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Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

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

Mar 21, 2027 → Mar 28, 2027 • San Juan ↔

$440 above typical

From $1,669

$238/night

Priced high

↑36% above typical

Norwegian Cruise Line

Norwegian Viva • Norwegian Cruise Line

7-night ABC Islands Loop via Basseterre, Saint Kitts & Castries

Nov 14, 2027 → Nov 21, 2027 • San Juan ↔

$320 above typical

From $1,219

$174/night

Priced high

↑36% above typical

P&O Cruises

Iona • P&O Cruises

14-night Southern Caribbean Loop via Tortola, Philipsburg & Fort-de-France

Nov 29, 2027 → Dec 13, 2027 • Basseterre, Saint Kitts ↔

$632 above typical

From $2,431

$174/night

Priced high

↑35% above typical

MSC Cruises

MSC Seaview • MSC Cruises

14-night Eastern Caribbean Loop via Kingstown, Saint George & Castries

Dec 29, 2026 → Jan 12, 2027 • Bridgetown ↔

From $2,621

$187/night

P&O Cruises

Britannia • P&O Cruises

14-night Southern Caribbean Loop via Saint George's, Curaçao & Oranjestad

Jan 22, 2027 → Feb 5, 2027 • Bridgetown ↔

$781 above typical

From $3,080

$220/night

Priced high

↑34% above typical

P&O Cruises

Iona • P&O Cruises

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

Dec 24, 2027 → Jan 7, 2028 • Bridgetown ↔

$770 above typical

From $3,039

$217/night

Priced high

↑34% above typical

Regent Seven Seas Cruises

Seven Seas Voyager • Regent Seven Seas Cruises

21-night Amazon River Repositioning via Recife, Manaus & Castries

Feb 26, 2028 → Mar 18, 2028 • Rio de Janeiro → Miami

$5,086 above typical

From $20,097

$957/night

Priced high

↑34% above typical

Explora III

8-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Road Bay & Saint-Pierre

Jan 21, 2027 → Jan 29, 2027 • Miami → San Juan

$1,909 above typical

From $7,690

$961/night

Priced high

↑33% above typical

Norwegian Cruise Line

Norwegian Viva • Norwegian Cruise Line

7-night Eastern Caribbean Loop via Philipsburg & Willemstad

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

$290 above typical

From $1,169

$167/night

Priced high

↑33% above typical

MSC Cruises

MSC World Europa • MSC Cruises

7-night Eastern Caribbean Loop via Pointe-à-Pitre, Philipsburg & Saint John's

Dec 19, 2026 → Dec 26, 2026 • Fort-de-France ↔

$301 above typical ↘ Trending down

From $1,251

$179/night

Priced high

↑32% above typical

Oceania Cruises

Oceania Allura • Oceania Cruises

17-night Eastern Caribbean Loop via Costa Maya, Roatán & Cozumel

Dec 21, 2026 → Jan 7, 2027 • Miami ↔

$2,400 above typical

From $10,049

$591/night

Priced high

↑31% above typical

Royal Caribbean International

Grandeur of the Seas • Royal Caribbean International

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

May 22, 2027 → May 29, 2027 • San Juan ↔

$225 above typical

From $960

$137/night

Priced high

↑31% above typical

Explora Journeys

Explora I • Explora Journeys

24-night Southern Caribbean Loop via Saint-Barthélemy, Saint-Pierre & Bridgetown

Feb 5, 2027 → Mar 1, 2027 • San Juan ↔

$4,335 above typical

From $19,095

$796/night

Priced high

↑29% above typical

MSC Cruises

MSC Seashore • MSC Cruises

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

Jan 23, 2028 → Feb 6, 2028 • Miami ↔

$350 above typical ↗ Trending up

From $1,608

$115/night

Priced high

↑28% above typical

Emerald Cruises

Emerald Sakara • Emerald Cruises

14-night Eastern Caribbean Arc: Soufriere, Terre-de-Haut & Road Bay

Mar 31, 2029 → Apr 14, 2029 • Bridgetown → Philipsburg

$3,178 above typical

From $15,119

$1,080/night

Priced high

↑27% above typical

Norwegian Cruise Line

Norwegian Bliss • Norwegian Cruise Line

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

Feb 1, 2027 → Feb 13, 2027 • New York ↔

$350 above typical

From $1,669

$139/night

Priced high

↑27% above typical

Norwegian Cruise Line

Norwegian Viva • Norwegian Cruise Line

7-night ABC Islands Loop via Oranjestad & Willemstad

Nov 28, 2027 → Dec 5, 2027 • San Juan ↔

$230 above typical

From $1,129

$161/night

Priced high

↑26% above typical

Holland America

Rotterdam • Holland America

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

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

$309 above typical

From $1,534

$139/night

Priced high

↑25% above typical

Holland America

Rotterdam • Holland America

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

Feb 2, 2027 → Feb 13, 2027 • Fort Lauderdale ↔

$309 above typical

From $1,534

$139/night

Priced high

↑25% above typical

Explora IV

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

Dec 23, 2027 → Dec 30, 2027 • Miami → San Juan

$985 above typical

From $4,900

$700/night

Priced high

↑25% above typical

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