Jibhop

Iona • P&O Cruises

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

Jan 21, 2028 → Feb 4, 2028 • Bridgetown ↔

11% below typical

From $2,296

$2,296 · $164/night · good value · ↓11% below typical

$164/night

Good value

↓11% below typical

Iona • P&O Cruises

14-night Southern Caribbean Loop via Basseterre, Saint Kitts, Philipsburg & Fort-de-France

Dec 10, 2027 → Dec 24, 2027 • Bridgetown ↔

From $1,796

$1,796 · $128/night · great deal · ↓20% below typical

$128/night

Great deal

↓20% below typical

Vista

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

Oct 28, 2026 → Nov 11, 2026 • New York → Miami

$681 below typical

From $5,349

$5,349 · $382/night · good value · ↓11% below typical

$382/night

Good value

↓11% below typical

Crown Princess • Princess Cruises

7-night Southern Caribbean Arc via Philipsburg, Fort-de-France & Roseau

Feb 28, 2027 → Mar 7, 2027 • San Juan ↔

22% below typical

From $743

$743 · $106/night · great deal · ↓22% below typical

$106/night

Great deal

↓22% 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

From $5,298

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

$662/night

Typical price

↓10% below typical

Seabourn Ovation • Seabourn

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

Mar 6, 2027 → Mar 13, 2027 • Philipsburg → Bridgetown

Lowest in 180 days ↘

From $3,909

$3,909 · $558/night · typical price · ↓5% below typical

$558/night

Typical price

↓5% below typical

Seabourn Ovation • Seabourn

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

Mar 11, 2028 → Mar 25, 2028 • Bridgetown ↔

Lowest in 30 days ↘

From $7,819

$7,819 · $559/night · typical price · ↓5% below typical

$559/night

Typical price

↓5% below typical

Silver Spirit • Silversea Cruises

12-night Southern Caribbean Loop via Port Elizabeth, Bequia, Fort-de-France & Saint-Barthélemy

Feb 5, 2028 → Feb 17, 2028 • Bridgetown ↔

From $7,100

$7,100 · $592/night · great deal · ↓21% below typical

$592/night

Great deal

↓21% below typical

Silver Spirit • Silversea Cruises

12-night Southern Caribbean Loop via Port Elizabeth, Bequia, Castries & Oranjestad

Feb 17, 2028 → Feb 29, 2028 • Bridgetown ↔

From $7,100

$7,100 · $592/night · great deal · ↓21% below typical

$592/night

Great deal

↓21% below typical

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 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

Vista

14-night Southern Caribbean Loop via Georgetown, South Carolina, Falmouth & Oranjestad

Nov 11, 2026 → Nov 25, 2026 • Miami ↔

$631 below typical ↗

From $5,399

$5,399 · $386/night · good value · ↓10% below typical

$386/night

Good value

↓10% below typical

Silver Spirit • Silversea Cruises

11-night Southern Caribbean Loop via Port Elizabeth, Bequia, Saint George's & Willemstad

Feb 29, 2028 → Mar 11, 2028 • Bridgetown ↔

From $6,600

$6,600 · $600/night · great deal · ↓20% below typical

$600/night

Great deal

↓20% below typical

Oceania Vista • Oceania Cruises

14-night New York → Charlotte Amalie, Saint Thomas → Tortola → Saint John's + 6 more

Oct 28, 2026 → Nov 11, 2026 • New York → Miami

22% below typical

From $4,999

$4,999 · $357/night · great deal · ↓22% below typical

$357/night

Great deal

↓22% below typical

Arvia • P&O Cruises

14-night Eastern Caribbean Loop via Fort-de-France, Basseterre, Saint Kitts & Tortola

Nov 21, 2026 → Dec 5, 2026 • Bridgetown ↔

16% below typical

From $1,823

$1,823 · $130/night · good value · ↓16% below typical

$130/night

Good value

↓16% 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

Silver Spirit • Silversea Cruises

12-night Southern Caribbean Loop via Port Elizabeth, Bequia, Castries & Kralendijk

Jan 10, 2028 → Jan 22, 2028 • Bridgetown ↔

From $7,400

$7,400 · $617/night · good value · ↓18% below typical

$617/night

Good value

↓18% below typical

Iona • P&O Cruises

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

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

8% below typical

From $2,363

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

$169/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

Seven Seas Grandeur • Regent Seven Seas Cruises

14-night Southern Caribbean Loop via Ocho Rios, Oranjestad & Willemstad

Dec 8, 2027 → Dec 22, 2027 • Miami ↔

From $7,874

$7,874 · $562/night · great deal · ↓20% below typical

$562/night

Great deal

↓20% below typical