Jibhop

Iona • P&O Cruises

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

Nov 12, 2027 → Nov 26, 2027 • Bridgetown ↔

$335 above typical

From $2,134

$2,134 · $152/night · priced high · ↑19% above typical

$152/night

Priced high

↑19% above typical

Crown Princess • Princess Cruises

7-night Eastern Caribbean Loop via San Juan, Saint Thomas & Philipsburg

Mar 5, 2027 → Mar 12, 2027 • Bridgetown ↔

$181 above typical

From $1,194

$1,194 · $171/night · priced high · ↑18% above typical

$171/night

Priced high

↑18% above typical

Norwegian Bliss • Norwegian Cruise Line

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

Feb 7, 2028 → Feb 19, 2028 • New York ↔

$240 above typical ↗

From $1,589

$1,589 · $132/night · priced high · ↑18% above typical

$132/night

Priced high

↑18% above typical

Norwegian Bliss • Norwegian Cruise Line

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

Mar 6, 2028 → Mar 18, 2028 • New York ↔

$250 above typical ↗

From $1,679

$1,679 · $140/night · priced high · ↑18% above typical

$140/night

Priced high

↑18% above typical

Emerald Princess • Princess Cruises

7-night Eastern Caribbean Loop via San Juan, Saint Thomas & Philipsburg

Dec 31, 2027 → Jan 7, 2028 • Bridgetown ↔

$280 above typical

From $1,936

$1,936 · $277/night · priced high · ↑17% above typical

$277/night

Priced high

↑17% above typical

Valiant Lady • Virgin Voyages

7-night ABC Islands Loop via Willemstad & Cruz Bay, Saint John

Mar 27, 2027 → Apr 3, 2027 • San Juan ↔

From $1,708

$1,708 · $244/night · priced high · ↑17% above typical

$244/night

Priced high

↑17% above typical

Carnival Vista • Carnival Cruise Line

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

Jan 9, 2027 → Jan 17, 2027 • Port Canaveral ↔

$106 above typical ↗

From $739

$739 · $92/night · priced high · ↑17% above typical

$92/night

Priced high

↑17% above typical

Harmony of the Seas • Royal Caribbean International

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

Aug 21, 2027 → Aug 28, 2027 • Port Canaveral ↔

$167 above typical

From $1,178

$1,178 · $168/night · priced high · ↑17% above typical

$168/night

Priced high

↑17% above typical

Regal Princess • Princess Cruises

14-night Eastern Caribbean Loop via Puerto Plata, San Juan & Cozumel

Sep 26, 2026 → Oct 10, 2026 • Fort Lauderdale ↔

$221 above typical ↗

From $1,563

$1,563 · $112/night · priced high · ↑16% above typical

$112/night

Priced high

↑16% above typical

Explora I • Explora Journeys

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

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

$660 above typical ↗

From $4,680

$4,680 · $669/night · priced high · ↑16% above typical

$669/night

Priced high

↑16% above typical

Britannia • P&O Cruises

14-night Southern Caribbean Loop via Philipsburg, Antigua & Basseterre, Saint Kitts

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

$375 above typical

From $2,674

$2,674 · $191/night · priced high · ↑16% above typical

$191/night

Priced high

↑16% above typical

Celebrity Constellation • Celebrity Cruises

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

Jan 23, 2027 → Jan 30, 2027 • San Juan ↔

$114 above typical ↗

From $823

$823 · $118/night · priced high · ↑16% above typical

$118/night

Priced high

↑16% above typical

Celebrity Ascent • Celebrity Cruises

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

Feb 25, 2028 → Mar 6, 2028 • Fort Lauderdale ↔

$236 above typical

From $1,715

$1,715 · $172/night · priced high · ↑16% above typical

$172/night

Priced high

↑16% above typical

Brilliant Lady • Virgin Voyages

10-night Itinerary SXPHI-VGTOV-VIFRD-PRSJU-DOPOP-BSBIM

Feb 8, 2027 → Feb 18, 2027 • Miami ↔

$244 above typical

From $1,791

$1,791 · $179/night · priced high · ↑16% above typical

$179/night

Priced high

↑16% above typical

Regal Princess • Princess Cruises

14-night Eastern Caribbean Loop via Roatán, Belize City & Cozumel

Sep 19, 2026 → Oct 3, 2026 • Fort Lauderdale ↔

$210 above typical ↗

From $1,552

$1,552 · $111/night · priced high · ↑16% above typical

$111/night

Priced high

↑16% above typical

Oceania Allura • Oceania Cruises

20-night Eastern Caribbean Arc via Saint-Barthélemy, Philipsburg & Basseterre, Saint Kitts

Feb 19, 2027 → Mar 11, 2027 • San Juan → Miami

$1,251 above typical

From $9,249

$9,249 · $462/night · priced high · ↑16% above typical

$462/night

Priced high

↑16% above typical

MSC Seaview • MSC Cruises

14-night Eastern Caribbean Loop via Kingstown, Saint George & Fort-de-France

Dec 15, 2026 → Dec 29, 2026 • Bridgetown ↔

From $2,254

$2,254 · $161/night · priced high · ↑16% above typical

$161/night

Priced high

↑16% above typical

Rhapsody of the Seas • Royal Caribbean International

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

Aug 8, 2026 → Aug 15, 2026 • San Juan ↔

$147 above typical ↗

From $1,093

$1,093 · $156/night · priced high · ↑16% above typical

$156/night

Priced high

↑16% above typical

Celebrity Beyond • Celebrity Cruises

7-night Eastern Caribbean Loop via Puerto Plata & Tortola

Sep 27, 2026 → Oct 4, 2026 • Miami ↔

$133 above typical ↗

From $995

$995 · $142/night · priced high · ↑15% above typical

$142/night

Priced high

↑15% above typical

Celebrity Apex • Celebrity Cruises

7-night Eastern Caribbean Loop via Puerto Plata & Charlotte Amalie, Saint Thomas

Feb 19, 2028 → Feb 26, 2028 • Port Canaveral ↔

$158 above typical

From $1,182

$1,182 · $169/night · priced high · ↑15% above typical

$169/night

Priced high

↑15% above typical