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Princess Cruises

Emerald Princess • Princess Cruises

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

Feb 18, 2028 → Feb 25, 2028 • Bridgetown ↔

Lowest in 180 days $679 above typical

From $1,655

$236/night

Priced high

↑70% above typical

Princess Cruises

Emerald Princess • Princess Cruises

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

Dec 24, 2027 → Dec 31, 2027 • Bridgetown ↔

Lowest in 180 days $690 above typical

From $1,709

$244/night

Priced high

↑68% above typical

Cunard Line

Queen Mary 2 • Cunard Line

13-night Southern Caribbean Arc via Road Town, Tortola, Basseterre, Saint Kitts & Castries

Dec 22, 2028 → Jan 4, 2029 • New York ↔

Lowest in 180 days $1,464 above typical

From $3,748

$288/night

Priced high

↑64% above typical

MSC Cruises

MSC Meraviglia • MSC Cruises

11-night Eastern Caribbean Loop via Fort-de-France, Pointe-à-Pitre & Antigua

Nov 19, 2027 → Nov 30, 2027 • Bridgetown ↔

Lowest in 30 days $609 above typical

From $1,590

$145/night

Priced high

↑62% above typical

MSC Cruises

MSC Opera • MSC Cruises

14-night Eastern Caribbean Loop via Fort-de-France, Antigua & Road Town, Tortola

Dec 31, 2026 → Jan 14, 2027 • Bridgetown ↔

Lowest in 30 days $914 above typical

From $2,579

$184/night

Priced high

↑55% above typical

Virgin Voyages

Brilliant Lady • Virgin Voyages

10-night Eastern Caribbean Loop via Philipsburg, Basseterre, Saint Kitts & Cruz Bay, Saint John

Dec 28, 2026 → Jan 7, 2027 • Miami ↔

Lowest in 90 days $700 above typical

From $1,990

$199/night

Priced high

↑54% above typical

MSC Cruises

MSC Seashore • MSC Cruises

15-night Eastern Caribbean Loop via Philipsburg, Basseterre, Saint Kitts & Ocean Cay

Dec 18, 2027 → Jan 2, 2028 • Miami ↔

Lowest in 30 days $767 above typical

From $2,181

$145/night

Priced high

↑54% 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 $908 above typical

From $2,685

$192/night

Priced high

↑51% above typical

Princess Cruises

Enchanted Princess • Princess Cruises

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

Dec 27, 2026 → Jan 6, 2027 • Fort Lauderdale ↔

Lowest in 30 days $601 above typical

From $1,793

$179/night

Priced high

↑50% above typical

MSC Cruises

MSC Meraviglia • MSC Cruises

14-night Eastern Caribbean Loop via Kingstown, Saint George & Fort-de-France

Nov 30, 2027 → Dec 14, 2027 • Bridgetown ↔

Lowest in 30 days $594 above typical

From $1,842

$132/night

Priced high

↑48% above typical

Royal Caribbean International

Symphony of the Seas • Royal Caribbean International

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

Nov 20, 2027 → Nov 28, 2027 • Fort Lauderdale ↔

Lowest in 180 days $464 above typical

From $1,494

$187/night

Priced high

↑45% 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

From $3,177

$227/night

Priced high

↑45% above typical

Princess Cruises

Emerald Princess • Princess Cruises

8-night Eastern Caribbean Loop via Castries, San Juan & Saint Thomas

Jan 20, 2028 → Jan 28, 2028 • Bridgetown ↔

Lowest in 180 days $451 above typical

From $1,514

$189/night

Priced high

↑42% above typical

Princess Cruises

Enchanted Princess • Princess Cruises

10-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Antigua & Princess Cays

Feb 15, 2027 → Feb 25, 2027 • Fort Lauderdale ↔

Lowest in 30 days $452 above typical

From $1,644

$164/night

Priced high

↑38% 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

From $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

From $4,520

$215/night

Priced high

↑38% above typical

MSC Cruises

MSC Opera • MSC Cruises

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

Dec 17, 2026 → Dec 31, 2026 • Bridgetown ↔

Lowest in 90 days $621 above typical

From $2,286

$163/night

Priced high

↑37% above typical

Carnival Cruise Line

Carnival Firenze • Carnival Cruise Line

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

Dec 17, 2027 → Dec 26, 2027 • Port Canaveral ↔

Lowest in 180 days $285 above typical

From $1,075

$119/night

Priced high

↑36% 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 $1,273 above typical

From $4,963

$236/night

Priced high

↑35% 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 $1,159 above typical

From $4,673

$234/night

Priced high

↑33% above typical

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