Jibhop

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

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

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

$750 below typical

From $3,635

$3,635 · $130/night · good value · ↓17% below typical

$130/night

Good value

↓17% 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

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

Grandeur of the Seas • Royal Caribbean International

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

Jun 12, 2027 → Jun 19, 2027 • San Juan ↔

Lowest in 180 days $99 below typical ↘

From $906

$906 · $129/night · typical price · ↓10% below typical

$129/night

Typical price

↓10% 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

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

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 $804 below typical ↘

From $7,394

$7,394 · $528/night · typical price · ↓10% below typical

$528/night

Typical price

↓10% below typical

Celebrity Ascent • Celebrity Cruises

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

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

$320 below typical

From $1,540

$1,540 · $154/night · good value · ↓17% below typical

$154/night

Good value

↓17% below typical

Carnival Firenze • Carnival Cruise Line

10-night Eastern Caribbean Loop via Philipsburg, Basseterre, Saint Kitts & Castries

Mar 8, 2027 → Mar 18, 2027 • Miami ↔

$141 below typical

From $738

$738 · $74/night · good value · ↓16% below typical

$74/night

Good value

↓16% below typical

Queen Mary 2 • Cunard Line

21-night Southern Caribbean Arc via New York, Road Town, Tortola & Philipsburg

Dec 12, 2026 → Jan 2, 2027 • Southampton → New York

Lowest in 180 days $324 below typical

From $3,289

$3,289 · $157/night · typical price · ↓9% below typical

$157/night

Typical price

↓9% below typical

Seabourn Ovation • Seabourn

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

Jan 9, 2027 → Jan 16, 2027 • Bridgetown → Philipsburg

Lowest in 180 days $350 below typical ↘

From $4,249

$4,249 · $607/night · typical price · ↓8% below typical

$607/night

Typical price

↓8% below typical

Scarlet Lady • Virgin Voyages

7-night Eastern Caribbean Loop via Oranjestad & Castries

Mar 18, 2028 → Mar 25, 2028 • San Juan ↔

Lowest in 180 days $70 below typical

From $903

$903 · $129/night · typical price · ↓7% below typical

$129/night

Typical price

↓7% below typical

Seabourn Ovation • Seabourn

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

Dec 19, 2026 → Jan 2, 2027 • Bridgetown ↔

Lowest in 180 days $572 below typical ↘

From $7,224

$7,224 · $516/night · typical price · ↓7% below typical

$516/night

Typical price

↓7% below typical

Seven Seas Prestige • Regent Seven Seas Cruises

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

Apr 9, 2027 → Apr 23, 2027 • Miami → New York

From $9,643

$9,643 · $689/night · great deal · ↓30% below typical

$689/night

Great deal

↓30% below typical

Queen Elizabeth • Cunard Line

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

Nov 17, 2026 → Dec 8, 2026 • Miami ↔

$306 below typical

From $1,844

$1,844 · $88/night · good value · ↓14% below typical

$88/night

Good value

↓14% below typical

Queen Mary 2 • Cunard Line

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

Nov 19, 2027 → Dec 2, 2027 • New York ↔

Lowest in 180 days $170 below typical

From $1,863

$1,863 · $143/night · typical price · ↓8% below typical

$143/night

Typical price

↓8% below typical