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Departures Itineraries
Norwegian Cruise Line

Norwegian Pearl • Norwegian Cruise Line

10-night Eastern Caribbean Loop via Puerto Plata & Cruz Bay, Saint John

Dec 13, 2027 → Dec 23, 2027 • Philadelphia ↔

Lowest in 30 days $95 above typical
$1,049 · $105/night · priced high · ↑10% above typical
Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

10-night Eastern Caribbean Arc via Kings Wharf, Tortola & Basseterre, Saint Kitts

Nov 3, 2027 → Nov 13, 2027 • New York → San Juan

Lowest in 30 days $182 above typical
$2,009 · $201/night · typical price · ↑10% above typical
Royal Caribbean International

Rhapsody of the Seas • Royal Caribbean International

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

Jan 22, 2028 → Jan 29, 2028 • San Juan ↔

Lowest in 180 days $67 above typical
$767 · $110/night · typical price · ↑10% above typical
Explora Journeys

Explora I • Explora Journeys

7-night Eastern Caribbean Arc via Puerto Plata & Philipsburg

Jan 29, 2027 → Feb 5, 2027 • Miami → San Juan

Lowest in 30 days $400 above typical
$4,600 · $657/night · typical price · ↑10% above typical
Disney Cruise Line

Disney Dream • Disney Cruise Line

7-night Eastern Caribbean Loop via Philipsburg & Disney Castaway Cay

Feb 19, 2027 → Feb 26, 2027 • Fort Lauderdale ↔

Lowest in 90 days $186 above typical
$2,363 · $338/night · typical price · ↑9% above typical
Holland America

Rotterdam • Holland America

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

Mar 16, 2027 → Mar 27, 2027 • Fort Lauderdale ↔

Lowest in 30 days $125 above typical
$1,584 · $144/night · typical price · ↑9% above typical
Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

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

Nov 22, 2026 → Nov 29, 2026 • San Juan ↔

Lowest in 180 days $110 above typical ↘
$1,419 · $203/night · typical price · ↑8% above typical
Holland America

Rotterdam • Holland America

21-night Eastern Caribbean Loop via Philipsburg, Basseterre, Saint Kitts & Cozumel

Dec 22, 2026 → Jan 12, 2027 • Fort Lauderdale ↔

Lowest in 30 days $210 above typical
$2,709 · $129/night · typical price · ↑8% above typical
Norwegian Cruise Line

Norwegian Bliss • Norwegian Cruise Line

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

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

Lowest in 30 days $140 above typical
$1,819 · $152/night · typical price · ↑8% above typical
Norwegian Cruise Line

Norwegian Dawn • Norwegian Cruise Line

12-night Eastern Caribbean Loop via Great Stirrup Cay, Puerto Plata & Cruz Bay, Saint John

Jan 2, 2028 → Jan 14, 2028 • Jacksonville ↔

Lowest in 30 days $102 above typical
$1,389 · $116/night · typical price · ↑8% 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

Lowest in 30 days $433 above typical
$6,330 · $791/night · typical price · ↑7% above typical
Virgin Voyages

Valiant Lady • Virgin Voyages

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

Mar 6, 2027 → Mar 13, 2027 • San Juan ↔

Lowest in 90 days $70 above typical
$1,043 · $149/night · typical price · ↑7% above typical
Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

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

Jan 1, 2028 → Jan 8, 2028 • San Juan ↔

Lowest in 30 days $80 above typical
$1,339 · $191/night · typical price · ↑6% above typical
Royal Caribbean International

Star of the Seas • Royal Caribbean International

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

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

Lowest in 180 days $106 above typical
$1,797 · $257/night · typical price · ↑6% above typical
Royal Caribbean International

Hero Of The Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Philipsburg & Coco Cay

Jan 15, 2028 → Jan 22, 2028 • Miami ↔

Lowest in 180 days $94 above typical
$1,708 · $244/night · typical price · ↑6% above typical
Royal Caribbean International

Star of the Seas • Royal Caribbean International

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

Mar 5, 2028 → Mar 12, 2028 • Port Canaveral ↔

Lowest in 180 days $96 above typical ↘
$1,787 · $255/night · typical price · ↑6% above typical
Royal Caribbean International

Vision of the Seas • Royal Caribbean International

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

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

Lowest in 180 days
$771 · $110/night · typical price · ↑6% above typical
Royal Caribbean International

Grandeur of the Seas • Royal Caribbean International

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

Jul 17, 2027 → Jul 24, 2027 • San Juan ↔

Lowest in 180 days $52 above typical
$1,021 · $146/night · typical price · ↑5% above typical
Seabourn

Seabourn Ovation • Seabourn

7-night Eastern Caribbean Arc via Tortola, South Friars Bay & Les Trois-Îlets

Feb 20, 2027 → Feb 27, 2027 • Philipsburg → Bridgetown

Lowest in 180 days $245 above typical ↘
$4,844 · $692/night · typical price · ↑5% above typical
Oceania Cruises

Oceania Sonata • Oceania Cruises

12-night Eastern Caribbean Arc: Charlotte Amalie, Saint Thomas, Philipsburg & Saint John's

Jan 11, 2029 → Jan 23, 2029 • Miami ↔

Lowest in 180 days
$6,199 · $517/night · typical price · ↑5% above typical