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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

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

Holland America

Rotterdam • Holland America

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

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

$809 above typical

From $2,034

$185/night

Priced high

↑66% 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

Princess Cruises

Crown Princess • Princess Cruises

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

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

$1,180 above typical

From $3,084

$220/night

Priced high

↑62% 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 ↔

$1,564 above typical

From $4,093

$292/night

Priced high

↑62% 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

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

P&O Cruises

Iona • P&O Cruises

14-night Eastern Caribbean Loop via Castries, Saint George's & Bridgetown

Dec 18, 2027 → Jan 1, 2028 • Antigua ↔

$1,108 above typical

From $3,377

$241/night

Priced high

↑49% above typical

P&O Cruises

Iona • P&O Cruises

14-night Eastern Caribbean Loop via Tortola, Philipsburg & Antigua

Dec 27, 2027 → Jan 10, 2028 • Basseterre, Saint Kitts ↔

$973 above typical

From $3,242

$232/night

Priced high

↑43% above typical

P&O Cruises

Iona • P&O Cruises

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

Nov 15, 2027 → Nov 29, 2027 • Basseterre, Saint Kitts ↔

$767 above typical

From $2,566

$183/night

Priced high

↑43% above typical

P&O Cruises

Arvia • P&O Cruises

14-night Southern Caribbean Loop via Roseau, Castries & Saint George's

Dec 26, 2026 → Jan 9, 2027 • Antigua ↔

$983 above typical

From $3,512

$251/night

Priced high

↑39% above typical

P&O Cruises

Iona • P&O Cruises

14-night Southern Caribbean Loop via Basseterre, Saint Kitts, Philipsburg & Fort-de-France

Mar 3, 2028 → Mar 17, 2028 • Bridgetown ↔

$783 above typical

From $2,836

$203/night

Priced high

↑38% above typical

P&O Cruises

Iona • P&O Cruises

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

Nov 29, 2027 → Dec 13, 2027 • Basseterre, Saint Kitts ↔

$632 above typical

From $2,431

$174/night

Priced high

↑35% above typical

Princess Cruises

Crown Princess • Princess Cruises

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

Feb 5, 2027 → Feb 12, 2027 • Bridgetown ↔

$321 above typical

From $1,238

$177/night

Priced high

↑35% above typical

Carnival Cruise Line

Carnival Pride • Carnival Cruise Line

14-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Roseau

Jan 10, 2027 → Jan 24, 2027 • Baltimore ↔

$522 above typical ↗ Trending up

From $2,040

$146/night

Priced high

↑34% above typical

P&O Cruises

Iona • P&O Cruises

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

Dec 24, 2027 → Jan 7, 2028 • Bridgetown ↔

$770 above typical

From $3,039

$217/night

Priced high

↑34% above typical

MSC Cruises

MSC Opera • MSC Cruises

7-night Eastern Caribbean Loop: Catalina Island, Spanish Town & Philipsburg

Apr 19, 2027 → Apr 26, 2027 • La Romana ↔

Great balance

From $959

$137/night

Emerald Cruises

Emerald Sakara • Emerald Cruises

14-night Eastern Caribbean Arc: Soufriere, Terre-de-Haut & Road Bay

Mar 31, 2029 → Apr 14, 2029 • Bridgetown → Philipsburg

$3,178 above typical

From $15,119

$1,080/night

Priced high

↑27% above typical

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