Sailing Search

8 Cruises

7 Nights Caribbean Cruise

Duration

7 Nights

Ship

Wind Surf

Port of Call

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

Itinerary Details

7 Nights Caribbean Cruise

Avg. per person

From

$3,151

as little as

$450/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 - Deshaies - Basseterre - Gustavia - Philipsburg, St MaartenItinerary Details

Itinerary Details

Avg. per person

From

$3,151

as little as

$450/night

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

What's Included?

Feb 28, 2026 - Mar 7, 2026 Sat - Sat

Interior

Oceanview

Balcony

Suite

Feb 28, 2026 - Mar 7, 2026 Sat - Sat

Bonus Details

$3,151 USD

$4,051 USD

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Bonus Details

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

8 Nights Caribbean Cruise

Duration

8 Nights

Ship

Wind Surf

Port of Call

Oranjestad - Cartagena - Cartagena - Bocas Del Toro - ColonItinerary Details

Itinerary Details

8 Nights Caribbean Cruise

Avg. per person

From

$3,441

as little as

$430/night

What's Included?

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

Duration

8 Nights

Ship

Wind Surf

Port of Call

Oranjestad - Cartagena - Cartagena - Bocas Del Toro - ColonItinerary Details

Itinerary Details

Avg. per person

From

$3,441

as little as

$430/night

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

What's Included?

Feb 1, 2026 - Feb 9, 2026 Sun - Mon

Interior

Oceanview

Balcony

Suite

Feb 1, 2026 - Feb 9, 2026 Sun - Mon

Bonus Details

$3,441 USD

$4,341 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

8 Nights Mexico Cruise

Duration

8 Nights

Ship

Wind Surf

Port of Call

Colon - Bocas Del Toro - Isla San Andres - Roatan - Belize City - Costa Maya - CozumelItinerary Details

Itinerary Details

8 Nights Mexico Cruise

Avg. per person

From

$3,444

as little as

$431/night

What's Included?

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

Duration

8 Nights

Ship

Wind Surf

Port of Call

Colon - Bocas Del Toro - Isla San Andres - Roatan - Belize City - Costa Maya - CozumelItinerary Details

Itinerary Details

Avg. per person

From

$3,444

as little as

$431/night

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

What's Included?

Feb 9, 2026 - Feb 17, 2026 Mon - Tue

Interior

Oceanview

Balcony

Suite

Feb 9, 2026 - Feb 17, 2026 Mon - Tue

Bonus Details

$3,444 USD

$4,344 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

11 Nights Caribbean Cruise

Duration

11 Nights

Ship

Wind Surf

Port of Call

Cozumel - Grand Cayman - Cayman Brac - Ocho Rios, Jamaica - Santo Domingo - La Romana - Jost Van Dyke, Great Harbour - Virgin Gorda / Prickly Pear, British Virgin Islands - Philipsburg, St MaartenItinerary Details

Itinerary Details

11 Nights Caribbean Cruise

Avg. per person

From

$4,463

as little as

$406/night

What's Included?

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

Duration

11 Nights

Ship

Wind Surf

Port of Call

Itinerary Details

Avg. per person

From

$4,463

as little as

$406/night

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

What's Included?

Feb 17, 2026 - Feb 28, 2026 Tue - Sat

Interior

Oceanview

Balcony

Suite

Feb 17, 2026 - Feb 28, 2026 Tue - Sat

Bonus Details

$4,463 USD

$5,463 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

16 Nights Caribbean Cruise

Duration

16 Nights

Ship

Wind Surf

Port of Call

Oranjestad - Cartagena - Cartagena - Bocas Del Toro - Colon - Bocas Del Toro - Isla San Andres - Roatan - Belize City - Costa Maya - CozumelItinerary Details

Itinerary Details

16 Nights Caribbean Cruise

Avg. per person

From

$5,386

as little as

$337/night

What's Included?

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

Duration

16 Nights

Ship

Wind Surf

Port of Call

Oranjestad - Cartagena - Cartagena - Bocas Del Toro - Colon - Bocas Del Toro - Isla San Andres - Roatan - Belize City - Costa Maya - CozumelItinerary Details

Itinerary Details

Avg. per person

From

$5,386

as little as

$337/night

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

What's Included?

Feb 1, 2026 - Feb 17, 2026 Sun - Tue

Interior

Oceanview

Balcony

Suite

Feb 1, 2026 - Feb 17, 2026 Sun - Tue

Bonus Details

$5,386 USD

$7,086 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

Filter Cruises

8 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.

8 Nights Caribbean Cruise

8 Nights Caribbean Cruise

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

8 Nights Mexico Cruise

8 Nights Mexico Cruise

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

11 Nights Caribbean Cruise

11 Nights Caribbean Cruise

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

16 Nights Caribbean Cruise

16 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