Jibhop

Explora III

14-night Eastern Caribbean Loop via Cruz Bay, Saint John, Terre-de-Haut & Philipsburg

Nov 22, 2026 → Dec 6, 2026 • Miami ↔

$600 below typical

From $9,160

$9,160 · $654/night · typical price · ↓6% below typical

$654/night

Typical price

↓6% below typical

Oceania Vista • Oceania Cruises

12-night Miami → Charlotte Amalie, Saint Thomas → Philipsburg → Saint-Barthélemy + 5 more

Nov 25, 2026 → Dec 7, 2026 • Miami ↔

14% below typical

From $4,749

$4,749 · $396/night · good value · ↓14% below typical

$396/night

Good value

↓14% below typical

Explora III

8-night Eastern Caribbean Arc via Ocho Rios, Catalina Island & Jost Van Dyke

Dec 20, 2026 → Dec 28, 2026 • Miami → San Juan

$339 below typical ↘

From $5,240

$5,240 · $655/night · typical price · ↓6% below typical

$655/night

Typical price

↓6% below typical

MSC Opera • MSC Cruises

14-night Eastern Caribbean Loop via Fort-de-France, Pointe-à-Pitre & Road Town, Tortola

Aug 5, 2027 → Aug 19, 2027 • Bridgetown ↔

16% below typical

From $1,998

$1,998 · $143/night · good value · ↓16% below typical

$143/night

Good value

↓16% below typical

Emerald Sakara • Emerald Cruises

9-night Eastern Caribbean Loop via South Friars Bay, Deshaies & Little Bay

Dec 18, 2027 → Dec 27, 2027 • Philipsburg ↔

4% below typical

From $7,094

$7,094 · $788/night · typical price · ↓4% below typical

$788/night

Typical price

↓4% below typical

MSC Opera • MSC Cruises

14-night Eastern Caribbean Loop via Catalina Island, Oranjestad & Willemstad

Dec 20, 2027 → Jan 3, 2028 • La Romana ↔

17% below typical

From $1,379

$1,379 · $99/night · good value · ↓17% below typical

$99/night

Good value

↓17% below typical

MSC Opera • MSC Cruises

7-night Eastern Caribbean Loop: Catalina Island, Spanish Town & Philipsburg

Sep 20, 2027 → Sep 27, 2027 • La Romana ↔

Great balance

From $629

$629 · $90/night · good value · ↓15% below typical

$90/night

Good value

↓15% below typical

MSC Opera • MSC Cruises

7-night Eastern Caribbean Loop: Catalina Island, Spanish Town & Philipsburg

Oct 4, 2027 → Oct 11, 2027 • La Romana ↔

Great balance

From $629

$629 · $90/night · good value · ↓15% below typical

$90/night

Good value

↓15% below typical

MSC Opera • MSC Cruises

7-night Eastern Caribbean Loop: Catalina Island, Spanish Town & Philipsburg

Oct 2, 2028 → Oct 9, 2028 • La Romana ↔

11% below typical

From $658

$658 · $94/night · good value · ↓11% below typical

$94/night

Good value

↓11% below typical

Resilient Lady • Virgin Voyages

8-night Eastern Caribbean Loop via Philipsburg & San Juan

Feb 26, 2028 → Mar 5, 2028 • Miami ↔

Lowest in 180 days

From $1,032

$1,032 · $129/night · typical price

$129/night

Typical price

Resilient Lady • Virgin Voyages

8-night Eastern Caribbean Loop via Philipsburg & San Juan

Jan 29, 2028 → Feb 6, 2028 • Miami ↔

Lowest in 180 days

From $952

$952 · $119/night · typical price

$119/night

Typical price

MSC Opera • MSC Cruises

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

Sep 3, 2027 → Sep 10, 2027 • Fort-de-France ↔

Great balance

From $630

$630 · $90/night · good value · ↓11% below typical

$90/night

Good value

↓11% below typical

Emerald Princess • Princess Cruises

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

Jan 16, 2028 → Jan 30, 2028 • San Juan ↔

9% below typical

From $1,666

$1,666 · $119/night · typical price · ↓9% below typical

$119/night

Typical price

↓9% below typical

Star of the Seas • Royal Caribbean International

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

Dec 26, 2027 → Jan 2, 2028 • Port Canaveral ↔

Lowest in 180 days $1,292 above typical

From $2,837

$2,837 · $405/night · priced high · ↑84% above typical

$405/night

Priced high

↑84% above typical

Scarlet Lady • Virgin Voyages

7-night Eastern Caribbean Loop via Philipsburg, Bridgetown & Fort-de-France

Dec 26, 2027 → Jan 2, 2028 • San Juan ↔

Lowest in 180 days $690 above typical

From $1,673

$1,673 · $239/night · priced high · ↑70% above typical

$239/night

Priced high

↑70% above typical

Norwegian Prima • Norwegian Cruise Line

7-night Eastern Caribbean Loop via Philipsburg, Basseterre, Saint Kitts & Bridgetown

Dec 27, 2026 → Jan 3, 2027 • San Juan ↔

Lowest in 30 days $1,010 above typical

From $2,499

$2,499 · $357/night · priced high · ↑68% above typical

$357/night

Priced high

↑68% above typical

Queen Mary 2 • Cunard Line

13-night Southern Caribbean Arc via Road Town, Tortola, Basseterre, Saint Kitts & Castries

Dec 22, 2028 → Jan 4, 2029 • New York ↔

Lowest in 180 days $1,511 above typical

From $3,748

$3,748 · $288/night · priced high · ↑68% above typical

$288/night

Priced high

↑68% above typical

Norwegian Bliss • Norwegian Cruise Line

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

Dec 23, 2026 → Jan 4, 2027 • New York ↔

Lowest in 30 days $900 above typical

From $2,319

$2,319 · $193/night · priced high · ↑63% above typical

$193/night

Priced high

↑63% above typical

Eurodam • Holland America

11-night Eastern Caribbean Arc: Half Moon Cay, Philipsburg & Antigua

Dec 22, 2027 → Jan 2, 2028 • Fort Lauderdale ↔

Lowest in 180 days $798 above typical

From $2,109

$2,109 · $192/night · priced high · ↑61% above typical

$192/night

Priced high

↑61% above typical

Norwegian Jewel • Norwegian Cruise Line

12-night Eastern Caribbean Loop via Great Stirrup Cay, Cabo Rojo & Oranjestad

Dec 23, 2026 → Jan 4, 2027 • Miami ↔

Lowest in 30 days $926 above typical

From $2,449

$2,449 · $204/night · priced high · ↑61% above typical

$204/night

Priced high

↑61% above typical