Sailing Search

9 Cruises

7 Nights Caribbean Cruise

Duration

7 Nights

Ship

Wind Surf

Port of Call

Philipsburg, St Maarten - Charlestown - Roseau - Mayreau - Les Saintes - Basseterre - Gustavia - Philipsburg, St MaartenItinerary Details

Itinerary Details

7 Nights Caribbean Cruise

Avg. per person

From

$1,591

as little as

$227/night

What's Included?

*Prices shown are per person and include all taxes and fees.

Duration

7 Nights

Ship

Wind Surf

Port of Call

Philipsburg, St Maarten - Charlestown - Roseau - Mayreau - Les Saintes - Basseterre - Gustavia - Philipsburg, St MaartenItinerary Details

Itinerary Details

Avg. per person

From

$1,591

as little as

$227/night

*Prices shown are per person and include all taxes and fees.

What's Included?

Dec 7, 2025 - Dec 14, 2025 Sun - Sun

Interior

Oceanview

Balcony

Suite

Dec 7, 2025 - Dec 14, 2025 Sun - Sun

Bonus Details

$1,591 USD

$1,921 USD

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Bonus Details

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CruiseDirector Exclusive: Up to $1,000 Visa Gift Card

Dec 21, 2025 - Dec 28, 2025 Sun - Sun

Bonus Details

$3,751 USD

$4,351 USD

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Bonus Details

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CruiseDirector Exclusive: Up to $1,000 Visa Gift Card

5 Nights Caribbean Cruise

Duration

5 Nights

Ship

Wind Surf

Port of Call

Itinerary Details

5 Nights Caribbean Cruise

Avg. per person

From

$2,049

as little as

$410/night

What's Included?

*Prices shown are per person and include all taxes and fees.

Duration

5 Nights

Ship

Wind Surf

Port of Call

Itinerary Details

Avg. per person

From

$2,049

as little as

$410/night

*Prices shown are per person and include all taxes and fees.

What's Included?

Dec 2, 2025 - Dec 7, 2025 Tue - Sun

Interior

Oceanview

Balcony

Suite

Dec 2, 2025 - Dec 7, 2025 Tue - Sun

Bonus Details

$2,049 USD

$3,250 USD

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Bonus Details

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CruiseDirector Exclusive: Up to $1,000 Visa Gift Card

7 Nights Caribbean Cruise

Duration

7 Nights

Ship

Wind Surf

Port of Call

Philipsburg, St Maarten - Falmouth Harbour - Road Bay - Sopers Hole - Jost Van Dyke, Great Harbour - Jost Van Dyke, Great Harbour - Virgin Gorda / Prickly Pear, British Virgin Islands - Gustavia - Philipsburg, St MaartenItinerary Details

Itinerary Details

7 Nights Caribbean Cruise

Avg. per person

From

$2,567

as little as

$367/night

What's Included?

*Prices shown are per person and include all taxes and fees.

Duration

7 Nights

Ship

Wind Surf

Port of Call

Itinerary Details

Avg. per person

From

$2,567

as little as

$367/night

*Prices shown are per person and include all taxes and fees.

What's Included?

Dec 14, 2025 - Dec 21, 2025 Sun - Sun

Interior

Oceanview

Balcony

Suite

Dec 14, 2025 - Dec 21, 2025 Sun - Sun

Bonus Details

$2,867 USD

$3,467 USD

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Bonus Details

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All the Cruise Line Offers & More

CruiseDirector Exclusive: Up to $1,000 Visa Gift Card

Dec 28, 2025 - Jan 4, 2026 Sun - Sun

Bonus Details

$3,867 USD

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Bonus Details

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All the Cruise Line Offers & More

CruiseDirector Exclusive: Up to $1,000 Visa Gift Card

14 Nights Caribbean Cruise

Duration

14 Nights

Ship

Wind Surf

Port of Call

Itinerary Details

14 Nights Caribbean Cruise

Avg. per person

From

$3,599

as little as

$257/night

What's Included?

*Prices shown are per person and include all taxes and fees.

Duration

14 Nights

Ship

Wind Surf

Port of Call

Itinerary Details

Avg. per person

From

$3,599

as little as

$257/night

*Prices shown are per person and include all taxes and fees.

What's Included?

Dec 14, 2025 - Dec 28, 2025 Sun - Sun

Interior

Oceanview

Balcony

Suite

Dec 14, 2025 - Dec 28, 2025 Sun - Sun

Bonus Details

$3,599 USD

$4,319 USD

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Bonus Details

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CruiseDirector Exclusive: Up to $1,500 Visa Gift Card

12 Nights Caribbean Cruise

Duration

12 Nights

Ship

Wind Surf

Port of Call

Philipsburg, St Maarten - Sopers Hole - Jost Van Dyke, Great Harbour - Jost Van Dyke, Great Harbour - Virgin Gorda / Prickly Pear, British Virgin Islands - Gustavia - Philipsburg, St Maarten - Charlestown - Roseau - Mayreau - Les Saintes - Basseterre - Gustavia - Philipsburg, St MaartenItinerary Details

Itinerary Details

12 Nights Caribbean Cruise

Avg. per person

From

$4,402

as little as

$367/night

What's Included?

*Prices shown are per person and include all taxes and fees.

Duration

12 Nights

Ship

Wind Surf

Port of Call

Itinerary Details

Avg. per person

From

$4,402

as little as

$367/night

*Prices shown are per person and include all taxes and fees.

What's Included?

Dec 2, 2025 - Dec 14, 2025 Tue - Sun

Interior

Oceanview

Balcony

Suite

Dec 2, 2025 - Dec 14, 2025 Tue - Sun

Bonus Details

$4,402 USD

$5,602 USD

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Bonus Details

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All the Cruise Line Offers & More

CruiseDirector Exclusive: Up to $1,500 Visa Gift Card

Filter Cruises

9 Cruises

7 Nights Caribbean Cruise

7 Nights Caribbean Cruise

DO YOU HAVE A FUTURE CRUISE CREDIT? Redeem your future cruise credit with CruiseDirector. Call us today 1-888-409-2784.

5 Nights Caribbean Cruise

5 Nights Caribbean Cruise

JOIN THE VOYAGER CLUB! Members receive Airport Club Access, Concierge Support, Price Assurance & More.

7 Nights Caribbean Cruise

7 Nights Caribbean Cruise

MAKE THE WORLD GREENER CruiseDirector and One Tree Planted are planting a tree for every passenger who sails with us.

14 Nights Caribbean Cruise

14 Nights Caribbean Cruise

BEST PRICE GUARANTEE! If you find a lower price online, we’ll match it!

12 Nights Caribbean Cruise

12 Nights Caribbean Cruise

FREE HOLDS Lock in a great price, finalize plans & pay later. Free Holds available on the final step

DO YOU HAVE A FUTURE CRUISE CREDIT?

Redeem your future cruise credit with CruiseDirector. Call us today 1-888-409-2784.

JOIN THE VOYAGER CLUB!

Members receive Airport Club Access, Concierge Support, Price Assurance & More.

MAKE THE WORLD GREENER

CruiseDirector and One Tree Planted are planting a tree for every passenger who sails with us.

BEST PRICE GUARANTEE!

If you find a lower price online, we’ll match it!

FREE HOLDS

Lock in a great price, finalize plans & pay later. Free Holds available on the final step