Sailing Search

28 Cruises

19 Nights Caribbean Cruise

Duration

19 Nights

Ship

Star Pride

Port of Call

Montreal - Quebec City - Quebec City - Gaspe - Cap Aux Meules - Sydney, Nova Scotia, Canada - Halifax - Portland - Rockland - Boston - Hamilton - Hamilton - St Georges - St Georges - San JuanItinerary Details

Itinerary Details

19 Nights Caribbean Cruise

Avg. per person

From

$6,922

as little as

$364/night

What's Included?

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

Duration

19 Nights

Ship

Star Pride

Port of Call

Itinerary Details

Avg. per person

From

$6,922

as little as

$364/night

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

What's Included?

Oct 9, 2026 - Oct 28, 2026 Fri - Wed

Interior

Oceanview

Balcony

Suite

Oct 9, 2026 - Oct 28, 2026 Fri - Wed

Bonus Details

$6,922 USD

$10,262 USD

$15,612 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

14 Nights Caribbean Cruise

Departing From

Miami

Duration

14 Nights

Port of Call

Miami - Saint John/cruz Bay - St Johns (antigua) - Terre-de-haut - St Maarten/philipsburg - San Juan - Tortola/road Town - Basseterre - Gustavia - Gustavia - Road Bay - MiamiItinerary Details

Itinerary Details

14 Nights Caribbean Cruise

Departing From

Miami

Avg. per person

From

$8,170

as little as

$584/night

What's Included?

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

Duration

14 Nights

Port of Call

Miami - Saint John/cruz Bay - St Johns (antigua) - Terre-de-haut - St Maarten/philipsburg - San Juan - Tortola/road Town - Basseterre - Gustavia - Gustavia - Road Bay - MiamiItinerary Details

Itinerary Details

Avg. per person

From

$8,170

as little as

$584/night

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

What's Included?

Oct 25, 2026 - Nov 8, 2026 Sun - Sun

Interior

Oceanview

Balcony

Suite

Oct 25, 2026 - Nov 8, 2026 Sun - Sun

Bonus Details

$8,170 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

25 Nights Caribbean Cruise

1 Reviews

Duration

25 Nights

Ship

Silver Shadow

Port of Call

Montreal - Quebec City - Charlottetown - Halifax - Boston Massachusetts - Cape Cod Canal Transit (canal Transit - Newport - New York - Miami - Miami - San Juan - St John - Gustavia - St Kitts - Little Bay - Jost Van Dyke - MiamiItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

25 Nights Caribbean Cruise

1 Reviews

Avg. per person

From

$10,700

as little as

$428/night

What's Included?

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

Duration

25 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

$10,700

as little as

$428/night

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

What's Included?

Oct 24, 2026 - Nov 18, 2026 Sat - Wed

Interior

Oceanview

Balcony

Suite

Oct 24, 2026 - Nov 18, 2026 Sat - Wed

Bonus Details

$10,700 USD

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Bonus Details

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All the Cruise Line Offers & More

17 Nights Caribbean Cruise

Duration

17 Nights

Port of Call

Quebec City - La Baie (saguenay) - Sept-iles - Sydney - Halifax - New York City - Miami - Saint John/cruz Bay - St Johns (antigua) - Terre-de-haut - St Maarten/philipsburg - San JuanItinerary Details

Itinerary Details

17 Nights Caribbean Cruise

Avg. per person

From

$10,750

as little as

$632/night

What's Included?

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

Duration

17 Nights

Port of Call

Quebec City - La Baie (saguenay) - Sept-iles - Sydney - Halifax - New York City - Miami - Saint John/cruz Bay - St Johns (antigua) - Terre-de-haut - St Maarten/philipsburg - San JuanItinerary Details

Itinerary Details

Avg. per person

From

$10,750

as little as

$632/night

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

What's Included?

Oct 15, 2026 - Nov 1, 2026 Thu - Sun

Interior

Oceanview

Balcony

Suite

Oct 15, 2026 - Nov 1, 2026 Thu - Sun

Bonus Details

$10,750 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

New Ship

16 Nights Eastern Caribbean Cruise

Duration

16 Nights

Ship

Seven Seas Splendor

Port of Call

Montreal - Quebec City - Saguenay - Sydney - Halifax - Philipsburg - St Johns - Basseterre - Tortola - San Juan - MiamiItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Itinerary Details

16 Nights Eastern Caribbean Cruise

Avg. per person

From

$11,799

as little as

$737/night

What's Included?

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

Duration

16 Nights

Ship

Seven Seas Splendor

Port of Call

Montreal - Quebec City - Saguenay - Sydney - Halifax - Philipsburg - St Johns - Basseterre - Tortola - San Juan - MiamiItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Itinerary Details

Avg. per person

From

$11,799

as little as

$737/night

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

What's Included?

Oct 30, 2026 - Nov 15, 2026 Fri - Sun

Interior

Oceanview

Balcony

Suite

Oct 30, 2026 - Nov 15, 2026 Fri - Sun

Bonus Details

$11,799 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

Filter Cruises

28 Cruises

19 Nights Caribbean Cruise

19 Nights Caribbean Cruise

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

14 Nights Caribbean Cruise

14 Nights Caribbean Cruise

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

25 Nights Caribbean Cruise

25 Nights Caribbean Cruise

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

17 Nights Caribbean Cruise

17 Nights Caribbean Cruise

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

16 Nights Eastern Caribbean Cruise

16 Nights Eastern 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