Jibhop

Silver Shadow • Silversea Cruises

12-night Eastern Caribbean Loop via San Juan, Saint-Barthélemy & Little Bay

Nov 18, 2026 → Nov 30, 2026 • Miami ↔

From $7,400

$7,400 · $617/night · great deal · ↓26% below typical

$617/night

Great deal

↓26% below typical

MS Aurelia • Phoenix Reisen

12-night Eastern Caribbean Arc: Charlotte Amalie, Saint Thomas, Tortola & Philipsburg

Oct 27, 2028 → Nov 8, 2028 • Miami → Bridgetown

Lowest in 180 days $370 below typical

From $5,749

$5,749 · $479/night · typical price · ↓6% below typical

$479/night

Typical price

↓6% below typical

Celebrity Xcel • Celebrity Cruises

8-night Eastern Caribbean Loop via Puerto Plata & Charlotte Amalie, Saint Thomas

Nov 20, 2027 → Nov 28, 2027 • Fort Lauderdale ↔

$194 below typical

From $1,261

$1,261 · $158/night · good value · ↓13% below typical

$158/night

Good value

↓13% below typical

Oceania Sirena • Oceania Cruises

31-night Eastern Caribbean Arc via Cozumel, Roatán & Harvest Caye

Nov 21, 2027 → Dec 22, 2027 • Miami ↔

Lowest in 180 days

From $8,299

$8,299 · $268/night · typical price · ↓3% below typical

$268/night

Typical price

↓3% below typical

Grandeur of the Seas • Royal Caribbean International

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

Jul 31, 2027 → Aug 7, 2027 • San Juan ↔

Lowest in 30 days $53 below typical

From $916

$916 · $131/night · typical price · ↓5% below typical

$131/night

Typical price

↓5% below typical

Vista

12-night Eastern Caribbean Arc: Charlotte Amalie, Saint Thomas, Saint-Barthélemy & Saint John's

Nov 13, 2028 → Nov 25, 2028 • Miami ↔

Lowest in 180 days $270 below typical

From $4,899

$4,899 · $408/night · typical price · ↓5% below typical

$408/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 ↔

$84 below typical

From $615

$615 · $88/night · good value · ↓12% below typical

$88/night

Good value

↓12% 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

Grandeur of the Seas • Royal Caribbean International

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

Oct 23, 2027 → Oct 30, 2027 • San Juan ↔

Lowest in 180 days

From $663

$663 · $95/night · typical price · ↓5% below typical

$95/night

Typical price

↓5% below typical

Silver Spirit • Silversea Cruises

12-night Southern Caribbean Loop via Port Elizabeth, Bequia, Castries & Oranjestad

Feb 17, 2028 → Feb 29, 2028 • Bridgetown ↔

From $7,100

$7,100 · $592/night · great deal · ↓21% below typical

$592/night

Great deal

↓21% below typical

Celebrity Xcel • Celebrity Cruises

7-night Eastern Caribbean Loop via Nassau & Charlotte Amalie, Saint Thomas

Dec 6, 2026 → Dec 13, 2026 • Miami ↔

$137 below typical ↘

From $987

$987 · $141/night · good value · ↓12% below typical

$141/night

Good value

↓12% 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

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

Celebrity Summit • Celebrity Cruises

7-night Southern Caribbean Loop via Roseau, Bridgetown & Castries

Dec 5, 2027 → Dec 12, 2027 • San Juan ↔

$84 below typical

From $626

$626 · $89/night · good value · ↓12% below typical

$89/night

Good value

↓12% below typical

Celebrity Ascent • Celebrity Cruises

11-night Eastern Caribbean Loop via Philipsburg, Saint John's & Castries

Jan 4, 2027 → Jan 15, 2027 • Fort Lauderdale ↔

$171 below typical ↘

From $1,451

$1,451 · $132/night · good value · ↓11% below typical

$132/night

Good value

↓11% below typical

Emerald Kaia • Emerald Cruises

7-night Eastern Caribbean Arc via Basseterre, Saint Kitts, Deshaies & Saint-Barthélemy

Nov 27, 2027 → Dec 4, 2027 • Saint John's → San Juan

$633 below typical

From $6,151

$6,151 · $879/night · typical price · ↓9% below typical

$879/night

Typical price

↓9% below typical

Silver Spirit • Silversea Cruises

11-night Southern Caribbean Loop via Port Elizabeth, Bequia, Saint George's & Willemstad

Feb 29, 2028 → Mar 11, 2028 • Bridgetown ↔

From $6,600

$6,600 · $600/night · great deal · ↓20% below typical

$600/night

Great deal

↓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

Grandeur of the Seas • Royal Caribbean International

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

Oct 9, 2027 → Oct 16, 2027 • San Juan ↔

Lowest in 180 days

From $671

$671 · $96/night · typical price · ↓4% below typical

$96/night

Typical price

↓4% 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 ↔

Great balance

From $759

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

$108/night

Good value

↓18% below typical