Sailing Search

347 Cruises

14 Nights Eastern Caribbean Cruise

Departing From

Miami

Duration

14 Nights

Port of Call

Miami - Oranjestad - Willemstad - Bonaire (kralendijk) - St Georges - Castries - Gustavia - San Juan - Royal Naval Dockyard - New YorkItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Itinerary Details

14 Nights Eastern Caribbean Cruise

Departing From

Miami

Avg. per person

From

$10,299

as little as

$736/night

What's Included?

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

Duration

14 Nights

Port of Call

Miami - Oranjestad - Willemstad - Bonaire (kralendijk) - St Georges - Castries - Gustavia - San Juan - Royal Naval Dockyard - New YorkItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Itinerary Details

Avg. per person

From

$10,299

as little as

$736/night

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

What's Included?

Apr 9, 2027 - Apr 23, 2027 Fri - Fri

Interior

Oceanview

Balcony

Suite

Apr 9, 2027 - Apr 23, 2027 Fri - Fri

Bonus Details

$10,299 USD

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Bonus Details

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17 Nights Caribbean Cruise

Departing From

San Juan

Duration

17 Nights

Port of Call

San Juan - Gustavia - Gustavia - Little Bay - Basseterre - Key West - Miami - Ocho Rios - Willemstad - Oranjestad - Santa Marta - Cartagena - Cartagena - Crossing The Panama Canal - Panama City (amador) - Panama City (amador)Itinerary Details

Itinerary Details

17 Nights Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$10,395

as little as

$611/night

What's Included?

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

Duration

17 Nights

Port of Call

Itinerary Details

Avg. per person

From

$10,395

as little as

$611/night

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

What's Included?

Apr 5, 2027 - Apr 22, 2027 Mon - Thu

Interior

Oceanview

Balcony

Suite

Apr 5, 2027 - Apr 22, 2027 Mon - Thu

Bonus Details

$10,395 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

16 Nights Caribbean Cruise

Departing From

San Juan

Duration

16 Nights

Port of Call

San Juan - St Maarten/philipsburg - Terre-de-haut - St Georges (grenada) - Castries - Puerto Plata, Dominican Republic - Miami - Charlotte Amalie (saint Thomas) - Road Bay - Saint-pierre - Basseterre - St Maarten/philipsburg - San JuanItinerary Details

Itinerary Details

16 Nights Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$10,800

as little as

$675/night

What's Included?

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

Duration

16 Nights

Port of Call

Itinerary Details

Avg. per person

From

$10,800

as little as

$675/night

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

What's Included?

Jan 13, 2027 - Jan 29, 2027 Wed - Fri

Interior

Oceanview

Balcony

Suite

Jan 13, 2027 - Jan 29, 2027 Wed - Fri

Bonus Details

$10,800 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

12 Nights Eastern Caribbean Cruise

Departing From

Miami

Duration

12 Nights

Port of Call

Miami - Charlotte Amalie - Basseterre - Roseau - Castries - Bridgetown - Pointe A Pitre - Tortola - MiamiItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Itinerary Details

12 Nights Eastern Caribbean Cruise

Departing From

Miami

Avg. per person

From

$10,849

as little as

$904/night

What's Included?

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

Duration

12 Nights

Port of Call

Miami - Charlotte Amalie - Basseterre - Roseau - Castries - Bridgetown - Pointe A Pitre - Tortola - MiamiItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Itinerary Details

Avg. per person

From

$10,849

as little as

$904/night

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

What's Included?

Mar 5, 2027 - Mar 17, 2027 Fri - Wed

Interior

Oceanview

Balcony

Suite

Mar 5, 2027 - Mar 17, 2027 Fri - Wed

Bonus Details

$10,849 USD

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Bonus Details

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All the Cruise Line Offers & More

15 Nights Caribbean Cruise

Departing From

San Juan

Duration

15 Nights

Ship

Explora I

Port of Call

San Juan - Basseterre - Tortola/road Town - Gustavia - Gustavia - Road Bay - Miami - Puerto Plata, Dominican Republic - Isla Catalina - Saint John/cruz Bay - New Year Fireworks Sju - New Year Fireworks Sju - Jost Van Dyke - Basseterre - Charlotte Amalie (saint Thomas) - San JuanItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Itinerary Details

15 Nights Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$10,880

as little as

$725/night

What's Included?

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

Duration

15 Nights

Ship

Explora I

Port of Call

Best For

Gourmet

Honeymoon

Luxury

Itinerary Details

Avg. per person

From

$10,880

as little as

$725/night

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

What's Included?

Dec 20, 2026 - Jan 4, 2027 Sun - Mon

Interior

Oceanview

Balcony

Suite

Dec 20, 2026 - Jan 4, 2027 Sun - Mon

Bonus Details

$10,880 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

Filter Cruises

347 Cruises

14 Nights Eastern Caribbean Cruise

14 Nights Eastern Caribbean Cruise

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

17 Nights Caribbean Cruise

17 Nights Caribbean Cruise

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

16 Nights Caribbean Cruise

16 Nights Caribbean Cruise

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

12 Nights Eastern Caribbean Cruise

12 Nights Eastern Caribbean Cruise

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

15 Nights Caribbean Cruise

15 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