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Your dedicated Personal Travel Advisor is here to help you plan the vacation of your dreams. From finding the best price to answering every question, we are with you every step of the way at no extra cost.

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7-night caribbean cruise

$2,443

Windstar Cruises – Star Pride

4.5 (95)

Date:

Nov 15, 2026 View Other Dates

Ports:

Departs Nov 15, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,443

14-night caribbean cruise

$4,644

Windstar Cruises – Star Pride

4.5 (95)

Date:

Nov 15, 2026

Ports:

Departs Nov 15, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,644

7-night caribbean cruise

$2,411

Windstar Cruises – Star Pride

4.5 (95)

Date:

Nov 22, 2026 View Other Dates

Ports:

Departs Nov 22, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$2,411

14-night caribbean cruise

$5,344

Windstar Cruises – Star Pride

4.5 (95)

Date:

Nov 22, 2026 View Other Dates

Ports:

Departs Nov 22, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,344

7-night caribbean cruise

$3,143

Windstar Cruises – Star Pride

4.5 (95)

Date:

Nov 29, 2026 View Other Dates

Ports:

Departs Nov 29, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,143

14-night caribbean cruise

$5,344

Windstar Cruises – Star Pride

4.5 (95)

Date:

Nov 29, 2026 View Other Dates

Ports:

Departs Nov 29, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,344

7-night caribbean cruise

$2,411

Windstar Cruises – Star Pride

4.5 (95)

Date:

Dec 06, 2026 View Other Dates

Ports:

Departs Dec 06, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,411

14-night caribbean cruise

$4,434

Windstar Cruises – Star Pride

4.5 (95)

Date:

Dec 06, 2026 View Other Dates

Ports:

Departs Dec 06, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,434

7-night caribbean cruise

$2,443

Windstar Cruises – Star Pride

4.5 (95)

Date:

Dec 13, 2026 View Other Dates

Ports:

Departs Dec 13, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,443

14-night caribbean cruise

$5,064

Windstar Cruises – Star Pride

4.5 (95)

Date:

Dec 13, 2026 View Other Dates

Ports:

Departs Dec 13, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,064

7-night caribbean cruise

$2,831

Windstar Cruises – Star Pride

4.5 (95)

Date:

Dec 20, 2026 View Other Dates

Ports:

Departs Dec 20, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Inside From

$2,831

14-night caribbean cruise

$5,064

Windstar Cruises – Star Pride

4.5 (95)

Date:

Dec 20, 2026 View Other Dates

Ports:

Departs Dec 20, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,064

7-night caribbean cruise

$2,443

Windstar Cruises – Star Pride

4.5 (95)

Date:

Dec 27, 2026 View Other Dates

Ports:

Departs Dec 27, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,443

14-night caribbean cruise

$4,784

Windstar Cruises – Star Pride

4.5 (95)

Date:

Dec 27, 2026 View Other Dates

Ports:

Departs Dec 27, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,784

7-night caribbean cruise

$2,551

Windstar Cruises – Star Pride

4.5 (95)

Date:

Jan 03, 2027 View Other Dates

Ports:

Departs Jan 03, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,551

14-night caribbean cruise

$5,204

Windstar Cruises – Star Pride

4.5 (95)

Date:

Jan 03, 2027

Ports:

Departs Jan 03, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,204

7-night caribbean cruise

$2,863

Windstar Cruises – Star Pride

4.5 (95)

Date:

Jan 10, 2027 View Other Dates

Ports:

Departs Jan 10, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,863

16-night repositioning cruise

$2,760

Windstar Cruises – Star Pride

4.5 (95)

Date:

Mar 30, 2027

Ports:

San Juan → Lisbon → London (Dover)

Departs Mar 30, 2027 from San Juan, Puerto Rico

Up to 1 deal including an Avoya Exclusive

View Details

Oceanview From

$2,760

7-night northern europe cruise

$4,011

Windstar Cruises – Star Pride

4.5 (95)

Date:

Apr 15, 2027

Ports:

London (Dover) → Mystery Port → Mystery Port 5 → Mystery Port 6 → Amsterdam

Departs Apr 15, 2027 from London (Dover), United Kingdom

Up to 2 deals including an Avoya Exclusive

View Details

Inside From

$4,011

7-night northern europe cruise

$4,254

Windstar Cruises – Star Pride

4.5 (95)

Date:

Apr 22, 2027

Ports:

Amsterdam → Harlingen → Oudeschild / Texel → Bruges → Antwerp → Amsterdam

Departs Apr 22, 2027 from Amsterdam, Netherlands

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,254

8-night northern europe cruise

$3,838

Windstar Cruises – Star Pride

4.5 (95)

Date:

Apr 29, 2027

Ports:

Amsterdam → Oudeschild / Texel → Harlingen → Bruges → Antwerp → London (Dover)

Departs Apr 29, 2027 from Amsterdam, Netherlands

Up to 2 deals including an Avoya Exclusive

View Details

Inside From

$3,838

3-night northern europe cruise

$2,307

Windstar Cruises – Star Pride

4.5 (95)

Date:

May 07, 2027

Ports:

London (Dover) → Antwerp → Bruges → London

Departs May 07, 2027 from London (Dover), United Kingdom

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,307

3-night northern europe cruise

$1,312

Windstar Cruises – Star Pride

4.5 (95)

Date:

May 10, 2027

Ports:

London (Dover) → Bruges → Harlingen → Amsterdam

Departs May 10, 2027 from London (Dover), United Kingdom

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$1,312

8-night northern europe cruise

$3,434

Windstar Cruises – Star Pride

4.5 (95)

Date:

May 10, 2027

Ports:

London (Dover) → Bruges → Harlingen → Amsterdam → Antwerp → Honfleur → London

Departs May 10, 2027 from London (Dover), United Kingdom

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,434

5-night northern europe cruise

$2,612

Windstar Cruises – Star Pride

4.5 (95)

Date:

May 13, 2027

Ports:

Amsterdam → Antwerp → Honfleur → London (Dover)

Departs May 13, 2027 from Amsterdam, Netherlands

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,612