Sailing Search

19 Cruises

5 Nights Caribbean Cruise

Departing From

San Juan

3 Reviews

Duration

5 Nights

Port of Call

San Juan - Jost Van Dyke (british Virgin Islands) - Oranjestad, Aruba - Cartagena - CartagenaItinerary Details

Best For

Gourmet

River Cruises

Honeymoon

Luxury

Romantic

Senior

Itinerary Details

5 Nights Caribbean Cruise

Departing From

San Juan

3 Reviews

Avg. per person

From

$3,000

as little as

$600/night

What's Included?

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

Duration

5 Nights

Port of Call

San Juan - Jost Van Dyke (british Virgin Islands) - Oranjestad, Aruba - Cartagena - CartagenaItinerary Details

Best For

Gourmet

River Cruises

Honeymoon

Luxury

Romantic

Senior

Itinerary Details

Avg. per person

From

$3,000

as little as

$600/night

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

What's Included?

Nov 27, 2026 - Dec 2, 2026 Fri - Wed

Interior

Oceanview

Balcony

Suite

Nov 27, 2026 - Dec 2, 2026 Fri - Wed

Bonus Details

$3,000 USD

$3,600 USD

$3,300 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

Departing From

San Juan

1 Reviews

Duration

7 Nights

Port of Call

San Juan - Jost Van Dyke (british Virgin Islands) - St Johns - Gustavia, St Barthelemy - St Thomas - Fort LauderdaleItinerary Details

Best For

Gourmet

River Cruises

Honeymoon

Luxury

Romantic

Senior

Itinerary Details

7 Nights Caribbean Cruise

Departing From

San Juan

1 Reviews

Avg. per person

From

$3,000

as little as

$429/night

What's Included?

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

Duration

7 Nights

Port of Call

San Juan - Jost Van Dyke (british Virgin Islands) - St Johns - Gustavia, St Barthelemy - St Thomas - Fort LauderdaleItinerary Details

Best For

Gourmet

River Cruises

Honeymoon

Luxury

Romantic

Senior

Itinerary Details

Avg. per person

From

$3,000

as little as

$429/night

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

What's Included?

Nov 4, 2026 - Nov 11, 2026 Wed - Wed

Interior

Oceanview

Balcony

Suite

Nov 4, 2026 - Nov 11, 2026 Wed - Wed

Bonus Details

$3,000 USD

$3,900 USD

$4,200 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

7 Nights Caribbean Cruise

Departing From

San Juan

Duration

7 Nights

Ship

Star Pride

Port of Call

San Juan - Cruz Bay, St John, Virgin Islands (us) - Gustavia - Basseterre - Philipsburg, St Maarten - Jost Van Dyke, Great Harbour - Virgin Gorda / Prickly Pear, British Virgin Islands - San JuanItinerary Details

Itinerary Details

7 Nights Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$3,099

as little as

$443/night

What's Included?

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

Duration

7 Nights

Ship

Star Pride

Port of Call

Itinerary Details

Avg. per person

From

$3,099

as little as

$443/night

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

What's Included?

Nov 29, 2026 - Dec 6, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Nov 29, 2026 - Dec 6, 2026 Sun - Sun

Bonus Details

$3,099 USD

$4,359 USD

$5,599 USD

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Bonus Details

Select

All the Cruise Line Offers & More

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

7 Nights Caribbean Cruise

Departing From

San Juan

Duration

7 Nights

Ship

Star Pride

Port of Call

San Juan - St Georges - Bequia - Mayreau - Les Saintes - Marigot, St Martin - San JuanItinerary Details

Itinerary Details

7 Nights Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$2,899

as little as

$414/night

What's Included?

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

Duration

7 Nights

Ship

Star Pride

Port of Call

San Juan - St Georges - Bequia - Mayreau - Les Saintes - Marigot, St Martin - San JuanItinerary Details

Itinerary Details

Avg. per person

From

$2,899

as little as

$414/night

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

What's Included?

Nov 8, 2026 - Nov 15, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Nov 8, 2026 - Nov 15, 2026 Sun - Sun

Bonus Details

$3,299 USD

$4,559 USD

$5,799 USD

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Bonus Details

Select

All the Cruise Line Offers & More

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

Nov 22, 2026 - Nov 29, 2026 Sun - Sun

Bonus Details

$3,299 USD

$4,559 USD

$5,799 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

7 Nights Caribbean Cruise

Departing From

San Juan

Duration

7 Nights

Ship

Star Pride

Port of Call

San Juan - Cruz Bay, St John, Virgin Islands (us) - Basseterre - Gustavia - Philipsburg, St Maarten - Jost Van Dyke, Great Harbour - Virgin Gorda / Prickly Pear, British Virgin Islands - San JuanItinerary Details

Itinerary Details

7 Nights Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$2,799

as little as

$400/night

What's Included?

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

Duration

7 Nights

Ship

Star Pride

Port of Call

Itinerary Details

Avg. per person

From

$2,799

as little as

$400/night

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

What's Included?

Nov 15, 2026 - Nov 22, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Nov 15, 2026 - Nov 22, 2026 Sun - Sun

Bonus Details

$3,399 USD

$4,399 USD

$5,399 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

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19 Cruises

5 Nights Caribbean Cruise

5 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!

7 Nights Caribbean Cruise

7 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