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388 Cruises

14 Nights Central America Cruise

Duration

14 Nights

Ship

Wind Surf

Port of Call

Philipsburg, St Maarten - Basseterre - Gustavia - St Johns - Les Saintes - Roseau - Mayreau - Bridgetown - Anse Mitan - Castries - Pigeon Island - Pigeon Island - Bequia - Mayreau - St Georges - BridgetownItinerary Details

Itinerary Details

14 Nights Central America Cruise

Avg. per person

From

$7,959

as little as

$569/night

What's Included?

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

Duration

14 Nights

Ship

Wind Surf

Port of Call

Itinerary Details

Avg. per person

From

$7,959

as little as

$569/night

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

What's Included?

Jan 11, 2026 - Jan 25, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 11, 2026 - Jan 25, 2026 Sun - Sun

Bonus Details

$7,959 USD

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Bonus Details

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

8 Nights Caribbean Cruise

Departing From

Miami

Duration

8 Nights

Ship

Star Seeker

Port of Call

Miami - Puerto Plata, Dominican Republic - Samana - Jost Van Dyke, Great Harbour - Virgin Gorda / Prickly Pear, British Virgin Islands - Sopers Hole - San JuanItinerary Details

Itinerary Details

8 Nights Caribbean Cruise

Departing From

Miami

Avg. per person

From

$7,996

as little as

$1,000/night

What's Included?

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

Duration

8 Nights

Ship

Star Seeker

Port of Call

Miami - Puerto Plata, Dominican Republic - Samana - Jost Van Dyke, Great Harbour - Virgin Gorda / Prickly Pear, British Virgin Islands - Sopers Hole - San JuanItinerary Details

Itinerary Details

Avg. per person

From

$7,996

as little as

$1,000/night

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

What's Included?

Jan 15, 2026 - Jan 23, 2026 Thu - Fri

Interior

Oceanview

Balcony

Suite

Jan 15, 2026 - Jan 23, 2026 Thu - Fri

Bonus Details

$7,996 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

USA Today: Best Ocean Cruise

14 Nights Caribbean Cruise

Duration

14 Nights

Ship

Seabourn Ovation

Port of Call

Bridgetown, Barbados - Rodney Bay, Saint Lucia - Oranjestad, Aruba - Kralendijk, Bonaire - Willemstad, Curacao - 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

$8,098

as little as

$578/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

$8,098

as little as

$578/night

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

What's Included?

Jan 3, 2026 - Jan 17, 2026 Sat - Sat

Interior

Oceanview

Balcony

Suite

Jan 3, 2026 - Jan 17, 2026 Sat - Sat

Bonus Details

$8,098 USD

$18,698 USD

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Bonus Details

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All the Cruise Line Offers & More

14 Nights Caribbean Cruise

Duration

14 Nights

Ship

Wind Surf

Port of Call

Bridgetown - Anse Mitan - Castries - Pigeon Island - Pigeon Island - Bequia - Mayreau - St Georges - Bridgetown - Bequia - Mayreau - Soufriere - Kralendijk - Willemstad - OranjestadItinerary Details

Itinerary Details

14 Nights Caribbean Cruise

Avg. per person

From

$8,147

as little as

$582/night

What's Included?

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

Duration

14 Nights

Ship

Wind Surf

Port of Call

Bridgetown - Anse Mitan - Castries - Pigeon Island - Pigeon Island - Bequia - Mayreau - St Georges - Bridgetown - Bequia - Mayreau - Soufriere - Kralendijk - Willemstad - OranjestadItinerary Details

Itinerary Details

Avg. per person

From

$8,147

as little as

$582/night

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

What's Included?

Jan 18, 2026 - Feb 1, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 18, 2026 - Feb 1, 2026 Sun - Sun

Bonus Details

$8,147 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

Conde Naste: Best Small Ship

14 Nights Caribbean Cruise

1 Reviews

Duration

14 Nights

Ship

Silver Shadow

Port of Call

Philipsburg - St Johns - St Thomas - Little Bay - Castries - Mayreau Island - Les Saintes - Philipsburg - Philipsburg - St John - Gustavia - Roseau - St Georges - Trois Ilets - Kingstown - BridgetownItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

14 Nights Caribbean Cruise

1 Reviews

Avg. per person

From

$8,000

as little as

$571/night

What's Included?

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

Duration

14 Nights

Ship

Silver Shadow

Port of Call

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$8,000

as little as

$571/night

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

What's Included?

Jan 11, 2026 - Jan 25, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Jan 11, 2026 - Jan 25, 2026 Sun - Sun

Bonus Details

$8,200 USD

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Bonus Details

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All the Cruise Line Offers & More

Jan 11, 2026 - Jan 25, 2026 Sun - Sun

Bonus Details

$8,300 USD

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Bonus Details

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All the Cruise Line Offers & More

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388 Cruises

14 Nights Central America Cruise

14 Nights Central America Cruise

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

8 Nights Caribbean Cruise

8 Nights Caribbean Cruise

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

14 Nights Caribbean Cruise

14 Nights 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!

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