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10 Cruises

7 Nights Caribbean Cruise

Duration

7 Nights

Ship

Wind Surf

Port of Call

Philipsburg, St Maarten - Basseterre - Gustavia - St Johns - Les Saintes - Roseau - Mayreau - BridgetownItinerary Details

Itinerary Details

7 Nights Caribbean Cruise

Avg. per person

From

$2,676

as little as

$382/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 - Basseterre - Gustavia - St Johns - Les Saintes - Roseau - Mayreau - BridgetownItinerary Details

Itinerary Details

Avg. per person

From

$2,676

as little as

$382/night

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

What's Included?

Jan 11, 2026 - Jan 18, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 11, 2026 - Jan 18, 2026 Sun - Sun

Bonus Details

$2,676 USD

$6,436 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

7 Nights Caribbean Cruise

Duration

7 Nights

Ship

Wind Surf

Port of Call

Bridgetown - Anse Mitan - Castries - Pigeon Island - Pigeon Island - Bequia - Mayreau - St Georges - BridgetownItinerary Details

Itinerary Details

7 Nights Caribbean Cruise

Avg. per person

From

$3,422

as little as

$489/night

What's Included?

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

Duration

7 Nights

Ship

Wind Surf

Port of Call

Bridgetown - Anse Mitan - Castries - Pigeon Island - Pigeon Island - Bequia - Mayreau - St Georges - BridgetownItinerary Details

Itinerary Details

Avg. per person

From

$3,422

as little as

$489/night

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

What's Included?

Jan 18, 2026 - Jan 25, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 18, 2026 - Jan 25, 2026 Sun - Sun

Bonus Details

$3,422 USD

$7,622 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 Caribbean Cruise

Duration

7 Nights

Ship

Wind Surf

Port of Call

Bridgetown - Bequia - Mayreau - Soufriere - Kralendijk - Willemstad - OranjestadItinerary Details

Itinerary Details

7 Nights Caribbean Cruise

Avg. per person

From

$3,624

as little as

$518/night

What's Included?

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

Duration

7 Nights

Ship

Wind Surf

Port of Call

Bridgetown - Bequia - Mayreau - Soufriere - Kralendijk - Willemstad - OranjestadItinerary Details

Itinerary Details

Avg. per person

From

$3,624

as little as

$518/night

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

What's Included?

Jan 25, 2026 - Feb 1, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 25, 2026 - Feb 1, 2026 Sun - Sun

Bonus Details

$3,624 USD

$4,524 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 - 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

$1,607

as little as

$230/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

$1,607

as little as

$230/night

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

What's Included?

Jan 4, 2026 - Jan 11, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 4, 2026 - Jan 11, 2026 Sun - Sun

Bonus Details

$3,660 USD

$4,210 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 Central America Cruise

Duration

14 Nights

Ship

Wind Surf

Port of Call

Philipsburg, St Maarten - Basseterre - Gustavia - St Johns - Les Saintes - Roseau - Mayreau - Bridgetown - Anse Mitan - Castries - Pigeon Island - Pigeon Island - Bequia - Mayreau - St Georges - BridgetownItinerary Details

Itinerary Details

14 Nights Central America Cruise

Avg. per person

From

$6,459

as little as

$461/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

$6,459

as little as

$461/night

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

What's Included?

Jan 11, 2026 - Jan 25, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 11, 2026 - Jan 25, 2026 Sun - Sun

Bonus Details

$6,459 USD

$14,759 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

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10 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 Caribbean Cruise

7 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.

7 Nights Caribbean Cruise

7 Nights Caribbean Cruise

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

14 Nights Central America Cruise

14 Nights Central America 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