Sailing Search

7 Cruises

Conde Naste: Best Small Ship

14 Nights Caribbean Cruise

Departing From

San Juan

1 Reviews

Duration

14 Nights

Ship

Silver Shadow

Port of Call

San Juan - Jost Van Dyke (british Virgin Islands) - St Johns - Santa Cruz De La Palma (canary Islands) - Santa Cruz De Tenerife - LisbonItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

14 Nights Caribbean Cruise

Departing From

San Juan

1 Reviews

Avg. per person

From

$4,300

as little as

$307/night

What's Included?

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

Duration

14 Nights

Ship

Silver Shadow

Port of Call

San Juan - Jost Van Dyke (british Virgin Islands) - St Johns - Santa Cruz De La Palma (canary Islands) - Santa Cruz De Tenerife - LisbonItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$4,300

as little as

$307/night

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

What's Included?

Mar 9, 2027 - Mar 23, 2027 Tue - Tue

Interior

Oceanview

Balcony

Suite

Mar 9, 2027 - Mar 23, 2027 Tue - Tue

Bonus Details

$4,300 USD

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Bonus Details

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All the Cruise Line Offers & More

Conde Naste: Best Small Ship

13 Nights Caribbean Cruise

3 Reviews

Duration

13 Nights

Ship

Silver Spirit

Port of Call

Bridgetown - Mindelo - Las Palmas, Canary Islands - Funchal, Madeira - Funchal, Madeira - LisbonItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

13 Nights Caribbean Cruise

3 Reviews

Avg. per person

From

$4,400

as little as

$338/night

What's Included?

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

Duration

13 Nights

Ship

Silver Spirit

Port of Call

Bridgetown - Mindelo - Las Palmas, Canary Islands - Funchal, Madeira - Funchal, Madeira - LisbonItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$4,400

as little as

$338/night

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

What's Included?

Mar 31, 2027 - Apr 13, 2027 Wed - Tue

Interior

Oceanview

Balcony

Suite

Mar 31, 2027 - Apr 13, 2027 Wed - Tue

Bonus Details

$4,400 USD

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Bonus Details

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All the Cruise Line Offers & More

14 Nights Southern Europe Cruise

Departing From

Miami

Duration

14 Nights

Ship

Silver Nova

Port of Call

Miami, Fl - Royal Naval Dockyard, Bermuda - Royal Naval Dockyard, Bermuda - Funchal, Madeira - Funchal, Madeira - LisbonItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

14 Nights Southern Europe Cruise

Departing From

Miami

Avg. per person

From

$4,700

as little as

$336/night

What's Included?

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

Duration

14 Nights

Ship

Silver Nova

Port of Call

Miami, Fl - Royal Naval Dockyard, Bermuda - Royal Naval Dockyard, Bermuda - Funchal, Madeira - Funchal, Madeira - LisbonItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$4,700

as little as

$336/night

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

What's Included?

Mar 23, 2027 - Apr 6, 2027 Tue - Tue

Interior

Oceanview

Balcony

Suite

Mar 23, 2027 - Apr 6, 2027 Tue - Tue

Bonus Details

$4,700 USD

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Bonus Details

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All the Cruise Line Offers & More

14 Nights Southern Europe Cruise

Departing From

Miami

Duration

14 Nights

Ship

Silver Ray

Port of Call

Miami, Fl - Royal Naval Dockyard, Bermuda - Funchal, Madeira - Funchal, Madeira - LisbonItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

14 Nights Southern Europe Cruise

Departing From

Miami

Avg. per person

From

$5,000

as little as

$357/night

What's Included?

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

Duration

14 Nights

Ship

Silver Ray

Port of Call

Miami, Fl - Royal Naval Dockyard, Bermuda - Funchal, Madeira - Funchal, Madeira - LisbonItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$5,000

as little as

$357/night

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

What's Included?

Mar 10, 2027 - Mar 24, 2027 Wed - Wed

Interior

Oceanview

Balcony

Suite

Mar 10, 2027 - Mar 24, 2027 Wed - Wed

Bonus Details

$5,000 USD

Select

Bonus Details

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All the Cruise Line Offers & More

Conde Naste: Best Small Ship

9 Nights Mediterranean Cruise

Departing From

Lisbon

1 Reviews

Duration

9 Nights

Ship

Silver Shadow

Port of Call

Lisbon - Portimao - Cadiz - Sevilla - Sevilla - Valencia - Barcelona - Marseille - NiceItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

9 Nights Mediterranean Cruise

Departing From

Lisbon

1 Reviews

Avg. per person

From

$5,700

as little as

$633/night

What's Included?

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

Duration

9 Nights

Ship

Silver Shadow

Port of Call

Lisbon - Portimao - Cadiz - Sevilla - Sevilla - Valencia - Barcelona - Marseille - NiceItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$5,700

as little as

$633/night

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

What's Included?

Mar 23, 2027 - Apr 1, 2027 Tue - Thu

Interior

Oceanview

Balcony

Suite

Mar 23, 2027 - Apr 1, 2027 Tue - Thu

Bonus Details

$5,700 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

Filter Cruises

7 Cruises

14 Nights Caribbean Cruise

14 Nights Caribbean Cruise

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

13 Nights Caribbean Cruise

13 Nights Caribbean Cruise

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

14 Nights Southern Europe Cruise

14 Nights Southern Europe Cruise

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

14 Nights Southern Europe Cruise

14 Nights Southern Europe Cruise

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

9 Nights Mediterranean Cruise

9 Nights Mediterranean 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