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Viking Cruises

Viking Sea • Viking Cruises

21-night Amazon River Loop via Bridgetown, Kourou / Îles du Salut & Santarém

Dec 15, 2026 → Jan 5, 2027 • San Juan ↔

From $11,499

$548/night

Crystal Cruises

Crystal Serenity • Crystal Cruises

30-night Eastern Caribbean Arc via Kings Wharf, Antigua & Pointe-à-Pitre

Oct 12, 2027 → Nov 11, 2027 • New York → Buenos Aires

From $13,000

$433/night

Regent Seven Seas Cruises

Seven Seas Prestige • Regent Seven Seas Cruises

11-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Cruz Bay, Saint John & Castries

Dec 7, 2027 → Dec 18, 2027 • Miami ↔

From $7,874

$716/night

Princess Cruises

Emerald Princess • Princess Cruises

14-night Eastern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Roseau

Dec 26, 2027 → Jan 9, 2028 • San Juan ↔

0% below typical

From $2,036

$145/night

Typical price
Princess Cruises

Emerald Princess • Princess Cruises

7-night Eastern Caribbean Loop via San Juan, Saint Thomas & Philipsburg

Mar 10, 2028 → Mar 17, 2028 • Bridgetown ↔

$991 above typical

From $2,024

$289/night

Priced high

↑96% above typical

Norwegian Cruise Line

Norwegian Pearl • Norwegian Cruise Line

11-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Castries & Antigua

Dec 23, 2027 → Jan 3, 2028 • Philadelphia ↔

$930 above typical

From $1,979

$180/night

Priced high

↑89% above typical

MSC Cruises

MSC Seaview • MSC Cruises

7-night Southern Caribbean Loop via Pointe-à-Pitre, Bridgetown & Kingstown

Dec 26, 2026 → Jan 2, 2027 • Fort-de-France ↔

Great balance

From $1,803

$258/night

Princess Cruises

Crown Princess • Princess Cruises

7-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Antigua

Dec 27, 2026 → Jan 3, 2027 • San Juan ↔

$791 above typical

From $1,863

$266/night

Priced high

↑74% above typical

P&O Cruises

Iona • P&O Cruises

14-night Southern Caribbean Loop via Philipsburg, Fort-de-France & Antigua

Dec 13, 2027 → Dec 27, 2027 • Basseterre, Saint Kitts ↔

$1,649 above typical

From $3,918

$280/night

Priced high

↑73% above typical

Virgin Voyages

Valiant Lady • Virgin Voyages

7-night Southern Caribbean Loop via Philipsburg, Fort-de-France & Bridgetown

Dec 26, 2026 → Jan 2, 2027 • San Juan ↔

$724 above typical

From $1,837

$262/night

Priced high

↑65% above typical

Holland America

Rotterdam • Holland America

11-night Eastern Caribbean Arc via Philipsburg, Basseterre, Saint Kitts & Roseau

Dec 22, 2026 → Jan 2, 2027 • Fort Lauderdale ↔

$800 above typical

From $2,034

$185/night

Priced high

↑65% above typical

Princess Cruises

Crown Princess • Princess Cruises

14-night Eastern Caribbean Arc via Saint Thomas, Philipsburg & Antigua

Dec 27, 2026 → Jan 10, 2027 • San Juan ↔

$1,177 above typical

From $3,084

$220/night

Priced high

↑62% above typical

MSC Cruises

MSC World Europa • MSC Cruises

7-night Southern Caribbean Loop via Pointe-à-Pitre, Bridgetown & Kingstown

Dec 26, 2026 → Jan 2, 2027 • Fort-de-France ↔

$726 above typical ↗ Trending up

From $1,916

$274/night

Priced high

↑61% above typical

Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

7-night Eastern Caribbean Loop via Philipsburg, Basseterre, Saint Kitts & Bridgetown

Dec 27, 2026 → Jan 3, 2027 • San Juan ↔

$960 above typical

From $2,569

$367/night

Priced high

↑60% above typical

P&O Cruises

Arvia • P&O Cruises

14-night Southern Caribbean Loop via Philipsburg, Roseau & Antigua

Dec 20, 2027 → Jan 3, 2028 • Basseterre, Saint Kitts ↔

$1,527 above typical

From $4,093

$292/night

Priced high

↑60% above typical

P&O Cruises

Britannia • P&O Cruises

14-night Southern Caribbean Loop via Philipsburg, Antigua & Basseterre, Saint Kitts

Mar 6, 2027 → Mar 20, 2027 • Bridgetown ↔

$1,081 above typical

From $2,904

$207/night

Priced high

↑59% above typical

MSC Cruises

MSC Seaview • MSC Cruises

14-night Eastern Caribbean Loop via Saint George, Kingstown & Fort-de-France

Mar 23, 2027 → Apr 6, 2027 • Bridgetown ↔

From $2,243

$160/night

Princess Cruises

Crown Princess • Princess Cruises

7-night Southern Caribbean Loop via San Juan, Philipsburg & Fort-de-France

Jan 15, 2027 → Jan 22, 2027 • Bridgetown ↔

$455 above typical

From $1,270

$181/night

Priced high

↑56% above typical

P&O Cruises

Britannia • P&O Cruises

14-night Southern Caribbean Loop via Philipsburg, Antigua & Basseterre, Saint Kitts

Mar 5, 2027 → Mar 19, 2027 • Bridgetown ↔

$1,013 above typical

From $2,836

$203/night

Priced high

↑56% above typical

Norwegian Cruise Line

Norwegian Viva • Norwegian Cruise Line

7-night Southern Caribbean Loop via Oranjestad & Bridgetown

Dec 19, 2027 → Dec 26, 2027 • San Juan ↔

$630 above typical

From $1,769

$253/night

Priced high

↑55% above typical

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