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Silversea Cruises

Silver Spirit • Silversea Cruises

12-night Southern Caribbean Loop via Port Elizabeth, Bequia, Castries & Kralendijk

Jan 10, 2028 → Jan 22, 2028 • Bridgetown ↔

From $7,400

$617/night

Regent Seven Seas Cruises

Seven Seas Mariner • Regent Seven Seas Cruises

14-night Eastern Caribbean Arc via Georgetown, Grand Cayman, Ocho Rios & Oranjestad

Dec 21, 2026 → Jan 4, 2027 • Tampa → Miami

From $9,561

$683/night

Princess Cruises

Emerald Princess • Princess Cruises

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

Nov 28, 2027 → Dec 12, 2027 • San Juan ↔

$144 below typical

From $1,586

$113/night

Typical price

↓8% below typical

P&O Cruises

Arvia • P&O Cruises

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

Jan 16, 2027 → Jan 30, 2027 • Bridgetown ↔

$210 below typical

From $2,296

$164/night

Typical price

↓8% below typical

P&O Cruises

Iona • P&O Cruises

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

Dec 11, 2027 → Dec 25, 2027 • Bridgetown ↔

Lowest in 30 days

From $2,228

$159/night

Typical price

↓2% below typical

MSC Cruises

MSC Meraviglia • MSC Cruises

14-night Southern Caribbean Loop via Kingstown, Port-of-Spain & Saint George

Feb 22, 2028 → Mar 7, 2028 • Bridgetown ↔

Lowest in 30 days

From $2,262

$162/night

Typical price

↓2% below typical

Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

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

Dec 13, 2026 → Dec 20, 2026 • San Juan ↔

$140 below typical

From $1,469

$210/night

Typical price

↓9% below typical

Emerald Cruises

Emerald Sakara • Emerald Cruises

14-night Eastern Caribbean Arc via Basseterre, Saint Kitts, Road Bay & Spanish Town

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

$776 below typical

From $11,054

$790/night

Typical price

↓7% below typical

Silversea Cruises

Silver Shadow • Silversea Cruises

10-night Eastern Caribbean Arc via Philipsburg, Basseterre, Saint Kitts & Little Bay

Dec 10, 2026 → Dec 20, 2026 • Miami → San Juan

From $6,300

$630/night

P&O Cruises

Arvia • P&O Cruises

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

Nov 6, 2026 → Nov 20, 2026 • Bridgetown ↔

Lowest in 180 days

From $2,134

$152/night

Typical price

↓1% below typical

P&O Cruises

Arvia • P&O Cruises

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

Nov 14, 2026 → Nov 28, 2026 • Antigua ↔

Lowest in 180 days

From $2,134

$152/night

Typical price

↓1% below typical

P&O Cruises

Arvia • P&O Cruises

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

Nov 6, 2027 → Nov 20, 2027 • Bridgetown ↔

Lowest in 30 days

From $2,134

$152/night

Typical price

↓1% below typical

P&O Cruises

Arvia • P&O Cruises

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

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

Lowest in 30 days

From $2,134

$152/night

Typical price

↓1% below typical

Regent Seven Seas Cruises

Seven Seas Grandeur • Regent Seven Seas Cruises

10-night Southern Caribbean Loop via Saint George's, Oranjestad & Willemstad

Feb 4, 2028 → Feb 14, 2028 • Bridgetown ↔

From $5,960

$596/night

Princess Cruises

Coral Princess • Princess Cruises

11-night Eastern Caribbean Loop via Saint Thomas, Basseterre, Saint Kitts & Fort-de-France

Dec 26, 2026 → Jan 6, 2027 • Fort Lauderdale ↔

Lowest in 180 days

From $1,588

$144/night

Typical price

↓1% below typical

Carnival Cruise Line

Carnival Pride • Carnival Cruise Line

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

Oct 31, 2027 → Nov 14, 2027 • Baltimore ↔

$116 below typical

From $1,572

$112/night

Typical price

↓7% below typical

MSC Cruises

MSC Seaview • MSC Cruises

7-night Eastern Caribbean Loop via Pointe-à-Pitre, Philipsburg & Saint John's

Jan 30, 2027 → Feb 6, 2027 • Fort-de-France ↔

Great balance

From $770

$110/night

Royal Caribbean International

Vision of the Seas • Royal Caribbean International

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

Nov 22, 2026 → Nov 29, 2026 • San Juan ↔

↘ Trending down

From $661

$94/night

Typical price

↓6% below typical

Norwegian Cruise Line

Norwegian Bliss • Norwegian Cruise Line

12-night Eastern Caribbean Loop via Puerto Plata, San Juan & Basseterre, Saint Kitts

Dec 11, 2026 → Dec 23, 2026 • New York ↔

$100 below typical

From $1,219

$102/night

Typical price

↓8% below typical

Emerald Cruises

Emerald Sakara • Emerald Cruises

14-night Eastern Caribbean Arc via Soufriere, Antigua & Road Bay

Nov 13, 2027 → Nov 27, 2027 • Bridgetown → Philipsburg

$719 below typical

From $11,111

$794/night

Typical price

↓6% below typical

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