Jibhop

Enchanted Princess • Princess Cruises

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

Mar 7, 2027 → Mar 17, 2027 • Fort Lauderdale ↔

40% below typical

From $998

$998 · $100/night · great deal · ↓40% below typical

$100/night

Great deal

↓40% below typical

MSC Meraviglia • MSC Cruises

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

Feb 7, 2027 → Feb 21, 2027 • Miami ↔

48% below typical

From $1,196

$1,196 · $85/night · great deal · ↓48% below typical

$85/night

Great deal

↓48% below typical

MSC Meraviglia • MSC Cruises

14-night Eastern Caribbean Loop via Nassau, San Juan & Ocean Cay

Jan 30, 2027 → Feb 13, 2027 • Miami ↔

From $1,066

$1,066 · $76/night · great deal · ↓40% below typical

$76/night

Great deal

↓40% below typical

Grandeur of the Seas • Royal Caribbean International

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

Oct 2, 2027 → Oct 9, 2027 • San Juan ↔

Lowest in 180 days $86 below typical

From $731

$731 · $104/night · good value · ↓11% below typical

$104/night

Good value

↓11% below typical

MSC Opera • MSC Cruises

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

Aug 23, 2027 → Aug 30, 2027 • La Romana ↔

Great balance

From $709

$709 · $101/night · great deal · ↓41% below typical

$101/night

Great deal

↓41% below typical

Oceania Sonata • Oceania Cruises

44-night Eastern Caribbean Arc via Puerto Quetzal, Panama Canal & Cozumel

Jan 6, 2028 → Feb 19, 2028 • Los Angeles → Miami

Lowest in 180 days $1,173 below typical

From $20,549

$20,549 · $467/night · typical price · ↓5% below typical

$467/night

Typical price

↓5% below typical

Icon of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Philipsburg & Coco Cay

Mar 13, 2027 → Mar 20, 2027 • Miami ↔

Lowest in 180 days $153 below typical

From $1,454

$1,454 · $208/night · typical price · ↓10% below typical

$208/night

Typical price

↓10% below typical

MSC Meraviglia • MSC Cruises

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

Jan 2, 2027 → Jan 16, 2027 • Miami ↔

43% below typical

From $1,016

$1,016 · $73/night · great deal · ↓43% below typical

$73/night

Great deal

↓43% below typical

MSC Meraviglia • MSC Cruises

14-night Eastern Caribbean Loop via Nassau, Ocean Cay & Puerto Plata

Jan 24, 2027 → Feb 7, 2027 • Miami ↔

From $1,016

$1,016 · $73/night · great deal · ↓43% below typical

$73/night

Great deal

↓43% below typical

MSC Meraviglia • MSC Cruises

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

Jan 10, 2027 → Jan 24, 2027 • Miami ↔

From $1,096

$1,096 · $78/night · great deal · ↓38% below typical

$78/night

Great deal

↓38% below typical

Star of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Coco Cay & Charlotte Amalie, Saint Thomas

Jan 23, 2028 → Jan 30, 2028 • Port Canaveral ↔

Lowest in 180 days $147 below typical

From $1,323

$1,323 · $189/night · good value · ↓10% below typical

$189/night

Good value

↓10% below typical

Allure of the Seas • Royal Caribbean International

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

Mar 28, 2027 → Apr 4, 2027 • Miami ↔

Lowest in 180 days $103 below typical ↘

From $997

$997 · $142/night · typical price · ↓9% below typical

$142/night

Typical price

↓9% below typical

Seabourn Ovation • Seabourn

7-night Eastern Caribbean Arc via Castries, Little Bay & South Friars Bay

Nov 27, 2027 → Dec 4, 2027 • Bridgetown → Philipsburg

Lowest in 90 days $460 below typical ↘

From $3,739

$3,739 · $534/night · good value · ↓11% below typical

$534/night

Good value

↓11% below typical

Carnival Magic • Carnival Cruise Line

8-night Eastern Caribbean Loop via Half Moon Cay & San Juan

Oct 31, 2026 → Nov 8, 2026 • Miami ↔

$107 below typical ↘

From $567

$567 · $71/night · good value · ↓16% below typical

$71/night

Good value

↓16% below typical

Grandeur of the Seas • Royal Caribbean International

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

Oct 30, 2027 → Nov 6, 2027 • San Juan ↔

Lowest in 180 days $80 below typical

From $738

$738 · $105/night · typical price · ↓10% below typical

$105/night

Typical price

↓10% below typical

Grandeur of the Seas • Royal Caribbean International

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

Jun 19, 2027 → Jun 26, 2027 • San Juan ↔

Lowest in 180 days $102 below typical ↘

From $866

$866 · $124/night · good value · ↓11% below typical

$124/night

Good value

↓11% below typical

Queen Mary 2 • Cunard Line

20-night Southern Caribbean Arc via Saint Thomas, Basseterre, Saint Kitts & Castries

Nov 19, 2027 → Dec 9, 2027 • New York → Southampton

Lowest in 180 days $355 below typical

From $2,773

$2,773 · $139/night · good value · ↓11% below typical

$139/night

Good value

↓11% below typical

Carnival Magic • Carnival Cruise Line

8-night Eastern Caribbean Loop via Half Moon Cay & San Juan

Nov 28, 2026 → Dec 6, 2026 • Miami ↔

$106 below typical ↗

From $568

$568 · $71/night · good value · ↓16% below typical

$71/night

Good value

↓16% below typical

Allure of the Seas • Royal Caribbean International

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

Sep 19, 2026 → Sep 27, 2026 • Fort Lauderdale ↔

$114 below typical

From $909

$909 · $114/night · good value · ↓11% below typical

$114/night

Good value

↓11% below typical

Enchanted Princess • Princess Cruises

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

Jan 6, 2027 → Jan 16, 2027 • Fort Lauderdale ↔

From $823

$823 · $82/night · great deal · ↓31% below typical

$82/night

Great deal

↓31% below typical