Jibhop

Crown Princess • Princess Cruises

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

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

From $1,238

$1,238 · $177/night · priced high · ↑31% above typical

$177/night

Priced high

↑31% above typical

MSC Opera • MSC Cruises

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

Apr 29, 2027 → May 13, 2027 • Bridgetown ↔

From $1,908

$1,908 · $136/night · priced high · ↑30% above typical

$136/night

Priced high

↑30% above typical

MSC Opera • MSC Cruises

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

Apr 19, 2027 → Apr 26, 2027 • La Romana ↔

Great balance

From $959

$959 · $137/night · priced high · ↑30% above typical

$137/night

Priced high

↑30% above typical

Regal Princess • Princess Cruises

8-night Itinerary DOPOP-PRSJU-SXPHI-VGTOV

Dec 19, 2027 → Dec 27, 2027 • Miami ↔

Great balance

From $1,487

$1,487 · $186/night · priced high · ↑29% above typical

$186/night

Priced high

↑29% above typical

Celebrity Ascent • Celebrity Cruises

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

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

$427 above typical ↗

From $1,901

$1,901 · $190/night · priced high · ↑29% above typical

$190/night

Priced high

↑29% above typical

Rotterdam • Holland America

11-night Eastern Caribbean Loop via Philipsburg, Antigua & Roseau

Jan 12, 2027 → Jan 23, 2027 • Fort Lauderdale ↔

$388 above typical ↗

From $1,734

$1,734 · $158/night · priced high · ↑29% above typical

$158/night

Priced high

↑29% above typical

Norwegian Viva • Norwegian Cruise Line

7-night Eastern Caribbean Loop via Philipsburg & Willemstad

Jan 9, 2028 → Jan 16, 2028 • San Juan ↔

From $1,169

$1,169 · $167/night · priced high · ↑29% above typical

$167/night

Priced high

↑29% above typical

Norwegian Prima • Norwegian Cruise Line

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

Jan 10, 2027 → Jan 17, 2027 • San Juan ↔

$360 above typical

From $1,619

$1,619 · $231/night · priced high · ↑29% above typical

$231/night

Priced high

↑29% above typical

Celebrity Beyond • Celebrity Cruises

7-night Eastern Caribbean Loop via Puerto Plata & Tortola

Oct 25, 2026 → Nov 1, 2026 • Miami ↔

$240 above typical ↗

From $1,088

$1,088 · $155/night · priced high · ↑28% above typical

$155/night

Priced high

↑28% above typical

Regal Princess • Princess Cruises

14-night Itinerary P221398-DOPOP-PRSJU-TCGDT-USMIA-P221398-VISTT-SXPHI

Apr 2, 2028 → Apr 16, 2028 • Miami ↔

From $2,278

$2,278 · $163/night · priced high · ↑28% above typical

$163/night

Priced high

↑28% above typical

MSC Seashore • MSC Cruises

14-night Itinerary DOPOP-BSOCE-BSNAS-USMIA-SXPHI-KNBAS-VICHA-DOPOP

Jan 23, 2028 → Feb 6, 2028 • Miami ↔

From $1,608

$1,608 · $115/night · priced high · ↑28% above typical

$115/night

Priced high

↑28% 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 ↔

$260 above typical ↗

From $1,201

$1,201 · $172/night · priced high · ↑28% above typical

$172/night

Priced high

↑28% above typical

Norwegian Prima • Norwegian Cruise Line

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

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

$340 above typical

From $1,599

$1,599 · $228/night · priced high · ↑27% above typical

$228/night

Priced high

↑27% above typical

Rhapsody of the Seas • Royal Caribbean International

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

Aug 15, 2026 → Aug 22, 2026 • San Juan ↔

$257 above typical ↗

From $1,225

$1,225 · $175/night · priced high · ↑27% above typical

$175/night

Priced high

↑27% 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 ↔

$203 above typical ↗

From $970

$970 · $139/night · priced high · ↑26% above typical

$139/night

Priced high

↑26% 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

$1,990 above typical ↗

From $10,099

$10,099 · $505/night · priced high · ↑25% above typical

$505/night

Priced high

↑25% above typical

Regal Princess • Princess Cruises

14-night Itinerary DOPOP-PRSJU-SXPHI-TCGDT-USFLL-P221398-TCGDT-BSNAS

Dec 26, 2026 → Jan 9, 2027 • Fort Lauderdale ↔

From $2,500

$2,500 · $179/night · priced high · ↑24% above typical

$179/night

Priced high

↑24% above typical

Celebrity Apex • Celebrity Cruises

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

Mar 4, 2028 → Mar 11, 2028 • Port Canaveral ↔

$216 above typical ↗

From $1,112

$1,112 · $159/night · priced high · ↑24% above typical

$159/night

Priced high

↑24% above typical

Celebrity Apex • Celebrity Cruises

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

Mar 18, 2028 → Mar 25, 2028 • Port Canaveral ↔

$216 above typical ↗

From $1,112

$1,112 · $159/night · priced high · ↑24% above typical

$159/night

Priced high

↑24% above typical

MSC Poesia • MSC Cruises

21-night Itinerary VICHA-KNBAS-SXPHI-AGSJO-PRSJU-DOPOP-USMIA-JMOCJ-COCTG-PAONX-CRLIO-HNRTB-BZBZE

Nov 12, 2026 → Dec 3, 2026 • Miami ↔

From $2,445

$2,445 · $116/night · priced high · ↑24% above typical

$116/night

Priced high

↑24% above typical