Sailing Search

99 Cruises

14 Nights Caribbean Cruise

Duration

14 Nights

Ship

Wind Surf

Port of Call

Bridgetown - Anse Mitan - Castries - Pigeon Island - Pigeon Island - Bequia - Mayreau - St Georges - Bridgetown - Bequia - Mayreau - Soufriere - Kralendijk - Willemstad - OranjestadItinerary Details

Itinerary Details

14 Nights Caribbean Cruise

Avg. per person

From

$6,647

as little as

$475/night

What's Included?

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

Duration

14 Nights

Ship

Wind Surf

Port of Call

Bridgetown - Anse Mitan - Castries - Pigeon Island - Pigeon Island - Bequia - Mayreau - St Georges - Bridgetown - Bequia - Mayreau - Soufriere - Kralendijk - Willemstad - OranjestadItinerary Details

Itinerary Details

Avg. per person

From

$6,647

as little as

$475/night

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

What's Included?

Jan 18, 2026 - Feb 1, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 18, 2026 - Feb 1, 2026 Sun - Sun

Bonus Details

$6,647 USD

$8,047 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

15 Nights Caribbean Cruise

Duration

15 Nights

Ship

Wind Surf

Port of Call

Bridgetown - Bequia - Mayreau - Soufriere - Kralendijk - Willemstad - Oranjestad - Cartagena - Cartagena - Bocas Del Toro - ColonItinerary Details

Itinerary Details

15 Nights Caribbean Cruise

Avg. per person

From

$6,766

as little as

$451/night

What's Included?

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

Duration

15 Nights

Ship

Wind Surf

Port of Call

Bridgetown - Bequia - Mayreau - Soufriere - Kralendijk - Willemstad - Oranjestad - Cartagena - Cartagena - Bocas Del Toro - ColonItinerary Details

Itinerary Details

Avg. per person

From

$6,766

as little as

$451/night

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

What's Included?

Jan 25, 2026 - Feb 9, 2026 Sun - Mon

Interior

Oceanview

Balcony

Suite

Jan 25, 2026 - Feb 9, 2026 Sun - Mon

Bonus Details

$6,766 USD

$8,166 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

11 Nights Caribbean Cruise

Departing From

Fort Lauderdale

Duration

11 Nights

Ship

Silver Ray

Port of Call

Fort Lauderdale, Florida - San Juan - St John - Gustavia, St Barthelemy - St Kitts (basseterre) - Deshaies - St Thomas - Fort Lauderdale, FloridaItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

11 Nights Caribbean Cruise

Departing From

Fort Lauderdale

Avg. per person

From

$6,800

as little as

$618/night

What's Included?

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

Duration

11 Nights

Ship

Silver Ray

Port of Call

Fort Lauderdale, Florida - San Juan - St John - Gustavia, St Barthelemy - St Kitts (basseterre) - Deshaies - St Thomas - Fort Lauderdale, FloridaItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$6,800

as little as

$618/night

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

What's Included?

Jan 16, 2026 - Jan 27, 2026 Fri - Tue

Interior

Oceanview

Balcony

Suite

Jan 16, 2026 - Jan 27, 2026 Fri - Tue

Bonus Details

$6,800 USD

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Bonus Details

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All the Cruise Line Offers & More

8 Nights Caribbean Cruise

Departing From

Miami

Duration

8 Nights

Ship

Star Seeker

Port of Call

Miami - Puerto Plata, Dominican Republic - Samana - Jost Van Dyke, Great Harbour - Virgin Gorda / Prickly Pear, British Virgin Islands - Sopers Hole - San JuanItinerary Details

Itinerary Details

8 Nights Caribbean Cruise

Departing From

Miami

Avg. per person

From

$6,946

as little as

$868/night

What's Included?

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

Duration

8 Nights

Ship

Star Seeker

Port of Call

Miami - Puerto Plata, Dominican Republic - Samana - Jost Van Dyke, Great Harbour - Virgin Gorda / Prickly Pear, British Virgin Islands - Sopers Hole - San JuanItinerary Details

Itinerary Details

Avg. per person

From

$6,946

as little as

$868/night

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

What's Included?

Jan 15, 2026 - Jan 23, 2026 Thu - Fri

Interior

Oceanview

Balcony

Suite

Jan 15, 2026 - Jan 23, 2026 Thu - Fri

Bonus Details

$6,946 USD

$7,996 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 Spirit

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 Maarten - Charlestown - Roseau - Mayreau - Fort-de-france - Basseterre - Gustavia - Philipsburg, St MaartenItinerary Details

Itinerary Details

14 Nights Caribbean Cruise

Avg. per person

From

$7,278

as little as

$520/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

$7,278

as little as

$520/night

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

What's Included?

Jan 31, 2026 - Feb 14, 2026 Sat - Sat

Interior

Oceanview

Balcony

Suite

Jan 31, 2026 - Feb 14, 2026 Sat - Sat

Bonus Details

$7,278 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

Filter Cruises

99 Cruises

14 Nights Caribbean Cruise

14 Nights Caribbean Cruise

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

15 Nights Caribbean Cruise

15 Nights Caribbean Cruise

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

11 Nights Caribbean Cruise

11 Nights Caribbean Cruise

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

8 Nights Caribbean Cruise

8 Nights Caribbean Cruise

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

14 Nights Caribbean Cruise

14 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