Windstar Cruises repositioning cruises to Caribbean

Compare Windstar Cruises repositioning cruises ending in Caribbean.

51 cruisesfrom $325/pp5 ships

Sailing to:Asia Atlantic - North America Caribbean Central America Hawaii / Mid-Pacific Mediterranean Northern Europe Pacific - North America Western Europe

17 repositioning cruises match your filters

Wind Star

Oct 31

Barcelona

Spain

Nov 25

Bridgetown

Barbados

25 nights from

$4,540/pp

$182/night

View details

Wind Star

Oct 31BarcelonaSpain

Nov 25BridgetownBarbados

25 nights from$4,540/pp$182/night

View details

Price drop

Wind Star

Nov 10

Lisbon

Portugal

Nov 25

Bridgetown

Barbados

15 nights from

$2,115/pp

$1,800/pp

$120/night

View details

Price drop

Wind Star

Nov 10LisbonPortugal

Nov 25BridgetownBarbados

15 nights from$2,115/pp$1,800/pp$120/night

View details

Under $100/night

Wind Star

Nov 10

Lisbon

Portugal

Dec 6

Colon

Panama

26 nights from

$1,055/pp

$41/night

View details

Under $100/night

Wind Star

Nov 10LisbonPortugal

Dec 6ColonPanama

26 nights from$1,055/pp$41/night

View details

Star Legend

Nov 12

Malaga

Spain

Nov 28

Bridgetown

Barbados

16 nights from

$2,140/pp

$134/night

View details

Star Legend

Nov 12MalagaSpain

Nov 28BridgetownBarbados

16 nights from$2,140/pp$134/night

View details

Price drop

Wind Star

Dec 12

Puntarenas

Costa Rica

Dec 20

Colon

Panama

8 nights from

$1,885/pp

$1,675/pp

$209/night

View details

Price drop

Wind Star

Dec 12PuntarenasCosta Rica

Dec 20ColonPanama

8 nights from$1,885/pp$1,675/pp$209/night

View details

Price drop

Wind Star

Dec 26

Puntarenas

Costa Rica

Jan 3

Colon

Panama

8 nights from

$2,385/pp

$2,075/pp

$259/night

View details

Price drop

Wind Star

Dec 26PuntarenasCosta Rica

Jan 3ColonPanama

8 nights from$2,385/pp$2,075/pp$259/night

View details

Star Legend

Dec 28

Puntarenas

Costa Rica

Jan 6

Colon

Panama

9 nights from

$2,380/pp

$264/night

View details

Star Legend

Dec 28PuntarenasCosta Rica

Jan 6ColonPanama

9 nights from$2,380/pp$264/night

View details

Star Legend

Jan 12

Puntarenas

Costa Rica

Jan 20

Colon

Panama

8 nights from

$1,370/pp

$171/night

View details

Star Legend

Jan 12PuntarenasCosta Rica

Jan 20ColonPanama

8 nights from$1,370/pp$171/night

View details

Price drop

Wind Star

Jan 24

Puntarenas

Costa Rica

Feb 1

Colon

Panama

8 nights from

$2,185/pp

$2,025/pp

$253/night

View details

Price drop

Wind Star

Jan 24PuntarenasCosta Rica

Feb 1ColonPanama

8 nights from$2,185/pp$2,025/pp$253/night

View details

Star Legend

Feb 9

Puntarenas

Costa Rica

Feb 23

Oranjestad Aruba

Aruba

14 nights from

$4,355/pp

$311/night

View details

Star Legend

Feb 9PuntarenasCosta Rica

Feb 23Oranjestad ArubaAruba

14 nights from$4,355/pp$311/night

View details

Price drop

Star Legend

Feb 16

Panama City

Panama

Mar 3

Bridgetown

Barbados

15 nights from

$2,205/pp

$610/pp

$41/night

View details

Price drop

Star Legend

Feb 16Panama CityPanama

Mar 3BridgetownBarbados

15 nights from$2,205/pp$610/pp$41/night

View details

Star Legend

Feb 16

Panama City

Panama

Feb 23

Oranjestad Aruba

Aruba

7 nights from

$2,870/pp

$410/night

View details

Star Legend

Feb 16Panama CityPanama

Feb 23Oranjestad ArubaAruba

7 nights from$2,870/pp$410/night

View details

Wind Surf

Nov 5

Lisbon

Portugal

Nov 29

Philipsburg St Maarten

Sint Maarten

24 nights from

$2,450/pp

$102/night

View details

Wind Surf

Nov 5LisbonPortugal

Nov 29Philipsburg St MaartenSint Maarten

24 nights from$2,450/pp$102/night

View details

Price drop

Star Pride

Dec 13

Puntarenas

Costa Rica

Dec 21

Colon

Panama

8 nights from

$1,510/pp

$1,490/pp

$186/night

View details

Price drop

Star Pride

Dec 13PuntarenasCosta Rica

Dec 21ColonPanama

8 nights from$1,510/pp$1,490/pp$186/night

View details

Price drop

Star Pride

Dec 27

Puntarenas

Costa Rica

Jan 4

Colon

Panama

8 nights from

$1,665/pp

$1,630/pp

$204/night

View details

Price drop

Star Pride

Dec 27PuntarenasCosta Rica

Jan 4ColonPanama

8 nights from$1,665/pp$1,630/pp$204/night

View details

Price drop

Star Pride

Jan 10

Puntarenas

Costa Rica

Jan 18

Colon

Panama

8 nights from

$1,615/pp

$1,510/pp

$189/night

View details

Price drop

Star Pride

Jan 10PuntarenasCosta Rica

Jan 18ColonPanama

8 nights from$1,615/pp$1,510/pp$189/night

View details

Star Pride

Jan 24

Puntarenas

Costa Rica

Feb 1

Colon

Panama

8 nights from

$1,420/pp

$178/night

View details

Star Pride

Jan 24PuntarenasCosta Rica

Feb 1ColonPanama

8 nights from$1,420/pp$178/night

View details

Home

Wishlist

17 repositioning cruises match your filters

Wind Star

Oct 31

Barcelona

Spain

Nov 25

Bridgetown

Barbados

25 nights from

$4,540/pp

$182/night

View details

Wind Star

Oct 31BarcelonaSpain

Nov 25BridgetownBarbados

25 nights from$4,540/pp$182/night

View details

Price drop

Wind Star

Nov 10

Lisbon

Portugal

Nov 25

Bridgetown

Barbados

15 nights from

$2,115/pp

$1,800/pp

$120/night

View details

Price drop

Wind Star

Nov 10LisbonPortugal

Nov 25BridgetownBarbados

15 nights from$2,115/pp$1,800/pp$120/night

View details

Under $100/night

Wind Star

Nov 10

Lisbon

Portugal

Dec 6

Colon

Panama

26 nights from

$1,055/pp

$41/night

View details

Under $100/night

Wind Star

Nov 10LisbonPortugal

Dec 6ColonPanama

26 nights from$1,055/pp$41/night

View details

Star Legend

Nov 12

Malaga

Spain

Nov 28

Bridgetown

Barbados

16 nights from

$2,140/pp

$134/night

View details

Star Legend

Nov 12MalagaSpain

Nov 28BridgetownBarbados

16 nights from$2,140/pp$134/night

View details

Price drop

Wind Star

Dec 12

Puntarenas

Costa Rica

Dec 20

Colon

Panama

8 nights from

$1,885/pp

$1,675/pp

$209/night

View details

Price drop

Wind Star

Dec 12PuntarenasCosta Rica

Dec 20ColonPanama

8 nights from$1,885/pp$1,675/pp$209/night

View details

Price drop

Wind Star

Dec 26

Puntarenas

Costa Rica

Jan 3

Colon

Panama

8 nights from

$2,385/pp

$2,075/pp

$259/night

View details

Price drop

Wind Star

Dec 26PuntarenasCosta Rica

Jan 3ColonPanama

8 nights from$2,385/pp$2,075/pp$259/night

View details

Star Legend

Dec 28

Puntarenas

Costa Rica

Jan 6

Colon

Panama

9 nights from

$2,380/pp

$264/night

View details

Star Legend

Dec 28PuntarenasCosta Rica

Jan 6ColonPanama

9 nights from$2,380/pp$264/night

View details

Star Legend

Jan 12

Puntarenas

Costa Rica

Jan 20

Colon

Panama

8 nights from

$1,370/pp

$171/night

View details

Star Legend

Jan 12PuntarenasCosta Rica

Jan 20ColonPanama

8 nights from$1,370/pp$171/night

View details

Price drop

Wind Star

Jan 24

Puntarenas

Costa Rica

Feb 1

Colon

Panama

8 nights from

$2,185/pp

$2,025/pp

$253/night

View details

Price drop

Wind Star

Jan 24PuntarenasCosta Rica

Feb 1ColonPanama

8 nights from$2,185/pp$2,025/pp$253/night

View details

Star Legend

Feb 9

Puntarenas

Costa Rica

Feb 23

Oranjestad Aruba

Aruba

14 nights from

$4,355/pp

$311/night

View details

Star Legend

Feb 9PuntarenasCosta Rica

Feb 23Oranjestad ArubaAruba

14 nights from$4,355/pp$311/night

View details

Price drop

Star Legend

Feb 16

Panama City

Panama

Mar 3

Bridgetown

Barbados

15 nights from

$2,205/pp

$610/pp

$41/night

View details

Price drop

Star Legend

Feb 16Panama CityPanama

Mar 3BridgetownBarbados

15 nights from$2,205/pp$610/pp$41/night

View details

Star Legend

Feb 16

Panama City

Panama

Feb 23

Oranjestad Aruba

Aruba

7 nights from

$2,870/pp

$410/night

View details

Star Legend

Feb 16Panama CityPanama

Feb 23Oranjestad ArubaAruba

7 nights from$2,870/pp$410/night

View details

Wind Surf

Nov 5

Lisbon

Portugal

Nov 29

Philipsburg St Maarten

Sint Maarten

24 nights from

$2,450/pp

$102/night

View details

Wind Surf

Nov 5LisbonPortugal

Nov 29Philipsburg St MaartenSint Maarten

24 nights from$2,450/pp$102/night

View details

Price drop

Star Pride

Dec 13

Puntarenas

Costa Rica

Dec 21

Colon

Panama

8 nights from

$1,510/pp

$1,490/pp

$186/night

View details

Price drop

Star Pride

Dec 13PuntarenasCosta Rica

Dec 21ColonPanama

8 nights from$1,510/pp$1,490/pp$186/night

View details

Price drop

Star Pride

Dec 27

Puntarenas

Costa Rica

Jan 4

Colon

Panama

8 nights from

$1,665/pp

$1,630/pp

$204/night

View details

Price drop

Star Pride

Dec 27PuntarenasCosta Rica

Jan 4ColonPanama

8 nights from$1,665/pp$1,630/pp$204/night

View details

Price drop

Star Pride

Jan 10

Puntarenas

Costa Rica

Jan 18

Colon

Panama

8 nights from

$1,615/pp

$1,510/pp

$189/night

View details

Price drop

Star Pride

Jan 10PuntarenasCosta Rica

Jan 18ColonPanama

8 nights from$1,615/pp$1,510/pp$189/night

View details

Star Pride

Jan 24

Puntarenas

Costa Rica

Feb 1

Colon

Panama

8 nights from

$1,420/pp

$178/night

View details

Star Pride

Jan 24PuntarenasCosta Rica

Feb 1ColonPanama

8 nights from$1,420/pp$178/night

View details