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Oceania Cruises

Oceania Allura • Oceania Cruises

20-night Eastern Caribbean Arc via Saint-Barthélemy, Philipsburg & Basseterre, Saint Kitts

Feb 19, 2027 → Mar 11, 2027 • San Juan → Miami

$1,201 above typical

From $9,199

$460/night

Priced high

↑15% above typical

Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

10-night Eastern Caribbean Arc via Kings Wharf, Tortola & Basseterre, Saint Kitts

Nov 3, 2027 → Nov 13, 2027 • New York → San Juan

$260 above typical

From $2,009

$201/night

Priced high

↑15% above typical

Virgin Voyages

Valiant Lady • Virgin Voyages

7-night Southern Caribbean Loop via Philipsburg, Bridgetown & Castries

Jan 16, 2027 → Jan 23, 2027 • San Juan ↔

$140 above typical

From $1,113

$159/night

Priced high

↑14% above typical

MSC Cruises

MSC Poesia • MSC Cruises

21-night Eastern Caribbean Loop via Ocho Rios, Cartagena & Colón

Nov 1, 2026 → Nov 22, 2026 • Miami ↔

$283 above typical ↘ Trending down

From $2,255

$107/night

Priced high

↑14% above typical

Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

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

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

$180 above typical

From $1,439

$206/night

Priced high

↑14% above typical

Norwegian Cruise Line

Norwegian Bliss • Norwegian Cruise Line

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

Dec 10, 2027 → Dec 22, 2027 • New York ↔

$180 above typical

From $1,499

$125/night

Priced high

↑14% above typical

Holland America

Rotterdam • Holland America

21-night Western Caribbean Loop via Philipsburg, Antigua & Cozumel

Feb 23, 2027 → Mar 16, 2027 • Fort Lauderdale ↔

$320 above typical

From $2,659

$127/night

Priced high

↑14% above typical

P&O Cruises

Britannia • P&O Cruises

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

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

$308 above typical

From $2,607

$186/night

Priced high

↑13% above typical

Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

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

Mar 25, 2028 → Apr 1, 2028 • San Juan ↔

$160 above typical

From $1,359

$194/night

Priced high

↑13% above typical

Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

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

Apr 8, 2028 → Apr 15, 2028 • San Juan ↔

$160 above typical

From $1,359

$194/night

Priced high

↑13% above typical

Holland America

Rotterdam • Holland America

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

Mar 16, 2027 → Mar 27, 2027 • Fort Lauderdale ↔

$185 above typical

From $1,584

$144/night

Priced high

↑13% above typical

Holland America

Rotterdam • Holland America

21-night Western Caribbean Arc via Philipsburg, Antigua & Cozumel

Feb 2, 2027 → Feb 23, 2027 • Fort Lauderdale ↔

$300 above typical

From $2,639

$126/night

Priced high

↑13% above typical

Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

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

Feb 14, 2027 → Feb 21, 2027 • San Juan ↔

$160 above typical

From $1,419

$203/night

Priced high

↑13% above typical

Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

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

Apr 22, 2028 → Apr 29, 2028 • San Juan → New York

$140 above typical

From $1,289

$184/night

Priced high

↑12% above typical

Norwegian Cruise Line

Norwegian Bliss • Norwegian Cruise Line

12-night Eastern Caribbean Loop via Puerto Plata, San Juan & Basseterre, Saint Kitts

Jan 4, 2027 → Jan 16, 2027 • New York ↔

$150 above typical

From $1,469

$122/night

Priced high

↑11% above typical

Oceania Cruises

Oceania Marina • Oceania Cruises

10-night Eastern Caribbean Loop via San Juan, Basseterre, Saint Kitts & Great Stirrup Cay

Feb 23, 2027 → Mar 5, 2027 • Miami ↔

$350 above typical

From $3,449

$345/night

Priced high

↑11% above typical

Holland America

Rotterdam • Holland America

21-night Western Caribbean Arc via Key West, Georgetown, Grand Cayman & Cozumel

Feb 13, 2027 → Mar 6, 2027 • Fort Lauderdale ↔

$260 above typical

From $2,599

$124/night

Priced high

↑11% above typical

Regent Seven Seas Cruises

Seven Seas Prestige • Regent Seven Seas Cruises

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

Jan 27, 2028 → Feb 5, 2028 • Miami ↔

From $7,179

$798/night

Princess Cruises

Island Princess • Princess Cruises

10-night Eastern Caribbean Loop via Puerto Plata, San Juan & Basseterre, Saint Kitts

Nov 5, 2027 → Nov 15, 2027 • Fort Lauderdale ↔

$124 above typical

From $1,275

$128/night

Priced high

↑11% above typical

Norwegian Cruise Line

Norwegian Bliss • Norwegian Cruise Line

11-night Eastern Caribbean Loop via Puerto Plata, San Juan & Basseterre, Saint Kitts

Jan 15, 2028 → Jan 26, 2028 • New York ↔

$130 above typical

From $1,339

$122/night

Priced high

↑11% above typical

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