Azamara Cruises

Azamara Quest

San Juan → Spanish Town (Virgin Gorda) → Scarborough → Bridgetown

Dec 19, 2027 · 8 nights

$2,409 interior · $301/night

Viking Cruises

Viking Sky

San Juan → Saint Thomas → Frederiksted, Saint Croix → San Juan

Dec 19, 2027 · 10 nights

$3,599 balcony · $360/night

Azamara Cruises

Azamara Quest

San Juan → Spanish Town (Virgin Gorda) → Nassau → Miami

Dec 19, 2027 · 17 nights

$4,929 interior · $290/night

Windstar Cruises

Star Legend

San Juan → Basseterre, Saint Kitts → Saint-Barthélemy → San Juan

Dec 20, 2027 · 7 nights

$2,443 oceanview · $349/night

Princess Cruises

Emerald Princess

San Juan → Tortola → Castries → San Juan

Dec 26, 2027 · 14 nights

$1,613 interior · $115/night

5% below typical
Silversea Cruises

Silver Ray

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

Dec 26, 2027 · 8 nights

$5,500 suite · $688/night

2% below typical
Viking Cruises

Viking Sky

San Juan → Saint Thomas → Frederiksted, Saint Croix → San Juan

Dec 29, 2027 · 10 nights

$3,799 balcony · $380/night

3% below typical
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

Viking Cruises

Viking Sea

San Juan → Saint Thomas → Frederiksted, Saint Croix → San Juan

Dec 17, 2027 · 10 nights

$3,699 balcony · $370/night

3% above typical
SeaDream Yacht Club

SeaDream II

San Juan → Culebra Island → Saint-Barthélemy → San Juan

Dec 27, 2027 · 7 nights

$9,314 oceanview · $1,331/night

Viking Cruises

Viking Sea

San Juan → Saint Thomas → Frederiksted, Saint Croix → San Juan

Dec 27, 2027 · 10 nights

$3,699 balcony · $370/night

3% above typical
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
Celebrity Cruises

Celebrity Summit

San Juan → Charlotte Amalie, Saint Thomas → Philipsburg → San Juan

Dec 26, 2027 · 7 nights

$1,177 oceanview · $168/night

5% above typical
SeaDream Yacht Club

SeaDream II

San Juan → Culebra Island → Jost Van Dyke → San Juan

Dec 4, 2027 · 7 nights

$4,183 oceanview · $598/night

2% above typical
SeaDream Yacht Club

SeaDream II

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

Dec 19, 2027 · 8 nights

$5,016 oceanview · $627/night

Disney Cruise Line

Disney Fantasy

San Juan → Oranjestad → Antigua → San Juan

Dec 3, 2027 · 7 nights

$2,094 interior · $299/night

4% above typical
Disney Cruise Line

Disney Fantasy

San Juan → Saint Thomas → Disney Castaway Cay → Fort Lauderdale

Dec 10, 2027 · 5 nights

$1,358 interior · $272/night

4% above typical
Windstar Cruises

Star Legend

San Juan → Basseterre, Saint Kitts → Marmaris → San Juan

Dec 20, 2027 · 14 nights

$4,504 oceanview · $322/night

2% above typical
Windstar Cruises

Star Legend

San Juan → Saint George's → Spanish Town (Virgin Gorda) → San Juan

Dec 27, 2027 · 14 nights

$4,504 oceanview · $322/night

2% above typical
Windstar Cruises

Star Legend

San Juan → Saint George's → Marmaris → San Juan

Dec 27, 2027 · 7 nights

$2,691 oceanview · $384/night

1% above typical

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