Cunard Line

Queen Mary 2 • Cunard Line

20-night Eastern Caribbean Arc via New York, Road Town, Tortola & Basseterre, Saint Kitts

Dec 15, 2028 → Jan 4, 2029 • Southampton → New York

Lowest in 180 days $1,232 above typical
$4,673 · $234/night · priced high · ↑36% above typical
Holland America

Eurodam • Holland America

21-night Eastern Caribbean Arc: Philipsburg, Antigua & Roseau

Feb 12, 2028 → Mar 4, 2028 • Fort Lauderdale ↔

Lowest in 180 days $836 above typical
$3,339 · $159/night · priced high · ↑33% above typical
Oceania Cruises

Oceania Allura • Oceania Cruises

7-night Eastern Caribbean Arc via Charlotte Amalie, Saint Thomas & Philipsburg

Feb 5, 2027 → Feb 12, 2027 • Miami → San Juan

Lowest in 30 days $911 above typical
$3,749 · $536/night · priced high · ↑32% above typical
Virgin Voyages

Valiant Lady • Virgin Voyages

6-night Eastern Caribbean Loop via Tortola & Cruz Bay, Saint John

Nov 14, 2026 → Nov 20, 2026 • San Juan ↔

Lowest in 90 days $240 above typical
$1,014 · $169/night · priced high · ↑31% above typical
Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

7-night Eastern Caribbean Loop via Tortola, Cruz Bay, Saint John & Bridgetown

Nov 15, 2026 → Nov 22, 2026 • San Juan ↔

Lowest in 30 days $380 above typical
$1,659 · $237/night · priced high · ↑30% 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 ↔

Lowest in 30 days $420 above typical
$1,909 · $273/night · priced high · ↑28% above typical
Royal Caribbean International

Rhapsody of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Philipsburg & Saint John's

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

Lowest in 90 days $237 above typical
$1,079 · $154/night · priced high · ↑28% above typical
Royal Caribbean International

Grandeur of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Tortola, Philipsburg & Saint John's

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

Lowest in 180 days $194 above typical
$889 · $127/night · priced high · ↑28% above typical
Holland America

Eurodam • Holland America

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

Mar 15, 2028 → Mar 26, 2028 • Fort Lauderdale ↔

Lowest in 180 days $385 above typical
$1,919 · $174/night · priced high · ↑25% above typical
Holland America

Eurodam • Holland America

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

Dec 1, 2027 → Dec 22, 2027 • Fort Lauderdale ↔

Lowest in 180 days $611 above typical
$3,114 · $148/night · priced high · ↑24% 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 ↔

Lowest in 30 days $300 above typical
$1,559 · $223/night · priced high · ↑24% above typical
Virgin Voyages

Valiant Lady • Virgin Voyages

7-night Eastern Caribbean Loop via Saint Thomas, Road Town, Tortola & Basseterre, Saint Kitts

Nov 28, 2026 → Dec 5, 2026 • San Juan ↔

Lowest in 30 days $210 above typical
$1,113 · $159/night · priced high · ↑23% above typical

Explora IV

7-night Eastern Caribbean Arc via Charlotte Amalie, Saint Thomas & Cruz Bay, Saint John

Dec 23, 2027 → Dec 30, 2027 • Miami → San Juan

Lowest in 30 days $880 above typical
$4,900 · $700/night · priced high · ↑22% 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 ↔

Lowest in 30 days $240 above typical
$1,499 · $214/night · priced high · ↑19% above typical
Holland America

Eurodam • Holland America

17-night Eastern Caribbean Arc: Philipsburg, Antigua & Roseau

Mar 15, 2028 → Apr 1, 2028 • Fort Lauderdale ↔

Lowest in 180 days $413 above typical
$2,784 · $164/night · priced high · ↑17% above typical
Cunard Line

Queen Mary 2 • Cunard Line

28-night Eastern Caribbean Loop via New York, Road Town, Tortola & Basseterre, Saint Kitts

Dec 15, 2028 → Jan 12, 2029 • Southampton ↔

Lowest in 180 days $807 above typical
$5,625 · $201/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 ↔

Lowest in 30 days $600 above typical
$4,499 · $450/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

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

Lowest in 30 days $190 above typical
$1,449 · $207/night · priced high · ↑15% above typical
Cunard Line

Queen Elizabeth • Cunard Line

14-night Eastern Caribbean Loop via Saint Thomas, Basseterre, Saint Kitts & Saint George's

Nov 25, 2027 → Dec 9, 2027 • Miami ↔

Lowest in 180 days $210 above typical
$1,643 · $117/night · priced high · ↑15% 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 ↔

Lowest in 30 days $157 above typical
$1,349 · $135/night · priced high · ↑13% above typical