Saintes, Marigot, San Juan, St. John, St. Barthelemy, St. Kitts, St. Maarten (Philipsburg), Jost Van Dyke and Virgin Gorda, with 1 day at sea.
Are there other dates with the same ports?
Yes. Star Pride sails this route on 7 dates between November 2026 and March 2028. Star Legend also sails the same route.
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