Jibhop

Disney Treasure • Disney Cruise Line

7-night Eastern Caribbean Loop via Tortola & Disney Castaway Cay

Sep 11, 2027 → Sep 18, 2027 • Port Canaveral ↔

Lowest in 90 days $268 below typical

From $2,036

$2,036 · $291/night · good value · ↓12% below typical

$291/night

Good value

↓12% below typical

Rhapsody of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Tortola, Philipsburg & Saint John's

Nov 28, 2026 → Dec 5, 2026 • San Juan ↔

$153 below typical ↘

From $572

$572 · $82/night · great deal · ↓21% below typical

$82/night

Great deal

↓21% below typical

Scarlet Lady • Virgin Voyages

7-night Eastern Caribbean Loop via Philipsburg & Saint John's

Dec 11, 2027 → Dec 18, 2027 • San Juan ↔

Lowest in 180 days $147 below typical

From $833

$833 · $119/night · good value · ↓15% below typical

$119/night

Good value

↓15% below typical

MSC Meraviglia • MSC Cruises

14-night Eastern Caribbean Loop via Grand Turk Island, Ocean Cay & Philipsburg

Nov 15, 2026 → Nov 29, 2026 • Miami ↔

68% below typical

From $398

$398 · $28/night · great deal · ↓68% below typical

$28/night

Great deal

↓68% below typical

Iona • P&O Cruises

14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg

Feb 4, 2028 → Feb 18, 2028 • Bridgetown ↔

Lowest in 180 days $279 below typical ↘

From $2,336

$2,336 · $167/night · good value · ↓11% below typical

$167/night

Good value

↓11% below typical

Enchanted Princess • Princess Cruises

10-night Eastern Caribbean Loop via Princess Cays, Puerto Plata & San Juan

Dec 17, 2026 → Dec 27, 2026 • Fort Lauderdale ↔

Lowest in 180 days $240 below typical

From $953

$953 · $95/night · great deal · ↓20% below typical

$95/night

Great deal

↓20% below typical

Iona • P&O Cruises

14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg

Jan 7, 2028 → Jan 21, 2028 • Bridgetown ↔

Lowest in 180 days $211 below typical ↘

From $2,363

$2,363 · $169/night · typical price · ↓8% below typical

$169/night

Typical price

↓8% below typical

Iona • P&O Cruises

14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg

Jan 8, 2028 → Jan 22, 2028 • Bridgetown ↔

Lowest in 180 days $211 below typical ↘

From $2,363

$2,363 · $169/night · typical price · ↓8% below typical

$169/night

Typical price

↓8% below typical

Icon of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Philipsburg & Coco Cay

Nov 7, 2026 → Nov 14, 2026 • Miami ↔

$285 below typical

From $1,349

$1,349 · $193/night · good value · ↓17% below typical

$193/night

Good value

↓17% below typical

Icon of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Philipsburg & Coco Cay

Feb 27, 2027 → Mar 6, 2027 • Miami ↔

Lowest in 30 days $194 below typical ↘

From $1,423

$1,423 · $203/night · good value · ↓12% below typical

$203/night

Good value

↓12% 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 $102 below typical ↘

From $716

$716 · $102/night · good value · ↓12% below typical

$102/night

Good value

↓12% below typical

Seabourn Ovation • Seabourn

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

Jan 30, 2027 → Feb 6, 2027 • Philipsburg → Bridgetown

Lowest in 180 days $600 below typical ↘

From $4,198

$4,198 · $600/night · good value · ↓13% below typical

$600/night

Good value

↓13% below typical

Seabourn Ovation • Seabourn

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

Nov 20, 2026 → Dec 5, 2026 • Miami → Philipsburg

$1,801 below typical

From $7,198

$7,198 · $480/night · great deal · ↓20% below typical

$480/night

Great deal

↓20% below typical

Seven Seas Splendor • Regent Seven Seas Cruises

17-night Eastern Caribbean Loop via Montego Bay, Ocho Rios & San Juan

Dec 11, 2026 → Dec 28, 2026 • Houston ↔

From $7,334

$7,334 · $431/night · great deal · ↓49% below typical

$431/night

Great deal

↓49% below typical

Icon of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Philipsburg & Coco Cay

Jan 30, 2027 → Feb 6, 2027 • Miami ↔

$283 below typical

From $1,334

$1,334 · $191/night · good value · ↓18% below typical

$191/night

Good value

↓18% below typical

MSC Opera • MSC Cruises

7-night Eastern Caribbean Loop: Catalina Island, Bridgetown & Fort-de-France

Feb 8, 2027 → Feb 15, 2027 • La Romana ↔

Great balance

From $579

$579 · $83/night · great deal · ↓34% below typical

$83/night

Great deal

↓34% below typical

MSC Opera • MSC Cruises

7-night Eastern Caribbean Loop via Spanish Town, Philipsburg & Basseterre, Saint Kitts

Feb 15, 2027 → Feb 22, 2027 • La Romana ↔

Great balance

From $579

$579 · $83/night · great deal · ↓34% below typical

$83/night

Great deal

↓34% below typical

MSC Opera • MSC Cruises

7-night Eastern Caribbean Loop via Catalina Island, Bridgetown & Fort-de-France

Feb 22, 2027 → Mar 1, 2027 • La Romana ↔

Great balance

From $579

$579 · $83/night · great deal · ↓34% below typical

$83/night

Great deal

↓34% below typical

MSC Opera • MSC Cruises

14-night Eastern Caribbean Loop via Catalina Island, Oranjestad & Willemstad

Dec 6, 2027 → Dec 20, 2027 • La Romana ↔

56% below typical

From $729

$729 · $52/night · great deal · ↓56% below typical

$52/night

Great deal

↓56% below typical

Carnival Magic • Carnival Cruise Line

6-night Eastern Caribbean Loop via Celebration Key & Puerto Plata

Oct 25, 2026 → Oct 31, 2026 • Miami ↔

Lowest in 30 days $59 below typical ↘

From $375

$375 · $63/night · good value · ↓14% below typical

$63/night

Good value

↓14% below typical