Sailing Search

8 Cruises

Conde Naste: Best Small Ship

7 Nights Caribbean Cruise

1 Reviews

Duration

7 Nights

Ship

Silver Shadow

Port of Call

Bridgetown - Trois Ilets - Kingstown, St Vincent - Roseau - Gustavia, St Barthelemy - St John - St Johns - 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

$3,700

as little as

$529/night

What's Included?

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

Duration

7 Nights

Ship

Silver Shadow

Port of Call

Bridgetown - Trois Ilets - Kingstown, St Vincent - Roseau - Gustavia, St Barthelemy - St John - St Johns - Philipsburg, St MaartenItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$3,700

as little as

$529/night

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

What's Included?

Feb 12, 2026 - Feb 19, 2026 Thu - Thu

Interior

Oceanview

Balcony

Suite

Feb 12, 2026 - Feb 19, 2026 Thu - Thu

Bonus Details

$3,700 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 John - Gustavia, St Barthelemy - Roseau - St Georges - Trois Ilets - Kingstown, St Vincent - BridgetownItinerary 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

$3,600

as little as

$514/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 John - Gustavia, St Barthelemy - Roseau - St Georges - Trois Ilets - Kingstown, St Vincent - BridgetownItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$3,600

as little as

$514/night

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

What's Included?

Feb 26, 2026 - Mar 5, 2026 Thu - Thu

Interior

Oceanview

Balcony

Suite

Feb 26, 2026 - Mar 5, 2026 Thu - Thu

Bonus Details

$3,800 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?

Feb 19, 2026 - Feb 26, 2026 Thu - Thu

Interior

Oceanview

Balcony

Suite

Feb 19, 2026 - Feb 26, 2026 Thu - Thu

Bonus Details

$3,800 USD

Select

Bonus Details

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All the Cruise Line Offers & More

Conde Naste: Best Small Ship

9 Nights Caribbean Cruise

1 Reviews

Duration

9 Nights

Ship

Silver Shadow

Port of Call

Cartagena - Santa Marta - Oranjestad, Aruba - Oranjestad, Aruba - Kralendijk, Bonaire - Willemstad, Curacao - Castries (st Lucia) - Bequia - BridgetownItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

9 Nights Caribbean Cruise

1 Reviews

Avg. per person

From

$4,100

as little as

$456/night

What's Included?

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

Duration

9 Nights

Ship

Silver Shadow

Port of Call

Cartagena - Santa Marta - Oranjestad, Aruba - Oranjestad, Aruba - Kralendijk, Bonaire - Willemstad, Curacao - Castries (st Lucia) - Bequia - BridgetownItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$4,100

as little as

$456/night

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

What's Included?

Feb 3, 2026 - Feb 12, 2026 Tue - Thu

Interior

Oceanview

Balcony

Suite

Feb 3, 2026 - Feb 12, 2026 Tue - Thu

Bonus Details

$4,100 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

Conde Naste: Best Small Ship

16 Nights Caribbean Cruise

1 Reviews

Duration

16 Nights

Ship

Silver Shadow

Port of Call

Cartagena - Santa Marta - Oranjestad - Oranjestad - Kralendijk - Willemstad - Castries - Bequia - Bridgetown - Bridgetown - Trois Ilets - Kingstown - Roseau - Gustavia - St John - St Johns - PhilipsburgItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

16 Nights Caribbean Cruise

1 Reviews

Avg. per person

From

$8,000

as little as

$500/night

What's Included?

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

Duration

16 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

$500/night

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

What's Included?

Feb 3, 2026 - Feb 19, 2026 Tue - Thu

Interior

Oceanview

Balcony

Suite

Feb 3, 2026 - Feb 19, 2026 Tue - Thu

Bonus Details

$8,000 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

Feb 3, 2026 - Feb 19, 2026 Tue - Thu

Bonus Details

$8,000 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

Filter Cruises

8 Cruises

7 Nights Caribbean Cruise

7 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.

9 Nights Caribbean Cruise

9 Nights Caribbean Cruise

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

16 Nights Caribbean Cruise

16 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