Leaving soon
Star Legend
Nov 12
Malaga
Spain
Nov 27
Bridgetown
Barbados
15 nights
Check fare
Windstar Cruises
Windstar Cruises runs 58 repositioning sailings in our directory, on 5 ships.
58 cruises5 ships
Sailing to:AsiaAtlantic - North AmericaCaribbeanCentral AmericaHawaii / Mid-PacificMediterraneanNorthern EuropePacific - North AmericaWestern Europe
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58 repositioning cruises
Leaving soonLeaving soonWind Star
Nov 24
Bridgetown
Barbados
Dec 12
Puntarenas
Costa Rica
18 nights
Check fare
Leaving soonWind Star
Nov 24BridgetownBarbados
Dec 12PuntarenasCosta Rica
18 nightsCheck fare
Leaving soonStar Legend
Dec 4
Bridgetown
Barbados
Dec 20
Panama City
Panama
16 nights
Check fare
Leaving soonStar Legend
Dec 4BridgetownBarbados
Dec 20Panama CityPanama
16 nightsCheck fare
Leaving soonStar Legend
Dec 12
Oranjestad Aruba
Aruba
Dec 28
Puntarenas
Costa Rica
16 nights
Check fare
Leaving soonStar Legend
Dec 12Oranjestad ArubaAruba
Dec 28PuntarenasCosta Rica
16 nightsCheck fare
Leaving soonWind Star
Dec 12
Puntarenas
Costa Rica
Dec 19
Colon
Panama
7 nights
Check fare
Wind Star
Dec 19
Colon
Panama
Dec 26
Puntarenas
Costa Rica
7 nights
Check fare
Wind Star
Dec 26
Puntarenas
Costa Rica
Jan 2, 2027
Colon
Panama
7 nights
Check fare
Star Legend
Dec 28
Puntarenas
Costa Rica
Jan 5, 2027
Colon
Panama
8 nights
Check fare
Wind Star
Jan 2, 2027
Colon
Panama
Jan 9, 2027
Puntarenas
Costa Rica
7 nights
Check fare
Star Legend
Jan 5, 2027
Colon
Panama
Jan 12, 2027
Puntarenas
Costa Rica
7 nights
Check fare
Star Legend
Jan 12, 2027
Puntarenas
Costa Rica
Jan 19, 2027
Colon
Panama
7 nights
Check fare
Star Legend
Jan 19, 2027
Colon
Panama
Jan 26, 2027
Puntarenas
Costa Rica
7 nights
Check fare
Wind Star
Jan 24, 2027
Puntarenas
Costa Rica
Jan 31, 2027
Colon
Panama
7 nights
Check fare
Wind Star
Jan 31, 2027
Colon
Panama
Feb 8, 2027
Puntarenas
Costa Rica
8 nights
Check fare
Wind Star
Jan 31, 2027
Colon
Panama
Mar 1, 2027
Papeete
French Polynesia
29 nights
Check fare
Star Legend
Feb 9, 2027
Puntarenas
Costa Rica
Feb 22, 2027
Oranjestad Aruba
Aruba
13 nights
Check fare
Star Legend
Feb 9, 2027PuntarenasCosta Rica
Feb 22, 2027Oranjestad ArubaAruba
13 nightsCheck fare
Star Legend
Feb 16, 2027
Panama City
Panama
Mar 2, 2027
Bridgetown
Barbados
14 nights
Check fare
Star Legend
Feb 16, 2027Panama CityPanama
Mar 2, 2027BridgetownBarbados
14 nightsCheck fare
Star Legend
Mar 2, 2027
Bridgetown
Barbados
Mar 25, 2027
Barcelona
Spain
23 nights
Check fare
Star Legend
Mar 2, 2027
Bridgetown
Barbados
Mar 17, 2027
Lisbon
Portugal
15 nights
Check fare
Star Pride
Mar 30, 2027
San Juan
Puerto Rico
Apr 15, 2027
London
England
16 nights
Check fare
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
Windstar Cruises repositioning cruises currently covers 58 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 November 12, 2026 to May 25, 2029. Voyage lengths range from 6 to 29 nights. These are the current catalogue dates, not a promise of future schedules.
The months with the most listed departures are December 2026 (8 sailings), January 2027 (7 sailings), February 2028 (6 sailings). Counts describe this catalogue selection, not historical seasonality or availability.
The median listed voyage length is 13 nights across 58 sailings. Compare the individual itineraries to choose the time at sea and port stops that suit your plans.
Departure cities in this selection include Bridgetown, Cadiz, Colon, Kobe-Osaka, Lisbon. Arrival cities include Amsterdam, Barcelona, Boston, Bridgetown, Colon. 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 (52)
- Star Legend: Oranjestad Aruba to Panama City, 2026-12-12
- Wind Star: Colon to Puntarenas, 2026-12-19
- Wind Star: Puntarenas to Colon, 2026-12-26
- Star Legend: Puntarenas to Colon, 2026-12-28
- Wind Star: Colon to Puntarenas, 2027-01-02
- Star Legend: Colon to Puntarenas, 2027-01-05
- Star Legend: Puntarenas to Colon, 2027-01-12
- Star Legend: Colon to Puntarenas, 2027-01-19
- Wind Star: Puntarenas to Colon, 2027-01-24
- Wind Star: Colon to Puntarenas, 2027-01-31
- Wind Star: Colon to Papeete, 2027-01-31
- 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
- Star Legend: Bridgetown to Barcelona, 2027-03-02
- Star Legend: Bridgetown to Lisbon, 2027-03-02
- Star Pride: San Juan to London, 2027-03-30
- Star Seeker: Kobe-Osaka to Seward, 2027-05-10
- Star Seeker: Tokyo to Seward, 2027-05-20
- Star Seeker: Tokyo to Vancouver, 2027-05-20
- Star Seeker: Vancouver to Sapporo-Otaru, 2027-08-21
- Star Pride: Reykjavik to Boston, 2027-08-26
- Star Seeker: Seward to Sapporo-Otaru, 2027-09-01
- Star Pride: Reykjavik to Boston, 2027-09-02
- Star Pride: Reykjavik to Montreal, 2027-09-02
- Wind Surf: Lisbon to Philipsburg St Maarten, 2027-11-05
- Star Pride: San Juan to Puntarenas, 2027-11-22
- Star Pride: San Juan to Puntarenas, 2027-11-29
- Star Pride: Colon to Puntarenas, 2027-12-06
- Star Legend: Cadiz to San Juan, 2027-12-06
- Star Pride: Puntarenas to Colon, 2027-12-13
- Star Pride: Colon to Puntarenas, 2027-12-20
- Star Pride: Puntarenas to Colon, 2027-12-27
- Star Pride: Colon to Puntarenas, 2028-01-03
- Star Pride: Puntarenas to Colon, 2028-01-10
- Star Pride: Colon to Puntarenas, 2028-01-17
- Star Pride: Puntarenas to Colon, 2028-01-24
- Star Pride: Colon to Puntarenas, 2028-01-31
- Star Pride: Puntarenas to Colon, 2028-02-07
- Star Pride: Colon to Puntarenas, 2028-02-14
- 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
- Star Pride: San Juan to Amsterdam, 2028-03-27
- Star Pride: San Juan to Amsterdam, 2028-04-03
- Star Seeker: Kobe-Osaka to Seward, 2028-05-25
- Star Seeker: Kobe-Osaka to Vancouver, 2028-05-25
- Star Seeker: Vancouver to Tokyo, 2028-08-19
- Star Seeker: Seward to Tokyo, 2028-08-30
- Star Seeker: Kobe-Osaka to Seward, 2029-05-15
- Star Seeker: Tokyo to Seward, 2029-05-25
Windstar Cruises repositioning cruises: questions and answers
What can I compare on this cruise page?
Windstar Cruises repositioning cruises currently covers 58 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 November 12, 2026 to May 25, 2029. Voyage lengths range from 6 to 29 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 Malaga 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. Listed fares are recent source observations, not guaranteed booking quotes. Check live cabin availability, currency, taxes, fees, gratuities and cancellation terms with the cruise line before booking.