Sailing Search

82 Cruises

11 Nights Caribbean Cruise

Duration

11 Nights

Ship

Wind Star

Port of Call

Bridgetown - Bequia - St Georges - Kralendijk - Willemstad - Oranjestad - Cartagena - San Blas, Panama - ColonItinerary Details

Itinerary Details

11 Nights Caribbean Cruise

Avg. per person

From

$4,530

as little as

$412/night

What's Included?

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

Duration

11 Nights

Ship

Wind Star

Port of Call

Bridgetown - Bequia - St Georges - Kralendijk - Willemstad - Oranjestad - Cartagena - San Blas, Panama - ColonItinerary Details

Itinerary Details

Avg. per person

From

$4,530

as little as

$412/night

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

What's Included?

Nov 24, 2026 - Dec 5, 2026 Tue - Sat

Interior

Oceanview

Balcony

Suite

Nov 24, 2026 - Dec 5, 2026 Tue - Sat

Bonus Details

$4,530 USD

$8,030 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 Eastern Caribbean Cruise

Departing From

San Juan

Duration

14 Nights

Ship

Star Pride

Port of Call

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

14 Nights Eastern Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$4,393

as little as

$314/night

What's Included?

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

Duration

14 Nights

Ship

Star Pride

Port of Call

Itinerary Details

Avg. per person

From

$4,393

as little as

$314/night

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

What's Included?

Nov 22, 2026 - Dec 6, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Nov 22, 2026 - Dec 6, 2026 Sun - Sun

Bonus Details

$4,593 USD

$7,013 USD

$9,493 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

Duration

15 Nights

Ship

Star Legend

Port of Call

Bridgetown - Anse Mitan - Pigeon Island - Pigeon Island - Castries - The Pitons - Mayreau - St Georges - Bequia - Bridgetown - Rodney Bay - The Pitons - Scarborough, Tobago - Bequia - Mayreau - Kralendijk - Willemstad - OranjestadItinerary Details

Itinerary Details

15 Nights Caribbean Cruise

Avg. per person

From

$4,658

as little as

$311/night

What's Included?

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

Duration

15 Nights

Ship

Star Legend

Port of Call

Itinerary Details

Avg. per person

From

$4,658

as little as

$311/night

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

What's Included?

Nov 27, 2026 - Dec 12, 2026 Fri - Sat

Interior

Oceanview

Balcony

Suite

Nov 27, 2026 - Dec 12, 2026 Fri - Sat

Bonus Details

$4,658 USD

$7,078 USD

$9,558 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

14 Nights Eastern Caribbean Cruise

Departing From

San Juan

Duration

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

Itinerary Details

14 Nights Eastern Caribbean Cruise

Departing From

San Juan

Sold Out

What's Included?

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

Duration

14 Nights

Ship

Star Pride

Port of Call

Itinerary Details

Sold Out

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

What's Included?

Nov 15, 2026 - Nov 29, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Nov 15, 2026 - Nov 29, 2026 Sun - Sun

Bonus Details

$4,693 USD

$7,113 USD

$9,593 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

14 Nights Eastern Caribbean Cruise

Departing From

San Juan

Duration

14 Nights

Ship

Star Pride

Port of Call

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

14 Nights Eastern Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$4,693

as little as

$335/night

What's Included?

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

Duration

14 Nights

Ship

Star Pride

Port of Call

Itinerary Details

Avg. per person

From

$4,693

as little as

$335/night

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

What's Included?

Nov 8, 2026 - Nov 22, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Nov 8, 2026 - Nov 22, 2026 Sun - Sun

Bonus Details

$4,693 USD

$7,113 USD

$9,593 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

Filter Cruises

82 Cruises

11 Nights Caribbean Cruise

11 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 Eastern Caribbean Cruise

14 Nights Eastern 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 Eastern Caribbean Cruise

14 Nights Eastern Caribbean Cruise

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

14 Nights Eastern Caribbean Cruise

14 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