Jibhop

Seabourn Ovation • Seabourn

14-night Southern Caribbean Arc via Tortola, South Friars Bay & Les Trois-Îlets

Dec 5, 2026 → Dec 19, 2026 • Philipsburg → Bridgetown

Lowest in 30 days $2,527 below typical ↘

From $5,269

$5,269 · $376/night · great deal · ↓32% below typical

$376/night

Great deal

↓32% below typical

Seabourn Quest • Seabourn

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

Nov 22, 2026 → Dec 6, 2026 • Miami ↔

Lowest in 30 days $2,845 below typical ↘

From $6,153

$6,153 · $440/night · great deal · ↓32% below typical

$440/night

Great deal

↓32% below typical

Seabourn Ovation • Seabourn

7-night Southern Caribbean Loop via South Friars Bay, Terre-de-Haut & Rodney Bay

Dec 12, 2026 → Dec 19, 2026 • Bridgetown ↔

Lowest in 180 days $1,009 below typical ↘

From $2,889

$2,889 · $413/night · great deal · ↓26% below typical

$413/night

Great deal

↓26% below typical

Seabourn Ovation • Seabourn

17-night Transatlantic Crossing via Rodney Bay, South Friars Bay & Road Bay

Dec 11, 2027 → Dec 28, 2027 • Bridgetown → Philipsburg

Lowest in 30 days $1,988 below typical ↘

From $7,479

$7,479 · $440/night · great deal · ↓21% below typical

$440/night

Great deal

↓21% 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

Explora III

7-night Eastern Caribbean Arc via Cruz Bay, Saint John & Terre-de-Haut

Mar 29, 2027 → Apr 5, 2027 • Miami → San Juan

Lowest in 30 days $797 below typical ↘

From $4,650

$4,650 · $664/night · good value · ↓15% below typical

$664/night

Good value

↓15% below typical

Explora III

7-night Eastern Caribbean Arc via Cruz Bay, Saint John & Terre-de-Haut

Oct 25, 2026 → Nov 1, 2026 • Miami → San Juan

Lowest in 90 days $850 below typical ↘

From $4,335

$4,335 · $619/night · good value · ↓16% below typical

$619/night

Good value

↓16% below typical

Seabourn Quest • Seabourn

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

Dec 6, 2026 → Dec 20, 2026 • Miami ↔

Lowest in 30 days $924 below typical

From $6,374

$6,374 · $455/night · good value · ↓13% below typical

$455/night

Good value

↓13% below typical

Seabourn Ovation • Seabourn

10-night Eastern Caribbean Arc via Saint George's, South Friars Bay & Road Bay

Dec 18, 2027 → Dec 28, 2027 • Bridgetown → Philipsburg

Lowest in 180 days $640 below typical ↘

From $4,929

$4,929 · $493/night · good value · ↓11% below typical

$493/night

Good value

↓11% below typical

SeaDream II • SeaDream Yacht Club

7-night Eastern Caribbean Arc via Terre-de-Haut & Charlestown

Mar 4, 2028 → Mar 11, 2028 • Bridgetown → San Juan

$1,192 below typical

From $4,591

$4,591 · $656/night · great deal · ↓21% below typical

$656/night

Great deal

↓21% below typical

Seabourn Ovation • Seabourn

11-night Eastern Caribbean Arc via Tortola, Road Bay & South Friars Bay

Dec 28, 2027 → Jan 8, 2028 • Philipsburg → Bridgetown

Lowest in 180 days $686 below typical ↘

From $5,439

$5,439 · $494/night · good value · ↓11% below typical

$494/night

Good value

↓11% below typical

SeaDream I • SeaDream Yacht Club

7-night Eastern Caribbean Arc via Port Elizabeth, Bequia, Soufriere & Terre-de-Haut

Dec 12, 2027 → Dec 19, 2027 • Bridgetown → Charlotte Amalie, Saint Thomas

$861 below typical ↗

From $3,716

$3,716 · $531/night · good value · ↓19% below typical

$531/night

Good value

↓19% below typical

Seabourn Ovation • Seabourn

7-night Southern Caribbean Loop via South Friars Bay, Saint-Pierre & Rodney Bay

Feb 6, 2027 → Feb 13, 2027 • Bridgetown ↔

Lowest in 180 days $435 below typical ↘

From $4,164

$4,164 · $595/night · typical price · ↓9% below typical

$595/night

Typical price

↓9% below typical

Explora III

16-night Eastern Caribbean Arc via Puerto Plata, Road Bay & Cruz Bay, Saint John

Feb 19, 2027 → Mar 7, 2027 • Miami → San Juan

$1,697 below typical

From $9,960

$9,960 · $623/night · good value · ↓15% below typical

$623/night

Good value

↓15% 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

Explora III

7-night Eastern Caribbean Loop via Cruz Bay, Saint John & Terre-de-Haut

Dec 6, 2026 → Dec 13, 2026 • Miami → San Juan

Lowest in 180 days $401 below typical ↘

From $4,480

$4,480 · $640/night · typical price · ↓8% below typical

$640/night

Typical price

↓8% below typical

Explora III

7-night Eastern Caribbean Arc via Cruz Bay, Saint John & Terre-de-Haut

Nov 22, 2026 → Nov 29, 2026 • Miami → San Juan

Lowest in 180 days $400 below typical ↘

From $4,480

$4,480 · $640/night · typical price · ↓8% below typical

$640/night

Typical price

↓8% below typical

Explora III

16-night Eastern Caribbean Arc via Cruz Bay, Saint John, Terre-de-Haut & Road Bay

Feb 12, 2027 → Feb 28, 2027 • San Juan → Miami

$1,417 below typical

From $10,240

$10,240 · $640/night · good value · ↓12% below typical

$640/night

Good value

↓12% 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

Explora I • Explora Journeys

16-night Eastern Caribbean Arc via Ocho Rios, Puerto Santo Tomás de Castilla & Roatán

Jan 20, 2027 → Feb 5, 2027 • Miami → San Juan

Lowest in 30 days

From $9,240

$9,240 · $578/night · typical price · ↓4% below typical

$578/night

Typical price

↓4% below typical