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

Suite From

$5,099

8-night caribbean cruise

$5,849

Windstar Cruises – Star Seeker

Date:

Jan 15, 2026

Ports:

Miami → Puerto Plata → Samana → Jost Van Dyke → Virgin Gorda → Soper's Hole → San Juan

Departs Jan 15, 2026 from Miami, Florida

Up to 1 deal

Suite From

$5,849

7-night caribbean cruise

$3,699

Windstar Cruises – Star Seeker

Date:

Jan 23, 2026 View Other Dates

Ports:

Departs Jan 23, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$3,699

Sponsored

14-night caribbean cruise

$6,399

Windstar Cruises – Star Seeker

Date:

Jan 23, 2026 View Other Dates

Ports:

Departs Jan 23, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$6,399

7-night caribbean cruise

$3,399

Windstar Cruises – Star Seeker

Date:

Jan 30, 2026 View Other Dates

Ports:

Departs Jan 30, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$3,399

14-night caribbean cruise

$6,699

Windstar Cruises – Star Seeker

Date:

Jan 30, 2026

Ports:

Departs Jan 30, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$6,699

7-night caribbean cruise

$3,999

Windstar Cruises – Star Seeker

Date:

Feb 06, 2026 View Other Dates

Ports:

Departs Feb 06, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$3,999

14-night caribbean cruise

$6,699

Windstar Cruises – Star Seeker

Date:

Feb 06, 2026 View Other Dates

Ports:

Departs Feb 06, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$6,699

7-night caribbean cruise

$3,399

Windstar Cruises – Star Seeker

Date:

Feb 13, 2026 View Other Dates

Ports:

Departs Feb 13, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$3,399

14-night caribbean cruise

$5,799

Windstar Cruises – Star Seeker

Date:

Feb 13, 2026

Ports:

Departs Feb 13, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$5,799

7-night caribbean cruise

$3,399

Windstar Cruises – Star Seeker

Date:

Feb 20, 2026

Ports:

Departs Feb 20, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$3,399

14-night caribbean cruise

$5,699

Windstar Cruises – Star Seeker

Date:

Feb 20, 2026

Ports:

Departs Feb 20, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$5,699

7-night caribbean cruise

$3,399

Windstar Cruises – Star Seeker

Date:

Feb 27, 2026

Ports:

Departs Feb 27, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$3,399

14-night caribbean cruise

$14,699

Windstar Cruises – Star Seeker

Date:

Feb 27, 2026

Ports:

Departs Feb 27, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$14,699

7-night caribbean cruise

$7,499

Windstar Cruises – Star Seeker

Date:

Mar 06, 2026 View Other Dates

Ports:

Departs Mar 06, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$7,499

14-night caribbean cruise

$13,599

Windstar Cruises – Star Seeker

Date:

Mar 06, 2026

Ports:

Departs Mar 06, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$13,599

7-night caribbean cruise

$2,999

Windstar Cruises – Star Seeker

Date:

Mar 13, 2026

Ports:

Departs Mar 13, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$2,999

10-night caribbean cruise

$4,099

Windstar Cruises – Star Seeker

Date:

Mar 27, 2026

Ports:

Departs Mar 27, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$4,099

17-night caribbean cruise

$5,799

Windstar Cruises – Star Seeker

Date:

Mar 27, 2026

Ports:

Departs Mar 27, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$5,799

24-night caribbean cruise

$8,899

Windstar Cruises – Star Seeker

Date:

Mar 27, 2026

Ports:

Departs Mar 27, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$8,899

49-night caribbean cruise

$20,359

Windstar Cruises – Star Seeker

Date:

Mar 27, 2026

Ports:

Departs Mar 27, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$20,359

7-night caribbean cruise

$3,199

Windstar Cruises – Star Seeker

Date:

Apr 06, 2026

Ports:

San Juan → Catalina Island → Santo Domingo → Cartagena → San Blas Island → Colon

Departs Apr 06, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$3,199

14-night caribbean cruise

$5,699

Windstar Cruises – Star Seeker

Date:

Apr 06, 2026

Ports:

Departs Apr 06, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$5,699

22-night caribbean cruise

$8,499

Windstar Cruises – Star Seeker

Date:

Apr 06, 2026

Ports:

Departs Apr 06, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$8,499

7-night panama canal cruise

$3,999

Windstar Cruises – Star Seeker

Date:

Apr 13, 2026

Ports:

Colon → Balboa → Panama Canal → Isla Parida → Quepos → Puerto Caldera (Puntarenas)

Departs Apr 13, 2026 from Colon, Panama

Up to 2 deals including an Avoya Exclusive

Suite From

$3,999