Jibhop

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 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

Dec 6, 2027 → Dec 20, 2027 • La Romana ↔

56% below typical

From $729

$729 · $52/night · great deal · ↓56% below typical

$52/night

Great deal

↓56% below typical

Arvia • P&O Cruises

14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Philipsburg & Tortola

Dec 3, 2027 → Dec 17, 2027 • Bridgetown ↔

From $1,890

$1,890 · $135/night · great deal · ↓26% below typical

$135/night

Great deal

↓26% below typical

Arvia • P&O Cruises

14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Philipsburg & Tortola

Dec 4, 2027 → Dec 18, 2027 • Bridgetown ↔

From $1,890

$1,890 · $135/night · great deal · ↓26% below typical

$135/night

Great deal

↓26% below typical

Queen Elizabeth • Cunard Line

14-night Eastern Caribbean Loop via Saint Thomas, Basseterre, Saint Kitts & Kingstown

Dec 9, 2027 → Dec 23, 2027 • Miami ↔

Lowest in 180 days $107 below typical

From $1,587

$1,587 · $113/night · typical price · ↓6% below typical

$113/night

Typical price

↓6% below typical

Emerald Princess • Princess Cruises

14-night Eastern Caribbean Arc via Tortola, Basseterre, Saint Kitts & Fort-de-France

Dec 12, 2027 → Dec 26, 2027 • San Juan ↔

From $1,516

$1,516 · $108/night · great deal · ↓23% below typical

$108/night

Great deal

↓23% below typical

MS Europa 2 • Hapag-Lloyd Cruises

14-night Eastern Caribbean Loop via San Juan, Saint-Barthélemy & Saint John's

Dec 7, 2027 → Dec 21, 2027 • Miami ↔

From $9,419

$9,419 · $673/night · good value · ↓15% below typical

$673/night

Good value

↓15% below typical

Emerald Princess • Princess Cruises

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

Dec 5, 2027 → Dec 19, 2027 • San Juan ↔

20% below typical

From $1,566

$1,566 · $112/night · great deal · ↓20% below typical

$112/night

Great deal

↓20% below typical

MSC Opera • MSC Cruises

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

Dec 20, 2027 → Jan 3, 2028 • La Romana ↔

17% below typical

From $1,379

$1,379 · $99/night · good value · ↓17% below typical

$99/night

Good value

↓17% below typical

Zuiderdam • Holland America

14-night Eastern Caribbean Arc: Half Moon Cay, Grand Turk Island & Puerto Plata

Dec 23, 2027 → Jan 6, 2028 • Fort Lauderdale ↔

Lowest in 180 days $1,021 above typical

From $2,719

$2,719 · $194/night · priced high · ↑60% above typical

$194/night

Priced high

↑60% above typical

Rotterdam • Holland America

17-night Eastern Caribbean Arc: Grand Turk Island, San Juan & Saint Thomas

Dec 22, 2027 → Jan 8, 2028 • Fort Lauderdale ↔

Lowest in 180 days $1,076 above typical

From $3,099

$3,099 · $182/night · priced high · ↑53% above typical

$182/night

Priced high

↑53% above typical

Queen Elizabeth • Cunard Line

14-night Transatlantic Crossing via Saint Thomas, Basseterre, Saint Kitts & Kingstown

Dec 23, 2027 → Jan 6, 2028 • Miami ↔

Lowest in 180 days $711 above typical

From $2,405

$2,405 · $172/night · priced high · ↑42% above typical

$172/night

Priced high

↑42% above typical

Eurodam • Holland America

21-night Eastern Caribbean Arc: Half Moon Cay, Montego Bay & Cozumel

Dec 22, 2027 → Jan 12, 2028 • Fort Lauderdale ↔

Lowest in 180 days $1,001 above typical

From $3,504

$3,504 · $167/night · priced high · ↑40% above typical

$167/night

Priced high

↑40% above typical

Rotterdam • Holland America

17-night Eastern Caribbean Loop: Half Moon Cay, Cabo Rojo & Willemstad

Dec 29, 2027 → Jan 15, 2028 • Fort Lauderdale ↔

Lowest in 180 days $781 above typical

From $2,804

$2,804 · $165/night · priced high · ↑39% above typical

$165/night

Priced high

↑39% above typical

Eurodam • Holland America

21-night Western Caribbean Arc: Philipsburg, Antigua & Cozumel

Dec 1, 2027 → Dec 22, 2027 • Fort Lauderdale ↔

Lowest in 180 days $611 above typical

From $3,114

$3,114 · $148/night · priced high · ↑24% above typical

$148/night

Priced high

↑24% above typical

Emerald Princess • Princess Cruises

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

Dec 19, 2027 → Jan 2, 2028 • San Juan ↔

9% below typical

From $1,791

$1,791 · $128/night · typical price · ↓9% below typical

$128/night

Typical price

↓9% below typical

Iona • P&O Cruises

14-night Eastern Caribbean Loop via Castries, Saint George's & Bridgetown

Dec 18, 2027 → Jan 1, 2028 • Antigua ↔

From $3,174

$3,174 · $227/night · priced high · ↑41% above typical

$227/night

Priced high

↑41% above typical

Iona • P&O Cruises

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

Dec 27, 2027 → Jan 10, 2028 • Basseterre, Saint Kitts ↔

From $3,174

$3,174 · $227/night · priced high · ↑41% above typical

$227/night

Priced high

↑41% above typical

Iona • P&O Cruises

14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg

Dec 24, 2027 → Jan 7, 2028 • Bridgetown ↔

From $2,701

$2,701 · $193/night · priced high · ↑20% above typical

$193/night

Priced high

↑20% above typical