Jibhop

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

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

Celebrity Eclipse • Celebrity Cruises

10-night Southern Caribbean Loop via Saint John's, Castries & Bridgetown

Mar 12, 2027 → Mar 22, 2027 • Fort Lauderdale ↔

$117 below typical ↗

From $1,313

$1,313 · $131/night · typical price · ↓8% below typical

$131/night

Typical price

↓8% below typical

Arvia • P&O Cruises

14-night Southern Caribbean Loop via Philipsburg, Tortola & Roseau

Dec 6, 2027 → Dec 20, 2027 • Basseterre, Saint Kitts ↔

From $2,269

$2,269 · $162/night · good value · ↓12% below typical

$162/night

Good value

↓12% below typical

MSC Seaview • MSC Cruises

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

Dec 12, 2026 → Dec 19, 2026 • Fort-de-France ↔

Great balance

From $799

$799 · $114/night · good value · ↓18% below typical

$114/night

Good value

↓18% 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

Queen Mary 2 • Cunard Line

20-night Southern Caribbean Arc via New York, Basseterre, Saint Kitts & Castries

Dec 14, 2027 → Jan 3, 2028 • Southampton → New York

$240 below typical ↗

From $3,201

$3,201 · $160/night · typical price · ↓7% below typical

$160/night

Typical price

↓7% 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

Valiant Lady • Virgin Voyages

7-night Southern Caribbean Loop via Philipsburg, Fort-de-France & Bridgetown

Dec 26, 2026 → Jan 2, 2027 • San Juan ↔

Lowest in 30 days $724 above typical

From $1,837

$1,837 · $262/night · priced high · ↑65% above typical

$262/night

Priced high

↑65% above typical

Queen Mary 2 • Cunard Line

14-night Southern Caribbean Arc via Saint Thomas, Bridgetown & Castries

Nov 24, 2028 → Dec 8, 2028 • New York ↔

Lowest in 180 days $988 above typical

From $3,177

$3,177 · $227/night · priced high · ↑45% above typical

$227/night

Priced high

↑45% above typical

Valiant Lady • Virgin Voyages

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

Nov 7, 2026 → Nov 14, 2026 • San Juan ↔

Lowest in 30 days $420 above typical

From $1,533

$1,533 · $219/night · priced high · ↑38% above typical

$219/night

Priced high

↑38% above typical

Queen Mary 2 • Cunard Line

21-night Southern Caribbean Arc via New York, Saint Thomas & Bridgetown

Nov 17, 2028 → Dec 8, 2028 • Southampton → New York

Lowest in 180 days $1,236 above typical

From $4,520

$4,520 · $215/night · priced high · ↑38% above typical

$215/night

Priced high

↑38% above typical

Explora I • Explora Journeys

12-night Southern Caribbean Arc via Saint-Barthélemy, Saint-Pierre & Bridgetown

Feb 5, 2027 → Feb 17, 2027 • San Juan → Manaus

Lowest in 30 days $1,740 above typical ↘

From $9,120

$9,120 · $760/night · priced high · ↑24% above typical

$760/night

Priced high

↑24% 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