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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

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

Princess Cruises

Coral Princess • Princess Cruises

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

Oct 15, 2026 → Oct 29, 2026 • Fort Lauderdale ↔

$138 above typical

From $1,994

$142/night

Typical price

↑7% above typical

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 ↔

$115 above typical

From $1,739

$124/night

Typical price

↑7% above typical

Princess Cruises

Emerald Princess • Princess Cruises

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

Mar 5, 2028 → Mar 12, 2028 • San Juan ↔

$65 above typical

From $1,090

$156/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

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

Azamara Cruises

Azamara Journey • Azamara Cruises

7-night Southern Caribbean Arc via Spanish Town, Antigua & Saint-Pierre

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

Great balance

From $1,859

$266/night

Princess Cruises

Emerald Princess • Princess Cruises

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

Mar 19, 2028 → Mar 26, 2028 • San Juan ↔

$55 above typical

From $1,080

$154/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

Silversea Cruises

Silver Shadow • Silversea Cruises

10-night Southern Caribbean Arc via Port Elizabeth, Bequia, Saint George's & Castries

Feb 16, 2027 → Feb 26, 2027 • Bridgetown → San Juan

From $7,500

$750/night

Princess Cruises

Emerald Princess • Princess Cruises

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

Feb 27, 2028 → Mar 12, 2028 • San Juan ↔

From $2,016

$144/night

Typical price

↑3% above typical

Princess Cruises

Emerald Princess • Princess Cruises

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

Mar 5, 2028 → Mar 19, 2028 • San Juan ↔

From $2,116

$151/night

Typical price

↑3% above typical

Princess Cruises

Emerald Princess • Princess Cruises

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

Mar 12, 2028 → Mar 26, 2028 • San Juan ↔

From $2,106

$150/night

Typical price

↑3% above typical

Silversea Cruises

Silver Spirit • Silversea Cruises

10-night Southern Caribbean Loop via Port Elizabeth, Bequia, Saint George's & Oranjestad

Jan 15, 2027 → Jan 25, 2027 • Bridgetown ↔

From $7,800

$780/night

P&O Cruises

Arvia • P&O Cruises

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

Jan 23, 2027 → Feb 6, 2027 • Antigua ↔

From $2,566

$183/night

Typical price

↑2% above typical

P&O Cruises

Arvia • P&O Cruises

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

Jan 8, 2028 → Jan 22, 2028 • Antigua ↔

From $2,566

$183/night

Typical price

↑2% above typical

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