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46 Cruises

9 Nights Caribbean Cruise

Departing From

San Juan

1 Reviews

Duration

9 Nights

Port of Call

San Juan - Punta Cana - Santo Domingo - Santo Domingo - Port Antonio - Montego Bay - George Town (grand Cayman) - Fort LauderdaleItinerary Details

Best For

Gourmet

River Cruises

Honeymoon

Luxury

Romantic

Senior

Itinerary Details

9 Nights Caribbean Cruise

Departing From

San Juan

1 Reviews

Avg. per person

From

$3,800

as little as

$422/night

What's Included?

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

Duration

9 Nights

Port of Call

San Juan - Punta Cana - Santo Domingo - Santo Domingo - Port Antonio - Montego Bay - George Town (grand Cayman) - Fort LauderdaleItinerary Details

Best For

Gourmet

River Cruises

Honeymoon

Luxury

Romantic

Senior

Itinerary Details

Avg. per person

From

$3,800

as little as

$422/night

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

What's Included?

Feb 17, 2027 - Feb 26, 2027 Wed - Fri

Interior

Oceanview

Balcony

Suite

Feb 17, 2027 - Feb 26, 2027 Wed - Fri

Bonus Details

$3,800 USD

$4,800 USD

$5,000 USD

Select

Bonus Details

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All the Cruise Line Offers & More

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

10 Nights Caribbean Cruise

Departing From

Fort Lauderdale

1 Reviews

Duration

10 Nights

Port of Call

Fort Lauderdale - Colon - Puerto Limon - Roatan Island - Belize City - Cozumel Quintana Roo - Fort LauderdaleItinerary Details

Best For

Gourmet

River Cruises

Honeymoon

Luxury

Romantic

Senior

Itinerary Details

10 Nights Caribbean Cruise

Departing From

Fort Lauderdale

1 Reviews

Avg. per person

From

$4,300

as little as

$430/night

What's Included?

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

Duration

10 Nights

Port of Call

Fort Lauderdale - Colon - Puerto Limon - Roatan Island - Belize City - Cozumel Quintana Roo - Fort LauderdaleItinerary Details

Best For

Gourmet

River Cruises

Honeymoon

Luxury

Romantic

Senior

Itinerary Details

Avg. per person

From

$4,300

as little as

$430/night

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

What's Included?

Feb 26, 2027 - Mar 8, 2027 Fri - Mon

Interior

Oceanview

Balcony

Suite

Feb 26, 2027 - Mar 8, 2027 Fri - Mon

Bonus Details

$4,300 USD

$5,400 USD

$5,700 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

Conde Naste: Best Small Ship

10 Nights Caribbean Cruise

1 Reviews

Duration

10 Nights

Ship

Silver Shadow

Port of Call

Bridgetown - Bequia - St Georges - Castries (st Lucia) - Trois Ilets - Roseau - Les Saintes - St Kitts (basseterre) - Gustavia, St Barthelemy - Jost Van Dyke (british Virgin Islands) - San JuanItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

10 Nights Caribbean Cruise

1 Reviews

Avg. per person

From

$5,000

as little as

$500/night

What's Included?

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

Duration

10 Nights

Ship

Silver Shadow

Port of Call

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$5,000

as little as

$500/night

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

What's Included?

Feb 16, 2027 - Feb 26, 2027 Tue - Fri

Interior

Oceanview

Balcony

Suite

Feb 16, 2027 - Feb 26, 2027 Tue - Fri

Bonus Details

$5,000 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

Conde Naste: Best Small Ship

7 Nights Caribbean Cruise

Departing From

San Juan

1 Reviews

Duration

7 Nights

Ship

Silver Shadow

Port of Call

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

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

7 Nights Caribbean Cruise

Departing From

San Juan

1 Reviews

Avg. per person

From

$5,000

as little as

$714/night

What's Included?

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

Duration

7 Nights

Ship

Silver Shadow

Port of Call

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

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$5,000

as little as

$714/night

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

What's Included?

Feb 26, 2027 - Mar 5, 2027 Fri - Fri

Interior

Oceanview

Balcony

Suite

Feb 26, 2027 - Mar 5, 2027 Fri - Fri

Bonus Details

$5,000 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

Conde Naste: Best Small Ship

10 Nights Caribbean Cruise

Departing From

San Juan

1 Reviews

Duration

10 Nights

Ship

Silver Shadow

Port of Call

San Juan - Jost Van Dyke (british Virgin Islands) - Gustavia, St Barthelemy - St Kitts (basseterre) - Little Bay, Montserrat - Les Saintes - Roseau - Trois Ilets - Castries (st Lucia) - St Georges - BridgetownItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

10 Nights Caribbean Cruise

Departing From

San Juan

1 Reviews

Avg. per person

From

$5,280

as little as

$528/night

What's Included?

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

Duration

10 Nights

Ship

Silver Shadow

Port of Call

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$5,280

as little as

$528/night

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

What's Included?

Feb 6, 2027 - Feb 16, 2027 Sat - Tue

Interior

Oceanview

Balcony

Suite

Feb 6, 2027 - Feb 16, 2027 Sat - Tue

Bonus Details

$5,280 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

Filter Cruises

46 Cruises

9 Nights Caribbean Cruise

9 Nights Caribbean Cruise

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

10 Nights Caribbean Cruise

10 Nights Caribbean Cruise

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

10 Nights Caribbean Cruise

10 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!

10 Nights Caribbean Cruise

10 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