Jibhop

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

Oceania Sonata • Oceania Cruises

11-night Eastern Caribbean Loop via Puerto Plata, San Juan & Charlotte Amalie, Saint Thomas

Feb 19, 2028 → Mar 1, 2028 • Miami ↔

Lowest in 180 days

From $5,299

$5,299 · $482/night · typical price · ↓2% below typical

$482/night

Typical price

↓2% 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

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 · ↓22% below typical

$108/night

Great deal

↓22% below typical

Icon of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Philipsburg & Coco Cay

Nov 21, 2026 → Nov 28, 2026 • Miami ↔

$163 below typical ↘

From $1,444

$1,444 · $206/night · good value · ↓10% below typical

$206/night

Good value

↓10% 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

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

Allure of the Seas • Royal Caribbean International

8-night Eastern Caribbean Loop via Basseterre, Saint Kitts & Coco Cay

Aug 22, 2026 → Aug 30, 2026 • Fort Lauderdale ↔

$147 below typical ↗

From $1,157

$1,157 · $145/night · good value · ↓11% below typical

$145/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

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

Rhapsody of the Seas • Royal Caribbean International

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

Dec 5, 2026 → Dec 12, 2026 • San Juan ↔

$80 below typical ↗

From $619

$619 · $88/night · good value · ↓12% below typical

$88/night

Good value

↓12% 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

Coral Princess • Princess Cruises

10-night Eastern Caribbean Loop via Antigua, Philipsburg & Roseau

Nov 8, 2026 → Nov 18, 2026 • Fort Lauderdale ↔

From $1,094

$1,094 · $109/night · great deal · ↓26% below typical

$109/night

Great deal

↓26% 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

Vision of the Seas • Royal Caribbean International

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

Nov 29, 2026 → Dec 6, 2026 • San Juan ↔

$72 below typical ↗

From $601

$601 · $86/night · good value · ↓11% below typical

$86/night

Good value

↓11% 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

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

Rhapsody of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Tortola, Philipsburg & Saint John's

Oct 24, 2026 → Oct 31, 2026 • San Juan ↔

$80 below typical

From $615

$615 · $88/night · good value · ↓11% below typical

$88/night

Good value

↓11% below typical