Jibhop

Silver Dawn • Silversea Cruises

11-night Eastern Caribbean Loop via San Juan, Basseterre, Saint Kitts & Saint John's

Mar 14, 2028 → Mar 25, 2028 • Miami ↔

From $6,300

$6,300 · $573/night · great deal · ↓35% below typical

$573/night

Great deal

↓35% below typical

Seabourn Quest • Seabourn

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

Dec 18, 2027 → Dec 28, 2027 • Miami ↔

Lowest in 180 days $539 below typical ↘

From $4,674

$4,674 · $467/night · good value · ↓10% below typical

$467/night

Good value

↓10% below typical

Seabourn Quest • Seabourn

10-night Eastern Caribbean Loop via San Juan, South Friars Bay & Little Bay

Dec 28, 2027 → Jan 7, 2028 • Miami ↔

Lowest in 180 days $539 below typical ↘

From $4,674

$4,674 · $467/night · good value · ↓10% below typical

$467/night

Good value

↓10% 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

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

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

Seabourn Ovation • Seabourn

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

Jan 9, 2027 → Jan 23, 2027 • Bridgetown ↔

Lowest in 180 days $615 below typical ↘

From $8,584

$8,584 · $613/night · typical price · ↓7% below typical

$613/night

Typical price

↓7% below typical

Seabourn Ovation • Seabourn

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

Jan 16, 2027 → Jan 30, 2027 • Philipsburg ↔

Lowest in 30 days $615 below typical ↘

From $8,584

$8,584 · $613/night · typical price · ↓7% below typical

$613/night

Typical price

↓7% below typical

Seabourn Ovation • Seabourn

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

Mar 11, 2028 → Mar 18, 2028 • Bridgetown → Philipsburg

Lowest in 180 days $290 below typical ↘

From $3,909

$3,909 · $558/night · typical price · ↓7% below typical

$558/night

Typical price

↓7% below typical

Seabourn Ovation • Seabourn

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

Mar 11, 2028 → Mar 25, 2028 • Bridgetown ↔

Lowest in 30 days $579 below typical ↘

From $7,819

$7,819 · $559/night · typical price · ↓7% below typical

$559/night

Typical price

↓7% below typical

Silver Shadow • Silversea Cruises

12-night Eastern Caribbean Loop via San Juan, Saint-Barthélemy & Little Bay

Nov 18, 2026 → Nov 30, 2026 • Miami ↔

From $7,400

$7,400 · $617/night · great deal · ↓26% below typical

$617/night

Great deal

↓26% below typical

Silver Spirit • Silversea Cruises

7-night Eastern Caribbean Loop via Castries, Terre-de-Haut & Philipsburg

Mar 11, 2028 → Mar 18, 2028 • Bridgetown ↔

From $5,400

$5,400 · $771/night · great deal · ↓25% below typical

$771/night

Great deal

↓25% below typical

Silver Shadow • Silversea Cruises

11-night Eastern Caribbean Loop via San Juan, Saint-Barthélemy & Little Bay

Nov 7, 2026 → Nov 18, 2026 • Miami ↔

From $7,000

$7,000 · $636/night · great deal · ↓24% below typical

$636/night

Great deal

↓24% below typical

Silver Ray • Silversea Cruises

12-night Eastern Caribbean Arc via Port Elizabeth, Bequia, Castries & Fort-de-France

Mar 20, 2028 → Apr 1, 2028 • Bridgetown → Miami

From $8,200

$8,200 · $683/night · great deal · ↓25% below typical

$683/night

Great deal

↓25% below typical

Silver Shadow • Silversea Cruises

10-night Eastern Caribbean Loop via San Juan & Saint-Barthélemy

Nov 30, 2026 → Dec 10, 2026 • Miami ↔

From $6,500

$6,500 · $650/night · great deal · ↓22% below typical

$650/night

Great deal

↓22% 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

Explora III

7-night Itinerary TCPLS-DOPOP-DOLRM-VGJVD-BLSBH

Nov 8, 2026 → Nov 15, 2026 • Miami → San Juan

Lowest in 30 days ↘

From $4,760

$4,760 · $680/night · typical price · ↓2% below typical

$680/night

Typical price

↓2% below typical

MS Europa • Hapag-Lloyd Cruises

14-night Southern Caribbean Arc via Cockburn Town, Saint-Barthélemy & Cruz Bay, Saint John

Dec 3, 2028 → Dec 17, 2028 • Miami → Colón (Panama Canal)

From $7,061

$7,061 · $504/night · good value · ↓15% below typical

$504/night

Good value

↓15% 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