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Star Pride: 14-Night Caribbean

Star Pride

This 14-night Caribbean (Eastern) cruise aboard the Star Pride by Windstar Cruises departs San Juan on November 15, 2027, calling at St. John, St. Kitts, St. Barthelemy, and 9 more ports, and returns November 29, 2027.

Days
14 nights
Departs
Nov 15, 2027
Ports
12
Returns
Nov 29, 2027
Sea days
1
Distance
1,552nm
About this sailing

How this date compares

This route

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. 3 of the 6 other dates in the table below call at them in the same order.

Same ports, other ship

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.

Itinerary
Embark Port Sea
Day 1
Nov 15
Embark
San Juan, Puerto Rico
dep 19:00

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.

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Day 2
Nov 16
St. John, US Virgin Islands
arr 08:00 · dep 18:00
Day 3
Nov 17
St. Kitts, Saint Kitts and Nevis
arr 08:00 · dep 17:00

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.

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Day 4
Nov 18
St. Barthelemy, Saint Barthelemy
arr 07:00 · dep 22:00
Day 5
Nov 19
St. Maarten (Philipsburg)
arr 08:00 · dep 22:00

St. Maarten cruise port is one of the busiest in the Caribbean, with ships docking at the A.C.

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Day 6
Nov 20
Jost Van Dyke, British Virgin Islands
arr 09:00 · dep 22:00
Day 7
Nov 21
Virgin Gorda, British Virgin Islands
arr 08:00 · dep 17:00
Day 8
Nov 22
San Juan, Puerto Rico
arr 07:00 · dep 19:00

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.

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Day 9
Nov 23
At Sea
Day 10
Nov 24
St Georges, Grenada
arr 09:00 · dep 22:00
Day 11
Nov 25
Bequia, St Vincent and the Grenadines
arr 08:00 · dep 22:00
Day 12
Nov 26
Mayreau, Grenadines
arr 08:00 · dep 17:00
Day 13
Nov 27
Les Saintes, Guadeloupe
arr 10:00 · dep 17:00
Day 14
Nov 28
Marigot, Saint Martin
arr 08:00 · dep 15:00
Day 15
Nov 29
Disembark
San Juan, Puerto Rico
arr 07:00
Loading map...
1Embark/Debark3Port of CallRoute
Distance
≈ 1,552nm
At sea
1 of 14 nights
Type
Round-trip
Price history

Starting cabin

$4,593May 5Last available May 5

New to these charts? How to read cruise price history

Same ship, same ports, other dates

Star Pride to these 12 ports on other dates

DepartsPort orderInterior from
Nov 15, 2026St. John, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda, San Juan, St Georges, Bequia, Mayreau, Les Saintes, MarigotNo current price
Nov 22, 2026St Georges, Bequia, Mayreau, Les Saintes, Marigot, San Juan, St. John, St. Barthelemy, St. Kitts, St. Maarten (Philipsburg), Jost Van Dyke, Virgin GordaNo current price
Nov 1, 2027St. John, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda, San Juan, St Georges, Bequia, Mayreau, Les Saintes, MarigotNo current price
Nov 8, 2027St Georges, Bequia, Mayreau, Les Saintes, Marigot, San Juan, St. John, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Jost Van Dyke, Virgin GordaNo current price
Nov 15, 2027St. John, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda, San Juan, St Georges, Bequia, Mayreau, Les Saintes, MarigotSold out
Mar 13, 2028St Georges, Bequia, Mayreau, Les Saintes, Marigot, San Juan, St. John, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Jost Van Dyke, Virgin GordaNo current price
Mar 20, 2028St. John, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda, San Juan, St Georges, Bequia, Mayreau, Les Saintes, MarigotNo current price

Star Pride, round trip from San Juan, 14 nights. Interior cabin, per person, two sharing, taxes and port fees included.

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Questions

Questions about this sailing

Which ports does it visit?

It sails round trip from San Juan and calls at St. John, St. Kitts, St. Barthelemy, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda, San Juan, St Georges, Bequia, Mayreau, Les Saintes and Marigot, 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.

This sailing appears to be sold out. Prices below are the last we saw.
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Star Pride
Your ship
Star Pride
Windstar Cruises · Star Ship Megayacht class · Built 1988
Passengers
312
Tonnage
12,995
Length
159m
Crew
188
Onboard
PoolWhirlpoolCasinoTheaterPiano BarSpaFitness CenterSaunaSteam RoomHair SalonLibraryObservation Lounge
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