Jibhop

Rotterdam • Holland America

21-night Eastern Caribbean Loop via Philipsburg, Antigua & Roseau

Dec 1, 2026 → Dec 22, 2026 • Fort Lauderdale ↔

Lowest in 30 days $510 below typical

From $1,989

$1,989 · $95/night · great deal · ↓20% below typical

$95/night

Great deal

↓20% below typical

Queen Mary 2 • Cunard Line

14-night Eastern Caribbean Loop via Road Town, Tortola, Philipsburg & Bridgetown

Dec 19, 2026 → Jan 2, 2027 • New York ↔

Lowest in 180 days $450 below typical

From $1,959

$1,959 · $140/night · good value · ↓19% below typical

$140/night

Good value

↓19% below typical

Oceania Marina • Oceania Cruises

17-night Eastern Caribbean Loop via Puerto Plata, San Juan & Cozumel

Feb 17, 2028 → Mar 5, 2028 • Miami ↔

Lowest in 180 days $675 below typical

From $4,849

$4,849 · $285/night · good value · ↓12% below typical

$285/night

Good value

↓12% below typical

Seabourn Ovation • Seabourn

21-night Eastern Caribbean Loop via Saint George's, South Friars Bay & Road Bay

Dec 18, 2027 → Jan 8, 2028 • Bridgetown ↔

Lowest in 30 days $1,835 below typical ↘

From $9,859

$9,859 · $469/night · good value · ↓16% below typical

$469/night

Good value

↓16% below typical

Seabourn Ovation • Seabourn

14-night Eastern Caribbean Loop via Tortola, South Friars Bay & Les Trois-Îlets

Mar 6, 2027 → Mar 20, 2027 • Philipsburg ↔

Lowest in 30 days $1,484 below typical ↘

From $6,714

$6,714 · $480/night · good value · ↓18% below typical

$480/night

Good value

↓18% below typical

Seabourn Ovation • Seabourn

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

Feb 12, 2028 → Feb 26, 2028 • Bridgetown ↔

Lowest in 30 days $1,379 below typical ↘

From $7,819

$7,819 · $559/night · good value · ↓15% below typical

$559/night

Good value

↓15% below typical

Queen Mary 2 • Cunard Line

21-night Southern Caribbean Arc via Basseterre, Saint Kitts, Castries & Bridgetown

Dec 21, 2027 → Jan 11, 2028 • New York → Southampton

Lowest in 180 days $622 below typical

From $2,991

$2,991 · $142/night · good value · ↓17% below typical

$142/night

Good value

↓17% below typical

Seabourn Ovation • Seabourn

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

Nov 27, 2027 → Dec 11, 2027 • Bridgetown ↔

Lowest in 180 days $1,429 below typical ↘

From $6,969

$6,969 · $498/night · good value · ↓17% below typical

$498/night

Good value

↓17% below typical

Seabourn Quest • Seabourn

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

Dec 4, 2027 → Dec 18, 2027 • Miami ↔

Lowest in 180 days $1,094 below typical ↘

From $6,204

$6,204 · $443/night · good value · ↓15% below typical

$443/night

Good value

↓15% below typical

MSC Opera • MSC Cruises

14-night Eastern Caribbean Loop via Catalina Island, Oranjestad & Willemstad

Feb 28, 2028 → Mar 13, 2028 • La Romana ↔

48% below typical

From $909

$909 · $65/night · great deal · ↓48% below typical

$65/night

Great deal

↓48% below typical

MSC Opera • MSC Cruises

14-night Eastern Caribbean Loop via Catalina Island, Oranjestad & Willemstad

Mar 27, 2028 → Apr 10, 2028 • La Romana ↔

49% below typical

From $939

$939 · $67/night · great deal · ↓49% below typical

$67/night

Great deal

↓49% below typical

MSC Opera • MSC Cruises

14-night Eastern Caribbean Loop via Catalina Island, Oranjestad & Willemstad

Jan 17, 2028 → Jan 31, 2028 • La Romana ↔

55% below typical

From $709

$709 · $51/night · great deal · ↓55% below typical

$51/night

Great deal

↓55% below typical

MSC Opera • MSC Cruises

14-night Eastern Caribbean Loop via Catalina Island, Spanish Town & Philipsburg

Jan 10, 2028 → Jan 24, 2028 • La Romana ↔

59% below typical

From $649

$649 · $46/night · great deal · ↓59% below typical

$46/night

Great deal

↓59% below typical

MSC Grandiosa • MSC Cruises

14-night Port Canaveral → Nassau → Ocean Cay → Cozumel + 6 more

Jan 9, 2027 → Jan 23, 2027 • Port Canaveral ↔

50% below typical

From $847

$847 · $61/night · great deal · ↓50% below typical

$61/night

Great deal

↓50% below typical

MSC Opera • MSC Cruises

14-night Eastern Caribbean Loop via Catalina Island, Spanish Town & Philipsburg

Feb 21, 2028 → Mar 6, 2028 • La Romana ↔

45% below typical

From $969

$969 · $69/night · great deal · ↓45% below typical

$69/night

Great deal

↓45% below typical

Zuiderdam • Holland America

14-night Western Caribbean Loop via Key West, Ocho Rios & Cozumel

Nov 21, 2026 → Dec 5, 2026 • Miami ↔

Lowest in 180 days $190 below typical ↘

From $1,109

$1,109 · $79/night · good value · ↓15% below typical

$79/night

Good value

↓15% below typical

Queen Mary 2 • Cunard Line

23-night Southern Caribbean Arc via Road Town, Tortola, Philipsburg & Bridgetown

Dec 19, 2026 → Jan 11, 2027 • New York → Southampton

$909 below typical

From $3,049

$3,049 · $133/night · great deal · ↓23% below typical

$133/night

Great deal

↓23% below typical

Carnival Firenze • Carnival Cruise Line

14-night Eastern Caribbean Loop via Saint Thomas, Antigua & Castries

Mar 19, 2028 → Apr 2, 2028 • Port Canaveral ↔

Lowest in 30 days $196 below typical

From $1,035

$1,035 · $74/night · good value · ↓16% below typical

$74/night

Good value

↓16% below typical

MSC Opera • MSC Cruises

14-night Eastern Caribbean Loop via Catalina Island, Spanish Town & Philipsburg

Mar 20, 2028 → Apr 3, 2028 • La Romana ↔

49% below typical

From $939

$939 · $67/night · great deal · ↓49% below typical

$67/night

Great deal

↓49% below typical

Seven Seas Splendor • Regent Seven Seas Cruises

17-night Eastern Caribbean Loop via Montego Bay, Ocho Rios & San Juan

Dec 11, 2026 → Dec 28, 2026 • Houston ↔

From $7,334

$7,334 · $431/night · great deal · ↓49% below typical

$431/night

Great deal

↓49% below typical