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Holland America

Rotterdam • Holland America

11-night Eastern Caribbean Loop via Philipsburg, Antigua & Roseau

Jan 12, 2027 → Jan 23, 2027 • Fort Lauderdale ↔

$309 above typical

From $1,534

$139/night

Priced high

↑25% above typical

Holland America

Rotterdam • Holland America

11-night Eastern Caribbean Loop via Philipsburg, Antigua & Roseau

Feb 2, 2027 → Feb 13, 2027 • Fort Lauderdale ↔

$309 above typical

From $1,534

$139/night

Priced high

↑25% above typical

Holland America

Rotterdam • Holland America

21-night Eastern Caribbean Loop via Philipsburg, Basseterre, Saint Kitts & Cozumel

Dec 22, 2026 → Jan 12, 2027 • Fort Lauderdale ↔

$550 above typical

From $2,889

$138/night

Priced high

↑24% above typical

P&O Cruises

Arvia • P&O Cruises

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

Dec 18, 2026 → Jan 1, 2027 • Bridgetown ↔

$578 above typical

From $3,107

$222/night

Priced high

↑23% above typical

Princess Cruises

Crown Princess • Princess Cruises

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

Mar 19, 2027 → Mar 26, 2027 • Bridgetown ↔

$231 above typical

From $1,244

$178/night

Priced high

↑23% above typical

Holland America

Eurodam • Holland America

10-night Eastern Caribbean Loop via Half Moon Cay, San Juan & Tortola

Feb 27, 2027 → Mar 9, 2027 • Fort Lauderdale ↔

$250 above typical

From $1,349

$135/night

Priced high

↑23% above typical

Holland America

Rotterdam • Holland America

11-night Eastern Caribbean Loop via Philipsburg, Antigua & Roseau

Feb 23, 2027 → Mar 6, 2027 • Fort Lauderdale ↔

$259 above typical

From $1,484

$135/night

Priced high

↑21% above typical

P&O Cruises

Iona • P&O Cruises

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

Dec 25, 2027 → Jan 8, 2028 • Bridgetown ↔

$473 above typical

From $2,742

$196/night

Priced high

↑21% above typical

Princess Cruises

Emerald Princess • Princess Cruises

5-night Eastern Caribbean Arc via Saint Thomas & Philipsburg

Nov 21, 2027 → Nov 26, 2027 • San Juan → Bridgetown

$126 above typical

From $744

$149/night

Priced high

↑20% above typical

Regent Seven Seas Cruises

Seven Seas Grandeur • Regent Seven Seas Cruises

10-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Roseau & Antigua

Dec 19, 2026 → Dec 29, 2026 • Miami ↔

From $8,672

$867/night

P&O Cruises

Iona • P&O Cruises

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

Nov 13, 2027 → Nov 27, 2027 • Bridgetown ↔

$362 above typical

From $2,161

$154/night

Priced high

↑20% above typical

P&O Cruises

Iona • P&O Cruises

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

Nov 26, 2027 → Dec 10, 2027 • Bridgetown ↔

$362 above typical

From $2,161

$154/night

Priced high

↑20% above typical

Holland America

Rotterdam • Holland America

21-night Western Caribbean Loop via Half Moon Cay, Falmouth & Cozumel

Dec 12, 2026 → Jan 2, 2027 • Fort Lauderdale ↔

$460 above typical

From $2,799

$133/night

Priced high

↑20% above typical

P&O Cruises

Britannia • P&O Cruises

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

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

$443 above typical

From $2,742

$196/night

Priced high

↑19% above typical

Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

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

Dec 25, 2027 → Jan 1, 2028 • San Juan ↔

$300 above typical

From $1,909

$273/night

Priced high

↑19% above typical

P&O Cruises

Iona • P&O Cruises

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

Nov 12, 2027 → Nov 26, 2027 • Bridgetown ↔

$335 above typical

From $2,134

$152/night

Priced high

↑19% above typical

Princess Cruises

Crown Princess • Princess Cruises

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

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

$181 above typical

From $1,194

$171/night

Priced high

↑18% above typical

Holland America

Nieuw Amsterdam • Holland America

9-night Eastern Caribbean Loop

Mar 12, 2027 → Mar 21, 2027 • Fort Lauderdale ↔

$186 above typical

From $1,264

$140/night

Priced high

↑17% above typical

P&O Cruises

Britannia • P&O Cruises

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

Nov 13, 2026 → Nov 27, 2026 • Bridgetown ↔

$311 above typical

From $2,134

$152/night

Priced high

↑17% above typical

Princess Cruises

Emerald Princess • Princess Cruises

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

Nov 21, 2027 → Nov 28, 2027 • San Juan ↔

$137 above typical

From $1,002

$143/night

Priced high

↑16% above typical

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