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66 Cruises

16 Nights Caribbean Cruise

Departing From

Miami

Duration

16 Nights

Ship

Explora I

Port of Call

Miami - Ocho Rios - Santo Tomas - Roatan Island - Belize City - Key West - Miami - Puerto Plata, Dominican Republic - St Maarten/philipsburg - Terre-de-haut - Basseterre - San JuanItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Itinerary Details

16 Nights Caribbean Cruise

Departing From

Miami

Avg. per person

From

$7,000

as little as

$438/night

What's Included?

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

Duration

16 Nights

Ship

Explora I

Port of Call

Miami - Ocho Rios - Santo Tomas - Roatan Island - Belize City - Key West - Miami - Puerto Plata, Dominican Republic - St Maarten/philipsburg - Terre-de-haut - Basseterre - San JuanItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Itinerary Details

Avg. per person

From

$7,000

as little as

$438/night

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

What's Included?

Jan 20, 2027 - Feb 5, 2027 Wed - Fri

Interior

Oceanview

Balcony

Suite

Jan 20, 2027 - Feb 5, 2027 Wed - Fri

Bonus Details

$7,000 USD

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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

Departing From

Miami

Duration

15 Nights

Port of Call

Miami - Charlotte Amalie (saint Thomas) - Road Bay - Saint-pierre - Basseterre - St Maarten/philipsburg - San Juan - Tortola/road Town - St Johns (antigua) - Providenciales - Key West - MiamiItinerary Details

Itinerary Details

15 Nights Caribbean Cruise

Departing From

Miami

Avg. per person

From

$7,035

as little as

$469/night

What's Included?

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

Duration

15 Nights

Port of Call

Itinerary Details

Avg. per person

From

$7,035

as little as

$469/night

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

What's Included?

Jan 21, 2027 - Feb 5, 2027 Thu - Fri

Interior

Oceanview

Balcony

Suite

Jan 21, 2027 - Feb 5, 2027 Thu - Fri

Bonus Details

$7,035 USD

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Bonus Details

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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

$4,499

as little as

$321/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

$4,499

as little as

$321/night

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

What's Included?

Jan 3, 2027 - Jan 17, 2027 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 3, 2027 - Jan 17, 2027 Sun - Sun

Bonus Details

$7,199 USD

$9,619 USD

$16,099 USD

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Bonus Details

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All the Cruise Line Offers & More

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

14 Nights Caribbean Cruise

Departing From

San Juan

Duration

14 Nights

Port of Call

San Juan - Tortola/road Town - St Johns (antigua) - Providenciales - Key West - Miami - St Maarten/philipsburg - Gustavia - Basseterre - Saint John/cruz Bay - San JuanItinerary Details

Itinerary Details

14 Nights Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$7,210

as little as

$515/night

What's Included?

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

Duration

14 Nights

Port of Call

San Juan - Tortola/road Town - St Johns (antigua) - Providenciales - Key West - Miami - St Maarten/philipsburg - Gustavia - Basseterre - Saint John/cruz Bay - San JuanItinerary Details

Itinerary Details

Avg. per person

From

$7,210

as little as

$515/night

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

What's Included?

Jan 29, 2027 - Feb 12, 2027 Fri - Fri

Interior

Oceanview

Balcony

Suite

Jan 29, 2027 - Feb 12, 2027 Fri - Fri

Bonus Details

$7,210 USD

Select

Bonus Details

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All the Cruise Line Offers & More

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

Conde Naste: Best Small Ship

12 Nights Caribbean Cruise

3 Reviews

Duration

12 Nights

Ship

Silver Spirit

Port of Call

Bridgetown - Bequia - St Georges - Kralendijk, Bonaire - Willemstad, Curacao - Oranjestad, Aruba - St John - San Juan - Miami, FlItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

12 Nights Caribbean Cruise

3 Reviews

Avg. per person

From

$7,300

as little as

$608/night

What's Included?

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

Duration

12 Nights

Ship

Silver Spirit

Port of Call

Bridgetown - Bequia - St Georges - Kralendijk, Bonaire - Willemstad, Curacao - Oranjestad, Aruba - St John - San Juan - Miami, FlItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$7,300

as little as

$608/night

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

What's Included?

Jan 25, 2027 - Feb 6, 2027 Mon - Sat

Interior

Oceanview

Balcony

Suite

Jan 25, 2027 - Feb 6, 2027 Mon - Sat

Bonus Details

$12,000 USD

$7,300 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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66 Cruises

16 Nights Caribbean Cruise

16 Nights Caribbean Cruise

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

15 Nights Caribbean Cruise

15 Nights Caribbean Cruise

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

14 Nights Eastern Caribbean Cruise

14 Nights Eastern Caribbean Cruise

MAKE THE WORLD GREENER CruiseDirector and One Tree Planted are planting a tree for every passenger who sails with us.

14 Nights Caribbean Cruise

14 Nights Caribbean Cruise

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

12 Nights Caribbean Cruise

12 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