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

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 Bliss • Norwegian Cruise Line

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

Nov 29, 2026 → Dec 11, 2026 • New York ↔

$344 below typical

From $1,129

$1,129 · $94/night · great deal · ↓23% below typical

$94/night

Great deal

↓23% below typical

Independence of the Seas • Royal Caribbean International

9-night Eastern Caribbean Loop via Kings Wharf & Labadee

Jul 8, 2027 → Jul 17, 2027 • Cape Liberty, NJ (NYC) ↔

$391 below typical

From $1,457

$1,457 · $162/night · great deal · ↓21% below typical

$162/night

Great deal

↓21% below typical

Celebrity Ascent • Celebrity Cruises

10-night Eastern Caribbean Loop via Philipsburg, Castries & Bridgetown

Apr 7, 2028 → Apr 17, 2028 • Fort Lauderdale ↔

$396 below typical

From $1,465

$1,465 · $147/night · great deal · ↓21% below typical

$147/night

Great deal

↓21% below typical

MSC Meraviglia • MSC Cruises

8-night Eastern Caribbean Loop via Nassau & San Juan

Jan 30, 2027 → Feb 7, 2027 • Miami ↔

Great balance

From $579

$579 · $72/night · great deal · ↓43% below typical

$72/night

Great deal

↓43% below typical

MSC Meraviglia • MSC Cruises

8-night Eastern Caribbean Arc via Philipsburg & Saint John's

Mar 13, 2027 → Mar 21, 2027 • Miami ↔

From $709

$709 · $89/night · great deal · ↓42% below typical

$89/night

Great deal

↓42% below typical

Silver Dawn • Silversea Cruises

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

Mar 3, 2028 → Mar 14, 2028 • Miami ↔

From $6,300

$6,300 · $573/night · great deal · ↓37% below typical

$573/night

Great deal

↓37% below typical

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 · ↓37% below typical

$573/night

Great deal

↓37% below typical