Jibhop

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

$1,456 below typical

From $21,099

$21,099 · $449/night · typical price · ↓6% below typical

$449/night

Typical price

↓6% below typical

Brilliant Lady • Virgin Voyages

10-night Eastern Caribbean Loop via Philipsburg, Basseterre, Saint Kitts & Cruz Bay, Saint John

Dec 28, 2026 → Jan 7, 2027 • Miami ↔

Lowest in 90 days $700 above typical

From $1,990

$1,990 · $199/night · priced high · ↑54% above typical

$199/night

Priced high

↑54% above typical

Valiant Lady • Virgin Voyages

6-night Eastern Caribbean Loop via Tortola & Cruz Bay, Saint John

Nov 14, 2026 → Nov 20, 2026 • San Juan ↔

Lowest in 90 days $240 above typical

From $1,014

$1,014 · $169/night · priced high · ↑31% above typical

$169/night

Priced high

↑31% above typical

Norwegian Prima • Norwegian Cruise Line

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

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

Lowest in 30 days $380 above typical ↘

From $1,659

$1,659 · $237/night · priced high · ↑30% above typical

$237/night

Priced high

↑30% above typical

Explora II • Explora Journeys

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

Dec 19, 2027 → Dec 26, 2027 • San Juan → Miami

Lowest in 30 days $1,118 above typical

From $5,160

$5,160 · $737/night · priced high · ↑28% above typical

$737/night

Priced high

↑28% above typical

Explora IV

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

Dec 23, 2027 → Dec 30, 2027 • Miami → San Juan

Lowest in 30 days $880 above typical

From $4,900

$4,900 · $700/night · priced high · ↑22% above typical

$700/night

Priced high

↑22% above typical

Rhapsody of the Seas • Royal Caribbean International

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

Jan 15, 2028 → Jan 22, 2028 • San Juan ↔

Lowest in 180 days $112 above typical

From $756

$756 · $108/night · priced high · ↑17% above typical

$108/night

Priced high

↑17% above typical

Queen Elizabeth • Cunard Line

33-night Transatlantic Crossing via Cruz Bay, Saint John, Montego Bay & Cozumel

Dec 17, 2026 → Jan 19, 2027 • Miami → Southampton

Lowest in 30 days $479 above typical

From $4,472

$4,472 · $136/night · priced high · ↑12% above typical

$136/night

Priced high

↑12% above typical

Norwegian Pearl • Norwegian Cruise Line

10-night Eastern Caribbean Loop via Puerto Plata & Cruz Bay, Saint John

Dec 13, 2027 → Dec 23, 2027 • Philadelphia ↔

Lowest in 30 days $95 above typical

From $1,049

$1,049 · $105/night · priced high · ↑10% above typical

$105/night

Priced high

↑10% above typical

Norwegian Dawn • Norwegian Cruise Line

12-night Eastern Caribbean Loop via Great Stirrup Cay, Puerto Plata & Cruz Bay, Saint John

Jan 2, 2028 → Jan 14, 2028 • Jacksonville ↔

Lowest in 30 days $102 above typical

From $1,389

$1,389 · $116/night · typical price · ↑8% above typical

$116/night

Typical price

↑8% above typical

Explora III

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

Jan 29, 2027 → Feb 5, 2027 • San Juan → Miami

Lowest in 30 days $405 above typical

From $5,565

$5,565 · $795/night · typical price · ↑8% above typical

$795/night

Typical price

↑8% above typical

Explora II • Explora Journeys

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

Jan 9, 2028 → Jan 16, 2028 • Miami → San Juan

Lowest in 30 days $262 above typical

From $4,020

$4,020 · $574/night · typical price · ↑7% above typical

$574/night

Typical price

↑7% above typical

Explora II • Explora Journeys

7-night Eastern Caribbean Arc via Puerto Plata, Road Bay & Cruz Bay, Saint John

Jan 30, 2028 → Feb 6, 2028 • Miami → San Juan

Lowest in 30 days $262 above typical

From $4,020

$4,020 · $574/night · typical price · ↑7% above typical

$574/night

Typical price

↑7% above typical

Explora III

8-night Eastern Caribbean Arc via Cruz Bay, Saint John, Saint-Barthélemy & Saint John's

Jan 5, 2027 → Jan 13, 2027 • Miami → San Juan

Lowest in 30 days $393 above typical

From $6,290

$6,290 · $786/night · typical price · ↑7% above typical

$786/night

Typical price

↑7% above typical

Vision of the Seas • Royal Caribbean International

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

Jan 9, 2028 → Jan 16, 2028 • San Juan ↔

Lowest in 180 days

From $771

$771 · $110/night · typical price · ↑6% above typical

$110/night

Typical price

↑6% above typical

Explora IV

9-night Eastern Caribbean Loop via Puerto Plata, San Juan & Cruz Bay, Saint John

Dec 4, 2027 → Dec 13, 2027 • Miami ↔

Lowest in 30 days

From $5,415

$5,415 · $602/night · typical price · ↑5% above typical

$602/night

Typical price

↑5% above typical

Oceania Sonata • Oceania Cruises

14-night Southern Caribbean Arc: Charlotte Amalie, Saint Thomas, Cruz Bay, Saint John & Roseau

Feb 22, 2029 → Mar 8, 2029 • Miami ↔

Lowest in 180 days

From $7,199

$7,199 · $514/night · typical price · ↑4% above typical

$514/night

Typical price

↑4% above typical

Vista

11-night Southern Caribbean Arc: San Juan, Cruz Bay, Saint John & Castries

Mar 2, 2029 → Mar 13, 2029 • Miami ↔

Lowest in 180 days

From $4,999

$4,999 · $454/night · typical price · ↑4% above typical

$454/night

Typical price

↑4% above typical

Vista

11-night Southern Caribbean Arc: San Juan, Cruz Bay, Saint John & Castries

Mar 20, 2029 → Mar 31, 2029 • Miami ↔

Lowest in 180 days

From $4,999

$4,999 · $454/night · typical price · ↑4% above typical

$454/night

Typical price

↑4% above typical

Explora III

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

Feb 5, 2027 → Feb 12, 2027 • Miami → San Juan

Lowest in 30 days

From $5,270

$5,270 · $753/night · typical price · ↑3% above typical

$753/night

Typical price

↑3% above typical