Jibhop

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

Brilliant Lady • Virgin Voyages

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

Mar 8, 2027 → Mar 18, 2027 • Miami ↔

Lowest in 90 days $100 below typical

From $1,091

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

$109/night

Typical price

↓8% below typical

Queen Mary 2 • Cunard Line

21-night Southern Caribbean Arc via New York, Road Town, Tortola & Philipsburg

Dec 12, 2026 → Jan 2, 2027 • Southampton → New York

Lowest in 180 days $324 below typical

From $3,289

$3,289 · $157/night · typical price · ↓9% below typical

$157/night

Typical price

↓9% below typical

Carnival Firenze • Carnival Cruise Line

14-night Eastern Caribbean Loop via Saint Thomas, Antigua & Fort-de-France

Jan 23, 2028 → Feb 6, 2028 • Port Canaveral ↔

Lowest in 30 days $107 below typical

From $1,032

$1,032 · $74/night · typical price · ↓9% below typical

$74/night

Typical price

↓9% below typical

Vision of the Seas • Royal Caribbean International

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

Nov 15, 2026 → Nov 22, 2026 • San Juan ↔

$95 below typical ↗

From $599

$599 · $86/night · good value · ↓14% below typical

$86/night

Good value

↓14% below typical

MSC Meraviglia • MSC Cruises

8-night Eastern Caribbean Arc via Philipsburg & Saint John's

Feb 27, 2027 → Mar 7, 2027 • Miami ↔

Great balance

From $880

$880 · $110/night · great deal · ↓33% below typical

$110/night

Great deal

↓33% below typical

Grandeur of the Seas • Royal Caribbean International

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

Jun 5, 2027 → Jun 12, 2027 • San Juan ↔

Lowest in 180 days $83 below typical ↘

From $886

$886 · $127/night · typical price · ↓9% below typical

$127/night

Typical price

↓9% below typical

Brilliant Lady • Virgin Voyages

10-night Eastern Caribbean Loop via Philipsburg, Road Town, Tortola & Basseterre, Saint Kitts

Jan 25, 2027 → Feb 4, 2027 • Miami ↔

Lowest in 30 days $99 below typical

From $1,191

$1,191 · $119/night · typical price · ↓8% below typical

$119/night

Typical price

↓8% below typical

Carnival Miracle • Carnival Cruise Line

9-night Eastern Caribbean Loop via Puerto Plata & San Juan

Jan 27, 2028 → Feb 5, 2028 • Baltimore ↔

Lowest in 180 days $91 below typical

From $898

$898 · $100/night · typical price · ↓9% below typical

$100/night

Typical price

↓9% below typical

Seabourn Ovation • Seabourn

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

Jan 9, 2027 → Jan 16, 2027 • Bridgetown → Philipsburg

Lowest in 180 days $350 below typical ↘

From $4,249

$4,249 · $607/night · typical price · ↓8% below typical

$607/night

Typical price

↓8% below typical

Scarlet Lady • Virgin Voyages

7-night Eastern Caribbean Loop via Oranjestad & Castries

Mar 18, 2028 → Mar 25, 2028 • San Juan ↔

Lowest in 180 days $70 below typical

From $903

$903 · $129/night · typical price · ↓7% below typical

$129/night

Typical price

↓7% below typical

Scarlet Lady • Virgin Voyages

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

Mar 25, 2028 → Apr 1, 2028 • San Juan ↔

Lowest in 180 days $70 below typical

From $903

$903 · $129/night · typical price · ↓7% below typical

$129/night

Typical price

↓7% below typical

Seabourn Ovation • Seabourn

14-night Eastern Caribbean Loop via Castries, Little Bay & South Friars Bay

Dec 19, 2026 → Jan 2, 2027 • Bridgetown ↔

Lowest in 180 days $572 below typical ↘

From $7,224

$7,224 · $516/night · typical price · ↓7% below typical

$516/night

Typical price

↓7% below typical

MSC World Europa • MSC Cruises

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

Jan 30, 2027 → Feb 6, 2027 • Fort-de-France ↔

Great balance

From $643

$643 · $92/night · great deal · ↓32% below typical

$92/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

Feb 7, 2027 → Feb 14, 2027 • San Juan ↔

$96 below typical

From $549

$549 · $78/night · good value · ↓15% below typical

$78/night

Good value

↓15% below typical

Rhapsody of the Seas • Royal Caribbean International

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

Jan 16, 2027 → Jan 23, 2027 • San Juan ↔

$95 below typical

From $549

$549 · $78/night · good value · ↓15% below typical

$78/night

Good value

↓15% below typical

MSC Meraviglia • MSC Cruises

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

Mar 27, 2027 → Apr 4, 2027 • Miami ↔

Great balance

From $784

$784 · $98/night · great deal · ↓35% below typical

$98/night

Great deal

↓35% below typical

Enchanted Princess • Princess Cruises

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

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

31% below typical

From $1,153

$1,153 · $115/night · great deal · ↓31% below typical

$115/night

Great deal

↓31% below typical

Rhapsody of the Seas • Royal Caribbean International

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

Mar 25, 2028 → Apr 1, 2028 • San Juan ↔

Lowest in 180 days

From $787

$787 · $112/night · typical price · ↓4% below typical

$112/night

Typical price

↓4% below typical

Queen Mary 2 • Cunard Line

13-night Eastern Caribbean Loop via Saint Thomas, Basseterre, Saint Kitts & Castries

Nov 19, 2027 → Dec 2, 2027 • New York ↔

Lowest in 180 days $170 below typical

From $1,863

$1,863 · $143/night · typical price · ↓8% below typical

$143/night

Typical price

↓8% below typical