Jibhop

Enchanted Princess • Princess Cruises

10-night Eastern Caribbean Loop via Grand Turk Island, Puerto Plata & San Juan

Mar 17, 2027 → Mar 27, 2027 • Fort Lauderdale ↔

From $1,351

$1,351 · $135/night · good value · ↓19% below typical

$135/night

Good value

↓19% below typical

Grandeur of the Seas • Royal Caribbean International

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

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

Lowest in 180 days

From $1,062

$1,062 · $152/night · typical price · ↓1% below typical

$152/night

Typical price

↓1% below typical

Rhapsody of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Philipsburg & Saint John's

Apr 8, 2028 → Apr 15, 2028 • San Juan ↔

Lowest in 180 days

From $837

$837 · $120/night · typical price · ↓1% below typical

$120/night

Typical price

↓1% below typical

Regal Princess • Princess Cruises

14-night Eastern Caribbean Loop via Cozumel & Princess Cays

Jan 2, 2028 → Jan 16, 2028 • Miami ↔

16% below typical

From $1,478

$1,478 · $106/night · good value · ↓16% below typical

$106/night

Good value

↓16% 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

MSC World America • MSC Cruises

7-night Eastern Caribbean Loop via Puerto Plata & Ocean Cay

Oct 31, 2026 → Nov 7, 2026 • Miami ↔

Great balance

From $594

$594 · $85/night · good value · ↓15% below typical

$85/night

Good value

↓15% below typical

MSC World America • MSC Cruises

7-night Eastern Caribbean Loop via Puerto Plata & Ocean Cay

Nov 14, 2026 → Nov 21, 2026 • Miami ↔

Great balance

From $594

$594 · $85/night · good value · ↓15% below typical

$85/night

Good value

↓15% below typical

Vista

18-night Southern Caribbean Arc: San Juan, Cruz Bay, Saint John & Cozumel

Mar 2, 2029 → Mar 20, 2029 • Miami ↔

Lowest in 180 days

From $7,799

$7,799 · $433/night · typical price · ↓1% below typical

$433/night

Typical price

↓1% below typical

Sun Princess • Princess Cruises

14-night Eastern Caribbean Loop via Grand Turk Island, Princess Cays & Cozumel

Jan 31, 2027 → Feb 14, 2027 • Fort Lauderdale ↔

13% below typical

From $1,248

$1,248 · $89/night · good value · ↓13% below typical

$89/night

Good value

↓13% below typical

Sky Princess • Princess Cruises

8-night Eastern Caribbean Loop via Princess Cays & San Juan

Jan 10, 2027 → Jan 18, 2027 • Port Canaveral ↔

Great balance

From $709

$709 · $89/night · good value · ↓15% below typical

$89/night

Good value

↓15% below typical

Sky Princess • Princess Cruises

8-night Eastern Caribbean Loop via Princess Cays & San Juan

Nov 29, 2026 → Dec 7, 2026 • Port Canaveral ↔

Great balance

From $691

$691 · $86/night · good value · ↓17% below typical

$86/night

Good value

↓17% below typical

Disney Dream • Disney Cruise Line

7-night Eastern Caribbean Loop via Lighthouse Point, Florida & San Juan

Jan 22, 2027 → Jan 29, 2027 • Fort Lauderdale ↔

$149 below typical

From $2,016

$2,016 · $288/night · typical price · ↓7% below typical

$288/night

Typical price

↓7% below typical

Enchanted Princess • Princess Cruises

10-night Eastern Caribbean Loop via Puerto Plata, San Juan & Basseterre, Saint Kitts

Feb 5, 2028 → Feb 15, 2028 • Fort Lauderdale ↔

12% below typical

From $1,055

$1,055 · $106/night · good value · ↓12% below typical

$106/night

Good value

↓12% below typical

Grandeur of the Seas • Royal Caribbean International

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

Nov 6, 2027 → Nov 13, 2027 • San Juan ↔

Lowest in 180 days

From $686

$686 · $98/night · typical price · ↓1% below typical

$98/night

Typical price

↓1% below typical

Explora II • Explora Journeys

7-night Eastern Caribbean Arc via Saint-Barthélemy & Ocean Cay

Feb 27, 2028 → Mar 5, 2028 • San Juan → Miami

Lowest in 30 days

From $4,020

$4,020 · $574/night · typical price · ↓1% below typical

$574/night

Typical price

↓1% below typical

Star of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Coco Cay & San Juan

Oct 25, 2026 → Nov 1, 2026 • Port Canaveral ↔

$93 below typical

From $1,311

$1,311 · $187/night · typical price · ↓7% below typical

$187/night

Typical price

↓7% below typical

Explora II • Explora Journeys

7-night Eastern Caribbean Arc via Puerto Plata & Cruz Bay, Saint John

Dec 12, 2027 → Dec 19, 2027 • Miami → San Juan

Lowest in 30 days

From $4,020

$4,020 · $574/night · typical price · ↓1% below typical

$574/night

Typical price

↓1% below typical

Explora IV

7-night Eastern Caribbean Arc via Charlotte Amalie, Saint Thomas, Catalina Island & Ocean Cay

Nov 13, 2027 → Nov 20, 2027 • San Juan → Miami

$325 below typical

From $4,200

$4,200 · $600/night · typical price · ↓7% below typical

$600/night

Typical price

↓7% below typical

Explora IV

7-night Eastern Caribbean Arc via Saint-Barthélemy, Spanish Town & Ocean Cay

Nov 27, 2027 → Dec 4, 2027 • San Juan → Miami

$325 below typical

From $4,200

$4,200 · $600/night · typical price · ↓7% below typical

$600/night

Typical price

↓7% below typical

Explora IV

7-night Eastern Caribbean Arc via Charlotte Amalie, Saint Thomas, Cayo Levantado & Ocean Cay

Apr 1, 2028 → Apr 8, 2028 • San Juan → Miami

$325 below typical

From $4,200

$4,200 · $600/night · typical price · ↓7% below typical

$600/night

Typical price

↓7% below typical