Jibhop

Crown Princess • Princess Cruises

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

Jan 24, 2027 → Jan 31, 2027 • San Juan ↔

Great balance

From $788

$788 · $113/night · great deal · ↓26% below typical

$113/night

Great deal

↓26% below typical

Emerald Princess • Princess Cruises

14-night Eastern Caribbean Arc via Tortola, Basseterre, Saint Kitts & Fort-de-France

Dec 12, 2027 → Dec 26, 2027 • San Juan ↔

From $1,516

$1,516 · $108/night · great deal · ↓22% below typical

$108/night

Great deal

↓22% below typical

Nieuw Statendam • Holland America

7-night Eastern Caribbean Loop: Grand Turk Island & San Juan

Jan 24, 2027 → Jan 31, 2027 • Fort Lauderdale ↔

Lowest in 30 days $50 below typical ↘

From $894

$894 · $128/night · typical price · ↓5% below typical

$128/night

Typical price

↓5% below typical

Disney Fantasy • Disney Cruise Line

10-night Eastern Caribbean Loop via Philipsburg, Castries & Disney Castaway Cay

Jul 11, 2027 → Jul 21, 2027 • Port Canaveral ↔

Lowest in 180 days

From $4,049

$4,049 · $405/night · typical price · ↓3% below typical

$405/night

Typical price

↓3% below typical

Allure of the Seas • Royal Caribbean International

8-night Eastern Caribbean Loop via Basseterre, Saint Kitts & Coco Cay

Aug 22, 2026 → Aug 30, 2026 • Fort Lauderdale ↔

$147 below typical ↗

From $1,157

$1,157 · $145/night · good value · ↓11% below typical

$145/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 ↔

20% below typical

From $953

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

$95/night

Great deal

↓20% below typical

Rhapsody of the Seas • Royal Caribbean International

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

Dec 5, 2026 → Dec 12, 2026 • San Juan ↔

$80 below typical ↗

From $619

$619 · $88/night · good value · ↓12% below typical

$88/night

Good value

↓12% below typical

Crown Princess • Princess Cruises

7-night Southern Caribbean Arc via Philipsburg, Fort-de-France & Roseau

Feb 28, 2027 → Mar 7, 2027 • San Juan ↔

22% below typical

From $743

$743 · $106/night · great deal · ↓22% below typical

$106/night

Great deal

↓22% below typical

Silver Shadow • Silversea Cruises

10-night Eastern Caribbean Loop via San Juan & Saint-Barthélemy

Nov 30, 2026 → Dec 10, 2026 • Miami ↔

From $6,500

$6,500 · $650/night · great deal · ↓22% below typical

$650/night

Great deal

↓22% below typical

Vision of the Seas • Royal Caribbean International

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

Nov 29, 2026 → Dec 6, 2026 • San Juan ↔

$72 below typical ↗

From $601

$601 · $86/night · good value · ↓11% below typical

$86/night

Good value

↓11% below typical

Silver Shadow • Silversea Cruises

12-night Eastern Caribbean Loop via George Town, Great Exuma Island, Samana & San Juan

Dec 24, 2027 → Jan 5, 2028 • Miami ↔

From $7,000

$7,000 · $583/night · good value · ↓19% below typical

$583/night

Good value

↓19% below typical

Explora III

7-night Eastern Caribbean Arc via Cruz Bay, Saint John & Terre-de-Haut

Mar 29, 2027 → Apr 5, 2027 • Miami → San Juan

$572 below typical ↘

From $4,875

$4,875 · $696/night · good value · ↓11% below typical

$696/night

Good value

↓11% below typical

Rhapsody of the Seas • Royal Caribbean International

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

Oct 24, 2026 → Oct 31, 2026 • San Juan ↔

$80 below typical

From $615

$615 · $88/night · good value · ↓11% below typical

$88/night

Good value

↓11% below typical

Crown Princess • Princess Cruises

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

Feb 21, 2027 → Mar 7, 2027 • San Juan ↔

From $1,426

$1,426 · $102/night · great deal · ↓25% below typical

$102/night

Great deal

↓25% below typical

Star Princess • Princess Cruises

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

Dec 12, 2027 → Dec 22, 2027 • Port Canaveral ↔

25% below typical

From $937

$937 · $94/night · great deal · ↓25% below typical

$94/night

Great deal

↓25% below typical

Norwegian Pearl • Norwegian Cruise Line

10-night Eastern Caribbean Loop via Tortola & Saint Thomas

Jan 23, 2027 → Feb 2, 2027 • Philadelphia ↔

Lowest in 30 days ↘

From $909

$909 · $91/night · typical price · ↓5% below typical

$91/night

Typical price

↓5% below typical

Vision of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Tortola, Cruz Bay, Saint John & Philipsburg

Dec 6, 2026 → Dec 13, 2026 • San Juan ↔

$90 below typical ↗

From $659

$659 · $94/night · good value · ↓12% below typical

$94/night

Good value

↓12% below typical

Explora I • Explora Journeys

16-night Eastern Caribbean Arc via Philipsburg, Saint John's & Little Bay

Jan 4, 2027 → Jan 20, 2027 • San Juan → Miami

$640 below typical

From $8,960

$8,960 · $560/night · typical price · ↓7% below typical

$560/night

Typical price

↓7% below typical

Norwegian Prima • Norwegian Cruise Line

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

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

Lowest in 30 days

From $1,419

$1,419 · $203/night · typical price · ↓5% below typical

$203/night

Typical price

↓5% below typical

Emerald Kaia • Emerald Cruises

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

Nov 27, 2027 → Dec 4, 2027 • Saint John's → San Juan

$636 below typical

From $6,151

$6,151 · $879/night · typical price · ↓9% below typical

$879/night

Typical price

↓9% below typical