Jibhop

Enchanted Princess • Princess Cruises

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

Dec 17, 2026 → Dec 27, 2026 • Fort Lauderdale ↔

Lowest in 180 days $240 below typical

From $953

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

$95/night

Great deal

↓20% below typical

Iona • P&O Cruises

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

Jan 7, 2028 → Jan 21, 2028 • Bridgetown ↔

Lowest in 180 days $211 below typical ↘

From $2,363

$2,363 · $169/night · typical price · ↓8% below typical

$169/night

Typical price

↓8% below typical

Iona • P&O Cruises

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

Jan 8, 2028 → Jan 22, 2028 • Bridgetown ↔

Lowest in 180 days $211 below typical ↘

From $2,363

$2,363 · $169/night · typical price · ↓8% below typical

$169/night

Typical price

↓8% 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 ↔

Lowest in 30 days $365 below typical

From $1,153

$1,153 · $115/night · great deal · ↓24% below typical

$115/night

Great deal

↓24% below typical

Icon of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Philipsburg & Coco Cay

Feb 27, 2027 → Mar 6, 2027 • Miami ↔

Lowest in 30 days $194 below typical ↘

From $1,423

$1,423 · $203/night · good value · ↓12% below typical

$203/night

Good value

↓12% below typical

Grandeur of the Seas • Royal Caribbean International

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

Nov 13, 2027 → Nov 20, 2027 • San Juan ↔

Lowest in 180 days $102 below typical ↘

From $716

$716 · $102/night · good value · ↓12% below typical

$102/night

Good value

↓12% below typical

Seabourn Ovation • Seabourn

7-night Southern Caribbean Arc via Tortola, South Friars Bay & Les Trois-Îlets

Jan 30, 2027 → Feb 6, 2027 • Philipsburg → Bridgetown

Lowest in 180 days $600 below typical ↘

From $4,198

$4,198 · $600/night · good value · ↓13% below typical

$600/night

Good value

↓13% below typical

Icon of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Philipsburg & Coco Cay

Oct 3, 2026 → Oct 10, 2026 • Miami ↔

$283 below typical ↘

From $1,350

$1,350 · $193/night · good value · ↓17% below typical

$193/night

Good value

↓17% below typical

Seabourn Ovation • Seabourn

15-night Eastern Caribbean Arc via South Friars Bay, Rodney Bay & Little Bay

Nov 20, 2026 → Dec 5, 2026 • Miami → Philipsburg

$1,801 below typical

From $7,198

$7,198 · $480/night · great deal · ↓20% below typical

$480/night

Great deal

↓20% below typical

Costa Fascinosa • Costa Cruises

14-night Itinerary ESAGP-ESLPA-GPPTP-SXPHI

Dec 6, 2026 → Dec 20, 2026 • Barcelona → La Romana

$393 below typical

From $1,484

$1,484 · $106/night · great deal · ↓21% below typical

$106/night

Great deal

↓21% below typical

Icon of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Philipsburg & Coco Cay

Jan 30, 2027 → Feb 6, 2027 • Miami ↔

$283 below typical

From $1,334

$1,334 · $191/night · good value · ↓18% below typical

$191/night

Good value

↓18% below typical

Seven Seas Splendor • Regent Seven Seas Cruises

17-night Eastern Caribbean Loop via Montego Bay, Ocho Rios & San Juan

Dec 11, 2026 → Dec 28, 2026 • Houston ↔

From $7,334

$7,334 · $431/night · great deal · ↓49% below typical

$431/night

Great deal

↓49% below typical

Sea Cloud Spirit • Sea Cloud Cruises

8-night Southern Caribbean Arc via Terre-de-Haut & Soufriere

Dec 12, 2027 → Dec 20, 2027 • Philipsburg → Willemstad

Lowest in 30 days $585 below typical

From $5,298

$5,298 · $662/night · typical price · ↓10% below typical

$662/night

Typical price

↓10% below typical

MSC Opera • MSC Cruises

17-night Transatlantic Crossing via Livorno, Marseille & Barcelona

Oct 30, 2026 → Nov 16, 2026 • Genova → La Romana

Lowest in 30 days $352 below typical

From $1,246

$1,246 · $73/night · great deal · ↓22% below typical

$73/night

Great deal

↓22% below typical

MSC Opera • MSC Cruises

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

Feb 15, 2027 → Feb 22, 2027 • La Romana ↔

Great balance

From $579

$579 · $83/night · great deal · ↓34% below typical

$83/night

Great deal

↓34% below typical

MSC Opera • MSC Cruises

14-night Eastern Caribbean Loop via Catalina Island, Oranjestad & Willemstad

Dec 6, 2027 → Dec 20, 2027 • La Romana ↔

56% below typical

From $729

$729 · $52/night · great deal · ↓56% below typical

$52/night

Great deal

↓56% below typical

Rotterdam • Holland America

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

Nov 21, 2026 → Dec 12, 2026 • Fort Lauderdale ↔

$607 below typical ↗

From $2,064

$2,064 · $98/night · great deal · ↓23% below typical

$98/night

Great deal

↓23% below typical

Seabourn Ovation • Seabourn

14-night Southern Caribbean Arc via Tortola, South Friars Bay & Les Trois-Îlets

Feb 19, 2028 → Mar 4, 2028 • Philipsburg ↔

Lowest in 30 days $1,101 below typical ↘

From $8,398

$8,398 · $600/night · good value · ↓12% below typical

$600/night

Good value

↓12% below typical

Hero Of The Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Philipsburg & Coco Cay

Aug 28, 2027 → Sep 4, 2027 • Miami ↔

Lowest in 180 days $248 below typical ↘

From $1,815

$1,815 · $259/night · good value · ↓12% below typical

$259/night

Good value

↓12% below typical

Vision of the Seas • Royal Caribbean International

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

Nov 8, 2026 → Nov 15, 2026 • San Juan ↔

$130 below typical ↘

From $574

$574 · $82/night · good value · ↓19% below typical

$82/night

Good value

↓19% below typical