Jibhop

Regal Princess • Princess Cruises

8-night Eastern Caribbean Loop via Philipsburg & San Juan

Oct 31, 2026 → Nov 8, 2026 • Fort Lauderdale ↔

Great balance

From $807

$807 · $101/night · great deal · ↓41% below typical

$101/night

Great deal

↓41% below typical

Grandeur of the Seas • Royal Caribbean International

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

Aug 7, 2027 → Aug 14, 2027 • San Juan ↔

Lowest in 180 days $99 below typical

From $887

$887 · $127/night · good value · ↓10% below typical

$127/night

Good value

↓10% below typical

Grandeur of the Seas • Royal Caribbean International

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

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

Lowest in 180 days $99 below typical ↘

From $906

$906 · $129/night · typical price · ↓10% below typical

$129/night

Typical price

↓10% below typical

Rhapsody of the Seas • Royal Caribbean International

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

Nov 7, 2026 → Nov 14, 2026 • San Juan ↔

$104 below typical

From $568

$568 · $81/night · good value · ↓16% below typical

$81/night

Good value

↓16% below typical

Explora III

8-night Eastern Caribbean Loop via Philipsburg, Terre-de-Haut & Road Bay

Jan 13, 2027 → Jan 21, 2027 • San Juan → Miami

Lowest in 90 days $457 below typical ↘

From $5,440

$5,440 · $680/night · typical price · ↓8% below typical

$680/night

Typical price

↓8% below typical

Seabourn Ovation • Seabourn

7-night Southern Caribbean Arc via Tortola, South Friars Bay & Les Trois-Îlets

Dec 4, 2027 → Dec 11, 2027 • Philipsburg → Bridgetown

Lowest in 180 days $329 below typical ↘

From $3,569

$3,569 · $510/night · typical price · ↓8% below typical

$510/night

Typical price

↓8% below typical

Seabourn Ovation • Seabourn

14-night Eastern Caribbean Loop via Castries, Little Bay & South Friars Bay

Mar 13, 2027 → Mar 27, 2027 • Bridgetown ↔

Lowest in 30 days $804 below typical ↘

From $7,394

$7,394 · $528/night · typical price · ↓10% below typical

$528/night

Typical price

↓10% below typical

Celebrity Ascent • Celebrity Cruises

10-night Eastern Caribbean Loop via Philipsburg, Castries & Bridgetown

Nov 12, 2027 → Nov 22, 2027 • Fort Lauderdale ↔

$320 below typical

From $1,540

$1,540 · $154/night · good value · ↓17% below typical

$154/night

Good value

↓17% below typical

Icon of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Philipsburg & Coco Cay

Dec 5, 2026 → Dec 12, 2026 • Miami ↔

$230 below typical

From $1,384

$1,384 · $198/night · good value · ↓14% below typical

$198/night

Good value

↓14% below typical

Vision of the Seas • Royal Caribbean International

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

Dec 13, 2026 → Dec 20, 2026 • San Juan ↔

$103 below typical ↘

From $541

$541 · $77/night · good value · ↓16% below typical

$77/night

Good value

↓16% below typical

MSC Meraviglia • MSC Cruises

14-night Eastern Caribbean Loop via Philipsburg, Saint John's & Ocean Cay

Mar 13, 2027 → Mar 27, 2027 • Miami ↔

From $1,306

$1,306 · $93/night · great deal · ↓39% below typical

$93/night

Great deal

↓39% below typical

Carnival Firenze • Carnival Cruise Line

10-night Eastern Caribbean Loop via Philipsburg, Basseterre, Saint Kitts & Castries

Mar 8, 2027 → Mar 18, 2027 • Miami ↔

$141 below typical

From $738

$738 · $74/night · good value · ↓16% below typical

$74/night

Good value

↓16% below typical

Grandeur of the Seas • Royal Caribbean International

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

Sep 11, 2027 → Sep 18, 2027 • San Juan ↔

Lowest in 180 days $67 below typical

From $632

$632 · $90/night · typical price · ↓10% below typical

$90/night

Typical price

↓10% below typical

Explora III

7-night Eastern Caribbean Arc via Cruz Bay, Saint John & Terre-de-Haut

Nov 22, 2026 → Nov 29, 2026 • Miami → San Juan

Lowest in 180 days $400 below typical ↘

From $4,480

$4,480 · $640/night · typical price · ↓8% below typical

$640/night

Typical price

↓8% below typical

MSC Meraviglia • MSC Cruises

14-night Eastern Caribbean Loop via Philipsburg, Saint John's & Ocean Cay

Jan 16, 2027 → Jan 30, 2027 • Miami ↔

From $1,096

$1,096 · $78/night · great deal · ↓38% below typical

$78/night

Great deal

↓38% below typical

Carnival Firenze • Carnival Cruise Line

14-night Itinerary DOPOP-AWORJ-CWCUR-GDSTG-BBBGI-DMRSU-SXPHI-VISTT

Jan 9, 2028 → Jan 23, 2028 • Port Canaveral ↔

Lowest in 180 days $111 below typical

From $1,028

$1,028 · $73/night · typical price · ↓10% below typical

$73/night

Typical price

↓10% below typical

Rhapsody of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Tortola & Cruz Bay, Saint John

Sep 19, 2026 → Sep 26, 2026 • San Juan ↔

$149 below typical ↗

From $756

$756 · $108/night · good value · ↓16% below typical

$108/night

Good value

↓16% below typical

Brilliant Lady • Virgin Voyages

10-night Eastern Caribbean Loop via Philipsburg, Road Town, Tortola & Frederiksted, Saint Croix

Jan 11, 2027 → Jan 21, 2027 • Miami ↔

Lowest in 90 days $100 below typical

From $1,390

$1,390 · $139/night · typical price · ↓7% below typical

$139/night

Typical price

↓7% below typical

Resilient Lady • Virgin Voyages

8-night Eastern Caribbean Loop via Philipsburg & San Juan

Nov 20, 2027 → Nov 28, 2027 • Miami ↔

Lowest in 180 days $80 below typical

From $952

$952 · $119/night · typical price · ↓8% below typical

$119/night

Typical price

↓8% below typical

Icon of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Philipsburg & Coco Cay

Apr 24, 2027 → May 1, 2027 • Miami ↔

Lowest in 90 days $123 below typical ↘

From $1,484

$1,484 · $212/night · typical price · ↓8% below typical

$212/night

Typical price

↓8% below typical