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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

P&O Cruises

Iona • P&O Cruises

14-night Eastern Caribbean Loop via Castries, Saint George's & Bridgetown

Nov 20, 2027 → Dec 4, 2027 • Antigua ↔

Lowest in 30 days $564 above typical

From $2,363

$169/night

Priced high

↑31% 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 30 days $240 above typical

From $1,014

$169/night

Priced high

↑31% above typical

MSC Cruises

MSC World Europa • MSC Cruises

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

Dec 20, 2026 → Dec 27, 2026 • Pointe-à-Pitre ↔

Lowest in 30 days $354 above typical

From $1,544

$221/night

Priced high

↑30% above typical

Celebrity Cruises

Celebrity Eclipse • Celebrity Cruises

12-night Southern Caribbean Loop via Basseterre, Saint Kitts, Castries & Bridgetown

Jan 17, 2027 → Jan 29, 2027 • Fort Lauderdale ↔

Lowest in 90 days $441 above typical

From $1,944

$162/night

Priced high

↑29% above typical

Cunard Line

Queen Mary 2 • Cunard Line

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

Nov 24, 2028 → Dec 15, 2028 • New York → Southampton

Lowest in 180 days $938 above typical

From $4,222

$201/night

Priced high

↑29% above typical

P&O Cruises

Iona • P&O Cruises

14-night Southern Caribbean Loop via Basseterre, Saint Kitts, Philipsburg & Fort-de-France

Mar 4, 2028 → Mar 18, 2028 • Bridgetown ↔

Lowest in 90 days $581 above typical

From $2,634

$188/night

Priced high

↑28% above typical

P&O Cruises

Arvia • P&O Cruises

14-night Southern Caribbean Loop via Fort-de-France, Basseterre, Saint Kitts & Philipsburg

Dec 19, 2026 → Jan 2, 2027 • Bridgetown ↔

Lowest in 180 days $716 above typical

From $3,282

$234/night

Priced high

↑28% above typical

P&O Cruises

Arvia • P&O Cruises

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

Dec 18, 2027 → Jan 1, 2028 • Bridgetown ↔

Lowest in 30 days $676 above typical

From $3,242

$232/night

Priced high

↑26% 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 $857 above typical

From $4,157

$160/night

Priced high

↑26% above typical

Celebrity Cruises

Celebrity Constellation • Celebrity Cruises

7-night Southern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Roseau

Nov 28, 2026 → Dec 5, 2026 • San Juan ↔

Lowest in 30 days $199 above typical

From $1,048

$150/night

Priced high

↑23% above typical

Virgin Voyages

Valiant Lady • Virgin Voyages

7-night Eastern Caribbean Loop via Saint Thomas, Road Town, Tortola & Basseterre, Saint Kitts

Nov 28, 2026 → Dec 5, 2026 • San Juan ↔

Lowest in 30 days $210 above typical

From $1,113

$159/night

Priced high

↑23% above typical

Celebrity Cruises

Celebrity Xcel • Celebrity Cruises

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

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

Lowest in 90 days $229 above typical

From $1,228

$175/night

Priced high

↑23% above typical

Princess Cruises

Enchanted Princess • Princess Cruises

11-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Roseau & Bridgetown

Dec 24, 2027 → Jan 4, 2028 • Fort Lauderdale ↔

Lowest in 30 days $295 above typical

From $1,607

$146/night

Priced high

↑22% above typical

Royal Caribbean International

Rhapsody of the Seas • Royal Caribbean International

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

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

Lowest in 30 days $195 above typical

From $1,079

$154/night

Priced high

↑22% above typical

Royal Caribbean International

Grandeur of the Seas • Royal Caribbean International

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

Nov 20, 2027 → Nov 27, 2027 • San Juan ↔

Lowest in 180 days $155 above typical

From $889

$127/night

Priced high

↑21% above typical

Celebrity Cruises

Celebrity Apex • Celebrity Cruises

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

Dec 19, 2026 → Dec 26, 2026 • Port Canaveral ↔

Lowest in 90 days $207 above typical

From $1,206

$172/night

Priced high

↑21% 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

From $5,282

$189/night

Priced high

↑21% above typical

P&O Cruises

Iona • P&O Cruises

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

Nov 27, 2027 → Dec 11, 2027 • Bridgetown ↔

Lowest in 30 days $362 above typical

From $2,161

$154/night

Priced high

↑20% above typical

Oceania Cruises

Oceania Allura • Oceania Cruises

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

Jan 27, 2027 → Feb 5, 2027 • Miami ↔

Lowest in 90 days $700 above typical

From $4,349

$483/night

Priced high

↑19% above typical

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