14 Night Caribbean Cruise

Star Legend

This 14-night Caribbean (Eastern) cruise aboard the Star Legend by Windstar Cruises departs San Juan on January 31, 2028, calling at St. John, Gustavia St Barths, St. Maarten (Philipsburg), and 9 more ports, and returns February 14, 2028.

Days
14 nights
Departs
Jan 31, 2028
Ports
12
Returns
Feb 14, 2028
Sea days
1
Distance
1,577nm
Itinerary
Embark Port Sea
Day 1
Jan 31
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.

Read more →
Day 2
Feb 1
St. John, US Virgin Islands
arr 08:00 · dep 18:00
Day 3
Feb 2
Gustavia St Barths, Saint-Barthelemy Island France
arr 07:00 · dep 22:00
Day 4
Feb 3
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.

Read more →
Day 5
Feb 4
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.

Read more →
Day 6
Feb 5
Jost Van Dyke, British Virgin Islands
arr 09:00 · dep 22:00
Day 7
Feb 6
Day 8
Feb 7
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.

Read more →
Day 9
Feb 8
At Sea
Day 10
Feb 9
St Georges, Grenada
arr 09:00 · dep 22:00
Day 11
Feb 10
Bequia, St Vincent and the Grenadines
arr 08:00 · dep 22:00
Day 12
Feb 11
Mayreau Island, Grenadines
arr 08:00 · dep 17:00
Day 13
Feb 12
Terra de Haut, Guadeloupe
arr 10:00 · dep 17:00
Day 14
Feb 13
Marigot, Saint Martin
arr 08:00 · dep 15:00
Day 15
Feb 14
Disembark
San Juan, Puerto Rico
arr 07:00
Loading map...
1Embark/Debark3Port of CallRoute
Distance
≈ 1,577nm
At sea
1 of 14 nights
Type
Round-trip
Price history

Starting cabin

$3,902last available Jul 8
Low
$3,902
High
$4,893
Average
$4,398
$3,802$4,100$4,398$4,695$4,993Jun 29Jul 3Jul 8$4,893 · Jun 29$3,902 · Jul 8

New to these charts? How to read cruise price history

Similar sailings

Other Caribbean (Eastern) departures

View all →
This sailing appears to be sold out. Prices below are the last we saw.
From
—/person
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 Legend
Your ship
Star Legend
Windstar Cruises · Star Ship Megayacht class · Built 1992
Passengers
312
Tonnage
12,995
Length
159m
Crew
164
Onboard
PoolWhirlpoolCasinoTheaterPiano BarSpaFitness CenterSaunaSteam RoomHair SalonLibraryObservation Lounge
Full ship profile →
Book this cruiseInstant checkout

We may earn a commission when you book through this link, at no extra cost to you.