Jibhop

Queen Mary 2 • Cunard Line

28-night Southern Caribbean Loop via New York, Basseterre, Saint Kitts & Castries

Feb 27, 2028 → Mar 26, 2028 • Southampton ↔

$860 below typical

From $3,525

$3,525 · $126/night · good value · ↓20% below typical

$126/night

Good value

↓20% below typical

Seabourn Ovation • Seabourn

7-night Eastern Caribbean Arc via Castries, Little Bay & South Friars Bay

Feb 12, 2028 → Feb 19, 2028 • Bridgetown → Philipsburg

Lowest in 180 days $520 below typical ↘

From $4,079

$4,079 · $583/night · good value · ↓11% below typical

$583/night

Good value

↓11% below typical

Queen Elizabeth • Cunard Line

21-night Western Caribbean Loop via Cruz Bay, Saint John, Montego Bay & Cozumel

Nov 5, 2026 → Nov 26, 2026 • Miami ↔

Lowest in 30 days $266 below typical ↘

From $1,884

$1,884 · $90/night · good value · ↓12% below typical

$90/night

Good value

↓12% below typical

Britannia • P&O Cruises

14-night Eastern Caribbean Arc via Santa Cruz de Tenerife & Philipsburg

Oct 30, 2026 → Nov 13, 2026 • Southampton → Bridgetown

$297 below typical

From $1,323

$1,323 · $95/night · good value · ↓18% below typical

$95/night

Good value

↓18% below typical

Seabourn Ovation • Seabourn

14-night Eastern Caribbean Loop via Castries, Little Bay & South Friars Bay

Mar 13, 2027 → Mar 27, 2027 • Bridgetown ↔

Lowest in 30 days $1,004 below typical ↘

From $7,394

$7,394 · $528/night · good value · ↓12% below typical

$528/night

Good value

↓12% below typical

Aurora • P&O Cruises

24-night Southern Caribbean Arc via Santa Cruz de Tenerife, Bridgetown & Kingstown

Nov 3, 2026 → Nov 27, 2026 • Southampton ↔

Lowest in 180 days $355 below typical

From $2,701

$2,701 · $113/night · good value · ↓12% below typical

$113/night

Good value

↓12% below typical

Grandeur of the Seas • Royal Caribbean International

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

Oct 2, 2027 → Oct 9, 2027 • San Juan ↔

Lowest in 180 days $86 below typical

From $731

$731 · $104/night · good value · ↓11% below typical

$104/night

Good value

↓11% below typical

Grandeur of the Seas • Royal Caribbean International

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

Jun 26, 2027 → Jul 3, 2027 • San Juan ↔

Lowest in 180 days $109 below typical ↘

From $896

$896 · $128/night · good value · ↓11% below typical

$128/night

Good value

↓11% below typical

MSC World Europa • MSC Cruises

25-night Transatlantic Crossing via Pointe-à-Pitre, Castries & Bridgetown

Apr 3, 2027 → Apr 28, 2027 • Fort-de-France → Civitavecchia (Rome)

From $3,501

$3,501 · $140/night · great deal · ↓37% below typical

$140/night

Great deal

↓37% below typical

Oceania Sonata • Oceania Cruises

44-night Eastern Caribbean Arc via Puerto Quetzal, Panama Canal & Cozumel

Jan 6, 2028 → Feb 19, 2028 • Los Angeles → Miami

Lowest in 180 days $1,109 below typical

From $20,549

$20,549 · $467/night · typical price · ↓5% below typical

$467/night

Typical price

↓5% below typical

Seabourn Ovation • Seabourn

7-night Eastern Caribbean Arc via Castries, Little Bay & South Friars Bay

Nov 27, 2027 → Dec 4, 2027 • Bridgetown → Philipsburg

Lowest in 90 days $460 below typical ↘

From $3,739

$3,739 · $534/night · good value · ↓11% below typical

$534/night

Good value

↓11% below typical

Grandeur of the Seas • Royal Caribbean International

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

Oct 30, 2027 → Nov 6, 2027 • San Juan ↔

Lowest in 180 days $80 below typical

From $738

$738 · $105/night · typical price · ↓10% below typical

$105/night

Typical price

↓10% below typical

Queen Mary 2 • Cunard Line

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

Nov 19, 2027 → Dec 9, 2027 • New York → Southampton

Lowest in 180 days $355 below typical

From $2,773

$2,773 · $139/night · good value · ↓11% below typical

$139/night

Good value

↓11% below typical

MSC World Europa • 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 $743

$743 · $106/night · great deal · ↓38% below typical

$106/night

Great deal

↓38% below typical

Celebrity Ascent • Celebrity Cruises

10-night Eastern Caribbean Loop via Philipsburg, Castries & Bridgetown

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

$338 below typical

From $1,523

$1,523 · $152/night · good value · ↓18% below typical

$152/night

Good value

↓18% below typical

Grandeur of the Seas • Royal Caribbean International

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

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

Lowest in 180 days $99 below typical

From $887

$887 · $127/night · good value · ↓10% below typical

$127/night

Good value

↓10% below typical

Queen Elizabeth • Cunard Line

21-night Western Caribbean Loop via Cruz Bay, Saint John, Montego Bay & Cozumel

Nov 26, 2026 → Dec 17, 2026 • Miami ↔

$353 below typical ↗

From $1,797

$1,797 · $86/night · good value · ↓16% below typical

$86/night

Good value

↓16% below typical

Scarlet Lady • Virgin Voyages

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

Nov 27, 2027 → Dec 4, 2027 • San Juan ↔

Lowest in 180 days $70 below typical

From $763

$763 · $109/night · typical price · ↓8% below typical

$109/night

Typical price

↓8% below typical

Seabourn Ovation • Seabourn

12-night Transatlantic Crossing via Castries & Funchal, Madeira

Mar 25, 2028 → Apr 6, 2028 • Bridgetown → Lisboa

$1,200 below typical ↗

From $5,998

$5,998 · $500/night · good value · ↓17% below typical

$500/night

Good value

↓17% below typical

Explora III

8-night Eastern Caribbean Loop via Philipsburg, Terre-de-Haut & Road Bay

Jan 13, 2027 → Jan 21, 2027 • San Juan → Miami

Lowest in 90 days $457 below typical ↘

From $5,440

$5,440 · $680/night · typical price · ↓8% below typical

$680/night

Typical price

↓8% below typical