Jibhop

Seabourn Ovation • Seabourn

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

Feb 27, 2027 → Mar 6, 2027 • Bridgetown → Philipsburg

Lowest in 180 days $945 below typical ↘

From $3,654

$3,654 · $522/night · great deal · ↓21% below typical

$522/night

Great deal

↓21% below typical

Seabourn Ovation • Seabourn

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

Feb 26, 2028 → Mar 11, 2028 • Bridgetown ↔

Lowest in 180 days $1,889 below typical ↘

From $7,309

$7,309 · $522/night · great deal · ↓21% below typical

$522/night

Great deal

↓21% below typical

Queen Elizabeth • Cunard Line

21-night Eastern Caribbean Loop via Grand Turk Island, Willemstad & Cruz Bay, Saint John

Oct 27, 2026 → Nov 17, 2026 • Miami ↔

Lowest in 30 days $670 below typical

From $1,793

$1,793 · $85/night · great deal · ↓27% below typical

$85/night

Great deal

↓27% below typical

Rotterdam • Holland America

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

Nov 10, 2026 → Dec 1, 2026 • Fort Lauderdale ↔

Lowest in 30 days $725 below typical ↘

From $2,024

$2,024 · $96/night · great deal · ↓26% below typical

$96/night

Great deal

↓26% below typical

Rotterdam • Holland America

21-night Western Caribbean Loop via Half Moon Cay, Falmouth & Cozumel

Oct 31, 2026 → Nov 21, 2026 • Fort Lauderdale ↔

Lowest in 30 days $715 below typical ↘

From $2,034

$2,034 · $97/night · great deal · ↓26% below typical

$97/night

Great deal

↓26% below typical

Norwegian Breakaway • Norwegian Cruise Line

14-night Southern Caribbean Arc via Saint Thomas, Castries & Saint George's

Nov 8, 2026 → Nov 22, 2026 • Boston → New Orleans

Lowest in 180 days $380 below typical ↘

From $1,269

$1,269 · $91/night · great deal · ↓23% below typical

$91/night

Great deal

↓23% below typical

Norwegian Prima • Norwegian Cruise Line

7-night Eastern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Bridgetown

Dec 4, 2027 → Dec 11, 2027 • San Juan ↔

Lowest in 30 days $350 below typical

From $1,139

$1,139 · $163/night · great deal · ↓24% below typical

$163/night

Great deal

↓24% below typical

Queen Mary 2 • Cunard Line

27-night Eastern Caribbean Loop via New York, Saint Thomas & Basseterre, Saint Kitts

Nov 12, 2027 → Dec 9, 2027 • Southampton ↔

Lowest in 180 days $978 below typical

From $3,244

$3,244 · $120/night · great deal · ↓23% below typical

$120/night

Great deal

↓23% below typical

Carnival Freedom • Carnival Cruise Line

15-night Eastern Caribbean Arc via Oranjestad, Curaçao & Saint George's

May 8, 2027 → May 23, 2027 • Port Canaveral → Norfolk

$454 below typical

From $1,169

$1,169 · $78/night · great deal · ↓28% below typical

$78/night

Great deal

↓28% below typical

Seabourn Ovation • Seabourn

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

Jan 15, 2028 → Jan 29, 2028 • Bridgetown ↔

Lowest in 180 days $1,720 below typical ↘

From $7,479

$7,479 · $534/night · good value · ↓19% below typical

$534/night

Good value

↓19% below typical

Seabourn Ovation • Seabourn

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

Jan 29, 2028 → Feb 12, 2028 • Bridgetown ↔

Lowest in 30 days $1,720 below typical ↘

From $7,479

$7,479 · $534/night · good value · ↓19% below typical

$534/night

Good value

↓19% below typical

Queen Mary 2 • Cunard Line

28-night Southern Caribbean Loop via New York, Basseterre, Saint Kitts & Castries

Dec 14, 2027 → Jan 11, 2028 • Southampton ↔

Lowest in 180 days $1,010 below typical

From $3,808

$3,808 · $136/night · great deal · ↓21% below typical

$136/night

Great deal

↓21% below typical

Queen Mary 2 • Cunard Line

12-night Southern Caribbean Loop via Basseterre, Saint Kitts, Castries & Bridgetown

Mar 6, 2028 → Mar 18, 2028 • New York ↔

Lowest in 180 days $421 below typical

From $1,838

$1,838 · $153/night · good value · ↓19% below typical

$153/night

Good value

↓19% 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 $1,684 below typical ↘

From $6,714

$6,714 · $480/night · great deal · ↓20% below typical

$480/night

Great deal

↓20% below typical

Seabourn Ovation • Seabourn

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

Feb 26, 2028 → Mar 4, 2028 • Bridgetown → Philipsburg

Lowest in 180 days $775 below typical ↘

From $3,824

$3,824 · $546/night · good value · ↓17% below typical

$546/night

Good value

↓17% below typical

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

Grandeur of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg

Nov 13, 2027 → Nov 20, 2027 • San Juan ↔

Lowest in 180 days $142 below typical ↘

From $676

$676 · $97/night · good value · ↓17% below typical

$97/night

Good value

↓17% below typical

Queen Elizabeth • Cunard Line

12-night Eastern Caribbean Loop via San Juan, Cruz Bay, Saint John & Castries

Oct 15, 2026 → Oct 27, 2026 • Miami ↔

$412 below typical ↗

From $996

$996 · $83/night · great deal · ↓29% below typical

$83/night

Great deal

↓29% below typical

Nieuw Amsterdam • Holland America

21-night Transatlantic Crossing via Philipsburg, Fort-de-France & Bridgetown

Nov 29, 2026 → Dec 20, 2026 • Fort Lauderdale ↔

Lowest in 30 days $468 below typical

From $2,139

$2,139 · $102/night · good value · ↓18% below typical

$102/night

Good value

↓18% 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