Windstar Cruises

Star Pride

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

Mar 20, 2028 · 7 nights

$2,443 oceanview · $349/night

Princess Cruises

Emerald Princess

San Juan → Curaçao → Kralendijk → Fort Lauderdale

Mar 26, 2028 · 7 nights

$864 interior · $123/night

3% below typical
Royal Caribbean International

Vision of the Seas

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

Mar 26, 2028 · 7 nights

$812 oceanview · $116/night

1% below typical
Windstar Cruises

Star Pride

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

Mar 27, 2028 · 7 nights

$2,411 oceanview · $344/night

Virgin Voyages

Scarlet Lady

San Juan → Saint Thomas → Philipsburg → San Juan

Apr 15, 2028 · 7 nights

$973 interior · $139/night

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

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
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
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 → Culebra Island → Saint-Barthélemy → San Juan

Dec 27, 2027 · 7 nights

$9,314 oceanview · $1,331/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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