Jibhop

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

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

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

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 ↘

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

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

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

Crown Princess • Princess Cruises

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

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

20% below typical

From $738

$738 · $105/night · good value · ↓20% below typical

$105/night

Good value

↓20% below typical

Crown Princess • Princess Cruises

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

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

20% below typical

From $738

$738 · $105/night · good value · ↓20% below typical

$105/night

Good value

↓20% 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

MSC Opera • MSC Cruises

3-night Eastern Caribbean Arc via Antigua & Road Town, Tortola

Mar 12, 2027 → Mar 15, 2027 • Fort-de-France → La Romana

From $719

$719 · $240/night · good value · ↓20% below typical

$240/night

Good value

↓20% 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

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