Sailing Search

7 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

$1,579

as little as

$226/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

$1,579

as little as

$226/night

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

What's Included?

Mar 21, 2026 - Mar 28, 2026 Sat - Sat

Interior

Oceanview

Balcony

Suite

Mar 21, 2026 - Mar 28, 2026 Sat - Sat

Bonus Details

$2,390 USD

$2,845 USD

Select

Bonus Details

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All the Cruise Line Offers & More

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

7 Nights Eastern 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 Eastern Caribbean Cruise

Avg. per person

From

$3,367

as little as

$481/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

$3,367

as little as

$481/night

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

What's Included?

Mar 14, 2026 - Mar 21, 2026 Sat - Sat

Interior

Oceanview

Balcony

Suite

Mar 14, 2026 - Mar 21, 2026 Sat - Sat

Bonus Details

$3,367 USD

$4,267 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

Itinerary Details

7 Nights Caribbean Cruise

Avg. per person

From

$3,467

as little as

$495/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

$3,467

as little as

$495/night

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

What's Included?

Mar 7, 2026 - Mar 14, 2026 Sat - Sat

Interior

Oceanview

Balcony

Suite

Mar 7, 2026 - Mar 14, 2026 Sat - Sat

Bonus Details

$3,467 USD

$4,367 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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 - St Johns - 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

$3,667

as little as

$524/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

$3,667

as little as

$524/night

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

What's Included?

Mar 28, 2026 - Apr 4, 2026 Sat - Sat

Interior

Oceanview

Balcony

Suite

Mar 28, 2026 - Apr 4, 2026 Sat - Sat

Bonus Details

$3,667 USD

$4,567 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

21 Nights Caribbean Cruise

Duration

21 Nights

Ship

Wind Surf

Port of Call

Itinerary Details

21 Nights Caribbean Cruise

Avg. per person

From

$5,544

as little as

$264/night

What's Included?

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

Duration

21 Nights

Ship

Wind Surf

Port of Call

Itinerary Details

Avg. per person

From

$5,544

as little as

$264/night

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

What's Included?

Mar 28, 2026 - Apr 18, 2026 Sat - Sat

Interior

Oceanview

Balcony

Suite

Mar 28, 2026 - Apr 18, 2026 Sat - Sat

Bonus Details

$5,544 USD

$6,694 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

Filter Cruises

7 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.

7 Nights Eastern Caribbean Cruise

7 Nights Eastern 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.

7 Nights Caribbean Cruise

7 Nights Caribbean Cruise

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

21 Nights Caribbean Cruise

21 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