Sea Cloud Spirit • Sea Cloud Cruises
8-night Eastern Caribbean Loop via Saint-Pierre, Soufriere & Road Bay
Dec 6, 2026 → Dec 14, 2026 • Philipsburg ↔
From $5,883
$735/night
Typical price
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115 total
Seabourn Ovation • Seabourn
7-night Southern Caribbean Loop via South Friars Bay, Saint-Pierre & Rodney Bay
Feb 6, 2027 → Feb 13, 2027 • Bridgetown ↔
From $5,998
$857/night
Priced high
↑26% above typical
Sea Cloud II
10-night Eastern Caribbean Loop via Saint-Pierre, Port Elizabeth & Soufriere
Mar 5, 2027 → Mar 15, 2027 • Philipsburg ↔
From $6,900
$690/night
Typical price
↑5% above typical
Sea Cloud II
10-night Eastern Caribbean Arc via Soufriere, Port Elizabeth & Saint-Pierre
Mar 7, 2028 → Mar 17, 2028 • Bridgetown → Philipsburg
From $6,611
$661/night
Typical price
Seabourn Ovation • Seabourn
11-night Eastern Caribbean Arc via Tortola, Road Bay & South Friars Bay
Dec 28, 2027 → Jan 8, 2028 • Philipsburg → Bridgetown
From $6,398
$582/night
Typical price
Seabourn Ovation • Seabourn
10-night Eastern Caribbean Arc via Saint George's, South Friars Bay & Road Bay
Dec 18, 2027 → Dec 28, 2027 • Bridgetown → Philipsburg
From $5,798
$580/night
Typical price
Explora III
14-night Eastern Caribbean Loop via Cruz Bay, Saint John & Terre-de-Haut
Dec 6, 2026 → Dec 20, 2026 • Miami ↔
From $9,040
$646/night
Typical price
↓6% below typical
Emerald Kaia • Emerald Cruises
7-night Eastern Caribbean Arc via Basseterre, Saint Kitts, Deshaies & Saint-Barthélemy
Nov 27, 2027 → Dec 4, 2027 • Saint John's → San Juan
From $6,261
$894/night
Typical price
↓4% below typical
Explora I • Explora Journeys
16-night Eastern Caribbean Arc via Ocho Rios, Puerto Santo Tomás de Castilla & Roatán
Jan 20, 2027 → Feb 5, 2027 • Miami → San Juan
From $9,240
$578/night
Typical price
↓4% below typical
Le Ponant • Ponant Cruises
7-night Eastern Caribbean Arc via Charlestown & Falmouth
Apr 3, 2028 → Apr 10, 2028 • Saint-Barthélemy → Pointe-à-Pitre
From $7,910
$1,130/night
Explora III
16-night Eastern Caribbean Arc via Cruz Bay, Saint John, Saint-Barthélemy & Saint John's
Jan 5, 2027 → Jan 21, 2027 • Miami ↔
From $11,260
$704/night
Typical price
↓3% below typical
Le Ponant • Ponant Cruises
7-night Eastern Caribbean Arc via Charlestown & Falmouth
Mar 6, 2028 → Mar 13, 2028 • Saint-Barthélemy → Pointe-à-Pitre
From $7,910
$1,130/night
Explora III
14-night Eastern Caribbean Loop via Cruz Bay, Saint John, Terre-de-Haut & Philipsburg
Nov 22, 2026 → Dec 6, 2026 • Miami ↔
From $9,160
$654/night
Typical price
↓3% below typical
Emerald Sakara • Emerald Cruises
9-night Eastern Caribbean Loop via South Friars Bay, Deshaies & Little Bay
Dec 18, 2027 → Dec 27, 2027 • Philipsburg ↔
From $7,221
$802/night
Typical price
↓2% below typical
Explora I • Explora Journeys
15-night Western Caribbean Arc via Cozumel, Puerto Santo Tomás de Castilla & Cruz Bay, Saint John
Dec 5, 2026 → Dec 20, 2026 • Miami → San Juan
From $8,360
$557/night
Typical price
↓3% below typical
Silver Shadow • Silversea Cruises
10-night Eastern Caribbean Arc via Jost Van Dyke, Saint-Barthélemy & Little Bay
Jan 10, 2027 → Jan 20, 2027 • San Juan → Bridgetown
From $7,100
$710/night
Silver Shadow • Silversea Cruises
10-night Eastern Caribbean Arc via Jost Van Dyke, Saint-Barthélemy & Little Bay
Feb 6, 2027 → Feb 16, 2027 • San Juan → Bridgetown
From $7,100
$710/night
Emerald Sakara • Emerald Cruises
7-night Eastern Caribbean Arc via Soufriere, Antigua & Charlestown
Nov 13, 2027 → Nov 20, 2027 • Bridgetown → Philipsburg
From $5,810
$830/night
Typical price
↓2% below typical
Emerald Sakara • Emerald Cruises
14-night Eastern Caribbean Arc via Basseterre, Saint Kitts, Road Bay & Spanish Town
Mar 25, 2028 → Apr 8, 2028 • Philipsburg → Bridgetown
From $11,732
$838/night
Typical price
↓2% below typical
Silver Spirit • Silversea Cruises
7-night Eastern Caribbean Loop via Castries, Fort-de-France & Deshaies
Dec 12, 2026 → Dec 19, 2026 • Bridgetown ↔
From $5,400
$771/night