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Windstar Cruises to Caribbean

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14-night caribbean cruise

$4,099

Windstar Cruises – Star Pride

4.5 (93)

5 Star

65%

4 Star

26%

3 Star

2 Star

1 Star

Date:

Jan 03, 2027 View Other Dates

Ports:

San Juan → Saint George's → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Isle De Saintes → Saint Martin (Marigot) → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg) → Jost Van Dyke → Virgin Gorda → San Juan

Departs Jan 03, 2027 from San Juan, Puerto Rico

Up to 1 deal including an Avoya Exclusive

Suite From

$4,099

Top Picks Rank: 8

7-night caribbean cruise

$2,599

Windstar Cruises – Star Pride

4.5 (93)

5 Star

65%

4 Star

26%

3 Star

2 Star

1 Star

Date:

Jan 10, 2027 View Other Dates

Ports:

San Juan → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg) → Jost Van Dyke → Virgin Gorda → San Juan

Departs Jan 10, 2027 from San Juan, Puerto Rico

Up to 1 deal including an Avoya Exclusive

Suite From

$2,599

Top Picks Rank: 8

7-night caribbean cruise

$3,399

Windstar Cruises – Star Seeker

Date:

Feb 13, 2026 View Other Dates

Ports:

San Juan → Saint Vincent And Grenadines (Bequia) → Saint Vincent And Grenadines (Mayreau) → Saint Lucia (Soufriere) → Isle De Saintes → Saint Martin (Marigot) → San Juan

Departs Feb 13, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Oceanview From

$3,399

Top Picks Rank: -1

Showing 25 of 103 results

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