Jibhop

Regal Princess • Princess Cruises

8-night Eastern Caribbean Loop via Philipsburg & San Juan

Oct 31, 2026 → Nov 8, 2026 • Fort Lauderdale ↔

Great balance

From $807

$807 · $101/night · great deal · ↓41% below typical

$101/night

Great deal

↓41% below typical

Arvia • P&O Cruises

16-night Transatlantic Crossing via Bridgetown, Fort-de-France & Basseterre, Saint Kitts

Mar 12, 2027 → Mar 28, 2027 • Bridgetown → Southampton

$290 below typical ↗

From $1,715

$1,715 · $107/night · good value · ↓14% below typical

$107/night

Good value

↓14% below typical

Grandeur of the Seas • Royal Caribbean International

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

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

Lowest in 180 days $99 below typical

From $887

$887 · $127/night · good value · ↓10% below typical

$127/night

Good value

↓10% below typical

Queen Elizabeth • Cunard Line

21-night Western Caribbean Loop via Cruz Bay, Saint John, Montego Bay & Cozumel

Nov 26, 2026 → Dec 17, 2026 • Miami ↔

$353 below typical ↗

From $1,797

$1,797 · $86/night · good value · ↓16% below typical

$86/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

Jun 12, 2027 → Jun 19, 2027 • San Juan ↔

Lowest in 180 days $99 below typical ↘

From $906

$906 · $129/night · typical price · ↓10% below typical

$129/night

Typical price

↓10% below typical

Scarlet Lady • Virgin Voyages

7-night ABC Islands Loop via Oranjestad & Cruz Bay, Saint John

Nov 20, 2027 → Nov 27, 2027 • San Juan ↔

Lowest in 180 days $70 below typical

From $763

$763 · $109/night · typical price · ↓8% below typical

$109/night

Typical price

↓8% below typical

Scarlet Lady • Virgin Voyages

7-night Southern Caribbean Loop via Tortola, Bridgetown & Castries

Nov 27, 2027 → Dec 4, 2027 • San Juan ↔

Lowest in 180 days $70 below typical

From $763

$763 · $109/night · typical price · ↓8% below typical

$109/night

Typical price

↓8% below typical

MSC Opera • MSC Cruises

18-night Transatlantic Crossing via Civitavecchia, Livorno & Marseille

Oct 29, 2026 → Nov 16, 2026 • Civitavecchia (Rome) → La Romana

From $1,045

$1,045 · $58/night · great deal · ↓38% below typical

$58/night

Great deal

↓38% below typical

Rhapsody of the Seas • Royal Caribbean International

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

Nov 7, 2026 → Nov 14, 2026 • San Juan ↔

$104 below typical

From $568

$568 · $81/night · good value · ↓16% below typical

$81/night

Good value

↓16% below typical

Explora III

8-night Eastern Caribbean Loop via Philipsburg, Terre-de-Haut & Road Bay

Jan 13, 2027 → Jan 21, 2027 • San Juan → Miami

Lowest in 90 days $457 below typical ↘

From $5,440

$5,440 · $680/night · typical price · ↓8% below typical

$680/night

Typical price

↓8% below typical

Seabourn Ovation • Seabourn

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

Dec 4, 2027 → Dec 11, 2027 • Philipsburg → Bridgetown

Lowest in 180 days $329 below typical ↘

From $3,569

$3,569 · $510/night · typical price · ↓8% below typical

$510/night

Typical price

↓8% below typical

Seabourn Ovation • Seabourn

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

Mar 13, 2027 → Mar 27, 2027 • Bridgetown ↔

Lowest in 30 days $804 below typical ↘

From $7,394

$7,394 · $528/night · typical price · ↓10% below typical

$528/night

Typical price

↓10% below typical

Silver Nova • Silversea Cruises

15-night Eastern Caribbean Arc via Gibraltar & Philipsburg

Dec 3, 2027 → Dec 18, 2027 • Lisboa → Miami

$1,673 below typical ↗

From $9,100

$9,100 · $607/night · good value · ↓16% below typical

$607/night

Good value

↓16% below typical

Volendam • Holland America

27-night Fort Lauderdale → Philipsburg → Sint-Maarten Apt → Port de Fort-de-France Pt. + 16 more

Nov 25, 2026 → Dec 22, 2026 • Fort Lauderdale ↔

26% below typical

From $4,834

$4,834 · $179/night · great deal · ↓26% below typical

$179/night

Great deal

↓26% below typical

Celebrity Ascent • Celebrity Cruises

10-night Eastern Caribbean Loop via Philipsburg, Castries & Bridgetown

Nov 12, 2027 → Nov 22, 2027 • Fort Lauderdale ↔

$320 below typical

From $1,540

$1,540 · $154/night · good value · ↓17% below typical

$154/night

Good value

↓17% below typical

Icon of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Philipsburg & Coco Cay

Dec 5, 2026 → Dec 12, 2026 • Miami ↔

$230 below typical

From $1,384

$1,384 · $198/night · good value · ↓14% below typical

$198/night

Good value

↓14% below typical

Crown Princess • Princess Cruises

7-night ABC Islands One-Way via Philipsburg & Oranjestad

Mar 28, 2027 → Apr 4, 2027 • San Juan → Fort Lauderdale

From $685

$685 · $98/night · great deal · ↓32% below typical

$98/night

Great deal

↓32% below typical

Crown Princess • Princess Cruises

9-night ABC Islands One-Way via San Juan & Philipsburg

Mar 26, 2027 → Apr 4, 2027 • Bridgetown → Fort Lauderdale

From $881

$881 · $98/night · great deal · ↓32% below typical

$98/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

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

$103 below typical ↘

From $541

$541 · $77/night · good value · ↓16% below typical

$77/night

Good value

↓16% below typical

MSC Meraviglia • MSC Cruises

14-night Eastern Caribbean Loop via Philipsburg, Saint John's & Ocean Cay

Mar 13, 2027 → Mar 27, 2027 • Miami ↔

From $1,306

$1,306 · $93/night · great deal · ↓39% below typical

$93/night

Great deal

↓39% below typical