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Departures Itineraries
Virgin Voyages

Valiant Lady • Virgin Voyages

7-night Southern Caribbean Loop via Philipsburg, Fort-de-France & Bridgetown

Dec 26, 2026 → Jan 2, 2027 • San Juan ↔

Lowest in 30 days $724 above typical
$1,837 · $262/night · priced high · ↑65% above typical
Holland America

Rotterdam • Holland America

11-night Eastern Caribbean Arc via Philipsburg, Basseterre, Saint Kitts & Roseau

Dec 22, 2026 → Jan 2, 2027 • Fort Lauderdale ↔

Lowest in 30 days $725 above typical
$2,034 · $185/night · priced high · ↑55% above typical
Cunard Line

Queen Mary 2 • Cunard Line

14-night Southern Caribbean Arc via Saint Thomas, Bridgetown & Castries

Nov 24, 2028 → Dec 8, 2028 • New York ↔

Lowest in 180 days $988 above typical
$3,177 · $227/night · priced high · ↑45% above typical
Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

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

Dec 18, 2027 → Dec 25, 2027 • San Juan ↔

Lowest in 30 days $550 above typical
$1,809 · $258/night · priced high · ↑44% above typical
Cunard Line

Queen Elizabeth • Cunard Line

14-night Transatlantic Crossing via Saint Thomas, Basseterre, Saint Kitts & Kingstown

Dec 23, 2027 → Jan 6, 2028 • Miami ↔

Lowest in 180 days $711 above typical
$2,405 · $172/night · priced high · ↑42% above typical
Virgin Voyages

Valiant Lady • Virgin Voyages

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

Nov 7, 2026 → Nov 14, 2026 • San Juan ↔

Lowest in 30 days $420 above typical
$1,533 · $219/night · priced high · ↑38% above typical
Cunard Line

Queen Mary 2 • Cunard Line

21-night Southern Caribbean Arc via New York, Saint Thomas & Bridgetown

Nov 17, 2028 → Dec 8, 2028 • Southampton → New York

Lowest in 180 days $1,236 above typical
$4,520 · $215/night · priced high · ↑38% above typical
Cunard Line

Queen Mary 2 • Cunard Line

21-night Eastern Caribbean Arc via Road Town, Tortola, Basseterre, Saint Kitts & Castries

Dec 22, 2028 → Jan 12, 2029 • New York → Southampton

Lowest in 180 days $1,350 above typical
$4,963 · $236/night · priced high · ↑37% above typical
Cunard Line

Queen Mary 2 • Cunard Line

20-night Eastern Caribbean Arc via New York, Road Town, Tortola & Basseterre, Saint Kitts

Dec 15, 2028 → Jan 4, 2029 • Southampton → New York

Lowest in 180 days $1,232 above typical
$4,673 · $234/night · priced high · ↑36% above typical
Virgin Voyages

Valiant Lady • Virgin Voyages

6-night Eastern Caribbean Loop via Tortola & Cruz Bay, Saint John

Nov 14, 2026 → Nov 20, 2026 • San Juan ↔

Lowest in 90 days $240 above typical
$1,014 · $169/night · priced high · ↑31% above typical
Explora Journeys

Explora II • Explora Journeys

10-night Transatlantic Crossing via Parintins, Scarborough & Castries

Feb 17, 2028 → Feb 27, 2028 • Manaus → San Juan

Lowest in 30 days $1,591 above typical
$7,370 · $737/night · priced high · ↑28% above typical
Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

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

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

Lowest in 30 days $300 above typical
$1,559 · $223/night · priced high · ↑24% above typical
Norwegian Cruise Line

Norwegian Breakaway • Norwegian Cruise Line

14-night Southern Caribbean Arc via Georgetown, South Carolina, Oranjestad & Willemstad

Apr 4, 2027 → Apr 18, 2027 • New Orleans → Boston

Lowest in 30 days $401 above typical
$2,259 · $161/night · priced high · ↑22% above typical
Cunard Line

Queen Mary 2 • Cunard Line

28-night Southern Caribbean Loop via New York, Saint Thomas & Bridgetown

Nov 17, 2028 → Dec 15, 2028 • Southampton ↔

Lowest in 180 days $903 above typical
$5,282 · $189/night · priced high · ↑21% above typical
Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

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

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

Lowest in 30 days $240 above typical
$1,499 · $214/night · priced high · ↑19% above typical
Cunard Line

Queen Elizabeth • Cunard Line

26-night Transatlantic Crossing via Saint Thomas, Basseterre, Saint Kitts & Kingstown

Dec 23, 2027 → Jan 18, 2028 • Miami → Southampton

Lowest in 180 days $591 above typical
$3,737 · $144/night · priced high · ↑19% above typical
P&O Cruises

Arvia • P&O Cruises

22-night Transatlantic Crossing via Antigua, Castries & Oranjestad

Mar 4, 2028 → Mar 26, 2028 • Antigua → Southampton

Lowest in 180 days $486 above typical
$3,242 · $147/night · priced high · ↑18% above typical
Cunard Line

Queen Mary 2 • Cunard Line

28-night Eastern Caribbean Loop via New York, Road Town, Tortola & Basseterre, Saint Kitts

Dec 15, 2028 → Jan 12, 2029 • Southampton ↔

Lowest in 180 days $807 above typical
$5,625 · $201/night · priced high · ↑17% above typical
Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

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

Jan 24, 2027 → Jan 31, 2027 • San Juan ↔

Lowest in 30 days $200 above typical
$1,459 · $208/night · priced high · ↑16% above typical
Cunard Line

Queen Elizabeth • Cunard Line

14-night Eastern Caribbean Loop via Saint Thomas, Basseterre, Saint Kitts & Saint George's

Nov 25, 2027 → Dec 9, 2027 • Miami ↔

Lowest in 180 days $210 above typical
$1,643 · $117/night · priced high · ↑15% above typical