Sailing Search

21 Cruises

8 Nights Caribbean Cruise

Departing From

San Juan

Duration

8 Nights

Port of Call

San Juan - St Johns (antigua) - Pointe-a-pitre - Tortola/road Town - New Year Fireworks Sju - New Year Fireworks Sju - Samana - Puerto Plata, Dominican Republic - MiamiItinerary Details

Itinerary Details

8 Nights Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$6,440

as little as

$805/night

What's Included?

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

Duration

8 Nights

Port of Call

San Juan - St Johns (antigua) - Pointe-a-pitre - Tortola/road Town - New Year Fireworks Sju - New Year Fireworks Sju - Samana - Puerto Plata, Dominican Republic - MiamiItinerary Details

Itinerary Details

Avg. per person

From

$6,440

as little as

$805/night

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

What's Included?

Dec 28, 2026 - Jan 5, 2027 Mon - Tue

Interior

Oceanview

Balcony

Suite

Dec 28, 2026 - Jan 5, 2027 Mon - Tue

Bonus Details

$6,440 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

CruiseDirector Exclusive: Up to $1,000 Visa Gift Card

8 Nights Caribbean Cruise

Departing From

San Juan

Duration

8 Nights

Ship

Silver Nova

Port of Call

San Juan - St John - Sopers Hole - Roseau - St Johns - Jost Van Dyke (british Virgin Islands) - Miami, FlItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

8 Nights Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$7,800

as little as

$975/night

What's Included?

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

Duration

8 Nights

Ship

Silver Nova

Port of Call

San Juan - St John - Sopers Hole - Roseau - St Johns - 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

$7,800

as little as

$975/night

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

What's Included?

Dec 29, 2026 - Jan 6, 2027 Tue - Wed

Interior

Oceanview

Balcony

Suite

Dec 29, 2026 - Jan 6, 2027 Tue - Wed

Bonus Details

$7,800 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

15 Nights Caribbean Cruise

Departing From

San Juan

Duration

15 Nights

Port of Call

San Juan - Road Bay - St Johns (antigua) - Basseterre - Grand Turk - Miami - Ocho Rios - Isla Catalina - Jost Van Dyke - St Maarten/philipsburg - Charlotte Amalie (saint Thomas) - San JuanItinerary Details

Itinerary Details

15 Nights Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$8,225

as little as

$548/night

What's Included?

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

Duration

15 Nights

Port of Call

Itinerary Details

Avg. per person

From

$8,225

as little as

$548/night

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

What's Included?

Dec 13, 2026 - Dec 28, 2026 Sun - Mon

Interior

Oceanview

Balcony

Suite

Dec 13, 2026 - Dec 28, 2026 Sun - Mon

Bonus Details

$8,225 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

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 - Little Bay - Castries - Fort-de-france - Sopers Hole - San Juan - San Juan - St John - St Kitts - Les Saintes - Bequia - St Thomas - San JuanItinerary 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

$9,300

as little as

$664/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 - Little Bay - Castries - Fort-de-france - Sopers Hole - San Juan - San Juan - St John - St Kitts - Les Saintes - Bequia - St Thomas - San JuanItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Wedding

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$9,300

as little as

$664/night

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

What's Included?

Dec 20, 2026 - Jan 3, 2027 Sun - Sun

Interior

Oceanview

Balcony

Suite

Dec 20, 2026 - Jan 3, 2027 Sun - Sun

Bonus Details

$9,300 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

16 Nights Caribbean Cruise

Departing From

San Juan

Duration

16 Nights

Port of Call

San Juan - St Johns (antigua) - Pointe-a-pitre - Tortola/road Town - New Year Fireworks Sju - New Year Fireworks Sju - Samana - Puerto Plata, Dominican Republic - Miami - Saint John/cruz Bay - Gustavia - St Johns (antigua) - Tortola/road Town - Basseterre - San JuanItinerary Details

Itinerary Details

16 Nights Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$9,765

as little as

$610/night

What's Included?

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

Duration

16 Nights

Port of Call

Itinerary Details

Avg. per person

From

$9,765

as little as

$610/night

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

What's Included?

Dec 28, 2026 - Jan 13, 2027 Mon - Wed

Interior

Oceanview

Balcony

Suite

Dec 28, 2026 - Jan 13, 2027 Mon - Wed

Bonus Details

$9,765 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

Filter Cruises

21 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.

8 Nights Caribbean Cruise

8 Nights Caribbean Cruise

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

15 Nights Caribbean Cruise

15 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!

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