Jibhop

MSC Seaview • MSC Cruises

14-night Eastern Caribbean Loop via Kingstown, Saint George & Fort-de-France

Feb 23, 2027 → Mar 9, 2027 • Bridgetown ↔

From $2,128

$2,128 · $152/night · typical price · ↑5% above typical

$152/night

Typical price

↑5% above typical

Silver Shadow • Silversea Cruises

10-night Southern Caribbean Arc via Port Elizabeth, Bequia, Saint George's & Castries

Feb 16, 2027 → Feb 26, 2027 • Bridgetown → San Juan

From $7,500

$7,500 · $750/night · typical price · ↑4% above typical

$750/night

Typical price

↑4% above typical

Emerald Princess • Princess Cruises

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

Mar 12, 2028 → Mar 26, 2028 • San Juan ↔

From $2,181

$2,181 · $156/night · typical price · ↑4% above typical

$156/night

Typical price

↑4% above typical

Rotterdam • Holland America

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

Mar 6, 2027 → Mar 27, 2027 • Fort Lauderdale ↔

↗

From $2,749

$2,749 · $131/night · typical price · ↑3% above typical

$131/night

Typical price

↑3% above typical

Celebrity Constellation • Celebrity Cruises

7-night Southern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Roseau

Jan 30, 2027 → Feb 6, 2027 • San Juan ↔

Great balance

From $724

$724 · $103/night · typical price · ↑2% above typical

$103/night

Typical price

↑2% above typical

Caribbean Princess • Princess Cruises

12-night Southern Caribbean Loop via Oranjestad, Curaçao & Fort-de-France

Apr 9, 2027 → Apr 21, 2027 • Fort Lauderdale ↔

From $1,234

$1,234 · $103/night · typical price · ↑2% above typical

$103/night

Typical price

↑2% above typical

Emerald Princess • Princess Cruises

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

Jan 30, 2028 → Feb 13, 2028 • San Juan ↔

From $1,841

$1,841 · $132/night · typical price · ↑1% above typical

$132/night

Typical price

↑1% above typical

MSC Seaview • MSC Cruises

14-night Eastern Caribbean Loop via Kingstown, Saint George & Fort-de-France

Jan 26, 2027 → Feb 9, 2027 • Bridgetown ↔

From $1,846

$1,846 · $132/night · typical price · ↑1% above typical

$132/night

Typical price

↑1% above typical

Celebrity Constellation • Celebrity Cruises

7-night Southern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Roseau

Dec 19, 2026 → Dec 26, 2026 • San Juan ↔

Great balance

From $774

$774 · $111/night · typical price · ↑1% above typical

$111/night

Typical price

↑1% above typical

Seven Seas Prestige • Regent Seven Seas Cruises

12-night Southern Caribbean Arc via Panama Canal, Cartagena & Oranjestad

Mar 14, 2028 → Mar 26, 2028 • Panamá, Ciudad de → Miami

From $8,675

$8,675 · $723/night · typical price

$723/night

Typical price

Oceania Insignia • Oceania Cruises

47-night Transatlantic Crossing via Palma de Mallorca, Portimao & Cruz Bay, Saint John

Nov 2, 2026 → Dec 19, 2026 • Barcelona → Miami

From $14,949

$14,949 · $318/night · typical price

$318/night

Typical price

Explora III

7-night Eastern Caribbean Arc via Providenciales & Cruz Bay, Saint John

Mar 14, 2027 → Mar 21, 2027 • Miami → Bridgetown

From $5,360

$5,360 · $766/night · typical price

$766/night

Typical price

Rhapsody of the Seas • Royal Caribbean International

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

Oct 17, 2026 → Oct 24, 2026 • San Juan ↔

Great balance

From $562

$562 · $80/night

$80/night

Vision of the Seas • Royal Caribbean International

10-night Eastern Caribbean Arc via Grand Turk Island, Philipsburg & Roseau

Oct 22, 2026 → Nov 1, 2026 • Baltimore → San Juan

From $1,320

$1,320 · $132/night

$132/night

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 ↔

Great balance

From $490

$490 · $70/night

$70/night

Rhapsody of the Seas • Royal Caribbean International

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

Nov 14, 2026 → Nov 21, 2026 • San Juan ↔

From $574

$574 · $82/night

$82/night

Celebrity Constellation • Celebrity Cruises

11-night Southern Caribbean Loop via Tortola, Saint John's & Castries

Nov 17, 2026 → Nov 28, 2026 • San Juan ↔

From $1,164

$1,164 · $106/night

$106/night

Explorer of the Seas • Royal Caribbean International

9-night Eastern Caribbean Loop via Cruz Bay, Saint John & Bridgetown

Nov 18, 2026 → Nov 27, 2026 • Port Canaveral ↔

From $810

$810 · $90/night

$90/night

Celebrity Eclipse • Celebrity Cruises

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

Dec 3, 2026 → Dec 12, 2026 • Fort Lauderdale ↔

From $1,283

$1,283 · $143/night

$143/night

Celebrity Constellation • Celebrity Cruises

7-night Southern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Roseau

Dec 12, 2026 → Dec 19, 2026 • San Juan ↔

From $713

$713 · $102/night

$102/night