Wind Star
Oct 31
Barcelona
Spain
Nov 24
Bridgetown
Barbados
24 nights from
$9,070/pp
$378/night
Windstar Cruises repositioning cruises to Caribbean
Compare Windstar Cruises repositioning cruises ending in Caribbean.
23 cruisesfrom $1,130/pp4 ships
Sailing to:AsiaAtlantic - North AmericaCaribbeanCentral AmericaHawaii / Mid-PacificMediterraneanNorthern EuropePacific - North AmericaWestern Europe
Loading filters…Under $100/nightUnder $100/night 
Under $100/nightUnder $100/night 
23 repositioning cruises
Under $100/nightWind Star
Nov 10
Lisbon
Portugal
Dec 5
Colon
Panama
25 nights from
$2,030/pp
$81/night
Under $100/nightWind Star
Nov 10LisbonPortugal
Dec 5ColonPanama
25 nights from$2,030/pp$81/night
Star Legend
Nov 12
Malaga
Spain
Dec 4
Bridgetown
Barbados
22 nights from
$8,040/pp
$365/night
Wind Star
Dec 12
Puntarenas
Costa Rica
Dec 19
Colon
Panama
7 nights from
$3,340/pp
$477/night
Wind Star
Dec 26
Puntarenas
Costa Rica
Jan 2, 2027
Colon
Panama
7 nights from
$4,150/pp
$593/night
Wind Star
Dec 26PuntarenasCosta Rica
Jan 2, 2027ColonPanama
7 nights from$4,150/pp$593/night
Star Legend
Dec 28
Puntarenas
Costa Rica
Jan 5, 2027
Colon
Panama
8 nights from
$4,760/pp
$595/night
Star Legend
Dec 28PuntarenasCosta Rica
Jan 5, 2027ColonPanama
8 nights from$4,760/pp$595/night
Star Legend
Jan 12, 2027
Puntarenas
Costa Rica
Jan 19, 2027
Colon
Panama
7 nights from
$2,740/pp
$391/night
Star Legend
Jan 12, 2027PuntarenasCosta Rica
Jan 19, 2027ColonPanama
7 nights from$2,740/pp$391/night
Wind Star
Jan 24, 2027
Puntarenas
Costa Rica
Jan 31, 2027
Colon
Panama
7 nights from
$4,040/pp
$577/night
Wind Star
Jan 24, 2027PuntarenasCosta Rica
Jan 31, 2027ColonPanama
7 nights from$4,040/pp$577/night
Star Legend
Feb 9, 2027
Puntarenas
Costa Rica
Feb 22, 2027
Oranjestad Aruba
Aruba
13 nights from
$8,710/pp
$670/night
Star Legend
Feb 9, 2027PuntarenasCosta Rica
Feb 22, 2027Oranjestad ArubaAruba
13 nights from$8,710/pp$670/night
Under $100/nightStar Legend
Feb 16, 2027
Panama City
Panama
Mar 2, 2027
Bridgetown
Barbados
14 nights from
$1,130/pp
$81/night
Under $100/nightStar Legend
Feb 16, 2027Panama CityPanama
Mar 2, 2027BridgetownBarbados
14 nights from$1,130/pp$81/night
Wind Surf
Nov 5, 2027
Lisbon
Portugal
Nov 28, 2027
Philipsburg St Maarten
Sint Maarten
23 nights from
$4,890/pp
$213/night
Wind Surf
Nov 5, 2027LisbonPortugal
Nov 28, 2027Philipsburg St MaartenSint Maarten
23 nights from$4,890/pp$213/night
Star Legend
Dec 6, 2027
Cadiz
Spain
Dec 20, 2027
San Juan
Puerto Rico
14 nights from
$7,790/pp
$556/night
Star Legend
Dec 6, 2027CadizSpain
Dec 20, 2027San JuanPuerto Rico
14 nights from$7,790/pp$556/night
Star Pride
Dec 13, 2027
Puntarenas
Costa Rica
Dec 20, 2027
Colon
Panama
7 nights from
$2,980/pp
$426/night
Star Pride
Dec 13, 2027PuntarenasCosta Rica
Dec 20, 2027ColonPanama
7 nights from$2,980/pp$426/night
Star Pride
Dec 27, 2027
Puntarenas
Costa Rica
Jan 3, 2028
Colon
Panama
7 nights from
$3,260/pp
$466/night
Star Pride
Dec 27, 2027PuntarenasCosta Rica
Jan 3, 2028ColonPanama
7 nights from$3,260/pp$466/night
Star Pride
Jan 10, 2028
Puntarenas
Costa Rica
Jan 17, 2028
Colon
Panama
7 nights from
$3,020/pp
$431/night
Star Pride
Jan 10, 2028PuntarenasCosta Rica
Jan 17, 2028ColonPanama
7 nights from$3,020/pp$431/night
Star Pride
Jan 24, 2028
Puntarenas
Costa Rica
Jan 31, 2028
Colon
Panama
7 nights from
$2,840/pp
$406/night
Star Pride
Jan 24, 2028PuntarenasCosta Rica
Jan 31, 2028ColonPanama
7 nights from$2,840/pp$406/night
Star Pride
Feb 7, 2028
Puntarenas
Costa Rica
Feb 14, 2028
Colon
Panama
7 nights from
$2,980/pp
$426/night
Star Pride
Feb 7, 2028PuntarenasCosta Rica
Feb 14, 2028ColonPanama
7 nights from$2,980/pp$426/night
Star Pride
Feb 21, 2028
Puntarenas
Costa Rica
Mar 13, 2028
San Juan
Puerto Rico
21 nights from
$6,930/pp
$330/night
Star Pride
Feb 21, 2028PuntarenasCosta Rica
Mar 13, 2028San JuanPuerto Rico
21 nights from$6,930/pp$330/night
Star Pride
Feb 21, 2028
Puntarenas
Costa Rica
Mar 6, 2028
Oranjestad Aruba
Aruba
14 nights from
$4,690/pp
$335/night
Star Pride
Feb 21, 2028PuntarenasCosta Rica
Mar 6, 2028Oranjestad ArubaAruba
14 nights from$4,690/pp$335/night
Compare upcoming sailings
20 departures shown in date order. Open a sailing for its full details. Fares are per person and display in your selected currency; confirm occupancy and inclusions with the operator.
Scroll the table to compare all columns and departures.
Use the sailing list below to explore the rest of this selection.
How we check fares and itinerariesExplore Windstar Cruises repositioning cruises to Caribbean
Windstar Cruises repositioning cruises to Caribbean currently covers 23 sailings from 1 cruise line in the published catalogue. This page compares one-way sailings operated by the named cruise line. Ship, route and cabin availability can differ between departures.
Listed departures run from October 31, 2026 to February 28, 2028. Voyage lengths range from 6 to 25 nights. These are the current catalogue dates, not a promise of future schedules.
The months with the most listed departures are February 2028 (5 sailings), November 2026 (3 sailings), December 2026 (3 sailings). Counts describe this catalogue selection, not historical seasonality or availability.
The median listed voyage length is 8 nights across 23 sailings. Compare the individual itineraries to choose the time at sea and port stops that suit your plans.
Departure cities in this selection include Barcelona, Cadiz, Lisbon, Malaga, Panama City. Arrival cities include Bridgetown, Colon, Oranjestad Aruba, Philipsburg St Maarten, San Juan. Operators include Windstar Cruises. These are examples from the full page selection, before any additional filters.
Compare ships within the cruise line
The operator’s sailings can differ by vessel, cabin category and route. Compare the ship alongside dates and endpoints, then check the booking terms for the individual departure. Use the destination links to narrow the operator’s published catalogue.
Check the operator’s final quote
Confirm occupancy, cabin category, currency and inclusions directly with the cruise line or booking provider. Ask which charges and optional packages are additional and compare cancellation terms before choosing a fare.
Explore this selection
More sailing details (17)
- Star Legend: Puntarenas to Colon, 2026-12-28
- Star Legend: Puntarenas to Colon, 2027-01-12
- Wind Star: Puntarenas to Colon, 2027-01-24
- Star Legend: Puntarenas to Oranjestad Aruba, 2027-02-09
- Star Legend: Panama City to Oranjestad Aruba, 2027-02-16
- Star Legend: Panama City to Bridgetown, 2027-02-16
- Wind Surf: Lisbon to Philipsburg St Maarten, 2027-11-05
- Star Legend: Cadiz to San Juan, 2027-12-06
- Star Pride: Puntarenas to Colon, 2027-12-13
- Star Pride: Puntarenas to Colon, 2027-12-27
- Star Pride: Puntarenas to Colon, 2028-01-10
- Star Pride: Puntarenas to Colon, 2028-01-24
- Star Pride: Puntarenas to Colon, 2028-02-07
- Star Pride: Puntarenas to San Juan, 2028-02-21
- Star Pride: Puntarenas to Oranjestad Aruba, 2028-02-21
- Star Pride: Panama City to Oranjestad Aruba, 2028-02-28
- Star Pride: Panama City to San Juan, 2028-02-28
Windstar Cruises repositioning cruises to Caribbean: questions and answers
What can I compare on this cruise page?
Windstar Cruises repositioning cruises to Caribbean currently covers 23 sailings from 1 cruise line in the published catalogue. This page compares one-way sailings operated by the named cruise line. Ship, route and cabin availability can differ between departures.
Which dates and voyage lengths are currently listed?
Listed departures run from October 31, 2026 to February 28, 2028. Voyage lengths range from 6 to 25 nights. These are the current catalogue dates, not a promise of future schedules.
How should I compare the crossings?
Start with the departure and arrival cities, such as Barcelona and Bridgetown, then compare dates, nights, ship and price per person. Open the sailing for its listed port stops and fare details. Allow for travel to and from the two ends of a one-way trip.
Are the listed fares and cabins guaranteed?
No. RepoCruises is a comparison directory, not a reservation service. A listed fare may be an estimate or a previously observed price. Check live cabin availability, currency, taxes, fees, gratuities and cancellation terms with the cruise line before booking.