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.
61 cruisesfrom $570/pp5 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 Under $100/nightUnder $100/night
61 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
Wind Star
Nov 10
Lisbon
Portugal
Nov 24
Bridgetown
Barbados
14 nights from
$3,600/pp
$257/night
Star Legend
Nov 12
Malaga
Spain
Dec 4
Bridgetown
Barbados
22 nights from
$8,040/pp
$365/night
Under $100/nightWind Star
Nov 24
Bridgetown
Barbados
Dec 12
Puntarenas
Costa Rica
18 nights from
$1,460/pp
$81/night
Under $100/nightWind Star
Nov 24BridgetownBarbados
Dec 12PuntarenasCosta Rica
18 nights from$1,460/pp$81/night
Star Legend
Dec 4
Bridgetown
Barbados
Dec 20
Panama City
Panama
16 nights from
$6,010/pp
$376/night
Star Legend
Dec 4BridgetownBarbados
Dec 20Panama CityPanama
16 nights from$6,010/pp$376/night
Under $100/nightWind Star
Dec 5
Colon
Panama
Dec 12
Puntarenas
Costa Rica
7 nights from
$570/pp
$81/night
Under $100/nightWind Star
Dec 5ColonPanama
Dec 12PuntarenasCosta Rica
7 nights from$570/pp$81/night
Wind Star
Dec 12
Puntarenas
Costa Rica
Dec 19
Colon
Panama
7 nights from
$3,340/pp
$477/night
Star Legend
Dec 12
Oranjestad Aruba
Aruba
Dec 20
Panama City
Panama
8 nights from
$4,010/pp
$501/night
Star Legend
Dec 12Oranjestad ArubaAruba
Dec 20Panama CityPanama
8 nights from$4,010/pp$501/night
Star Legend
Dec 12
Oranjestad Aruba
Aruba
Dec 28
Puntarenas
Costa Rica
16 nights from
$6,630/pp
$414/night
Star Legend
Dec 12Oranjestad ArubaAruba
Dec 28PuntarenasCosta Rica
16 nights from$6,630/pp$414/night
Wind Star
Dec 19
Colon
Panama
Dec 26
Puntarenas
Costa Rica
7 nights from
$5,510/pp
$787/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
Wind Star
Jan 2, 2027
Colon
Panama
Jan 9, 2027
Puntarenas
Costa Rica
7 nights from
$3,520/pp
$503/night
Wind Star
Jan 2, 2027ColonPanama
Jan 9, 2027PuntarenasCosta Rica
7 nights from$3,520/pp$503/night
Star Legend
Jan 5, 2027
Colon
Panama
Jan 12, 2027
Puntarenas
Costa Rica
7 nights from
$3,610/pp
$516/night
Star Legend
Jan 5, 2027ColonPanama
Jan 12, 2027PuntarenasCosta Rica
7 nights from$3,610/pp$516/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
Star Legend
Jan 19, 2027
Colon
Panama
Jan 26, 2027
Puntarenas
Costa Rica
7 nights from
$3,020/pp
$431/night
Star Legend
Jan 19, 2027ColonPanama
Jan 26, 2027PuntarenasCosta Rica
7 nights from$3,020/pp$431/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
Wind Star
Jan 31, 2027
Colon
Panama
Feb 8, 2027
Puntarenas
Costa Rica
8 nights from
$6,730/pp
$841/night
Wind Star
Jan 31, 2027ColonPanama
Feb 8, 2027PuntarenasCosta Rica
8 nights from$6,730/pp$841/night
Wind Star
Jan 31, 2027
Colon
Panama
Mar 1, 2027
Papeete
French Polynesia
29 nights from
$9,950/pp
$343/night
Wind Star
Jan 31, 2027ColonPanama
Mar 1, 2027PapeeteFrench Polynesia
29 nights from$9,950/pp$343/night
Explore 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.
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.
Explore this selection
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.
