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Holland America

Volendam • Holland America

14-night Southern Caribbean Loop via Key West, Oranjestad & Charlotteville

Dec 22, 2026 → Jan 5, 2027 • Fort Lauderdale ↔

$140 above typical

From $1,939

$139/night

Typical price

↑8% above typical

P&O Cruises

Arvia • P&O Cruises

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

Jan 28, 2028 → Feb 11, 2028 • Bridgetown ↔

$195 above typical

From $2,701

$193/night

Typical price

↑8% above typical

Nicko Cruises

Vasco Da Gama • Nicko Cruises

20-night Southern Caribbean Arc via Mindelo, Belém & Fort-de-France

Nov 12, 2026 → Dec 2, 2026 • Santa Cruz de Tenerife → Bridgetown

$332 above typical

From $4,617

$231/night

Typical price

↑8% above typical

Explora III

8-night Eastern Caribbean Loop via Philipsburg, Terre-de-Haut & Road Bay

Jan 13, 2027 → Jan 21, 2027 • San Juan → Miami

$450 above typical

From $6,290

$786/night

Typical price

↑8% above typical

P&O Cruises

Iona • P&O Cruises

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

Feb 26, 2028 → Mar 11, 2028 • Antigua ↔

$202 above typical

From $2,836

$203/night

Typical price

↑8% above typical

P&O Cruises

Britannia • P&O Cruises

14-night Southern Caribbean Loop via Philipsburg, Antigua & Basseterre, Saint Kitts

Jan 8, 2027 → Jan 22, 2027 • Bridgetown ↔

$173 above typical

From $2,472

$177/night

Typical price

↑8% above typical

MSC Cruises

MSC Seaview • MSC Cruises

7-night Southern Caribbean Loop via Pointe-à-Pitre, Castries & Bridgetown

Jan 23, 2027 → Jan 30, 2027 • Fort-de-France ↔

Great balance

From $984

$141/night

Princess Cruises

Crown Princess • Princess Cruises

14-night Southern Caribbean Loop via Philipsburg, Fort-de-France & Saint George's

Jan 17, 2027 → Jan 31, 2027 • San Juan ↔

$108 above typical

From $1,739

$124/night

Typical price

↑7% above typical

Princess Cruises

Emerald Princess • Princess Cruises

7-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Antigua

Mar 12, 2028 → Mar 19, 2028 • San Juan ↔

$67 above typical

From $1,092

$156/night

Typical price

↑7% above typical

Virgin Voyages

Valiant Lady • Virgin Voyages

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

Dec 12, 2026 → Dec 19, 2026 • San Juan ↔

$70 above typical

From $1,183

$169/night

Typical price

↑6% above typical

Princess Cruises

Emerald Princess • Princess Cruises

14-night Eastern Caribbean Arc via Falmouth, Oranjestad & Curaçao

Nov 14, 2027 → Nov 28, 2027 • Fort Lauderdale → San Juan

$108 above typical

From $1,838

$131/night

Typical price

↑6% above typical

P&O Cruises

Arvia • P&O Cruises

14-night Southern Caribbean Loop via Philipsburg, Tortola & Roseau

Nov 22, 2027 → Dec 6, 2027 • Basseterre, Saint Kitts ↔

$135 above typical

From $2,296

$164/night

Typical price

↑6% above typical

Oceania Cruises

Oceania Insignia • Oceania Cruises

57-night Transatlantic Crossing via Rijeka, Kotor & Cruz Bay, Saint John

Oct 23, 2026 → Dec 19, 2026 • Fusina (Venice) → Miami

$1,055 above typical

From $19,099

$335/night

Typical price

↑6% above typical

P&O Cruises

Britannia • P&O Cruises

35-night Transatlantic Crossing via Santa Cruz de Tenerife, Bridgetown & Fort-de-France

Jan 4, 2028 → Feb 8, 2028 • Southampton ↔

$333 above typical

From $6,080

$174/night

Typical price

↑6% above typical

Princess Cruises

Emerald Princess • Princess Cruises

7-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Antigua

Jan 2, 2028 → Jan 9, 2028 • San Juan ↔

Great balance

From $962

$137/night

Typical price

↑5% above typical

P&O Cruises

Arvia • P&O Cruises

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

Jan 15, 2028 → Jan 29, 2028 • Bridgetown ↔

$128 above typical

From $2,634

$188/night

Typical price

↑5% above typical

Cunard Line

Queen Mary 2 • Cunard Line

34-night Itinerary PTFNC-VGRAD-BBBGI-LCCAS-GDSTG-DMRSU-KNBAS-DOPOP-SXPHI-ESSCT

Jan 11, 2027 → Feb 14, 2027 • Southampton ↔

$290 above typical

From $6,036

$178/night

Typical price

↑5% above typical

P&O Cruises

Arvia • P&O Cruises

14-night Southern Caribbean Loop via Tortola, Philipsburg & Roseau

Nov 8, 2027 → Nov 22, 2027 • Basseterre, Saint Kitts ↔

From $2,269

$162/night

Typical price

↑5% above typical

MSC Cruises

MSC Seaview • MSC Cruises

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

Feb 23, 2027 → Mar 9, 2027 • Bridgetown ↔

From $2,128

$152/night

Princess Cruises

Crown Princess • Princess Cruises

7-night Eastern Caribbean Loop via Saint Thomas, Philipsburg & Antigua

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

Great balance

From $1,138

$163/night

Typical price

↑4% above typical

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