Jibhop

Iona • P&O Cruises

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

Jan 22, 2028 → Feb 5, 2028 • Bridgetown ↔

13% below typical

From $2,228

$2,228 · $159/night · good value · ↓13% below typical

$159/night

Good value

↓13% below typical

Seabourn Ovation • Seabourn

7-night Eastern Caribbean Arc via Rodney Bay, Little Bay & South Friars Bay

Mar 11, 2028 → Mar 18, 2028 • Bridgetown → Philipsburg

Lowest in 180 days $290 below typical ↘

From $3,909

$3,909 · $558/night · typical price · ↓7% below typical

$558/night

Typical price

↓7% 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 $579 below typical ↘

From $7,819

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

$559/night

Typical price

↓7% below typical

Enchanted Princess • Princess Cruises

10-night Eastern Caribbean Loop via Princess Cays, Puerto Plata & San Juan

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

32% below typical

From $1,143

$1,143 · $114/night · great deal · ↓32% below typical

$114/night

Great deal

↓32% below typical

Coral Princess • Princess Cruises

10-night Eastern Caribbean Loop via Saint Thomas, Basseterre, Saint Kitts & Roseau

Nov 18, 2026 → Nov 28, 2026 • Fort Lauderdale ↔

From $1,044

$1,044 · $104/night · great deal · ↓29% below typical

$104/night

Great deal

↓29% below typical

Britannia • P&O Cruises

13-night Eastern Caribbean Arc via Castries & Basseterre, Saint Kitts

Mar 20, 2027 → Apr 2, 2027 • Bridgetown → Southampton

$219 below typical

From $1,445

$1,445 · $111/night · good value · ↓13% below typical

$111/night

Good value

↓13% below typical

MSC Opera • MSC Cruises

14-night Transatlantic Crossing: Tangier, Antigua & Philipsburg

Nov 2, 2026 → Nov 16, 2026 • Barcelona → La Romana

From $932

$932 · $67/night · great deal · ↓28% below typical

$67/night

Great deal

↓28% below typical

MSC Opera • MSC Cruises

7-night Eastern Caribbean Loop: Catalina Island, Spanish Town & Philipsburg

Aug 9, 2027 → Aug 16, 2027 • La Romana ↔

Great balance

From $879

$879 · $126/night · great deal · ↓26% below typical

$126/night

Great deal

↓26% below typical

Emerald Princess • Princess Cruises

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

Dec 12, 2027 → Dec 26, 2027 • San Juan ↔

From $1,516

$1,516 · $108/night · great deal · ↓23% below typical

$108/night

Great deal

↓23% below typical

Silver Ray • Silversea Cruises

12-night Eastern Caribbean Arc via Port Elizabeth, Bequia, Castries & Fort-de-France

Mar 20, 2028 → Apr 1, 2028 • Bridgetown → Miami

From $8,200

$8,200 · $683/night · great deal · ↓25% below typical

$683/night

Great deal

↓25% below typical

Crown Princess • Princess Cruises

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

Jan 8, 2027 → Jan 15, 2027 • Bridgetown ↔

Great balance

From $1,194

$1,194 · $171/night · great deal · ↓28% below typical

$171/night

Great deal

↓28% below typical

Crown Princess • Princess Cruises

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

Feb 19, 2027 → Feb 26, 2027 • Bridgetown ↔

Great balance

From $1,194

$1,194 · $171/night · great deal · ↓28% below typical

$171/night

Great deal

↓28% below typical

Crown Princess • Princess Cruises

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

Jan 24, 2027 → Jan 31, 2027 • San Juan ↔

Great balance

From $788

$788 · $113/night · great deal · ↓26% below typical

$113/night

Great deal

↓26% below typical

MSC Opera • MSC Cruises

7-night Eastern Caribbean Loop: Antigua & La Romana

Aug 13, 2027 → Aug 20, 2027 • Fort-de-France ↔

Great balance

From $889

$889 · $127/night · great deal · ↓26% below typical

$127/night

Great deal

↓26% below typical

Disney Fantasy • Disney Cruise Line

10-night Eastern Caribbean Loop via Philipsburg, Castries & Disney Castaway Cay

Jul 11, 2027 → Jul 21, 2027 • Port Canaveral ↔

Lowest in 180 days

From $4,049

$4,049 · $405/night · typical price · ↓3% below typical

$405/night

Typical price

↓3% below typical

Enchanted Princess • Princess Cruises

10-night Eastern Caribbean Loop via Princess Cays, Puerto Plata & San Juan

Dec 17, 2026 → Dec 27, 2026 • Fort Lauderdale ↔

20% below typical

From $953

$953 · $95/night · great deal · ↓20% below typical

$95/night

Great deal

↓20% 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

MSC Meraviglia • MSC Cruises

13-night Eastern Caribbean Arc via Ponta Delgada & Antigua

Nov 7, 2027 → Nov 20, 2027 • Le Havre → Fort-de-France

From $875

$875 · $67/night · great deal · ↓25% below typical

$67/night

Great deal

↓25% 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

Star Princess • Princess Cruises

10-night Eastern Caribbean Loop via San Juan, Basseterre, Saint Kitts & Castries

Dec 12, 2027 → Dec 22, 2027 • Port Canaveral ↔

25% below typical

From $937

$937 · $94/night · great deal · ↓25% below typical

$94/night

Great deal

↓25% below typical