Sailing Search

99 Cruises

16 Nights Caribbean Cruise

Duration

16 Nights

Ship

Explora I

Port of Call

Bridgetown - Martinique/fort De France - Basseterre - San Juan - Gustavia - St Johns (antigua) - Tortola/road Town - Road Bay - Miami - Saint John/cruz Bay - Deshaies - St Georges (grenada) - BridgetownItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Itinerary Details

16 Nights Caribbean Cruise

Avg. per person

From

$8,865

as little as

$554/night

What's Included?

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

Duration

16 Nights

Ship

Explora I

Port of Call

Best For

Gourmet

Honeymoon

Luxury

Itinerary Details

Avg. per person

From

$8,865

as little as

$554/night

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

What's Included?

Jan 3, 2026 - Jan 19, 2026 Sat - Mon

Interior

Oceanview

Balcony

Suite

Jan 3, 2026 - Jan 19, 2026 Sat - Mon

Bonus Details

$8,865 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

USA Today: Best Ocean Cruise

14 Nights Caribbean Cruise

Duration

14 Nights

Ship

Seabourn Ovation

Port of Call

Philipsburg, Sint Maarten - Sopers Hole (frenchmans Cay), Bvi - Carambola Beach, Saint Kitts And Nevis - Saint Pierre, Martinique - Port Elizabeth, Bequia, St Vincent And The Grenadines - Saint Georges, Grenada - Bridgetown, Barbados - Carambola Beach, Saint Kitts And Nevis - Trois Ilets, Martinique - Point-a-pitre, Guadeloupe - Roseau, Dominica - Rodney Bay, Saint Lucia - Bridgetown, BarbadosItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

14 Nights Caribbean Cruise

Avg. per person

From

$8,898

as little as

$636/night

What's Included?

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

Duration

14 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

$8,898

as little as

$636/night

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

What's Included?

Jan 31, 2026 - Feb 14, 2026 Sat - Sat

Interior

Oceanview

Balcony

Suite

Jan 31, 2026 - Feb 14, 2026 Sat - Sat

Bonus Details

$8,898 USD

$18,898 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

USA Today: Best Ocean Cruise

14 Nights Caribbean Cruise

Duration

14 Nights

Ship

Seabourn Ovation

Port of Call

Philipsburg, Sint Maarten - Sopers Hole (frenchmans Cay), Bvi - Carambola Beach, Saint Kitts And Nevis - Saint Pierre, Martinique - Port Elizabeth, Bequia, St Vincent And The Grenadines - Saint Georges, Grenada - Bridgetown, Barbados - Castries, Saint Lucia - Little Bay, Montserrat - St Johns, Antigua And Barbuda - Carambola Beach, Saint Kitts And Nevis - Great Harbour, Jost Van Dyke, British Virgin Islands - Philipsburg, Sint MaartenItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

14 Nights Caribbean Cruise

Avg. per person

From

$8,998

as little as

$643/night

What's Included?

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

Duration

14 Nights

Ship

Seabourn Ovation

Port of Call

Philipsburg, Sint Maarten - Sopers Hole (frenchmans Cay), Bvi - Carambola Beach, Saint Kitts And Nevis - Saint Pierre, Martinique - Port Elizabeth, Bequia, St Vincent And The Grenadines - Saint Georges, Grenada - Bridgetown, Barbados - Castries, Saint Lucia - Little Bay, Montserrat - St Johns, Antigua And Barbuda - Carambola Beach, Saint Kitts And Nevis - Great Harbour, Jost Van Dyke, British Virgin Islands - Philipsburg, Sint MaartenItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Romantic

Senior

Ocean Cruises

Yacht & Expedition Cruises

Itinerary Details

Avg. per person

From

$8,998

as little as

$643/night

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

What's Included?

Jan 17, 2026 - Jan 31, 2026 Sat - Sat

Interior

Oceanview

Balcony

Suite

Jan 17, 2026 - Jan 31, 2026 Sat - Sat

Bonus Details

$8,998 USD

$20,928 USD

Select

Bonus Details

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All the Cruise Line Offers & More

15 Nights Caribbean Cruise

Departing From

San Juan

Duration

15 Nights

Ship

Explora I

Port of Call

San Juan - Gustavia - Tortola/road Town - St Johns (antigua) - Road Bay - Miami - Charlotte Amalie (saint Thomas) - Terre-de-haut - Bridgetown - Martinique/fort De France - Basseterre - San JuanItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Itinerary Details

15 Nights Caribbean Cruise

Departing From

San Juan

Avg. per person

From

$9,225

as little as

$615/night

What's Included?

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

Duration

15 Nights

Ship

Explora I

Port of Call

Best For

Gourmet

Honeymoon

Luxury

Itinerary Details

Avg. per person

From

$9,225

as little as

$615/night

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

What's Included?

Jan 21, 2026 - Feb 5, 2026 Wed - Thu

Interior

Oceanview

Balcony

Suite

Jan 21, 2026 - Feb 5, 2026 Wed - Thu

Bonus Details

$9,225 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

15 Nights Caribbean Cruise

Departing From

Miami

Duration

15 Nights

Ship

Explora I

Port of Call

Miami - Saint John/cruz Bay - Deshaies - St Georges (grenada) - Bridgetown - Little Bay - San Juan - Gustavia - Tortola/road Town - St Johns (antigua) - Road Bay - MiamiItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Itinerary Details

15 Nights Caribbean Cruise

Departing From

Miami

Avg. per person

From

$9,225

as little as

$615/night

What's Included?

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

Duration

15 Nights

Ship

Explora I

Port of Call

Miami - Saint John/cruz Bay - Deshaies - St Georges (grenada) - Bridgetown - Little Bay - San Juan - Gustavia - Tortola/road Town - St Johns (antigua) - Road Bay - MiamiItinerary Details

Best For

Gourmet

Honeymoon

Luxury

Itinerary Details

Avg. per person

From

$9,225

as little as

$615/night

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

What's Included?

Jan 13, 2026 - Jan 28, 2026 Tue - Wed

Interior

Oceanview

Balcony

Suite

Jan 13, 2026 - Jan 28, 2026 Tue - Wed

Bonus Details

$9,225 USD

Select

Bonus Details

Select

All the Cruise Line Offers & More

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

Filter Cruises

99 Cruises

16 Nights Caribbean Cruise

16 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.

14 Nights Caribbean Cruise

14 Nights Caribbean Cruise

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

15 Nights Caribbean Cruise

15 Nights Caribbean Cruise

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

15 Nights Caribbean Cruise

15 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