Jibhop

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

From $1,014

$1,014 · $169/night · priced high · ↑31% above typical

$169/night

Priced high

↑31% above typical

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 ↘

From $1,659

$1,659 · $237/night · priced high · ↑30% above typical

$237/night

Priced high

↑30% above typical

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

From $1,909

$1,909 · $273/night · priced high · ↑28% above typical

$273/night

Priced high

↑28% above typical

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

From $1,079

$1,079 · $154/night · priced high · ↑28% above typical

$154/night

Priced high

↑28% above typical

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

From $889

$889 · $127/night · priced high · ↑28% above typical

$127/night

Priced high

↑28% above typical

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

From $1,919

$1,919 · $174/night · priced high · ↑25% above typical

$174/night

Priced high

↑25% above typical

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

From $3,114

$3,114 · $148/night · priced high · ↑24% above typical

$148/night

Priced high

↑24% above typical

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

From $1,559

$1,559 · $223/night · priced high · ↑24% above typical

$223/night

Priced high

↑24% above typical

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

From $1,113

$1,113 · $159/night · priced high · ↑23% above typical

$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

From $4,900

$4,900 · $700/night · priced high · ↑22% above typical

$700/night

Priced high

↑22% above typical

Queen Mary 2 • Cunard Line

28-night Southern Caribbean Loop via New York, Saint Thomas & Bridgetown

Nov 17, 2028 → Dec 15, 2028 • Southampton ↔

Lowest in 180 days $903 above typical

From $5,282

$5,282 · $189/night · priced high · ↑21% above typical

$189/night

Priced high

↑21% above typical

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

From $1,499

$1,499 · $214/night · priced high · ↑19% above typical

$214/night

Priced high

↑19% above typical

Eurodam • Holland America

22-night Western Caribbean Loop: Half Moon Cay, Ocho Rios & Cozumel

Mar 4, 2028 → Mar 26, 2028 • Fort Lauderdale ↔

Lowest in 180 days $551 above typical

From $3,619

$3,619 · $165/night · priced high · ↑18% above typical

$165/night

Priced high

↑18% above typical

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

From $2,784

$2,784 · $164/night · priced high · ↑17% above typical

$164/night

Priced high

↑17% above typical

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

From $5,625

$5,625 · $201/night · priced high · ↑17% above typical

$201/night

Priced high

↑17% above typical

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

From $4,499

$4,499 · $450/night · priced high · ↑15% above typical

$450/night

Priced high

↑15% above typical

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

From $1,449

$1,449 · $207/night · priced high · ↑15% above typical

$207/night

Priced high

↑15% above typical

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

From $1,643

$1,643 · $117/night · priced high · ↑15% above typical

$117/night

Priced high

↑15% above typical

Valiant Lady • Virgin Voyages

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

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

Lowest in 30 days $140 above typical

From $1,113

$1,113 · $159/night · priced high · ↑14% above typical

$159/night

Priced high

↑14% above typical

Valiant Lady • Virgin Voyages

7-night ABC Islands Loop via Willemstad & Oranjestad

Oct 31, 2026 → Nov 7, 2026 • San Juan ↔

Lowest in 30 days $131 above typical

From $1,113

$1,113 · $159/night · priced high · ↑13% above typical

$159/night

Priced high

↑13% above typical