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15 Cruises

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 - Little Bay, Montserrat - St Johns - Gustavia, St Barthelemy - St Kitts (basseterre) - 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

$2,880

as little as

$411/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 - Little Bay, Montserrat - St Johns - Gustavia, St Barthelemy - St Kitts (basseterre) - 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

$2,880

as little as

$411/night

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

What's Included?

Jan 30, 2027 - Feb 6, 2027 Sat - Sat

Interior

Oceanview

Balcony

Suite

Jan 30, 2027 - Feb 6, 2027 Sat - Sat

Bonus Details

$2,880 USD

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Bonus Details

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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 Johns - Little Bay, Montserrat - St Kitts (basseterre) - 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

$3,600

as little as

$514/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 Johns - Little Bay, Montserrat - St Kitts (basseterre) - 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

$3,600

as little as

$514/night

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

What's Included?

Jan 3, 2027 - Jan 10, 2027 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 3, 2027 - Jan 10, 2027 Sun - Sun

Bonus Details

$3,600 USD

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Bonus Details

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All the Cruise Line Offers & More

7 Nights Caribbean Cruise

Departing From

San Juan

Duration

7 Nights

Ship

Explora I

Port of Call

San Juan - St Maarten/philipsburg - St Johns (antigua) - Little Bay - Tortola/road Town - MiamiItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Itinerary Details

7 Nights Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$3,850

as little as

$550/night

What's Included?

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

Duration

7 Nights

Ship

Explora I

Port of Call

San Juan - St Maarten/philipsburg - St Johns (antigua) - Little Bay - Tortola/road Town - MiamiItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Itinerary Details

Avg. per person

From

$3,850

as little as

$550/night

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

What's Included?

Jan 4, 2027 - Jan 11, 2027 Mon - Mon

Interior

Oceanview

Balcony

Suite

Jan 4, 2027 - Jan 11, 2027 Mon - Mon

Bonus Details

$3,850 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

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?

Jan 10, 2027 - Jan 17, 2027 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 10, 2027 - Jan 17, 2027 Sun - Sun

Bonus Details

$3,999 USD

$5,259 USD

$8,499 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 - 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?

Jan 3, 2027 - Jan 10, 2027 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 3, 2027 - Jan 10, 2027 Sun - Sun

Bonus Details

$3,999 USD

$5,259 USD

$7,399 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

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15 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.

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