Sailing Search

445 Cruises

Travvy Award: Best Ship

7 Nights Caribbean Cruise

Departing From

San Juan

Duration

7 Nights

Ship

Valiant Lady

Port of Call

San Juan, Puerto Rico - Philipsburg - Basseterre, Saint Kitts And Nevis - Castries, St Lucia - Bridgetown, Barbados - St Croix, Us Virgin Islands - San Juan, Puerto RicoItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Wedding

Ocean Cruises

Itinerary Details

7 Nights Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$1,884

as little as

$269/night

What's Included?

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

Duration

7 Nights

Ship

Valiant Lady

Port of Call

San Juan, Puerto Rico - Philipsburg - Basseterre, Saint Kitts And Nevis - Castries, St Lucia - Bridgetown, Barbados - St Croix, Us Virgin Islands - San Juan, Puerto RicoItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Wedding

Ocean Cruises

Itinerary Details

Avg. per person

From

$1,884

as little as

$269/night

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

What's Included?

Dec 27, 2025 - Jan 3, 2026 Sat - Sat

Interior

Oceanview

Balcony

Suite

Dec 27, 2025 - Jan 3, 2026 Sat - Sat

Bonus Details

$2,030 USD

$1,884 USD

$2,163 USD

$4,893 USD

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Bonus Details

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5 Nights Caribbean Cruise

Duration

5 Nights

Ship

Wind Surf

Port of Call

Philipsburg, St Maarten - 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

5 Nights Caribbean Cruise

Avg. per person

From

$2,049

as little as

$410/night

What's Included?

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

Duration

5 Nights

Ship

Wind Surf

Port of Call

Itinerary Details

Avg. per person

From

$2,049

as little as

$410/night

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

What's Included?

Dec 2, 2025 - Dec 7, 2025 Tue - Sun

Interior

Oceanview

Balcony

Suite

Dec 2, 2025 - Dec 7, 2025 Tue - Sun

Bonus Details

$2,049 USD

$3,250 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

13 Nights Caribbean Cruise

Departing From

San Juan

Duration

13 Nights

Ship

Star Pride

Port of Call

San Juan - Santo Domingo - Cartagena - Cartagena - San Blas, Panama - Colon - Panama Canal - Balboa / Fuerte Amador - Balboa / Fuerte Amador - Isla Parida - Golfo Dulce - Quepos - Puerto CalderaItinerary Details

Itinerary Details

13 Nights Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$2,073

as little as

$159/night

What's Included?

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

Duration

13 Nights

Ship

Star Pride

Port of Call

Itinerary Details

Avg. per person

From

$2,073

as little as

$159/night

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

What's Included?

Dec 7, 2025 - Dec 20, 2025 Sun - Sat

Interior

Oceanview

Balcony

Suite

Dec 7, 2025 - Dec 20, 2025 Sun - Sat

Bonus Details

$2,073 USD

$3,039 USD

$9,493 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

Travel Weekly: Best New Ship

9 Nights Caribbean Cruise

Departing From

Miami

Duration

9 Nights

Ship

Brilliant Lady

Port of Call

Miami, Florida - Grand Turk, Turks And Caicos - Philipsburg - Basseterre, Saint Kitts And Nevis - San Juan, Puerto Rico - Miami, FloridaItinerary Details

Best For

Gourmet

River Cruises

Honeymoon

Luxury

Romantic

Wedding

Ocean Cruises

Itinerary Details

9 Nights Caribbean Cruise

Departing From

Miami

Avg. per person

From

$2,152

as little as

$239/night

What's Included?

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

Duration

9 Nights

Ship

Brilliant Lady

Port of Call

Miami, Florida - Grand Turk, Turks And Caicos - Philipsburg - Basseterre, Saint Kitts And Nevis - San Juan, Puerto Rico - Miami, FloridaItinerary Details

Best For

Gourmet

River Cruises

Honeymoon

Luxury

Romantic

Wedding

Ocean Cruises

Itinerary Details

Avg. per person

From

$2,152

as little as

$239/night

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

What's Included?

Dec 26, 2025 - Jan 4, 2026 Fri - Sun

Interior

Oceanview

Balcony

Suite

Dec 26, 2025 - Jan 4, 2026 Fri - Sun

Bonus Details

$2,152 USD

$2,511 USD

$2,871 USD

$7,065 USD

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Bonus Details

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All the Cruise Line Offers & More

Travel Weekly: Best Cuisine

10 Nights Eastern Caribbean Cruise

Departing From

Miami

Duration

10 Nights

Ship

Oceania Nautica

Port of Call

Miami - Charlotte Amalie - St Johns - Gustavia - Philipsburg - Tortola - MiamiItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Itinerary Details

10 Nights Eastern Caribbean Cruise

Departing From

Miami

Avg. per person

From

$2,400

as little as

$240/night

What's Included?

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

Duration

10 Nights

Ship

Oceania Nautica

Port of Call

Miami - Charlotte Amalie - St Johns - Gustavia - Philipsburg - Tortola - MiamiItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Itinerary Details

Avg. per person

From

$2,400

as little as

$240/night

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

What's Included?

Dec 17, 2025 - Dec 27, 2025 Wed - Sat

Interior

Oceanview

Balcony

Suite

Dec 17, 2025 - Dec 27, 2025 Wed - Sat

Bonus Details

$2,400 USD

$2,655 USD

$3,649 USD

$11,699 USD

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Bonus Details

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All the Cruise Line Offers & More

Filter Cruises

445 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.

5 Nights Caribbean Cruise

5 Nights Caribbean Cruise

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

13 Nights Caribbean Cruise

13 Nights Caribbean Cruise

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

9 Nights Caribbean Cruise

9 Nights Caribbean Cruise

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

10 Nights Eastern Caribbean Cruise

10 Nights Eastern 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