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6 Cruises

USA Today: Best Ocean Cruise

8 Nights Caribbean Cruise

Departing From

Miami

Duration

8 Nights

Ship

Seabourn Ovation

Port of Call

Miami, Florida, Us - San Juan, Puerto Rico - Great Harbour, Jost Van Dyke, British Virgin Islands - Carambola Beach, Saint Kitts And Nevis - Roseau, Dominica - Port Elizabeth, Bequia, St Vincent And The Grenadines - Bridgetown, BarbadosItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

8 Nights Caribbean Cruise

Departing From

Miami

Avg. per person

From

$3,798

as little as

$475/night

What's Included?

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

Duration

8 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

$3,798

as little as

$475/night

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

What's Included?

Nov 20, 2026 - Nov 28, 2026 Fri - Sat

Interior

Oceanview

Balcony

Suite

Nov 20, 2026 - Nov 28, 2026 Fri - Sat

Bonus Details

$3,798 USD

$6,998 USD

Select

Bonus Details

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All the Cruise Line Offers & More

Conde Naste: Best Small Ship

10 Nights Caribbean Cruise

Departing From

Miami

1 Reviews

Duration

10 Nights

Ship

Silver Shadow

Port of Call

Miami, Fl - San Juan - St John - Gustavia, St Barthelemy - St Kitts (basseterre) - Jost Van Dyke (british Virgin Islands) - Miami, FlItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

10 Nights Caribbean Cruise

Departing From

Miami

1 Reviews

Avg. per person

From

$6,000

as little as

$600/night

What's Included?

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

Duration

10 Nights

Ship

Silver Shadow

Port of Call

Miami, Fl - San Juan - St John - Gustavia, St Barthelemy - St Kitts (basseterre) - Jost Van Dyke (british Virgin Islands) - Miami, FlItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$6,000

as little as

$600/night

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

What's Included?

Nov 30, 2026 - Dec 10, 2026 Mon - Thu

Interior

Oceanview

Balcony

Suite

Nov 30, 2026 - Dec 10, 2026 Mon - Thu

Bonus Details

$6,000 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

Conde Naste: Best Small Ship

12 Nights Caribbean Cruise

Departing From

Miami

1 Reviews

Duration

12 Nights

Ship

Silver Shadow

Port of Call

Miami, Fl - San Juan - St John - Gustavia, St Barthelemy - St Johns - Little Bay, Montserrat - St Kitts (basseterre) - Jost Van Dyke (british Virgin Islands) - Miami, FlItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

12 Nights Caribbean Cruise

Departing From

Miami

1 Reviews

Avg. per person

From

$6,100

as little as

$508/night

What's Included?

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

Duration

12 Nights

Ship

Silver Shadow

Port of Call

Miami, Fl - San Juan - St John - Gustavia, St Barthelemy - St Johns - Little Bay, Montserrat - St Kitts (basseterre) - Jost Van Dyke (british Virgin Islands) - Miami, FlItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$6,100

as little as

$508/night

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

What's Included?

Nov 18, 2026 - Nov 30, 2026 Wed - Mon

Interior

Oceanview

Balcony

Suite

Nov 18, 2026 - Nov 30, 2026 Wed - Mon

Bonus Details

$6,100 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

Conde Naste: Best Small Ship

11 Nights Caribbean Cruise

Departing From

Miami

1 Reviews

Duration

11 Nights

Ship

Silver Shadow

Port of Call

Miami, Fl - San Juan - St John - Gustavia, St Barthelemy - St Kitts (basseterre) - Little Bay, Montserrat - Jost Van Dyke (british Virgin Islands) - Miami, FlItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

11 Nights Caribbean Cruise

Departing From

Miami

1 Reviews

Avg. per person

From

$6,200

as little as

$564/night

What's Included?

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

Duration

11 Nights

Ship

Silver Shadow

Port of Call

Miami, Fl - San Juan - St John - Gustavia, St Barthelemy - St Kitts (basseterre) - Little Bay, Montserrat - Jost Van Dyke (british Virgin Islands) - Miami, FlItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$6,200

as little as

$564/night

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

What's Included?

Nov 7, 2026 - Nov 18, 2026 Sat - Wed

Interior

Oceanview

Balcony

Suite

Nov 7, 2026 - Nov 18, 2026 Sat - Wed

Bonus Details

$6,200 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

USA Today: Best Ocean Cruise

14 Nights Caribbean Cruise

Departing From

Miami

Duration

14 Nights

Ship

Seabourn Quest

Port of Call

Miami, Florida, Us - San Juan, Puerto Rico - Road Bay, Anguilla - Carambola Beach, Saint Kitts And Nevis - Roseau, Dominica - Fort-de-france, Martinique - Terre-de-haut, Iles Des Saintes, Guadeloupe - Little Bay, Montserrat - Spanish Town, Virgin Gorda, British Virgin Islands - Great Harbour, Jost Van Dyke, British Virgin Islands - Miami, Florida, UsItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

14 Nights Caribbean Cruise

Departing From

Miami

Avg. per person

From

$6,498

as little as

$464/night

What's Included?

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

Duration

14 Nights

Ship

Seabourn Quest

Port of Call

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$6,498

as little as

$464/night

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

What's Included?

Nov 22, 2026 - Dec 6, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Nov 22, 2026 - Dec 6, 2026 Sun - Sun

Bonus Details

$6,498 USD

$7,998 USD

$13,998 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

Filter Cruises

6 Cruises

8 Nights Caribbean Cruise

8 Nights Caribbean Cruise

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

10 Nights Caribbean Cruise

10 Nights Caribbean Cruise

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

12 Nights Caribbean Cruise

12 Nights Caribbean Cruise

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

11 Nights Caribbean Cruise

11 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