7-night repositioning cruise

$2,399

Windstar Cruises – Star Pride

4.5 (91)

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 2 deals including an Avoya Exclusive

Suite From

$2,399

14-night repositioning cruise

$2,599

Windstar Cruises – Wind Spirit

4.8 (98)

Date:

Nov 04, 2025

Ports:

Lisbon → Bridgetown

Departs Nov 04, 2025 from Lisbon, Portugal

Up to 1 deal

Oceanview From

$2,599

25-night repositioning cruise

$5,999

Windstar Cruises – Wind Spirit

4.8 (98)

Date:

Nov 04, 2025

Ports:

Departs Nov 04, 2025 from Lisbon, Portugal

Up to 1 deal including an Avoya Exclusive

Oceanview From

$5,999

19-night repositioning cruise

$3,599

Windstar Cruises – Wind Surf

4.7 (146)

Date:

Nov 18, 2025

Ports:

Departs Nov 18, 2025 from Lisbon, Portugal

Up to 1 deal

Oceanview From

$3,599

22-night repositioning cruise

$4,099

Windstar Cruises – Wind Spirit

4.8 (98)

Date:

Mar 21, 2026

Ports:

Departs Mar 21, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

Oceanview From

$4,099

16-night repositioning cruise

$2,499

Windstar Cruises – Star Pride

4.5 (91)

Date:

Mar 22, 2026

Ports:

Bridgetown → Lisbon → Amsterdam

Departs Mar 22, 2026 from Bridgetown, Barbados

Up to 1 deal including an Avoya Exclusive

Suite From

$2,499

15-night repositioning cruise

$2,499

Windstar Cruises – Wind Spirit

4.8 (98)

Date:

Mar 28, 2026

Ports:

Bridgetown → Lisbon

Departs Mar 28, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

Oceanview From

$2,499

25-night repositioning cruise

$5,199

Windstar Cruises – Wind Spirit

4.8 (98)

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

Oceanview From

$5,199

14-night repositioning cruise

$2,499

Windstar Cruises – Wind Star

4.6 (89)

Date:

Nov 10, 2026

Ports:

Lisbon → Bridgetown

Departs Nov 10, 2026 from Lisbon, Portugal

Up to 1 deal including an Avoya Exclusive

Oceanview From

$2,499

25-night repositioning cruise

$5,299

Windstar Cruises – Wind Star

4.6 (89)

Date:

Nov 10, 2026

Ports:

Departs Nov 10, 2026 from Lisbon, Portugal

Up to 1 deal including an Avoya Exclusive

Oceanview From

$5,299

16-night repositioning cruise

$5,099

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

Balcony From

$5,099

14-night repositioning cruise

$2,599

Windstar Cruises – Wind Surf

4.7 (146)

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

Oceanview From

$2,599

22-night repositioning cruise

$5,299

Windstar Cruises – Wind Surf

4.7 (146)

Date:

Apr 04, 2026

Ports:

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

Up to 2 deals including an Avoya Exclusive

Oceanview 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

Oceanview From

$2,199

17-night repositioning cruise

$6,999

Windstar Cruises – Star Seeker

Date:

Apr 28, 2026

Ports:

Departs Apr 28, 2026 from Puerto Vallarta, Mexico

Up to 2 deals including an Avoya Exclusive

Oceanview 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

Oceanview From

$3,099

14-night repositioning cruise

$2,499

Windstar Cruises – Wind Surf

4.7 (146)

Date:

Nov 18, 2025

Ports:

Lisbon → San Jose → Saint Maarten (Phillipsburg)

Departs Nov 18, 2025 from Lisbon, Portugal

Oceanview From

$2,499

Windstar Cruises to Repositioning