P&O Cruises

Iona • P&O Cruises

15-night Transatlantic Crossing via Bridgetown, Roseau & Antigua

Mar 17, 2028 → Apr 1, 2028 • Bridgetown → Southampton

Lowest in 30 days $337 below typical
$1,863 · $124/night · good value · ↓15% below typical
Seabourn

Seabourn Ovation • Seabourn

15-night Eastern Caribbean Arc via South Friars Bay, Rodney Bay & Little Bay

Nov 20, 2026 → Dec 5, 2026 • Miami → Philipsburg

$1,801 below typical
$7,198 · $480/night · great deal · ↓20% below typical
Holland America

Rotterdam • Holland America

21-night Western Caribbean Loop via Half Moon Cay, Falmouth & Cozumel

Nov 21, 2026 → Dec 12, 2026 • Fort Lauderdale ↔

$607 below typical
$2,064 · $98/night · great deal · ↓23% below typical
Royal Caribbean International

Vision of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg

Nov 8, 2026 → Nov 15, 2026 • San Juan ↔

$130 below typical
$574 · $82/night · good value · ↓19% below typical
Royal Caribbean International

Vision of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg

Nov 29, 2026 → Dec 6, 2026 • San Juan ↔

$130 below typical
$574 · $82/night · good value · ↓19% below typical
Carnival Cruise Line

Carnival Venezia • Carnival Cruise Line

14-night Eastern Caribbean Loop via Grand Turk Island, Oranjestad & Curaçao

Jan 10, 2027 → Jan 24, 2027 • Port Canaveral ↔

Lowest in 30 days $131 below typical
$996 · $71/night · good value · ↓12% below typical
P&O Cruises

Iona • P&O Cruises

14-night Southern Caribbean Arc via Santa Cruz de Tenerife & Philipsburg

Oct 30, 2027 → Nov 13, 2027 • Southampton → Bridgetown

Lowest in 180 days $205 below typical
$1,485 · $106/night · good value · ↓12% below typical
P&O Cruises

Iona • P&O Cruises

21-night Transatlantic Crossing via Antigua, Castries & Saint George's

Mar 11, 2028 → Apr 1, 2028 • Antigua → Southampton

Lowest in 180 days $446 below typical
$2,634 · $125/night · good value · ↓14% below typical
Princess Cruises

Emerald Princess • Princess Cruises

14-night Eastern Caribbean Arc via Tortola, Basseterre, Saint Kitts & Fort-de-France

Dec 12, 2027 → Dec 26, 2027 • San Juan ↔

$446 below typical
$1,591 · $114/night · great deal · ↓22% below typical
Princess Cruises

Coral Princess • Princess Cruises

10-night Eastern Caribbean Loop via Saint Thomas, Basseterre, Saint Kitts & Roseau

Nov 18, 2026 → Nov 28, 2026 • Fort Lauderdale ↔

$387 below typical
$1,044 · $104/night · great deal · ↓27% below typical
Royal Caribbean International

Vision of the Seas • Royal Caribbean International

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

Mar 14, 2027 → Mar 21, 2027 • San Juan ↔

$137 below typical
$659 · $94/night · good value · ↓17% below typical
P&O Cruises

Arvia • P&O Cruises

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

Feb 11, 2028 → Feb 25, 2028 • Bridgetown ↔

Lowest in 180 days $311 below typical
$2,228 · $159/night · good value · ↓12% below typical
P&O Cruises

Arvia • P&O Cruises

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

Feb 12, 2028 → Feb 26, 2028 • Bridgetown ↔

Lowest in 180 days $311 below typical
$2,228 · $159/night · good value · ↓12% below typical
MSC Cruises

MSC World Europa • MSC Cruises

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

Jan 31, 2027 → Feb 7, 2027 • Pointe-à-Pitre ↔

Lowest in 180 days $163 below typical
$759 · $108/night · good value · ↓18% below typical
Princess Cruises

Crown Princess • Princess Cruises

7-night Southern Caribbean Arc via Philipsburg, Fort-de-France & Roseau

Feb 28, 2027 → Mar 7, 2027 • San Juan ↔

Lowest in 180 days $174 below typical
$743 · $106/night · good value · ↓19% below typical
Seabourn

Seabourn Ovation • Seabourn

7-night Southern Caribbean Loop via South Friars Bay, Terre-de-Haut & Rodney Bay

Dec 12, 2026 → Dec 19, 2026 • Bridgetown ↔

Lowest in 90 days $401 below typical
$3,598 · $514/night · good value · ↓10% below typical
Princess Cruises

Emerald Princess • Princess Cruises

7-night Southern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Fort-de-France

Dec 12, 2027 → Dec 19, 2027 • San Juan ↔

$204 below typical
$815 · $116/night · good value · ↓20% below typical
Cunard Line

Queen Mary 2 • Cunard Line

21-night Southern Caribbean Arc via New York, Road Town, Tortola & Philipsburg

Dec 12, 2026 → Jan 2, 2027 • Southampton → New York

Lowest in 180 days $400 below typical
$3,289 · $157/night · good value · ↓11% below typical
Royal Caribbean International

Rhapsody of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg

Jan 16, 2027 → Jan 23, 2027 • San Juan ↔

$113 below typical
$560 · $80/night · good value · ↓17% below typical
Royal Caribbean International

Vision of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg

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

$113 below typical
$561 · $80/night · good value · ↓17% below typical