Jibhop

Resilient Lady • Virgin Voyages

8-night Eastern Caribbean Loop via Frederiksted, Saint Croix & San Juan

Dec 5, 2026 → Dec 13, 2026 • Miami ↔

Lowest in 90 days $240 below typical

From $952

$952 · $119/night · great deal · ↓20% below typical

$119/night

Great deal

↓20% below typical

Norwegian Bliss • Norwegian Cruise Line

12-night Eastern Caribbean Loop via Puerto Plata, San Juan & Basseterre, Saint Kitts

Dec 11, 2026 → Dec 23, 2026 • New York ↔

Lowest in 30 days $250 below typical

From $1,169

$1,169 · $97/night · good value · ↓18% below typical

$97/night

Good value

↓18% below typical

Queen Elizabeth • Cunard Line

12-night Southern Caribbean Arc via San Juan, Cruz Bay, Saint John & Castries

Dec 17, 2026 → Dec 29, 2026 • Miami ↔

Lowest in 180 days $254 below typical

From $1,198

$1,198 · $100/night · good value · ↓18% below typical

$100/night

Good value

↓18% below typical

Nieuw Amsterdam • Holland America

9-night Eastern Caribbean Loop via Philipsburg, Antigua & Tortola

Dec 11, 2026 → Dec 20, 2026 • Fort Lauderdale ↔

Lowest in 30 days $163 below typical ↘

From $854

$854 · $95/night · good value · ↓16% below typical

$95/night

Good value

↓16% below typical

Brilliant Lady • Virgin Voyages

9-night Eastern Caribbean Loop via Philipsburg & Saint Thomas

Dec 14, 2026 → Dec 23, 2026 • Miami ↔

Lowest in 90 days $180 below typical

From $981

$981 · $109/night · good value · ↓16% below typical

$109/night

Good value

↓16% below typical

Norwegian Pearl • Norwegian Cruise Line

10-night Eastern Caribbean Loop via Puerto Plata & San Juan

Dec 8, 2026 → Dec 18, 2026 • Philadelphia ↔

Lowest in 30 days $115 below typical ↘

From $839

$839 · $84/night · good value · ↓12% below typical

$84/night

Good value

↓12% below typical

MSC Meraviglia • MSC Cruises

8-night Eastern Caribbean Arc via San Juan & Basseterre, Saint Kitts

Dec 5, 2026 → Dec 13, 2026 • Miami ↔

From $559

$559 · $70/night · great deal · ↓49% below typical

$70/night

Great deal

↓49% below typical

Norwegian Getaway • Norwegian Cruise Line

8-night Eastern Caribbean Loop via Puerto Plata, San Juan & Great Stirrup Cay

Dec 14, 2026 → Dec 22, 2026 • Port Canaveral ↔

Lowest in 30 days $100 below typical

From $829

$829 · $104/night · good value · ↓11% below typical

$104/night

Good value

↓11% below typical

Sky Princess • Princess Cruises

8-night Eastern Caribbean Loop via Princess Cays & Grand Turk Island

Dec 13, 2026 → Dec 21, 2026 • Port Canaveral ↔

From $710

$710 · $89/night · great deal · ↓35% below typical

$89/night

Great deal

↓35% below typical

Enchanted Princess • Princess Cruises

10-night Eastern Caribbean Loop via Princess Cays, Puerto Plata & San Juan

Dec 17, 2026 → Dec 27, 2026 • Fort Lauderdale ↔

20% below typical

From $953

$953 · $95/night · great deal · ↓20% below typical

$95/night

Great deal

↓20% below typical

Silver Shadow • Silversea Cruises

10-night Eastern Caribbean Arc via Philipsburg, Basseterre, Saint Kitts & Little Bay

Dec 10, 2026 → Dec 20, 2026 • Miami → San Juan

From $6,300

$6,300 · $630/night · good value · ↓13% below typical

$630/night

Good value

↓13% below typical

Explora III

8-night Eastern Caribbean Arc via Ocho Rios, Catalina Island & Jost Van Dyke

Dec 20, 2026 → Dec 28, 2026 • Miami → San Juan

$339 below typical ↘

From $5,240

$5,240 · $655/night · typical price · ↓6% below typical

$655/night

Typical price

↓6% below typical

Norwegian Bliss • Norwegian Cruise Line

12-night Eastern Caribbean Loop via Puerto Plata, San Juan & Basseterre, Saint Kitts

Dec 23, 2026 → Jan 4, 2027 • New York ↔

Lowest in 30 days $900 above typical

From $2,319

$2,319 · $193/night · priced high · ↑63% above typical

$193/night

Priced high

↑63% above typical

Norwegian Jewel • Norwegian Cruise Line

12-night Eastern Caribbean Loop via Great Stirrup Cay, Cabo Rojo & Oranjestad

Dec 23, 2026 → Jan 4, 2027 • Miami ↔

Lowest in 30 days $926 above typical

From $2,449

$2,449 · $204/night · priced high · ↑61% above typical

$204/night

Priced high

↑61% above typical

Carnival Sunshine • Carnival Cruise Line

8-night Eastern Caribbean Loop via Half Moon Cay & Grand Turk Island

Dec 18, 2026 → Dec 26, 2026 • Norfolk ↔

Lowest in 90 days $347 above typical

From $956

$956 · $120/night · priced high · ↑57% above typical

$120/night

Priced high

↑57% above typical

Rotterdam • Holland America

11-night Eastern Caribbean Arc via Philipsburg, Basseterre, Saint Kitts & Roseau

Dec 22, 2026 → Jan 2, 2027 • Fort Lauderdale ↔

Lowest in 30 days $725 above typical

From $2,034

$2,034 · $185/night · priced high · ↑55% above typical

$185/night

Priced high

↑55% above typical

Brilliant Lady • Virgin Voyages

10-night Eastern Caribbean Loop via Philipsburg, Basseterre, Saint Kitts & Cruz Bay, Saint John

Dec 28, 2026 → Jan 7, 2027 • Miami ↔

Lowest in 90 days $700 above typical

From $1,990

$1,990 · $199/night · priced high · ↑54% above typical

$199/night

Priced high

↑54% above typical

Norwegian Getaway • Norwegian Cruise Line

9-night Eastern Caribbean Loop via Puerto Plata, San Juan & Great Stirrup Cay

Dec 22, 2026 → Dec 31, 2026 • Port Canaveral ↔

Lowest in 30 days $424 above typical ↘

From $1,469

$1,469 · $163/night · priced high · ↑41% above typical

$163/night

Priced high

↑41% above typical

Norwegian Pearl • Norwegian Cruise Line

11-night Eastern Caribbean Loop via Philipsburg, Saint Thomas & Tortola

Dec 23, 2026 → Jan 3, 2027 • Philadelphia ↔

Lowest in 30 days $390 above typical ↘

From $1,439

$1,439 · $131/night · priced high · ↑37% above typical

$131/night

Priced high

↑37% above typical

Resilient Lady • Virgin Voyages

8-night Eastern Caribbean Loop via Puerto Plata & San Juan

Dec 19, 2026 → Dec 27, 2026 • Miami ↔

Lowest in 90 days $160 above typical

From $1,352

$1,352 · $169/night · priced high · ↑13% above typical

$169/night

Priced high

↑13% above typical