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25 Cruises

15 Nights Caribbean Cruise

Duration

15 Nights

Ship

Wind Spirit

Port of Call

Philipsburg, St Maarten - Basseterre - Gustavia - Falmouth Harbour - Les Saintes - Roseau - Mayreau - Bridgetown - Basseterre - St Johns - Les Saintes - Roseau - Mayreau - Anse Mitan - BridgetownItinerary Details

Itinerary Details

15 Nights Caribbean Cruise

Avg. per person

From

$8,199

as little as

$547/night

What's Included?

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

Duration

15 Nights

Ship

Wind Spirit

Port of Call

Itinerary Details

Avg. per person

From

$8,199

as little as

$547/night

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

What's Included?

Feb 28, 2026 - Mar 15, 2026 Sat - Sun

Interior

Oceanview

Balcony

Suite

Feb 28, 2026 - Mar 15, 2026 Sat - Sun

Bonus Details

$8,199 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

14 Nights Caribbean Cruise

Duration

14 Nights

Ship

Wind Spirit

Port of Call

Philipsburg, St Maarten - St Johns - Road Bay - Virgin Gorda / Prickly Pear, British Virgin Islands - Sopers Hole - Sopers Hole - Jost Van Dyke, Great Harbour - Gustavia - Philipsburg, St Maarten - Basseterre - Gustavia - Falmouth Harbour - Les Saintes - Roseau - Mayreau - BridgetownItinerary Details

Itinerary Details

14 Nights Caribbean Cruise

Avg. per person

From

$8,199

as little as

$586/night

What's Included?

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

Duration

14 Nights

Ship

Wind Spirit

Port of Call

Itinerary Details

Avg. per person

From

$8,199

as little as

$586/night

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

What's Included?

Feb 21, 2026 - Mar 7, 2026 Sat - Sat

Interior

Oceanview

Balcony

Suite

Feb 21, 2026 - Mar 7, 2026 Sat - Sat

Bonus Details

$8,199 USD

Select

Bonus Details

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All the Cruise Line Offers & More

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

15 Nights Caribbean Cruise

Departing From

Miami

Duration

15 Nights

Ship

Explora II

Port of Call

Miami - Charlotte Amalie (saint Thomas) - Jost Van Dyke - St Johns (antigua) - Gustavia - San Juan - St Georges (grenada) - Bequia - Bridgetown - Martinique/fort De France - Gustavia - Basseterre - San JuanItinerary Details

Best For

Gourmet

Luxury

Itinerary Details

15 Nights Caribbean Cruise

Departing From

Miami

Avg. per person

From

$8,685

as little as

$579/night

What's Included?

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

Duration

15 Nights

Ship

Explora II

Port of Call

Best For

Gourmet

Luxury

Itinerary Details

Avg. per person

From

$8,685

as little as

$579/night

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

What's Included?

Feb 24, 2026 - Mar 11, 2026 Tue - Wed

Interior

Oceanview

Balcony

Suite

Feb 24, 2026 - Mar 11, 2026 Tue - Wed

Bonus Details

$8,685 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

14 Nights Caribbean Cruise

Departing From

San Juan

Duration

14 Nights

Ship

Silver Ray

Port of Call

San Juan - St John - Gustavia, St Barthelemy - St Johns - Bequia - Soufriere, St Lucia - Bridgetown - Fort-de-france - Deshaies - St Kitts (basseterre) - Road Town, Tortola - Fort Lauderdale, FloridaItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

14 Nights Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$11,300

as little as

$807/night

What's Included?

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

Duration

14 Nights

Ship

Silver Ray

Port of Call

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$11,300

as little as

$807/night

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

What's Included?

Feb 24, 2026 - Mar 10, 2026 Tue - Tue

Interior

Oceanview

Balcony

Suite

Feb 24, 2026 - Mar 10, 2026 Tue - Tue

Bonus Details

$7,910 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

22 Nights Caribbean Cruise

Duration

22 Nights

Ship

Wind Spirit

Port of Call

Itinerary Details

22 Nights Caribbean Cruise

Avg. per person

From

$12,299

as little as

$559/night

What's Included?

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

Duration

22 Nights

Ship

Wind Spirit

Port of Call

Itinerary Details

Avg. per person

From

$12,299

as little as

$559/night

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

What's Included?

Feb 21, 2026 - Mar 15, 2026 Sat - Sun

Interior

Oceanview

Balcony

Suite

Feb 21, 2026 - Mar 15, 2026 Sat - Sun

Bonus Details

$12,299 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

Filter Cruises

25 Cruises

15 Nights Caribbean Cruise

15 Nights Caribbean Cruise

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

14 Nights Caribbean Cruise

14 Nights Caribbean Cruise

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

15 Nights Caribbean Cruise

15 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!

22 Nights Caribbean Cruise

22 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