Sailing Search

70 Cruises

22 Nights Caribbean Cruise

Duration

22 Nights

Ship

Star Legend

Port of Call

Malaga - Tangier - Casablanca, Morocco - Funchal - Bridgetown - Anse Mitan - Rodney Bay - Rodney Bay - Castries - The Pitons - Mayreau - St Georges - Bequia - BridgetownItinerary Details

Itinerary Details

22 Nights Caribbean Cruise

Avg. per person

From

$4,999

as little as

$227/night

What's Included?

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

Duration

22 Nights

Ship

Star Legend

Port of Call

Malaga - Tangier - Casablanca, Morocco - Funchal - Bridgetown - Anse Mitan - Rodney Bay - Rodney Bay - Castries - The Pitons - Mayreau - St Georges - Bequia - BridgetownItinerary Details

Itinerary Details

Avg. per person

From

$4,999

as little as

$227/night

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

What's Included?

Nov 12, 2026 - Dec 4, 2026 Thu - Fri

Interior

Oceanview

Balcony

Suite

Nov 12, 2026 - Dec 4, 2026 Thu - Fri

Bonus Details

$4,999 USD

$6,999 USD

$10,799 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) - 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

$5,099

as little as

$364/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

$5,099

as little as

$364/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

$5,099 USD

$7,519 USD

$9,999 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

Conde Naste: Best Small Ship

11 Nights Caribbean Cruise

Departing From

Miami

1 Reviews

Duration

11 Nights

Ship

Silver Shadow

Port of Call

Miami, Fl - San Juan - St John - Gustavia, St Barthelemy - St Kitts (basseterre) - Little Bay, Montserrat - Jost Van Dyke (british Virgin Islands) - Miami, FlItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

11 Nights Caribbean Cruise

Departing From

Miami

1 Reviews

Avg. per person

From

$5,100

as little as

$464/night

What's Included?

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

Duration

11 Nights

Ship

Silver Shadow

Port of Call

Miami, Fl - San Juan - St John - Gustavia, St Barthelemy - St Kitts (basseterre) - Little Bay, Montserrat - Jost Van Dyke (british Virgin Islands) - Miami, FlItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$5,100

as little as

$464/night

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

What's Included?

Nov 7, 2026 - Nov 18, 2026 Sat - Wed

Interior

Oceanview

Balcony

Suite

Nov 7, 2026 - Nov 18, 2026 Sat - Wed

Bonus Details

$5,100 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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) - Gustavia - Basseterre - Philipsburg, St Maarten - Jost Van Dyke, Great Harbour - Virgin Gorda / Prickly Pear, British Virgin Islands - San Juan - St Georges - Bequia - Mayreau - Deshaies - Marigot, St Martin - San JuanItinerary Details

Itinerary Details

14 Nights Eastern Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$5,299

as little as

$379/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

$5,299

as little as

$379/night

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

What's Included?

Nov 29, 2026 - Dec 13, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Nov 29, 2026 - Dec 13, 2026 Sun - Sun

Bonus Details

$5,299 USD

$7,719 USD

$10,199 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

13 Nights Caribbean Cruise

Departing From

Fort Lauderdale

1 Reviews

Duration

13 Nights

Port of Call

Fort Lauderdale - New Orleans - New Orleans - Cozumel Quintana Roo - Roatan Island - Santo Tomas - Montego Bay - George Town (grand Cayman) - Fort LauderdaleItinerary Details

Best For

Gourmet

River Cruises

Honeymoon

Luxury

Romantic

Senior

Itinerary Details

13 Nights Caribbean Cruise

Departing From

Fort Lauderdale

1 Reviews

Avg. per person

From

$5,300

as little as

$408/night

What's Included?

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

Duration

13 Nights

Port of Call

Fort Lauderdale - New Orleans - New Orleans - Cozumel Quintana Roo - Roatan Island - Santo Tomas - Montego Bay - George Town (grand Cayman) - Fort LauderdaleItinerary Details

Best For

Gourmet

River Cruises

Honeymoon

Luxury

Romantic

Senior

Itinerary Details

Avg. per person

From

$5,300

as little as

$408/night

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

What's Included?

Nov 11, 2026 - Nov 24, 2026 Wed - Tue

Interior

Oceanview

Balcony

Suite

Nov 11, 2026 - Nov 24, 2026 Wed - Tue

Bonus Details

$5,300 USD

$7,000 USD

$7,600 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

Filter Cruises

70 Cruises

22 Nights Caribbean Cruise

22 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.

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.

14 Nights Eastern Caribbean Cruise

14 Nights Eastern Caribbean Cruise

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

13 Nights Caribbean Cruise

13 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