Silversea Cruises

Silver Shadow

San Juan → Cruz Bay, Saint John → Saint-Barthélemy → San Juan

Dec 23, 2028 · 7 nights

$4,300 suite · $614/night

Silversea Cruises

Silver Shadow

San Juan → Jost Van Dyke → Charlestown → San Juan

Feb 10, 2029 · 7 nights

$3,900 suite · $557/night

Explora Journeys

Explora III

San Juan → Road Bay → Puerto Plata → Miami

Nov 15, 2026 · 7 nights

$4,270 suite · $610/night

Emerald Cruises

Emerald Sakara

San Juan → Cruz Bay, Saint John → Jost Van Dyke → Saint Thomas

Dec 7, 2026 · 6 nights

$5,635 balcony · $939/night

3% below typical
SeaDream Yacht Club

SeaDream I

San Juan → Culebra Island → Spanish Town (Virgin Gorda) → Charlotte Amalie, Saint Thomas

Dec 12, 2026 · 7 nights

$5,442 oceanview · $777/night

SeaDream Yacht Club

SeaDream II

San Juan → Cruz Bay, Saint John → Norman Island → Charlotte Amalie, Saint Thomas

Dec 27, 2026 · 7 nights

$11,251 oceanview · $1,607/night

SeaDream Yacht Club

SeaDream I

San Juan → Cruz Bay, Saint John → Jost Van Dyke → San Juan

Jan 3, 2027 · 6 nights

$4,899 oceanview · $817/night

Emerald Cruises

Emerald Sakara

San Juan → Cruz Bay, Saint John → Norman Island → Saint Thomas

Jan 9, 2027 · 7 nights

$17,160 suite · $2,451/night

3% below typical
SeaDream Yacht Club

SeaDream I

San Juan → Cruz Bay, Saint John → Road Bay → San Juan

Jan 9, 2027 · 7 nights

$6,120 oceanview · $874/night

Princess Cruises

Crown Princess

San Juan → Saint Thomas → Saint George's → San Juan

Jan 10, 2027 · 14 nights

$1,676 interior · $120/night

Explora Journeys

Explora III

San Juan → Philipsburg → Basseterre, Saint Kitts → San Juan

Jan 13, 2027 · 16 nights

$11,600 suite · $725/night

2% below typical
Emerald Cruises

Emerald Sakara

San Juan → Cruz Bay, Saint John → Norman Island → Saint Thomas

Feb 13, 2027 · 7 nights

$6,837 balcony · $977/night

3% below typical
Oceania Cruises

Oceania Allura

San Juan → Charlotte Amalie, Saint Thomas → Tortola → Miami

Feb 19, 2027 · 8 nights

$3,782 balcony · $473/night

1% above typical
Princess Cruises

Crown Princess

San Juan → Saint Thomas → Saint George's → San Juan

Mar 7, 2027 · 14 nights

$1,688 interior · $121/night

SeaDream Yacht Club

SeaDream II

San Juan → Cruz Bay, Saint John → Norman Island → San Juan

Nov 7, 2027 · 6 nights

$3,834 oceanview · $639/night

Explora Journeys

Explora IV

San Juan → Jeju → Ocean Cay → Miami

Nov 13, 2027 · 7 nights

$4,130 suite · $590/night

2% below typical
Emerald Cruises

Emerald Kaia

San Juan → Esperanza → Norman Island → San Juan

Nov 20, 2027 · 14 nights

$14,303 oceanview · $1,022/night

SeaDream Yacht Club

SeaDream II

San Juan → Spanish Town (Virgin Gorda) → Norman Island → Philipsburg

Nov 20, 2027 · 7 nights

$3,602 oceanview · $515/night

SeaDream Yacht Club

SeaDream II

San Juan → Cruz Bay, Saint John → Norman Island → San Juan

Dec 11, 2027 · 8 nights

$4,531 oceanview · $566/night

Explora Journeys

Explora IV

San Juan → Cruz Bay, Saint John → Ocean Cay → Miami

Dec 30, 2027 · 7 nights

$5,285 suite · $755/night

1% above typical

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