Jibhop

Seven Seas Prestige • Regent Seven Seas Cruises

12-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Basseterre, Saint Kitts & Roseau

Mar 5, 2027 → Mar 17, 2027 • Miami ↔

From $10,484

$10,484 · $874/night · priced high · ↑23% above typical

$874/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

Celebrity Summit • Celebrity Cruises

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

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

$130 above typical

From $839

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

$120/night

Priced high

↑18% above typical

MSC Seaview • MSC Cruises

7-night Southern Caribbean Loop via Pointe-à-Pitre, Castries & Bridgetown

Feb 20, 2027 → Feb 27, 2027 • Fort-de-France ↔

Great balance

From $1,204

$1,204 · $172/night · priced high · ↑18% above typical

$172/night

Priced high

↑18% above typical

Crown Princess • Princess Cruises

7-night Eastern Caribbean Loop via San Juan, Saint Thomas & Philipsburg

Mar 5, 2027 → Mar 12, 2027 • Bridgetown ↔

Great balance

From $1,194

$1,194 · $171/night · priced high · ↑18% above typical

$171/night

Priced high

↑18% above typical

Celebrity Summit • Celebrity Cruises

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

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

$103 above typical

From $697

$697 · $100/night · priced high · ↑17% above typical

$100/night

Priced high

↑17% above typical

Norwegian Viva • Norwegian Cruise Line

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

Jan 23, 2028 → Jan 30, 2028 • San Juan ↔

From $1,064

$1,064 · $152/night · priced high · ↑17% above typical

$152/night

Priced high

↑17% above typical

Celebrity Constellation • Celebrity Cruises

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

Dec 19, 2026 → Dec 26, 2026 • San Juan ↔

$125 above typical ↗

From $874

$874 · $125/night · priced high · ↑17% above typical

$125/night

Priced high

↑17% above typical

Celebrity Eclipse • Celebrity Cruises

12-night Southern Caribbean Loop via Basseterre, Saint Kitts, Castries & Bridgetown

Feb 28, 2027 → Mar 12, 2027 • Fort Lauderdale ↔

$237 above typical

From $1,750

$1,750 · $146/night · priced high · ↑16% above typical

$146/night

Priced high

↑16% above typical

Grandeur of the Seas • Royal Caribbean International

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

May 29, 2027 → Jun 5, 2027 • San Juan ↔

$125 above typical ↗

From $942

$942 · $135/night · priced high · ↑15% above typical

$135/night

Priced high

↑15% above typical

Celebrity Eclipse • Celebrity Cruises

9-night Eastern Caribbean Loop via Philipsburg & Saint John's

Feb 19, 2028 → Feb 28, 2028 • Fort Lauderdale ↔

$168 above typical ↗

From $1,303

$1,303 · $145/night · priced high · ↑15% above typical

$145/night

Priced high

↑15% above typical

Celebrity Constellation • Celebrity Cruises

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

Jan 23, 2027 → Jan 30, 2027 • San Juan ↔

$103 above typical ↘

From $870

$870 · $124/night · priced high · ↑13% above typical

$124/night

Priced high

↑13% above typical

Celebrity Ascent • Celebrity Cruises

11-night Eastern Caribbean Loop via Philipsburg, Saint John's & Castries

Feb 15, 2027 → Feb 26, 2027 • Fort Lauderdale ↔

$214 above typical

From $1,836

$1,836 · $167/night · priced high · ↑13% above typical

$167/night

Priced high

↑13% above typical

Star Princess • Princess Cruises

14-night Eastern Caribbean Loop via Princess Cays, Tortola & Philipsburg

Dec 22, 2027 → Jan 5, 2028 • Port Canaveral ↔

From $1,966

$1,966 · $140/night · priced high · ↑13% above typical

$140/night

Priced high

↑13% above typical

MSC Seaview • MSC Cruises

7-night Southern Caribbean Loop via Pointe-à-Pitre, Castries & Bridgetown

Apr 3, 2027 → Apr 10, 2027 • Fort-de-France ↔

From $1,035

$1,035 · $148/night · priced high · ↑13% above typical

$148/night

Priced high

↑13% above typical

Grandeur of the Seas • Royal Caribbean International

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

May 1, 2027 → May 8, 2027 • San Juan ↔

$100 above typical

From $917

$917 · $131/night · priced high · ↑12% above typical

$131/night

Priced high

↑12% above typical

Emerald Princess • Princess Cruises

7-night Eastern Caribbean Loop via San Juan, Saint Thomas & Philipsburg

Feb 25, 2028 → Mar 3, 2028 • Bridgetown ↔

Great balance

From $1,856

$1,856 · $265/night · priced high · ↑12% above typical

$265/night

Priced high

↑12% above typical

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

$7,179 · $798/night · priced high · ↑11% above typical

$798/night

Priced high

↑11% above typical

Explora III

16-night Eastern Caribbean Arc via Cruz Bay, Saint John, Saint-Barthélemy & Saint John's

Jan 5, 2027 → Jan 21, 2027 • Miami ↔

$1,336 above typical ↗

From $13,130

$13,130 · $821/night · priced high · ↑11% above typical

$821/night

Priced high

↑11% above typical

Seven Seas Prestige • Regent Seven Seas Cruises

15-night Southern Caribbean Loop via Tortola, Roseau & Castries

Feb 16, 2028 → Mar 2, 2028 • Miami ↔

From $11,909

$11,909 · $794/night · priced high · ↑11% above typical

$794/night

Priced high

↑11% above typical