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98 Cruises

Travel Weekly: Best Cuisine

12 Nights Caribbean Cruise

Departing From

Miami

Duration

12 Nights

Ship

Oceania Insignia

Port of Call

Miami - Oranjestad - Willemstad - Port Of Spain - St Georges - Castries - Kingstown - Roseau - Fort-de-france - BridgetownItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Itinerary Details

12 Nights Caribbean Cruise

Departing From

Miami

Avg. per person

From

$2,825

as little as

$235/night

What's Included?

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

Duration

12 Nights

Ship

Oceania Insignia

Port of Call

Miami - Oranjestad - Willemstad - Port Of Spain - St Georges - Castries - Kingstown - Roseau - Fort-de-france - BridgetownItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Itinerary Details

Avg. per person

From

$2,825

as little as

$235/night

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

What's Included?

Jan 15, 2026 - Jan 27, 2026 Thu - Tue

Interior

Oceanview

Balcony

Suite

Jan 15, 2026 - Jan 27, 2026 Thu - Tue

Bonus Details

$2,825 USD

$3,122 USD

$4,149 USD

$5,715 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

1 Reviews

Duration

7 Nights

Ship

Silver Shadow

Port of Call

Philipsburg, St Maarten - St Johns - St Thomas - Little Bay, Montserrat - Castries (st Lucia) - Mayreau Island - Les Saintes - Philipsburg, St MaartenItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

7 Nights Caribbean Cruise

1 Reviews

Avg. per person

From

$3,100

as little as

$443/night

What's Included?

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

Duration

7 Nights

Ship

Silver Shadow

Port of Call

Philipsburg, St Maarten - St Johns - St Thomas - Little Bay, Montserrat - Castries (st Lucia) - Mayreau Island - Les Saintes - Philipsburg, St MaartenItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$3,100

as little as

$443/night

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

What's Included?

Jan 4, 2026 - Jan 11, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 4, 2026 - Jan 11, 2026 Sun - Sun

Bonus Details

$3,100 USD

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Bonus Details

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All the Cruise Line Offers & More

Jan 11, 2026 - Jan 18, 2026 Sun - Sun

Bonus Details

$4,100 USD

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Bonus Details

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All the Cruise Line Offers & More

7 Nights Caribbean Cruise

Duration

7 Nights

Ship

Wind Surf

Port of Call

Philipsburg, St Maarten - Falmouth Harbour - Road Bay - Sopers Hole - Jost Van Dyke, Great Harbour - Jost Van Dyke, Great Harbour - Virgin Gorda / Prickly Pear, British Virgin Islands - Gustavia - Philipsburg, St MaartenItinerary Details

Itinerary Details

7 Nights Caribbean Cruise

Avg. per person

From

$2,567

as little as

$367/night

What's Included?

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

Duration

7 Nights

Ship

Wind Surf

Port of Call

Itinerary Details

Avg. per person

From

$2,567

as little as

$367/night

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

What's Included?

Jan 4, 2026 - Jan 11, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 4, 2026 - Jan 11, 2026 Sun - Sun

Bonus Details

$3,110 USD

$4,010 USD

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Bonus Details

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

7 Nights Caribbean Cruise

Duration

7 Nights

Ship

Wind Surf

Port of Call

Philipsburg, St Maarten - Basseterre - Gustavia - St Johns - Les Saintes - Roseau - Mayreau - BridgetownItinerary Details

Itinerary Details

7 Nights Caribbean Cruise

Avg. per person

From

$3,236

as little as

$462/night

What's Included?

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

Duration

7 Nights

Ship

Wind Surf

Port of Call

Philipsburg, St Maarten - Basseterre - Gustavia - St Johns - Les Saintes - Roseau - Mayreau - BridgetownItinerary Details

Itinerary Details

Avg. per person

From

$3,236

as little as

$462/night

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

What's Included?

Jan 11, 2026 - Jan 18, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 11, 2026 - Jan 18, 2026 Sun - Sun

Bonus Details

$3,236 USD

$4,136 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

Duration

7 Nights

Ship

Wind Surf

Port of Call

Bridgetown - Bequia - Mayreau - Soufriere - Kralendijk - Willemstad - OranjestadItinerary Details

Itinerary Details

7 Nights Caribbean Cruise

Avg. per person

From

$3,324

as little as

$475/night

What's Included?

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

Duration

7 Nights

Ship

Wind Surf

Port of Call

Bridgetown - Bequia - Mayreau - Soufriere - Kralendijk - Willemstad - OranjestadItinerary Details

Itinerary Details

Avg. per person

From

$3,324

as little as

$475/night

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

What's Included?

Jan 25, 2026 - Feb 1, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 25, 2026 - Feb 1, 2026 Sun - Sun

Bonus Details

$3,324 USD

$4,224 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

Filter Cruises

98 Cruises

12 Nights Caribbean Cruise

12 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