Jibhop

Crown Princess • Princess Cruises

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

Feb 21, 2027 → Mar 7, 2027 • San Juan ↔

From $1,426

$1,426 · $102/night · great deal · ↓25% below typical

$102/night

Great deal

↓25% below typical

MS Europa 2 • Hapag-Lloyd Cruises

14-night Eastern Caribbean Loop via San Juan, Saint-Barthélemy & Saint John's

Dec 7, 2027 → Dec 21, 2027 • Miami ↔

From $9,419

$9,419 · $673/night · good value · ↓15% below typical

$673/night

Good value

↓15% below typical

MS HANSEATIC inspiration • Hapag-Lloyd Cruises

16-night Southern Caribbean Arc via Kings Wharf, Road Bay & Saint-Barthélemy

Oct 20, 2027 → Nov 5, 2027 • Halifax → Curaçao

From $8,499

$8,499 · $531/night · good value · ↓18% below typical

$531/night

Good value

↓18% below typical

Celebrity Summit • Celebrity Cruises

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

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

$84 below typical

From $626

$626 · $89/night · good value · ↓12% below typical

$89/night

Good value

↓12% below typical

Emerald Princess • Princess Cruises

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

Dec 5, 2027 → Dec 19, 2027 • San Juan ↔

20% below typical

From $1,566

$1,566 · $112/night · great deal · ↓20% below typical

$112/night

Great deal

↓20% below typical

Celebrity Ascent • Celebrity Cruises

11-night Eastern Caribbean Loop via Philipsburg, Saint John's & Castries

Jan 4, 2027 → Jan 15, 2027 • Fort Lauderdale ↔

$171 below typical ↘

From $1,451

$1,451 · $132/night · good value · ↓11% below typical

$132/night

Good value

↓11% below typical

Emerald Princess • Princess Cruises

7-night Southern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Fort-de-France

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

From $790

$790 · $113/night · good value · ↓19% below typical

$113/night

Good value

↓19% below typical

MSC World Europa • MSC Cruises

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

Jan 31, 2027 → Feb 7, 2027 • Pointe-à-Pitre ↔

Great balance

From $759

$759 · $108/night · good value · ↓18% below typical

$108/night

Good value

↓18% below typical

Vision of the Seas • Royal Caribbean International

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

Feb 21, 2027 → Feb 28, 2027 • San Juan ↔

$66 below typical

From $579

$579 · $83/night · good value · ↓10% below typical

$83/night

Good value

↓10% below typical

Coral Princess • Princess Cruises

14-night Southern Caribbean Loop via Philipsburg, Basseterre, Saint Kitts & Roseau

Dec 6, 2027 → Dec 20, 2027 • Fort Lauderdale ↔

23% below typical

From $1,537

$1,537 · $110/night · great deal · ↓23% below typical

$110/night

Great deal

↓23% below typical

Arvia • P&O Cruises

14-night Southern Caribbean Loop via Fort-de-France, Castries & Bridgetown

Dec 11, 2027 → Dec 25, 2027 • Antigua ↔

From $2,134

$2,134 · $152/night · good value · ↓17% below typical

$152/night

Good value

↓17% below typical

Crown Princess • Princess Cruises

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

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

From $785

$785 · $112/night · good value · ↓17% below typical

$112/night

Good value

↓17% below typical

Celebrity Ascent • Celebrity Cruises

11-night Eastern Caribbean Loop via Philipsburg, Saint John's & Castries

Mar 29, 2027 → Apr 9, 2027 • Fort Lauderdale ↔

$145 below typical ↗

From $1,573

$1,573 · $143/night · typical price · ↓8% below typical

$143/night

Typical price

↓8% below typical

Oceania Sirena • Oceania Cruises

14-night Southern Caribbean Loop via Oranjestad, Willemstad & Kralendijk

Dec 22, 2027 → Jan 5, 2028 • Miami ↔

Lowest in 180 days

From $4,399

$4,399 · $314/night · typical price · ↓2% below typical

$314/night

Typical price

↓2% below typical

Crown Princess • Princess Cruises

14-night Southern Caribbean Loop via Philipsburg, Fort-de-France & Roseau

Feb 28, 2027 → Mar 14, 2027 • San Juan ↔

From $1,516

$1,516 · $108/night · great deal · ↓20% below typical

$108/night

Great deal

↓20% below typical

Crown Princess • Princess Cruises

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

Mar 7, 2027 → Mar 21, 2027 • San Juan ↔

20% below typical

From $1,619

$1,619 · $116/night · great deal · ↓20% below typical

$116/night

Great deal

↓20% below typical

Vision of the Seas • Royal Caribbean International

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

Dec 20, 2026 → Dec 27, 2026 • San Juan ↔

$69 below typical ↗

From $679

$679 · $97/night · typical price · ↓9% below typical

$97/night

Typical price

↓9% below typical

Crown Princess • Princess Cruises

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

Feb 7, 2027 → Feb 21, 2027 • San Juan ↔

15% below typical

From $1,615

$1,615 · $115/night · good value · ↓15% below typical

$115/night

Good value

↓15% below typical

Seven Seas Grandeur • Regent Seven Seas Cruises

10-night Southern Caribbean Loop via Saint George's, Kingstown & Castries

Feb 14, 2028 → Feb 24, 2028 • Bridgetown ↔

19% below typical

From $5,743

$5,743 · $574/night · good value · ↓19% below typical

$574/night

Good value

↓19% below typical

MSC World Europa • MSC Cruises

7-night Eastern Caribbean Loop via Pointe-à-Pitre, Antigua & Philipsburg

Dec 5, 2026 → Dec 12, 2026 • Fort-de-France ↔

Great balance

From $1,001

$1,001 · $143/night · good value · ↓16% below typical

$143/night

Good value

↓16% below typical