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Caribbean (Eastern)▼ 2% since Oct 10

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 8, 2027, calling at St Georges, Bequia, Mayreau Island, and 9 more ports, and returns November 22, 2027. Cabin prices start from $4,014 per person.

Days
14 nights
Departs
Nov 8, 2027
Ports
12
Returns
Nov 22, 2027
Sea days
1
Distance
1,552nm
About this sailing

How this date compares

This route

1 of 8 dates

Star Pride sails round trip from San Juan to these 12 ports on 8 dates between November 2026 and March 2028. In the table below, November 8, 2026 and March 13, 2028 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 8
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 9
At Sea
Day 3
Nov 10
St Georges, Grenada
arr 09:00 · dep 22:00
Day 4
Nov 11
Bequia, St Vincent and the Grenadines
arr 08:00 · dep 22:00
Day 5
Nov 12
Mayreau Island, Grenadines
arr 08:00 · dep 17:00
Day 6
Nov 13
Terra de Haut, Guadeloupe
arr 10:00 · dep 17:00
Day 7
Nov 14
Marigot, Saint Martin
arr 08:00 · dep 15:00
Day 8
Nov 15
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 16
St. John, US Virgin Islands
arr 08:00 · dep 18:00
Day 10
Nov 17
Basseterre St Kitts, Port Zante
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 11
Nov 18
Gustavia St Barths, Saint-Barthelemy Island France
arr 07:00 · dep 22:00
Day 12
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 13
Nov 20
Jost Van Dyke, British Virgin Islands
arr 09:00 · dep 22:00
Day 14
Nov 21
Virgin Gorda Island BVI, Spanish Town, UK Virgin Islands
arr 08:00 · dep 17:00
Day 15
Nov 22
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

$4,014▼ $579 (12.6%) vs Jun 29
Low
$3,902
High
$4,593
Average
$4,148
Vs avg
−3%
$3,832$4,040$4,248$4,455$4,663Jun 29Aug 25Oct 21$4,593 · Jun 29$3,902 · Sep 9$4,084 · Oct 10$4,014 · Oct 21

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 8, 2026St Georges, Bequia, Mayreau Island, Terra de Haut, Marigot, San Juan, St. John, Basseterre St Kitts, Gustavia St Barths, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda Island BVINo current price
Nov 15, 2026St. John, Basseterre St Kitts, Gustavia St Barths, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda Island BVI, San Juan, St Georges, Bequia, Mayreau Island, Terra de Haut, MarigotNo current price
Nov 22, 2026St Georges, Bequia, Mayreau Island, Terra de Haut, Marigot, San Juan, St. John, Gustavia St Barths, Basseterre St Kitts, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda Island BVINo current price
Nov 1, 2027St. John, Basseterre St Kitts, Gustavia St Barths, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda Island BVI, San Juan, St Georges, Bequia, Mayreau Island, Terra de Haut, MarigotNo current price
Nov 8, 2027St Georges, Bequia, Mayreau Island, Terra de Haut, Marigot, San Juan, St. John, Basseterre St Kitts, Gustavia St Barths, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda Island BVINo current price
Nov 15, 2027St. John, Basseterre St Kitts, Gustavia St Barths, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda Island BVI, San Juan, St Georges, Bequia, Mayreau Island, Terra de Haut, MarigotSold out
Mar 13, 2028St Georges, Bequia, Mayreau Island, Terra de Haut, Marigot, San Juan, St. John, Basseterre St Kitts, Gustavia St Barths, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda Island BVINo current price
Mar 20, 2028St. John, Basseterre St Kitts, Gustavia St Barths, St. Maarten (Philipsburg), Jost Van Dyke, Virgin Gorda Island BVI, San Juan, St Georges, Bequia, Mayreau Island, Terra de Haut, 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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Nov 8, 2027 · 14 nights
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Nov 8, 2027 · 12 nights
Norwegian Bliss
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▼ 25%
Questions

Questions about this sailing

Which ports does it visit?

It sails round trip from San Juan and calls at St Georges, Bequia, Mayreau Island, Terra de Haut, Marigot, San Juan, St. John, Basseterre St Kitts, Gustavia St Barths, St. Maarten (Philipsburg), Jost Van Dyke and Virgin Gorda Island BVI, with 1 day at sea.

Are there other dates with the same ports?

Yes. Star Pride sails this route on 8 dates between November 2026 and March 2028. Star Legend also sails the same route.

From
$4,014/person
Incl. taxes & port fees
Checked today · Oct 21
Last change Oct 21: $4,084 → $4,014 (−$70)
Per-cabin pricing not yet available. Click "Book this cruise" for full pricing.

Track prices

Cabin-level pricing isn't yet tracked for this cruise line, so price alerts aren't available here.

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
Full ship profile →
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