Jibhop

Enchanted Princess • Princess Cruises

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

Dec 5, 2027 → Dec 14, 2027 • Fort Lauderdale ↔

From $985

$985 · $109/night · typical price · ↓8% below typical

$109/night

Typical price

↓8% below typical

MSC Opera • MSC Cruises

7-night Eastern Caribbean Loop via Catalina Island, Spanish Town & Philipsburg

Dec 13, 2027 → Dec 20, 2027 • La Romana ↔

Great balance

From $729

$729 · $104/night · good value · ↓12% below typical

$104/night

Good value

↓12% below typical

Emerald Princess • Princess Cruises

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

Nov 28, 2027 → Dec 12, 2027 • San Juan ↔

7% below typical

From $1,616

$1,616 · $115/night · typical price · ↓7% below typical

$115/night

Typical price

↓7% below typical

Rotterdam • Holland America

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

Jan 2, 2027 → Jan 23, 2027 • Fort Lauderdale ↔

$145 below typical

From $2,424

$2,424 · $115/night · typical price · ↓6% below typical

$115/night

Typical price

↓6% below typical

Carnival Pride • Carnival Cruise Line

12-night Southern Caribbean Loop via Philipsburg, Fort-de-France & Bridgetown

Nov 28, 2027 → Dec 10, 2027 • Baltimore ↔

From $1,410

$1,410 · $118/night · typical price · ↓4% below typical

$118/night

Typical price

↓4% below typical

Emerald Sakara • Emerald Cruises

14-night Eastern Caribbean Arc via Soufriere, Antigua & Road Bay

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

5% below typical

From $11,747

$11,747 · $839/night · typical price · ↓5% below typical

$839/night

Typical price

↓5% below typical

Regal Princess • Princess Cruises

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

Jan 9, 2028 → Jan 16, 2028 • Miami ↔

Great balance

From $783

$783 · $112/night · good value · ↓11% below typical

$112/night

Good value

↓11% below typical

Silver Dawn • Silversea Cruises

10-night Eastern Caribbean Loop via Jost Van Dyke, Basseterre, Saint Kitts & Saint-Barthélemy

Dec 11, 2027 → Dec 21, 2027 • San Juan ↔

From $5,800

$5,800 · $580/night · typical price · ↓8% below typical

$580/night

Typical price

↓8% below typical

MSC Seaview • MSC Cruises

7-night Eastern Caribbean Loop via Pointe-à-Pitre, Philipsburg & Saint John's

Jan 16, 2027 → Jan 23, 2027 • Fort-de-France ↔

Great balance

From $846

$846 · $121/night · good value · ↓11% below typical

$121/night

Good value

↓11% below typical

Carnival Venezia • Carnival Cruise Line

14-night Eastern Caribbean Loop via Saint Thomas, Antigua & Roseau

Nov 29, 2026 → Dec 13, 2026 • Port Canaveral ↔

From $1,025

$1,025 · $73/night · good value · ↓10% below typical

$73/night

Good value

↓10% below typical

Iona • P&O Cruises

14-night Eastern Caribbean Loop via Saint George's, Castries & Bridgetown

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

3% below typical

From $2,499

$2,499 · $179/night · typical price · ↓3% below typical

$179/night

Typical price

↓3% below typical

Star Princess • Princess Cruises

10-night Eastern Caribbean Loop via San Juan, Basseterre, Saint Kitts & Castries

Mar 19, 2028 → Mar 29, 2028 • Port Canaveral ↔

11% below typical

From $1,237

$1,237 · $124/night · good value · ↓11% below typical

$124/night

Good value

↓11% below typical

Emerald Kaia • Emerald Cruises

7-night Eastern Caribbean Arc via Basseterre, Saint Kitts, Deshaies & Saint-Barthélemy

Mar 11, 2028 → Mar 18, 2028 • Saint John's → San Juan

Great balance

From $6,484

$6,484 · $926/night · typical price · ↓4% below typical

$926/night

Typical price

↓4% below typical

Emerald Kaia • Emerald Cruises

7-night Eastern Caribbean Arc via Basseterre, Saint Kitts, Deshaies & Saint-Barthélemy

Mar 25, 2028 → Apr 1, 2028 • Saint John's → San Juan

Great balance

From $6,484

$6,484 · $926/night · typical price · ↓4% below typical

$926/night

Typical price

↓4% below typical

Iona • P&O Cruises

14-night Southern Caribbean Loop via Basseterre, Saint Kitts, Philipsburg & Fort-de-France

Dec 11, 2027 → Dec 25, 2027 • Bridgetown ↔

From $2,134

$2,134 · $152/night · typical price · ↓5% below typical

$152/night

Typical price

↓5% below typical

Emerald Princess • Princess Cruises

14-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Antigua

Feb 13, 2028 → Feb 27, 2028 • San Juan ↔

From $1,828

$1,828 · $131/night · typical price · ↓6% below typical

$131/night

Typical price

↓6% below typical

MSC Seashore • MSC Cruises

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

Feb 6, 2028 → Feb 20, 2028 • Miami ↔

8% below typical

From $1,338

$1,338 · $96/night · typical price · ↓8% below typical

$96/night

Typical price

↓8% below typical

Arvia • P&O Cruises

14-night Eastern Caribbean Loop via Castries, Saint George's & Bridgetown

Feb 6, 2027 → Feb 20, 2027 • Antigua ↔

5% below typical

From $2,363

$2,363 · $169/night · typical price · ↓5% below typical

$169/night

Typical price

↓5% below typical

MSC Opera • MSC Cruises

19-night Transatlantic Crossing via Barcelona, Tangier & Antigua

Nov 1, 2026 → Nov 20, 2026 • Marseille → Fort-de-France

From $1,554

$1,554 · $82/night · good value · ↓11% below typical

$82/night

Good value

↓11% below typical

MSC World Europa • MSC Cruises

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

Dec 6, 2026 → Dec 13, 2026 • Pointe-à-Pitre ↔

Great balance

From $1,069

$1,069 · $153/night · good value · ↓10% below typical

$153/night

Good value

↓10% below typical