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347 Cruises

16 Nights Caribbean Cruise

Departing From

San Juan

Duration

16 Nights

Port of Call

San Juan - Charlotte Amalie (saint Thomas) - St Johns (antigua) - Terre-de-haut - Puerto Plata, Dominican Republic - Miami - Puerto Plata, Dominican Republic - Cayo Levantado, Dominican Republic - San Juan - Spanish Town (virgin Gorda) - Road Bay - MiamiItinerary Details

Itinerary Details

16 Nights Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$8,550

as little as

$534/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

$8,550

as little as

$534/night

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

What's Included?

Feb 12, 2027 - Feb 28, 2027 Fri - Sun

Interior

Oceanview

Balcony

Suite

Feb 12, 2027 - Feb 28, 2027 Fri - Sun

Bonus Details

$8,550 USD

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Bonus Details

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

18 Nights Caribbean Cruise

Departing From

Miami

Duration

18 Nights

Ship

Explora I

Port of Call

Miami - Puerto Plata, Dominican Republic - Cayo Levantado, Dominican Republic - San Juan - Charlotte Amalie (saint Thomas) - Spanish Town (virgin Gorda) - Miami - Ocho Rios - Santo Tomas - Roatan Island - Belize City - Key West - MiamiItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Itinerary Details

18 Nights Caribbean Cruise

Departing From

Miami

Avg. per person

From

$8,680

as little as

$482/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

$8,680

as little as

$482/night

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

What's Included?

Jan 11, 2027 - Jan 29, 2027 Mon - Fri

Interior

Oceanview

Balcony

Suite

Jan 11, 2027 - Jan 29, 2027 Mon - Fri

Bonus Details

$8,680 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

15 Nights Caribbean Cruise

Departing From

Miami

Duration

15 Nights

Port of Call

Miami - Providenciales - St Johns (antigua) - Roseau - Bequia - Bridgetown - St Georges (grenada) - Castries - Martinique/fort De France - Gustavia - Gustavia - Spanish Town (virgin Gorda) - MiamiItinerary Details

Itinerary Details

15 Nights Caribbean Cruise

Departing From

Miami

Avg. per person

From

$8,715

as little as

$581/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

$8,715

as little as

$581/night

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

What's Included?

Mar 14, 2027 - Mar 29, 2027 Sun - Mon

Interior

Oceanview

Balcony

Suite

Mar 14, 2027 - Mar 29, 2027 Sun - Mon

Bonus Details

$8,715 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

Travel Weekly: Best Cuisine

32 Nights Caribbean Cruise

Duration

32 Nights

Ship

Oceania Insignia

Port of Call

Venice (fusina) - Rijeka - Split - Kotor - Igoumenitsa - Gallipoli - Catania (sicily) - Naples/pompeii - Rome (civitavecchia) - Barcelona - Palma De Mallorca - Alicante - Cartagena - Malaga - Seville (cadiz) - Portimao - Lisbon - Arrecife (lanzarote) - Las Palmas De Gran Canaria - Santa Cruz De La Palma - San Juan - San Juan - Nassau - MiamiItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Itinerary Details

32 Nights Caribbean Cruise

Avg. per person

From

$8,899

as little as

$278/night

What's Included?

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

Duration

32 Nights

Ship

Oceania Insignia

Port of Call

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Itinerary Details

Avg. per person

From

$8,899

as little as

$278/night

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

What's Included?

Oct 23, 2026 - Nov 24, 2026 Fri - Tue

Interior

Oceanview

Balcony

Suite

Oct 23, 2026 - Nov 24, 2026 Fri - Tue

Bonus Details

$8,899 USD

$9,599 USD

$13,999 USD

$18,749 USD

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Bonus Details

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All the Cruise Line Offers & More

USA Today: Best Ocean Cruise

14 Nights Caribbean Cruise

Duration

14 Nights

Ship

Seabourn Ovation

Port of Call

Philipsburg, Sint Maarten - Sopers Hole (frenchmans Cay), Bvi - Carambola Beach, Saint Kitts And Nevis - Trois Ilets, Martinique - Port Elizabeth, Bequia, St Vincent And The Grenadines - Saint Georges, Grenada - Bridgetown, Barbados - Castries, Saint Lucia - Little Bay, Montserrat - St Johns, Antigua And Barbuda - Carambola Beach, Saint Kitts And Nevis - Great Harbour, Jost Van Dyke, British Virgin Islands - Philipsburg, Sint MaartenItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

14 Nights Caribbean Cruise

Avg. per person

From

$8,899

as little as

$636/night

What's Included?

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

Duration

14 Nights

Ship

Seabourn Ovation

Port of Call

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$8,899

as little as

$636/night

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

What's Included?

Jan 16, 2027 - Jan 30, 2027 Sat - Sat

Interior

Oceanview

Balcony

Suite

Jan 16, 2027 - Jan 30, 2027 Sat - Sat

Bonus Details

$10,199 USD

$21,599 USD

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Bonus Details

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All the Cruise Line Offers & More

Feb 20, 2027 - Mar 6, 2027 Sat - Sat

Bonus Details

$9,899 USD

$21,599 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

Mar 6, 2027 - Mar 20, 2027 Sat - Sat

Bonus Details

$8,899 USD

$21,599 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

Filter Cruises

347 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.

18 Nights Caribbean Cruise

18 Nights Caribbean Cruise

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

15 Nights Caribbean Cruise

15 Nights Caribbean Cruise

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

32 Nights Caribbean Cruise

32 Nights Caribbean Cruise

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

14 Nights Caribbean Cruise

14 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