Jibhop

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

Explora I • Explora Journeys

16-night Eastern Caribbean Arc via Philipsburg, Saint John's & Little Bay

Jan 4, 2027 → Jan 20, 2027 • San Juan → Miami

$640 below typical

From $8,960

$8,960 · $560/night · typical price · ↓7% below typical

$560/night

Typical price

↓7% 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

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 · good value · ↓20% below typical

$112/night

Good value

↓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

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

$644 below typical ↗

From $6,199

$6,199 · $443/night · typical price · ↓9% below typical

$443/night

Typical price

↓9% below typical

Zuiderdam • Holland America

20-night Eastern Caribbean Loop via Half Moon Cay, Cabo Rojo & Bonaire

Mar 28, 2027 → Apr 17, 2027 • Miami ↔

$339 below typical

From $2,489

$2,489 · $124/night · good value · ↓12% below typical

$124/night

Good value

↓12% below typical

Emerald Sakara • Emerald Cruises

14-night Eastern Caribbean Arc via Soufriere, Antigua & Road Bay

Apr 8, 2028 → Apr 22, 2028 • Bridgetown → Philipsburg

$661 below typical

From $11,359

$11,359 · $811/night · typical price · ↓6% below typical

$811/night

Typical price

↓6% 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

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

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

Zuiderdam • Holland America

14-night Eastern Caribbean Loop via Puerto Plata, Grand Turk Island & Half Moon Cay

Dec 19, 2026 → Jan 2, 2027 • Miami ↔

Lowest in 30 days ↘

From $1,659

$1,659 · $119/night · typical price · ↓2% below typical

$119/night

Typical price

↓2% below typical

Zuiderdam • Holland America

14-night Eastern Caribbean Loop: Half Moon Cay, Puerto Plata & Grand Turk Island

Nov 28, 2026 → Dec 12, 2026 • Miami ↔

Lowest in 30 days ↘

From $1,274

$1,274 · $91/night · typical price · ↓2% below typical

$91/night

Typical price

↓2% below typical

Emerald Sakara • Emerald Cruises

14-night Eastern Caribbean Arc via Basseterre, Saint Kitts, Road Bay & Spanish Town

Mar 25, 2028 → Apr 8, 2028 • Philipsburg → Bridgetown

$749 below typical

From $11,525

$11,525 · $823/night · typical price · ↓6% below typical

$823/night

Typical price

↓6% 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 ↔

11% 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 ↔

11% below typical

From $2,228

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

$159/night

Good value

↓11% below typical

Explora III

14-night Eastern Caribbean Loop via Cruz Bay, Saint John & Terre-de-Haut

Dec 6, 2026 → Dec 20, 2026 • Miami ↔

$723 below typical

From $9,040

$9,040 · $646/night · typical price · ↓7% below typical

$646/night

Typical price

↓7% 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

Iona • P&O Cruises

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

Feb 18, 2028 → Mar 3, 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 Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg

Feb 19, 2028 → Mar 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