Jibhop

MSC Opera • MSC Cruises

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

Aug 23, 2027 → Aug 30, 2027 • La Romana ↔

Great balance

From $709

$709 · $101/night · great deal · ↓41% below typical

$101/night

Great deal

↓41% below typical

Sea Cloud Spirit • Sea Cloud Cruises

16-night Transatlantic Crossing via Las Palmas de Gran Canaria & Philipsburg

Nov 13, 2026 → Nov 29, 2026 • Las Palmas de Gran Canaria → Philipsburg

$2,031 below typical

From $9,816

$9,816 · $614/night · good value · ↓17% below typical

$614/night

Good value

↓17% below typical

Sea Cloud Spirit • Sea Cloud Cruises

16-night Transatlantic Crossing via Las Palmas de Gran Canaria & Philipsburg

Nov 11, 2027 → Nov 27, 2027 • Las Palmas de Gran Canaria → Philipsburg

$2,031 below typical

From $9,816

$9,816 · $614/night · good value · ↓17% below typical

$614/night

Good value

↓17% below typical

Crown Princess • Princess Cruises

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

Jan 10, 2027 → Jan 17, 2027 • San Juan ↔

Lowest in 180 days $174 below typical

From $738

$738 · $105/night · good value · ↓19% below typical

$105/night

Good value

↓19% below typical

Crown Princess • Princess Cruises

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

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

Lowest in 180 days $174 below typical

From $738

$738 · $105/night · good value · ↓19% below typical

$105/night

Good value

↓19% below typical

Crown Princess • Princess Cruises

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

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

$462 below typical

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 ↔

$462 below typical

From $1,194

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

$171/night

Great deal

↓28% below typical

Arvia • P&O Cruises

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

Feb 12, 2027 → Feb 26, 2027 • Bridgetown ↔

Lowest in 30 days $311 below typical ↘

From $2,228

$2,228 · $159/night · good value · ↓12% below typical

$159/night

Good value

↓12% below typical

Arvia • P&O Cruises

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

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

Lowest in 180 days $311 below typical ↘

From $2,228

$2,228 · $159/night · good value · ↓12% below typical

$159/night

Good value

↓12% below typical

Arvia • P&O Cruises

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

Feb 12, 2028 → Feb 26, 2028 • Bridgetown ↔

Lowest in 180 days $311 below typical ↘

From $2,228

$2,228 · $159/night · good value · ↓12% below typical

$159/night

Good value

↓12% below typical

Icon of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Philipsburg & Coco Cay

Apr 10, 2027 → Apr 17, 2027 • Miami ↔

Lowest in 30 days $170 below typical

From $1,463

$1,463 · $209/night · good value · ↓10% below typical

$209/night

Good value

↓10% below typical

Crown Princess • Princess Cruises

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

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

$284 below typical

From $788

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

$113/night

Great deal

↓26% below typical

Rhapsody of the Seas • Royal Caribbean International

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

Nov 21, 2026 → Nov 28, 2026 • San Juan ↔

$123 below typical ↘

From $581

$581 · $83/night · good value · ↓17% below typical

$83/night

Good value

↓17% below typical

Seabourn Ovation • Seabourn

14-night Eastern Caribbean Loop via Tortola, South Friars Bay & Les Trois-Îlets

Feb 5, 2028 → Feb 19, 2028 • Philipsburg ↔

Lowest in 30 days $1,001 below typical

From $8,498

$8,498 · $607/night · good value · ↓11% below typical

$607/night

Good value

↓11% below typical

Vision of the Seas • Royal Caribbean International

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

Dec 13, 2026 → Dec 20, 2026 • San Juan ↔

$119 below typical ↘

From $554

$554 · $79/night · good value · ↓18% below typical

$79/night

Good value

↓18% below typical

Arvia • P&O Cruises

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

Jan 1, 2027 → Jan 15, 2027 • Bridgetown ↔

Lowest in 30 days $271 below typical

From $2,228

$2,228 · $159/night · good value · ↓11% below typical

$159/night

Good value

↓11% below typical

Arvia • P&O Cruises

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

Jan 2, 2027 → Jan 16, 2027 • Bridgetown ↔

Lowest in 30 days $271 below typical

From $2,228

$2,228 · $159/night · good value · ↓11% below typical

$159/night

Good value

↓11% 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 ↔

Lowest in 180 days $163 below typical ↘

From $759

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

$108/night

Good value

↓18% 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 ↔

Lowest in 180 days $174 below typical

From $743

$743 · $106/night · good value · ↓19% below typical

$106/night

Good value

↓19% below typical

Seabourn Ovation • Seabourn

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

Dec 19, 2026 → Dec 26, 2026 • Bridgetown → Philipsburg

Lowest in 180 days $401 below typical ↘

From $3,598

$3,598 · $514/night · good value · ↓10% below typical

$514/night

Good value

↓10% below typical