Jibhop

Norwegian Viva • Norwegian Cruise Line

7-night Southern Caribbean Loop via Oranjestad & Bridgetown

Dec 19, 2027 → Dec 26, 2027 • San Juan ↔

Great balance

From $1,769

$1,769 · $253/night · priced high · ↑46% above typical

$253/night

Priced high

↑46% above typical

Norwegian Viva • Norwegian Cruise Line

7-night Southern Caribbean Loop via Oranjestad & Bridgetown

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

Great balance

From $1,369

$1,369 · $196/night · priced high · ↑43% above typical

$196/night

Priced high

↑43% above typical

Celebrity Constellation • Celebrity Cruises

7-night Southern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Roseau

Feb 13, 2027 → Feb 20, 2027 • San Juan ↔

$301 above typical ↗

From $1,054

$1,054 · $151/night · priced high · ↑40% above typical

$151/night

Priced high

↑40% above typical

SeaDream I • SeaDream Yacht Club

7-night Eastern Caribbean Arc: Road Bay & Saint-Barthélemy

Apr 1, 2029 → Apr 8, 2029 • San Juan ↔

$1,373 above typical

From $4,892

$4,892 · $699/night · priced high · ↑39% above typical

$699/night

Priced high

↑39% above typical

Grandeur of the Seas • Royal Caribbean International

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

May 22, 2027 → May 29, 2027 • San Juan ↔

$261 above typical

From $960

$960 · $137/night · priced high · ↑37% above typical

$137/night

Priced high

↑37% above typical

Explora I • Explora Journeys

24-night Southern Caribbean Loop via Saint-Barthélemy, Saint-Pierre & Bridgetown

Feb 5, 2027 → Mar 1, 2027 • San Juan ↔

$5,095 above typical

From $19,855

$19,855 · $827/night · priced high · ↑35% above typical

$827/night

Priced high

↑35% above typical

Norwegian Viva • Norwegian Cruise Line

7-night ABC Islands Loop via Oranjestad & Willemstad

Jan 2, 2028 → Jan 9, 2028 • San Juan ↔

Great balance

From $1,219

$1,219 · $174/night · priced high · ↑34% above typical

$174/night

Priced high

↑34% above typical

Norwegian Prima • Norwegian Cruise Line

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

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

$410 above typical

From $1,719

$1,719 · $246/night · priced high · ↑31% above typical

$246/night

Priced high

↑31% above typical

Celebrity Constellation • Celebrity Cruises

7-night Southern Caribbean Loop via Charlotte Amalie, Saint Thomas, Basseterre, Saint Kitts & Roseau

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

$213 above typical ↗

From $916

$916 · $131/night · priced high · ↑30% above typical

$131/night

Priced high

↑30% above typical

Norwegian Viva • Norwegian Cruise Line

7-night Eastern Caribbean Loop via Philipsburg & Willemstad

Jan 9, 2028 → Jan 16, 2028 • San Juan ↔

From $1,169

$1,169 · $167/night · priced high · ↑29% above typical

$167/night

Priced high

↑29% above typical

Norwegian Viva • Norwegian Cruise Line

7-night ABC Islands Loop via Basseterre, Saint Kitts & Castries

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

From $1,219

$1,219 · $174/night · priced high · ↑27% above typical

$174/night

Priced high

↑27% above typical

Norwegian Prima • Norwegian Cruise Line

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

Feb 7, 2027 → Feb 14, 2027 • San Juan ↔

$340 above typical

From $1,599

$1,599 · $228/night · priced high · ↑27% above typical

$228/night

Priced high

↑27% above typical

Rhapsody of the Seas • Royal Caribbean International

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

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

$257 above typical ↗

From $1,225

$1,225 · $175/night · priced high · ↑27% above typical

$175/night

Priced high

↑27% above typical

SeaDream II • SeaDream Yacht Club

7-night Eastern Caribbean Arc via Samana & Grand Turk Island

Mar 13, 2027 → Mar 20, 2027 • San Juan → Freeport, Grand Bahama

$1,468 above typical

From $7,025

$7,025 · $1,004/night · priced high · ↑26% above typical

$1,004/night

Priced high

↑26% above typical

Vision of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg

Dec 27, 2026 → Jan 3, 2027 • San Juan ↔

$183 above typical ↘

From $882

$882 · $126/night · priced high · ↑26% above typical

$126/night

Priced high

↑26% above typical

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

$1,990 above typical ↗

From $10,099

$10,099 · $505/night · priced high · ↑25% above typical

$505/night

Priced high

↑25% above typical

Valiant Lady • Virgin Voyages

8-night Eastern Caribbean Loop via Saint Thomas, Willemstad & Oranjestad

Nov 20, 2026 → Nov 28, 2026 • San Juan ↔

From $1,272

$1,272 · $159/night · priced high · ↑23% above typical

$159/night

Priced high

↑23% above typical

Crown Princess • Princess Cruises

7-night Southern Caribbean Loop via Philipsburg, Fort-de-France & Saint George's

Jan 17, 2027 → Jan 24, 2027 • San Juan ↔

From $969

$969 · $138/night · priced high · ↑21% above typical

$138/night

Priced high

↑21% above typical

Explora I • Explora Journeys

7-night Eastern Caribbean Arc via Cruz Bay, Saint John & Road Bay

Mar 1, 2027 → Mar 8, 2027 • San Juan → Miami

$797 above typical

From $4,875

$4,875 · $696/night · priced high · ↑20% above typical

$696/night

Priced high

↑20% above typical

Celebrity Summit • Celebrity Cruises

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

Dec 19, 2027 → Dec 26, 2027 • San Juan ↔

$129 above typical

From $839

$839 · $120/night · priced high · ↑18% above typical

$120/night

Priced high

↑18% above typical