Sailing Search

94 Cruises

18 Nights Caribbean Cruise

Departing From

Miami

Duration

18 Nights

Ship

Explora I

Port of Call

Miami - Puerto Plata, Dominican Republic - Roseau - Bridgetown - Deshaies - Saint John/cruz Bay - San Juan - Oranjestad - Willemstad - Kralendijk - Bridgetown - Terre-de-haut - St Maarten/philipsburg - Jost Van Dyke - San JuanItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Itinerary Details

18 Nights Caribbean Cruise

Departing From

Miami

Avg. per person

From

$10,680

as little as

$593/night

What's Included?

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

Duration

18 Nights

Ship

Explora I

Port of Call

Best For

Gourmet

Honeymoon

Luxury

Itinerary Details

Avg. per person

From

$10,680

as little as

$593/night

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

What's Included?

Feb 12, 2026 - Mar 2, 2026 Thu - Mon

Interior

Oceanview

Balcony

Suite

Feb 12, 2026 - Mar 2, 2026 Thu - Mon

Bonus Details

$10,680 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

New Ship

14 Nights Eastern Caribbean Cruise

Departing From

Miami

Duration

14 Nights

Ship

Seven Seas Grandeur

Port of Call

Miami - Oranjestad - Willemstad - Bonaire (kralendijk) - St Georges - Pointe A Pitre - Fort De France - Basseterre - Gustavia - MiamiItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Itinerary Details

14 Nights Eastern Caribbean Cruise

Departing From

Miami

Avg. per person

From

$10,899

as little as

$779/night

What's Included?

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

Duration

14 Nights

Ship

Seven Seas Grandeur

Port of Call

Miami - Oranjestad - Willemstad - Bonaire (kralendijk) - St Georges - Pointe A Pitre - Fort De France - Basseterre - Gustavia - MiamiItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Itinerary Details

Avg. per person

From

$10,899

as little as

$779/night

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

What's Included?

Feb 28, 2026 - Mar 14, 2026 Sat - Sat

Interior

Oceanview

Balcony

Suite

Feb 28, 2026 - Mar 14, 2026 Sat - Sat

Bonus Details

$10,899 USD

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Bonus Details

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All the Cruise Line Offers & More

28 Nights Caribbean Cruise

Departing From

San Juan

Duration

28 Nights

Ship

Silver Ray

Port of Call

San Juan - St John - Gustavia - St Johns - Bequia - Soufriere - Bridgetown - Fort-de-france - Deshaies - St Kitts - Road Town - Fort Lauderdale - Fort Lauderdale - Royal Naval Dockyard - Royal Naval Dockyard - Funchal - Funchal - LisbonItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

28 Nights Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$10,900

as little as

$389/night

What's Included?

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

Duration

28 Nights

Ship

Silver Ray

Port of Call

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$10,900

as little as

$389/night

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

What's Included?

Feb 24, 2026 - Mar 24, 2026 Tue - Tue

Interior

Oceanview

Balcony

Suite

Feb 24, 2026 - Mar 24, 2026 Tue - Tue

Bonus Details

$10,900 USD

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Bonus Details

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All the Cruise Line Offers & More

20 Nights Caribbean Cruise

Departing From

Miami

Duration

20 Nights

Ship

Explora II

Port of Call

Miami - Charlotte Amalie (saint Thomas) - Pointe-a-pitre - Castries - Little Bay - Saint John/cruz Bay - Miami - Key West - New Orleans - New Orleans - Merida (progreso) - Merida (progreso) - Cozumel - MiamiItinerary Details

Best For

Gourmet

Luxury

Itinerary Details

20 Nights Caribbean Cruise

Departing From

Miami

Avg. per person

From

$11,250

as little as

$563/night

What's Included?

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

Duration

20 Nights

Ship

Explora II

Port of Call

Best For

Gourmet

Luxury

Itinerary Details

Avg. per person

From

$11,250

as little as

$563/night

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

What's Included?

Feb 4, 2026 - Feb 24, 2026 Wed - Tue

Interior

Oceanview

Balcony

Suite

Feb 4, 2026 - Feb 24, 2026 Wed - Tue

Bonus Details

$11,250 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 Seeker

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 - Bequia - Mayreau - Soufriere - Les Saintes - Marigot, St Martin - San JuanItinerary Details

Itinerary Details

14 Nights Eastern Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$11,250

as little as

$804/night

What's Included?

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

Duration

14 Nights

Ship

Star Seeker

Port of Call

Itinerary Details

Avg. per person

From

$11,250

as little as

$804/night

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

What's Included?

Feb 6, 2026 - Feb 20, 2026 Fri - Fri

Interior

Oceanview

Balcony

Suite

Feb 6, 2026 - Feb 20, 2026 Fri - Fri

Bonus Details

$11,250 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

Filter Cruises

94 Cruises

18 Nights Caribbean Cruise

18 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.

28 Nights Caribbean Cruise

28 Nights Caribbean Cruise

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

20 Nights Caribbean Cruise

20 Nights 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