Jibhop

Crown Princess • Princess Cruises

14-night Eastern Caribbean Loop via Saint Thomas, Basseterre, Saint Kitts & Roseau

Feb 14, 2027 → Feb 28, 2027 • San Juan ↔

More sea days than typical

From $1,559

$1,559 · $111/night · good value · ↓18% below typical

$111/night

Good value

↓18% below typical

Carnival Vista • Carnival Cruise Line

7-night Eastern Caribbean Loop via Celebration Key & San Juan

Sep 4, 2027 → Sep 11, 2027 • Port Canaveral ↔

Great balance

From $576

$576 · $82/night · typical price · ↓7% below typical

$82/night

Typical price

↓7% below typical

Silver Shadow • Silversea Cruises

10-night Eastern Caribbean Arc via Philipsburg, Basseterre, Saint Kitts & Little Bay

Dec 10, 2026 → Dec 20, 2026 • Miami → San Juan

From $6,300

$6,300 · $630/night · good value · ↓13% below typical

$630/night

Good value

↓13% below typical

MSC World America • MSC Cruises

14-night Western Caribbean Loop via Roatán, Cozumel & Ocean Cay

Apr 10, 2027 → Apr 24, 2027 • Miami ↔

20% below typical

From $877

$877 · $63/night · great deal · ↓20% below typical

$63/night

Great deal

↓20% below typical

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

MSC World America • MSC Cruises

14-night Western Caribbean Loop via Puerto Plata, Ocean Cay & Cozumel

Dec 26, 2026 → Jan 9, 2027 • Miami ↔

16% below typical

From $1,504

$1,504 · $107/night · good value · ↓16% below typical

$107/night

Good value

↓16% 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

Regal Princess • Princess Cruises

14-night Western Caribbean Loop via Princess Cays, San Juan & Cozumel

Aug 15, 2026 → Aug 29, 2026 • Fort Lauderdale ↔

14% below typical

From $1,363

$1,363 · $97/night · good value · ↓14% below typical

$97/night

Good value

↓14% 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

Vision of the Seas • Royal Caribbean International

7-night Southern Caribbean Loop via Charlotte Amalie, Saint Thomas, Cruz Bay, Saint John & Fort-de-France

Jan 23, 2028 → Jan 30, 2028 • San Juan ↔

Lowest in 180 days

From $722

$722 · $103/night · typical price · ↓1% below typical

$103/night

Typical price

↓1% below typical

Scarlet Lady • Virgin Voyages

8-night ABC Islands Loop via Philipsburg, Saint John's & Roseau

Dec 18, 2027 → Dec 26, 2027 • San Juan ↔

Lowest in 180 days

From $1,112

$1,112 · $139/night · typical price · ↓1% below typical

$139/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

Emerald Princess • Princess Cruises

7-night Southern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Fort-de-France

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

From $790

$790 · $113/night · good value · ↓19% below typical

$113/night

Good value

↓19% below typical