Seabourn Quest • Seabourn
14-night Eastern Caribbean Loop via South Friars Bay, Little Bay & Road Bay
Dec 6, 2026 → Dec 20, 2026 • Miami ↔
From $5,498
$393/night
Great deal
↓25% below typical
View by
115 total
Seabourn Ovation • Seabourn
14-night Southern Caribbean Arc via Tortola, South Friars Bay & Les Trois-Îlets
Dec 5, 2026 → Dec 19, 2026 • Philipsburg → Bridgetown
From $6,298
$450/night
Great deal
↓22% below typical
Sea Cloud Spirit • Sea Cloud Cruises
8-night Southern Caribbean Arc via Terre-de-Haut & Soufriere
Dec 12, 2027 → Dec 20, 2027 • Philipsburg → Willemstad
From $5,298
$662/night
Typical price
↓10% below typical
SeaDream I • SeaDream Yacht Club
7-night Eastern Caribbean Arc via Port Elizabeth, Bequia, Soufriere & Terre-de-Haut
Dec 12, 2027 → Dec 19, 2027 • Bridgetown → Charlotte Amalie, Saint Thomas
From $3,590
$513/night
Great deal
↓23% below typical
Seabourn Ovation • Seabourn
7-night Southern Caribbean Loop via South Friars Bay, Terre-de-Haut & Rodney Bay
Dec 12, 2026 → Dec 19, 2026 • Bridgetown ↔
From $3,598
$514/night
Good value
↓11% below typical
Explora III
17-night Eastern Caribbean Arc via Sept-Iles, New York & Cruz Bay, Saint John
Oct 15, 2026 → Nov 1, 2026 • Quebec → San Juan
From $9,900
$582/night
Great deal
↓21% below typical
Seabourn Ovation • Seabourn
17-night Transatlantic Crossing via Rodney Bay, South Friars Bay & Road Bay
Dec 11, 2027 → Dec 28, 2027 • Bridgetown → Philipsburg
From $8,798
$518/night
Good value
↓11% below typical
SeaDream II • SeaDream Yacht Club
7-night Eastern Caribbean Arc via Terre-de-Haut & Charlestown
Mar 4, 2028 → Mar 11, 2028 • Bridgetown → San Juan
From $4,554
$651/night
Good value
↓18% below typical
Seabourn Quest • Seabourn
14-night Eastern Caribbean Loop via Road Bay, South Friars Bay & Little Bay
Nov 22, 2026 → Dec 6, 2026 • Miami ↔
From $7,498
$536/night
Good value
↓17% below typical
Explora III
16-night Eastern Caribbean Arc via Puerto Plata, Road Bay & Cruz Bay, Saint John
Feb 19, 2027 → Mar 7, 2027 • Miami → San Juan
From $9,960
$623/night
Good value
↓12% below typical
Seabourn Ovation • Seabourn
21-night Eastern Caribbean Loop via Saint George's, South Friars Bay & Road Bay
Dec 18, 2027 → Jan 8, 2028 • Bridgetown ↔
From $11,598
$552/night
Typical price
↓5% below typical
Explora III
16-night Eastern Caribbean Arc via Cruz Bay, Saint John, Terre-de-Haut & Road Bay
Feb 12, 2027 → Feb 28, 2027 • San Juan → Miami
From $10,240
$640/night
Typical price
↓9% below typical
Explora III
7-night Eastern Caribbean Arc via Cruz Bay, Saint John & Terre-de-Haut
Mar 29, 2027 → Apr 5, 2027 • Miami → San Juan
From $4,650
$664/night
Typical price
↓10% below typical
Silver Spirit • Silversea Cruises
7-night Eastern Caribbean Loop via Castries, Terre-de-Haut & Philipsburg
Mar 11, 2028 → Mar 18, 2028 • Bridgetown ↔
From $5,400
$771/night
Explora III
14-night Eastern Caribbean Loop via Road Bay, Saint John's & Cruz Bay, Saint John
Nov 15, 2026 → Nov 29, 2026 • San Juan ↔
From $8,640
$617/night
Typical price
↓9% below typical
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
From $11,054
$790/night
Typical price
↓7% below typical
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
Emerald Sakara • Emerald Cruises
14-night Eastern Caribbean Arc via Soufriere, Antigua & Road Bay
Nov 13, 2027 → Nov 27, 2027 • Bridgetown → Philipsburg
From $11,111
$794/night
Typical price
↓6% below typical
Sea Cloud Spirit • Sea Cloud Cruises
8-night Eastern Caribbean Loop via Saint-Pierre & Road Bay
Nov 27, 2027 → Dec 5, 2027 • Philipsburg ↔
From $5,883
$735/night
Typical price
↓1% below typical
Emerald Sakara • Emerald Cruises
14-night Eastern Caribbean Arc via Soufriere, Antigua & Road Bay
Apr 8, 2028 → Apr 22, 2028 • Bridgetown → Philipsburg
From $11,562
$826/night
Typical price
↓4% below typical