Jibhop

Scarlet Lady • Virgin Voyages

7-night Southern Caribbean Loop via Tortola, Bridgetown & Castries

Nov 27, 2027 → Dec 4, 2027 • San Juan ↔

Lowest in 180 days $70 below typical

From $763

$763 · $109/night · typical price · ↓8% below typical

$109/night

Typical price

↓8% below typical

Carnival Firenze • Carnival Cruise Line

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

Apr 4, 2027 → Apr 11, 2027 • Miami ↔

$79 below typical

From $508

$508 · $73/night · good value · ↓13% below typical

$73/night

Good value

↓13% 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

$966 below typical

From $4,591

$4,591 · $656/night · good value · ↓17% below typical

$656/night

Good value

↓17% below typical

Rhapsody of the Seas • Royal Caribbean International

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

Nov 7, 2026 → Nov 14, 2026 • San Juan ↔

$104 below typical

From $568

$568 · $81/night · good value · ↓16% below typical

$81/night

Good value

↓16% 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

MSC Meraviglia • MSC Cruises

14-night Eastern Caribbean Loop via San Juan, Basseterre, Saint Kitts & Ocean Cay

Dec 5, 2026 → Dec 19, 2026 • Miami ↔

From $1,116

$1,116 · $80/night · great deal · ↓42% below typical

$80/night

Great deal

↓42% below typical

Norwegian Getaway • Norwegian Cruise Line

8-night Eastern Caribbean Loop via Puerto Plata, San Juan & Great Stirrup Cay

Dec 14, 2026 → Dec 22, 2026 • Port Canaveral ↔

Lowest in 30 days $100 below typical

From $829

$829 · $104/night · good value · ↓11% below typical

$104/night

Good value

↓11% below typical

Crown Princess • Princess Cruises

7-night ABC Islands One-Way via Philipsburg & Oranjestad

Mar 28, 2027 → Apr 4, 2027 • San Juan → Fort Lauderdale

From $685

$685 · $98/night · great deal · ↓32% below typical

$98/night

Great deal

↓32% below typical

Crown Princess • Princess Cruises

9-night ABC Islands One-Way via San Juan & Philipsburg

Mar 26, 2027 → Apr 4, 2027 • Bridgetown → Fort Lauderdale

From $881

$881 · $98/night · great deal · ↓32% below typical

$98/night

Great deal

↓32% below typical

Vision of the Seas • Royal Caribbean International

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

Dec 13, 2026 → Dec 20, 2026 • San Juan ↔

$103 below typical ↘

From $541

$541 · $77/night · good value · ↓16% below typical

$77/night

Good value

↓16% below typical

Caribbean Princess • Princess Cruises

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

Jul 26, 2026 → Aug 9, 2026 • Port Canaveral ↔

37% below typical

From $1,396

$1,396 · $100/night · great deal · ↓37% below typical

$100/night

Great deal

↓37% 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 Road Bay & Saint John's

Dec 13, 2026 → Dec 20, 2026 • San Juan → Miami

Lowest in 90 days $401 below typical ↘

From $4,480

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

$640/night

Typical price

↓8% below typical

Grandeur of the Seas • Royal Caribbean International

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

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

Lowest in 180 days $67 below typical

From $632

$632 · $90/night · typical price · ↓10% below typical

$90/night

Typical price

↓10% 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

MSC World America • MSC Cruises

14-night Western Caribbean Loop via Roatán, Cozumel & Ocean Cay

Jan 2, 2027 → Jan 16, 2027 • Miami ↔

38% below typical

From $947

$947 · $68/night · great deal · ↓38% below typical

$68/night

Great deal

↓38% below typical

Rhapsody of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Tortola & Cruz Bay, Saint John

Sep 19, 2026 → Sep 26, 2026 • San Juan ↔

$149 below typical ↗

From $756

$756 · $108/night · good value · ↓16% below typical

$108/night

Good value

↓16% below typical

Brilliant Lady • Virgin Voyages

10-night Eastern Caribbean Loop via Philipsburg, Road Town, Tortola & Frederiksted, Saint Croix

Jan 11, 2027 → Jan 21, 2027 • Miami ↔

Lowest in 90 days $100 below typical

From $1,390

$1,390 · $139/night · typical price · ↓7% below typical

$139/night

Typical price

↓7% below typical

Resilient Lady • Virgin Voyages

8-night Eastern Caribbean Loop via Philipsburg & San Juan

Nov 20, 2027 → Nov 28, 2027 • Miami ↔

Lowest in 180 days $80 below typical

From $952

$952 · $119/night · typical price · ↓8% below typical

$119/night

Typical price

↓8% below typical

Brilliant Lady • Virgin Voyages

10-night Eastern Caribbean Loop via Philipsburg, Road Town, Tortola & Frederiksted, Saint Croix

Nov 30, 2026 → Dec 10, 2026 • Miami ↔

Lowest in 30 days $100 below typical

From $1,091

$1,091 · $109/night · typical price · ↓8% below typical

$109/night

Typical price

↓8% below typical