Jibhop

Brilliant Lady • Virgin Voyages

10-night Eastern Caribbean Loop via Philipsburg, Road Town, Tortola & Basseterre, Saint Kitts

Feb 22, 2027 → Mar 4, 2027 • Miami ↔

Lowest in 90 days $99 below typical

From $1,191

$1,191 · $119/night · typical price · ↓8% below typical

$119/night

Typical price

↓8% 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 ↔

Lowest in 30 days $228 below typical

From $1,351

$1,351 · $135/night · good value · ↓14% below typical

$135/night

Good value

↓14% below typical

Oceania Sirena • Oceania Cruises

12-night Eastern Caribbean Loop via Nassau, Puerto Plata & San Juan

Dec 10, 2027 → Dec 22, 2027 • Miami ↔

Lowest in 180 days $272 below typical

From $3,499

$3,499 · $292/night · typical price · ↓7% below typical

$292/night

Typical price

↓7% below typical

Carnival Festivale • Carnival Cruise Line

8-night Eastern Caribbean Loop via Philipsburg & Celebration Key

Nov 27, 2027 → Dec 5, 2027 • Port Canaveral ↔

Lowest in 180 days $72 below typical

From $907

$907 · $113/night · typical price · ↓7% below typical

$113/night

Typical price

↓7% below typical

Crown Princess • Princess Cruises

14-night Eastern Caribbean Arc via Saint Thomas, Philipsburg & Antigua

Mar 7, 2027 → Mar 21, 2027 • San Juan ↔

$407 below typical

From $1,619

$1,619 · $116/night · great deal · ↓20% below typical

$116/night

Great deal

↓20% below typical

Arvia • P&O Cruises

14-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Tortola & Philipsburg

Jan 29, 2028 → Feb 12, 2028 • Bridgetown ↔

Lowest in 180 days $163 below typical ↘

From $2,336

$2,336 · $167/night · typical price · ↓7% below typical

$167/night

Typical price

↓7% 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 ↔

Lowest in 180 days $180 below typical

From $1,248

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

$89/night

Good value

↓13% below typical

MSC Opera • MSC Cruises

7-night Eastern Caribbean Loop: Pointe-à-Pitre, Road Town, Tortola & La Romana

Aug 20, 2027 → Aug 27, 2027 • Fort-de-France ↔

Great balance

From $799

$799 · $114/night · great deal · ↓33% below typical

$114/night

Great deal

↓33% below typical

Icon of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Philipsburg & Coco Cay

Jan 2, 2027 → Jan 9, 2027 • Miami ↔

Lowest in 180 days $103 below typical

From $1,514

$1,514 · $216/night · typical price · ↓6% below typical

$216/night

Typical price

↓6% below typical

MSC World Europa • MSC Cruises

7-night Eastern Caribbean Loop via Pointe-à-Pitre, Philipsburg & Saint John's

Mar 13, 2027 → Mar 20, 2027 • Fort-de-France ↔

Great balance

From $869

$869 · $124/night · great deal · ↓21% below typical

$124/night

Great deal

↓21% below typical

Icon of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Philipsburg & Coco Cay

Aug 22, 2026 → Aug 29, 2026 • Miami ↔

$260 below typical

From $1,803

$1,803 · $258/night · good value · ↓13% below typical

$258/night

Good value

↓13% below typical

Seabourn Ovation • Seabourn

7-night Eastern Caribbean Arc via Rodney Bay, Little Bay & South Friars Bay

Nov 28, 2026 → Dec 5, 2026 • Bridgetown → Philipsburg

Lowest in 180 days $302 below typical

From $3,898

$3,898 · $557/night · typical price · ↓7% below typical

$557/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 ↔

Lowest in 30 days $138 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 Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg

Jun 26, 2027 → Jul 3, 2027 • San Juan ↔

Lowest in 180 days $73 below typical

From $956

$956 · $137/night · typical price · ↓7% below typical

$137/night

Typical price

↓7% 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 $71 below typical

From $916

$916 · $131/night · typical price · ↓7% below typical

$131/night

Typical price

↓7% below typical

Vista

22-night Eastern Caribbean Arc: Charlotte Amalie, Saint Thomas, Saint-Barthélemy & Cozumel

Nov 13, 2028 → Dec 5, 2028 • Miami ↔

Lowest in 180 days $679 below typical

From $8,699

$8,699 · $395/night · typical price · ↓7% below typical

$395/night

Typical price

↓7% below typical

Rhapsody of the Seas • Royal Caribbean International

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

Oct 31, 2026 → Nov 7, 2026 • San Juan ↔

$90 below typical ↘

From $613

$613 · $88/night · good value · ↓13% below typical

$88/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 · ↓4% below typical

$268/night

Typical price

↓4% below typical

Carnival Celebration • Carnival Cruise Line

7-night Eastern Caribbean Loop via Saint Thomas & Celebration Key

Jan 3, 2027 → Jan 10, 2027 • Miami ↔

$52 below typical ↘

From $503

$503 · $72/night · typical price · ↓9% below typical

$72/night

Typical price

↓9% below typical

Disney Treasure • Disney Cruise Line

7-night Eastern Caribbean Loop via Tortola & Disney Castaway Cay

Aug 28, 2027 → Sep 4, 2027 • Port Canaveral ↔

$329 below typical

From $2,089

$2,089 · $298/night · good value · ↓14% below typical

$298/night

Good value

↓14% below typical