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Carnival Cruise Line

Carnival Vista • Carnival Cruise Line

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

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

$76 above typical

From $709

$89/night

Priced high

↑12% above typical

Princess Cruises

Island Princess • Princess Cruises

12-night Southern Caribbean Loop via Oranjestad, Curaçao & Castries

Nov 30, 2026 → Dec 12, 2026 • Fort Lauderdale ↔

$164 above typical

From $1,551

$129/night

Priced high

↑12% above typical

Royal Caribbean International

Allure of the Seas • Royal Caribbean International

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

Feb 14, 2027 → Feb 21, 2027 • Miami ↔

$130 above typical ↗ Trending up

From $1,228

$175/night

Priced high

↑12% above typical

Princess Cruises

Emerald Princess • Princess Cruises

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

Feb 25, 2028 → Mar 3, 2028 • Bridgetown ↔

$195 above typical

From $1,856

$265/night

Priced high

↑12% above typical

Princess Cruises

Emerald Princess • Princess Cruises

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

Jan 30, 2028 → Feb 6, 2028 • San Juan ↔

$105 above typical

From $1,017

$145/night

Priced high

↑12% above typical

Princess Cruises

Emerald Princess • Princess Cruises

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

Feb 27, 2028 → Mar 5, 2028 • San Juan ↔

$105 above typical

From $1,017

$145/night

Priced high

↑12% above typical

Princess Cruises

Regal Princess • Princess Cruises

15-night Itinerary DOPOP-PRSJU-SXPHI-VGTOV-USMIA-P221398-VISTT-SXPHI

Nov 27, 2027 → Dec 12, 2027 • Miami ↔

$202 above typical

From $1,969

$131/night

Priced high

↑11% above typical

Royal Caribbean International

Grandeur of the Seas • Royal Caribbean International

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

May 15, 2027 → May 22, 2027 • San Juan ↔

$93 above typical

From $911

$130/night

Priced high

↑11% above typical

Norwegian Cruise Line

Norwegian Bliss • Norwegian Cruise Line

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

Jan 4, 2027 → Jan 16, 2027 • New York ↔

$150 above typical ↗ Trending up

From $1,469

$122/night

Priced high

↑11% above typical

Oceania Cruises

Oceania Marina • Oceania Cruises

10-night Eastern Caribbean Loop via San Juan, Basseterre, Saint Kitts & Great Stirrup Cay

Feb 23, 2027 → Mar 5, 2027 • Miami ↔

$350 above typical

From $3,449

$345/night

Priced high

↑11% above typical

Regent Seven Seas Cruises

Seven Seas Prestige • Regent Seven Seas Cruises

9-night Eastern Caribbean Loop via Saint-Barthélemy & Basseterre, Saint Kitts

Jan 27, 2028 → Feb 5, 2028 • Miami ↔

From $7,179

$798/night

Royal Caribbean International

Allure of the Seas • Royal Caribbean International

8-night Eastern Caribbean Loop via Basseterre, Saint Kitts & Coco Cay

Jun 27, 2026 → Jul 5, 2026 • Fort Lauderdale ↔

$158 above typical ↗ Trending up

From $1,608

$201/night

Priced high

↑11% above typical

Princess Cruises

Emerald Princess • Princess Cruises

14-night Eastern Caribbean Arc via Falmouth, Oranjestad & Curaçao

Nov 14, 2027 → Nov 28, 2027 • Fort Lauderdale → San Juan

$183 above typical

From $1,913

$137/night

Priced high

↑11% above typical

Holland America

Nieuw Amsterdam • Holland America

12-night Transatlantic Crossing via Philipsburg, Fort-de-France & Bridgetown

Nov 29, 2026 → Dec 11, 2026 • Fort Lauderdale ↔

$151 above typical

From $1,589

$132/night

Priced high

↑10% above typical

Royal Caribbean International

Grandeur of the Seas • Royal Caribbean International

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

May 8, 2027 → May 15, 2027 • San Juan ↔

$77 above typical

From $810

$116/night

Priced high

↑10% above typical

Holland America

Rotterdam • Holland America

21-night Western Caribbean Arc via Key West, Georgetown, Grand Cayman & Cozumel

Feb 13, 2027 → Mar 6, 2027 • Fort Lauderdale ↔

$243 above typical

From $2,599

$124/night

Priced high

↑10% above 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

$537 above typical

From $6,040

$755/night

Typical price

↑10% above typical

Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

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

Mar 18, 2028 → Mar 25, 2028 • San Juan ↔

$120 above typical

From $1,359

$194/night

Typical price

↑10% above typical

Royal Caribbean International

Icon of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Philipsburg & Coco Cay

May 29, 2027 → Jun 5, 2027 • Miami ↔

$158 above typical

From $1,793

$256/night

Typical price

↑10% above typical

Princess Cruises

Star Princess • Princess Cruises

9-night Eastern Caribbean Loop via Grand Turk Island, Puerto Plata & San Juan

Nov 14, 2027 → Nov 23, 2027 • Port Canaveral ↔

$86 above typical

From $1,010

$112/night

Typical price

↑9% above typical

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