Jibhop

Coral Princess • Princess Cruises

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

Dec 6, 2027 → Dec 20, 2027 • Fort Lauderdale ↔

23% below typical

From $1,537

$1,537 · $110/night · great deal · ↓23% below typical

$110/night

Great deal

↓23% below typical

Silver Spirit • Silversea Cruises

12-night Southern Caribbean Loop via Port Elizabeth, Bequia, Castries & Kralendijk

Jan 10, 2028 → Jan 22, 2028 • Bridgetown ↔

From $7,400

$7,400 · $617/night · good value · ↓18% below typical

$617/night

Good value

↓18% below typical

Oceania Sirena • Oceania Cruises

14-night Southern Caribbean Loop via Oranjestad, Willemstad & Kralendijk

Dec 22, 2027 → Jan 5, 2028 • Miami ↔

Lowest in 180 days

From $4,399

$4,399 · $314/night · typical price · ↓2% below typical

$314/night

Typical price

↓2% below typical

Seven Seas Grandeur • Regent Seven Seas Cruises

14-night Southern Caribbean Loop via Ocho Rios, Oranjestad & Willemstad

Dec 8, 2027 → Dec 22, 2027 • Miami ↔

From $7,874

$7,874 · $562/night · great deal · ↓20% below typical

$562/night

Great deal

↓20% below typical

MS Europa • Hapag-Lloyd Cruises

17-night Southern Caribbean Loop via Saint-Barthélemy, Saint John's & Fort-de-France

Dec 20, 2026 → Jan 6, 2027 • Miami ↔

From $8,528

$8,528 · $502/night · good value · ↓15% below typical

$502/night

Good value

↓15% below typical

Crown Princess • Princess Cruises

14-night Southern Caribbean Loop via Philipsburg, Fort-de-France & Roseau

Feb 28, 2027 → Mar 14, 2027 • San Juan ↔

From $1,516

$1,516 · $108/night · great deal · ↓20% below typical

$108/night

Great deal

↓20% below typical

MS Europa • Hapag-Lloyd Cruises

14-night Southern Caribbean Arc via Cockburn Town, Saint-Barthélemy & Cruz Bay, Saint John

Dec 3, 2028 → Dec 17, 2028 • Miami → Colón (Panama Canal)

From $7,061

$7,061 · $504/night · good value · ↓15% below typical

$504/night

Good value

↓15% below typical

Celebrity Ascent • Celebrity Cruises

10-night Southern Caribbean Loop via Philipsburg, Castries & Saint George's

Jan 15, 2027 → Jan 25, 2027 • Fort Lauderdale ↔

$126 below typical ↘

From $1,349

$1,349 · $135/night · typical price · ↓9% below typical

$135/night

Typical price

↓9% below typical

Seven Seas Grandeur • Regent Seven Seas Cruises

10-night Southern Caribbean Loop via Saint George's, Kingstown & Castries

Feb 14, 2028 → Feb 24, 2028 • Bridgetown ↔

19% below typical

From $5,743

$5,743 · $574/night · good value · ↓19% below typical

$574/night

Good value

↓19% below typical

Celebrity Ascent • Celebrity Cruises

10-night Southern Caribbean Loop via Philipsburg, Castries & Saint George's

Dec 14, 2026 → Dec 24, 2026 • Fort Lauderdale ↔

$114 below typical ↗

From $1,360

$1,360 · $136/night · typical price · ↓8% below typical

$136/night

Typical price

↓8% below typical

Oceania Sonata • Oceania Cruises

11-night Southern Caribbean Loop via Philipsburg, Fort-de-France & Castries

Jan 22, 2028 → Feb 2, 2028 • Miami ↔

Lowest in 180 days

From $5,399

$5,399 · $491/night · typical price · ↓1% below typical

$491/night

Typical price

↓1% below typical

Vision of the Seas • Royal Caribbean International

7-night Southern Caribbean Loop via Charlotte Amalie, Saint Thomas, Cruz Bay, Saint John & Fort-de-France

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

Lowest in 180 days

From $722

$722 · $103/night · typical price · ↓1% below typical

$103/night

Typical price

↓1% below typical

Emerald Princess • Princess Cruises

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

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

Great balance

From $819

$819 · $117/night · good value · ↓11% below typical

$117/night

Good value

↓11% below typical

Emerald Princess • Princess Cruises

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

Feb 6, 2028 → Feb 13, 2028 • San Juan ↔

11% below typical

From $865

$865 · $124/night · good value · ↓11% below typical

$124/night

Good value

↓11% below typical

Azamara Journey • Azamara Cruises

7-night Southern Caribbean Arc via Spanish Town, Antigua & Saint-Pierre

Dec 5, 2026 → Dec 12, 2026 • San Juan → Bridgetown

Great balance

From $1,429

$1,429 · $204/night · good value · ↓15% below typical

$204/night

Good value

↓15% below typical

Seven Seas Grandeur • Regent Seven Seas Cruises

10-night Southern Caribbean Loop via Saint George's, Oranjestad & Willemstad

Feb 4, 2028 → Feb 14, 2028 • Bridgetown ↔

From $5,960

$5,960 · $596/night · good value · ↓16% below typical

$596/night

Good value

↓16% below typical

Crown Princess • Princess Cruises

7-night Eastern Caribbean Loop via Saint Thomas, Basseterre, Saint Kitts & Roseau

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

Great balance

From $859

$859 · $123/night · good value · ↓15% below typical

$123/night

Good value

↓15% below typical

Norwegian Breakaway • Norwegian Cruise Line

14-night Southern Caribbean Arc via Georgetown, South Carolina, Oranjestad & Willemstad

Apr 4, 2027 → Apr 18, 2027 • New Orleans → Boston

Lowest in 30 days $401 above typical

From $2,259

$2,259 · $161/night · priced high · ↑22% above typical

$161/night

Priced high

↑22% above typical

Vision of the Seas • Royal Caribbean International

7-night Southern Caribbean Loop via Bridgetown, Saint George's & Kingstown

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

Lowest in 180 days $140 above typical

From $834

$834 · $119/night · priced high · ↑20% above typical

$119/night

Priced high

↑20% above typical

Oceania Sonata • Oceania Cruises

14-night Southern Caribbean Arc: Georgetown, Grand Cayman, Ocho Rios & Oranjestad

Mar 15, 2029 → Mar 29, 2029 • Miami ↔

Lowest in 180 days $576 above typical

From $6,999

$6,999 · $500/night · typical price · ↑9% above typical

$500/night

Typical price

↑9% above typical