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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 Tortola, Basseterre, Saint Kitts & Bridgetown

Jan 10, 2027 → Jan 17, 2027 • San Juan ↔

$240 above typical

From $1,499

$214/night

Priced high

↑19% above typical

Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

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

Jan 24, 2027 → Jan 31, 2027 • San Juan ↔

$240 above typical

From $1,499

$214/night

Priced high

↑19% above typical

Celebrity Cruises

Celebrity Apex • Celebrity Cruises

7-night Eastern Caribbean Loop via Puerto Plata & Charlotte Amalie, Saint Thomas

Mar 13, 2027 → Mar 20, 2027 • Port Canaveral ↔

$198 above typical

From $1,240

$177/night

Priced high

↑19% above typical

Celebrity Cruises

Celebrity Apex • Celebrity Cruises

7-night Eastern Caribbean Loop via Puerto Plata & Charlotte Amalie, Saint Thomas

Dec 5, 2026 → Dec 12, 2026 • Port Canaveral ↔

$234 above typical ↘ Trending down

From $1,472

$210/night

Priced high

↑19% above typical

MSC Cruises

MSC Seashore • MSC Cruises

14-night Eastern Caribbean Loop via Ocean Cay, Puerto Plata & Philipsburg

Dec 12, 2027 → Dec 26, 2027 • Miami ↔

$248 above typical ↗ Trending up

From $1,568

$112/night

Priced high

↑19% above typical

Princess Cruises

Island Princess • Princess Cruises

7-night Eastern Caribbean Loop via Puerto Plata & San Juan

Oct 29, 2027 → Nov 5, 2027 • Fort Lauderdale ↔

$151 above typical

From $956

$137/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

Norwegian Cruise Line

Norwegian Bliss • Norwegian Cruise Line

12-night Eastern Caribbean Loop via Puerto Plata, San Juan & Tortola

Mar 6, 2028 → Mar 18, 2028 • New York ↔

$255 above typical

From $1,679

$140/night

Priced high

↑18% 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

Sky Princess • Princess Cruises

14-night Western Caribbean Loop via Princess Cays, Falmouth & Cozumel

Dec 19, 2027 → Jan 2, 2028 • Fort Lauderdale ↔

$320 above typical

From $2,220

$159/night

Priced high

↑17% above typical

Oceania Cruises

Oceania Allura • Oceania Cruises

10-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Philipsburg & Saint-Barthélemy

Mar 21, 2027 → Mar 31, 2027 • Miami ↔

$647 above typical

From $4,499

$450/night

Priced high

↑17% above typical

Celebrity Cruises

Celebrity Apex • Celebrity Cruises

7-night Eastern Caribbean Loop via Puerto Plata & Charlotte Amalie, Saint Thomas

Mar 27, 2027 → Apr 3, 2027 • Port Canaveral ↔

$172 above typical

From $1,214

$173/night

Priced high

↑17% above typical

Celebrity Cruises

Celebrity Beyond • Celebrity Cruises

7-night Eastern Caribbean Loop via Puerto Plata & Tortola

Jul 19, 2026 → Jul 26, 2026 • Miami ↔

Great balance

From $1,334

$191/night

MSC Cruises

MSC Seaview • MSC Cruises

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

Dec 15, 2026 → Dec 29, 2026 • Bridgetown ↔

From $2,254

$161/night

Explora Journeys

Explora I • Explora Journeys

7-night Eastern Caribbean Arc via Puerto Plata & Philipsburg

Jan 29, 2027 → Feb 5, 2027 • Miami → San Juan

$640 above typical

From $4,840

$691/night

Priced high

↑15% above typical

Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

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

Nov 20, 2027 → Nov 27, 2027 • San Juan ↔

$185 above typical

From $1,409

$201/night

Priced high

↑15% above typical

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