Windstar Cruises to Repositioning | Repositioning Cruises

14-Night Repositioning Cruise

$2,199

Windstar Cruises – Star Breeze

84 Reviews

Date:

Feb 02, 2025

Ports:

Puerto Caldera (Puntarenas) → Papeete (Tahiti)

Departs Feb 02, 2025 from Puerto Caldera (Puntarenas), Costa Rica

Up to 2 deals including an Avoya Exclusive

From

$2,199

15-Night Repositioning Cruise

$2,399

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Feb 22, 2025

Ports:

Bridgetown → Lisbon

Departs Feb 22, 2025 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

From

$2,399

15-Night Repositioning Cruise

$2,799

Windstar Cruises – Wind Star

89 Reviews

Date:

Mar 26, 2025

Ports:

Bridgetown → Lisbon

Departs Mar 26, 2025 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

From

$2,799

25-Night Repositioning Cruise

$7,599

Windstar Cruises – Wind Star

89 Reviews

Date:

Mar 26, 2025

Ports:

Bridgetown → Lisbon → Tangier → Malaga → Cartagena → Valencia → Mallorca → Tarragona → Barcelona

Departs Mar 26, 2025 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

From

$7,599

14-Night Repositioning Cruise

$2,699

Windstar Cruises – Wind Surf

145 Reviews

Date:

Mar 29, 2025

Ports:

Saint Maarten (Phillipsburg) → Ponta Delgada → Lisbon

Departs Mar 29, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

From

$2,699

22-Night Repositioning Cruise

$8,199

Windstar Cruises – Wind Surf

145 Reviews

Date:

Mar 29, 2025

Ports:

Departs Mar 29, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

From

$8,199

10-Night Repositioning Cruise

$2,399

Windstar Cruises – Star Pride

91 Reviews

Date:

Apr 05, 2025

Ports:

Bridgetown → Santa Cruz De Tenerife

Departs Apr 05, 2025 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

From

$2,399

18-Night Repositioning Cruise

$4,699

Windstar Cruises – Star Pride

91 Reviews

Date:

Apr 05, 2025

Ports:

Bridgetown → Santa Cruz De Tenerife → San Sebastian → Las Palmas → Lanzarote → Funchal → Lisbon

Departs Apr 05, 2025 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

From

$4,699

7-Night Repositioning Cruise

$2,159

Windstar Cruises – Star Pride

91 Reviews

Date:

Oct 19, 2025

Ports:

New York City → Saint George's → San Juan

Departs Oct 19, 2025 from New York City, New York

Up to 3 deals including Avoya Exclusives

From

$2,159

14-Night Repositioning Cruise

$2,599

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Nov 04, 2025

Ports:

Lisbon → Bridgetown

Departs Nov 04, 2025 from Lisbon, Portugal

Up to 2 deals including an Avoya Exclusive

From

$2,599

19-Night Repositioning Cruise

$3,599

Windstar Cruises – Wind Surf

145 Reviews

Date:

Nov 18, 2025

Ports:

Departs Nov 18, 2025 from Lisbon, Portugal

Up to 2 deals including an Avoya Exclusive

From

$3,599

16-Night Repositioning Cruise

$4,199

Windstar Cruises – Star Seeker

Date:

Dec 28, 2025

Ports:

Malaga → Santa Cruz De Tenerife → Freeport → Miami

Departs Dec 28, 2025 from Malaga, Spain

Up to 2 deals including an Avoya Exclusive

From

$4,199

22-Night Repositioning Cruise

$4,099

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Mar 21, 2026

Ports:

Departs Mar 21, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

From

$4,099

15-Night Repositioning Cruise

$2,499

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Mar 28, 2026

Ports:

Bridgetown → Lisbon

Departs Mar 28, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

From

$2,499

25-Night Repositioning Cruise

$5,199

Windstar Cruises – Wind Spirit

98 Reviews

Date:

Mar 28, 2026

Ports:

Bridgetown → Lisbon → Tangier → Malaga → Cartagena → Valencia → Mallorca → Tarragona → Barcelona

Departs Mar 28, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

From

$5,199

14-Night Repositioning Cruise

$2,599

Windstar Cruises – Wind Surf

145 Reviews

Date:

Apr 04, 2026

Ports:

Saint Maarten (Phillipsburg) → Ponta Delgada → Lisbon

Departs Apr 04, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

From

$2,599

22-Night Repositioning Cruise

$5,299

Windstar Cruises – Wind Surf

145 Reviews

Date:

Apr 04, 2026

Ports:

Departs Apr 04, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

From

$5,299

8-Night Repositioning Cruise

$2,199

Windstar Cruises – Star Seeker

Date:

Apr 28, 2026

Ports:

Puerto Vallarta → Seattle

Departs Apr 28, 2026 from Puerto Vallarta, Mexico

Up to 2 deals including an Avoya Exclusive

From

$2,199

17-Night Repositioning Cruise

$6,999

Windstar Cruises – Star Seeker

Date:

Apr 28, 2026

Ports:

Puerto Vallarta → Seattle → Vancouver → Ketchikan → Kiel Canal → Wrangell → Sitka → Tracy Arm Fjord → Haines → Juneau

Departs Apr 28, 2026 from Puerto Vallarta, Mexico

Up to 2 deals including an Avoya Exclusive

From

$6,999

14-Night Repositioning Cruise

$3,099

Windstar Cruises – Star Seeker

Date:

Sep 02, 2026

Ports:

Anchorage → Tokyo (Yokohama)

Departs Sep 02, 2026 from Anchorage, Alaska

Up to 2 deals including an Avoya Exclusive

From

$3,099

16-Night Repositioning Cruise

$2,499

Windstar Cruises – Star Pride

91 Reviews

Date:

Mar 22, 2026

Ports:

Bridgetown → Lisbon → Amsterdam

Departs Mar 22, 2026 from Bridgetown, Barbados

From

$2,499