Jibhop

Valiant Lady • Virgin Voyages

12-night Eastern Caribbean Arc via Kings Wharf, Bimini & Frederiksted, Saint Croix

Oct 19, 2026 → Oct 31, 2026 • New York → San Juan

Lowest in 90 days $616 below typical

From $1,068

$1,068 · $89/night · great deal · ↓37% below typical

$89/night

Great deal

↓37% below typical

SeaDream II • SeaDream Yacht Club

13-night Eastern Caribbean Arc via Philipsburg

Nov 14, 2026 → Nov 27, 2026 • Lisboa → San Juan

$7,246 below typical

From $5,078

$5,078 · $391/night · great deal · ↓59% below typical

$391/night

Great deal

↓59% below typical

Seabourn Quest • Seabourn

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

Nov 13, 2027 → Nov 23, 2027 • Miami ↔

Lowest in 180 days $2,603 below typical ↘

From $3,824

$3,824 · $382/night · great deal · ↓41% below typical

$382/night

Great deal

↓41% below typical

Seabourn Quest • Seabourn

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

Nov 23, 2027 → Dec 4, 2027 • Miami ↔

Lowest in 180 days $2,736 below typical ↘

From $4,334

$4,334 · $394/night · great deal · ↓39% below typical

$394/night

Great deal

↓39% below typical

Norwegian Sun • Norwegian Cruise Line

13-night Eastern Caribbean Arc via Kings Wharf, San Juan & Great Stirrup Cay

Oct 24, 2026 → Nov 6, 2026 • New York → Miami

Lowest in 30 days $888 below typical ↘

From $1,299

$1,299 · $100/night · great deal · ↓41% below typical

$100/night

Great deal

↓41% below typical

Queen Mary 2 • Cunard Line

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

Nov 17, 2026 → Nov 28, 2026 • New York ↔

Lowest in 180 days $582 below typical ↘

From $1,138

$1,138 · $103/night · great deal · ↓34% below typical

$103/night

Great deal

↓34% below typical

Norwegian Gem • Norwegian Cruise Line

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

Nov 28, 2026 → Dec 10, 2026 • Tampa ↔

Lowest in 30 days $588 below typical ↘

From $1,119

$1,119 · $93/night · great deal · ↓34% below typical

$93/night

Great deal

↓34% below typical

Zuiderdam • Holland America

11-night Eastern Caribbean Loop via Philipsburg, Antigua & Fort-de-France

Oct 31, 2026 → Nov 11, 2026 • Miami ↔

$952 below typical

From $1,294

$1,294 · $118/night · great deal · ↓42% below typical

$118/night

Great deal

↓42% below typical

Seabourn Ovation • Seabourn

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

Nov 20, 2026 → Nov 28, 2026 • Miami → Bridgetown

Lowest in 180 days $1,400 below typical ↘

From $3,399

$3,399 · $425/night · great deal · ↓29% below typical

$425/night

Great deal

↓29% below typical

Carnival Festivale • Carnival Cruise Line

8-night Eastern Caribbean Loop via Saint Thomas & Celebration Key

Aug 21, 2027 → Aug 29, 2027 • Port Canaveral ↔

$418 below typical

From $1,001

$1,001 · $125/night · great deal · ↓29% below typical

$125/night

Great deal

↓29% below typical

Carnival Freedom • Carnival Cruise Line

8-night Eastern Caribbean Loop via Puerto Plata & Grand Turk Island

Mar 4, 2028 → Mar 12, 2028 • Norfolk ↔

Lowest in 90 days $158 below typical

From $689

$689 · $86/night · good value · ↓19% below typical

$86/night

Good value

↓19% 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

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

Resilient Lady • Virgin Voyages

8-night Eastern Caribbean Loop via Philipsburg & San Juan

Dec 4, 2027 → Dec 12, 2027 • Miami ↔

Lowest in 180 days $240 below typical

From $952

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

$119/night

Great deal

↓20% below typical

Norwegian Escape • Norwegian Cruise Line

10-night Eastern Caribbean Loop via San Juan, Philipsburg & Saint Thomas

Aug 19, 2026 → Aug 29, 2026 • New York ↔

Lowest in 180 days $259 below typical

From $1,239

$1,239 · $124/night · good value · ↓17% below typical

$124/night

Good value

↓17% 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

Norwegian Dawn • Norwegian Cruise Line

9-night Eastern Caribbean Loop via Freeport, Grand Bahama, Great Stirrup Cay & San Juan

Dec 9, 2027 → Dec 18, 2027 • Jacksonville ↔

Lowest in 30 days $236 below typical

From $999

$999 · $111/night · good value · ↓19% below typical

$111/night

Good value

↓19% below typical

Norwegian Epic • Norwegian Cruise Line

10-night Itinerary DOPOP-PRSJU-VGTOV-KNBAS-SXPHI-VISTT-BSGSC

Dec 10, 2027 → Dec 20, 2027 • Port Canaveral ↔

Lowest in 90 days $257 below typical ↘

From $1,099

$1,099 · $110/night · good value · ↓19% below typical

$110/night

Good value

↓19% below typical

Explora III

9-night Eastern Caribbean Loop via Puerto Plata, San Juan & Road Bay

Feb 19, 2027 → Feb 28, 2027 • Miami ↔

Lowest in 180 days $930 below typical ↘

From $5,640

$5,640 · $627/night · good value · ↓14% below typical

$627/night

Good value

↓14% 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