Windstar Cruises

Star Legend

San Juan → Saint George's → Casablanca → Lisbon

Feb 21, 2028 · 20 nights

$4,376 oceanview · $219/night

2% above typical
Windstar Cruises

Star Pride

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

Dec 6, 2026 · 14 nights

$6,254 oceanview · $447/night

2% above typical
Windstar Cruises

Star Pride

San Juan → Saint-Barthélemy → Marmaris → San Juan

Nov 29, 2026 · 14 nights

$7,584 balcony · $542/night

3% above typical
Princess Cruises

Crown Princess

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

Feb 21, 2027 · 14 nights

$1,366 interior · $98/night

1% above typical
Explora Journeys

Explora III

San Juan → Saint John's → Basseterre, Saint Kitts → San Juan

Dec 28, 2026 · 16 nights

$14,960 suite · $935/night

6% above typical · Price trending up
Explora Journeys

Explora III

San Juan → Saint-Barthélemy → Cartagena → Panama City

Apr 5, 2027 · 17 nights

$13,725 suite · $807/night

7% above typical · Price trending up
Princess Cruises

Crown Princess

San Juan → Philipsburg → Castries → San Juan

Feb 28, 2027 · 14 nights

$1,566 oceanview · $112/night

4% above typical · Price trending up
Explora Journeys

Explora I

San Juan → Saint John's → Málaga → Barcelona

Mar 1, 2027 · 23 nights

$12,635 suite · $549/night

6% above typical · Price trending up
Windstar Cruises

Star Pride

San Juan → Saint-Barthélemy → Marmaris → San Juan

Dec 13, 2026 · 14 nights

$9,614 balcony · $687/night

5% above typical · Price trending up
Emerald Cruises

Emerald Kaia

San Juan → Esperanza → Nassau → Miami

Feb 5, 2028 · 14 nights

$26,459 suite · $1,890/night

7% above typical
SeaDream Yacht Club

SeaDream I

San Juan → Jost Van Dyke → Funchal, Madeira → Lisbon

Apr 17, 2027 · 14 nights

$5,093 oceanview · $364/night

13% above typical
Silversea Cruises

Silver Shadow

San Juan → Jost Van Dyke → Santa Cruz de La Palma → Barcelona

Mar 20, 2029 · 14 nights

$5,300 suite · $379/night

29% above typical
Explora Journeys

Explora I

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

Jan 4, 2027 · 16 nights

$12,410 suite · $776/night

41% above typical · Price trending up
Explora Journeys

Explora III

San Juan → Road Bay → Philipsburg → San Juan

Nov 15, 2026 · 14 nights

$15,785 suite · $1,128/night

55% above typical · Price trending up
Windstar Cruises

Star Pride

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

Nov 8, 2026 · 14 nights

No pricing

Viking Cruises

Viking Sea

San Juan → Bridgetown → Saint Thomas → San Juan

Dec 15, 2026 · 21 nights

No pricing

Azamara Cruises

Azamara Journey

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

Dec 18, 2026 · 18 nights

No pricing

Windstar Cruises

Star Pride

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

Dec 20, 2026 · 14 nights

No pricing

Princess Cruises

Caribbean Princess

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

Nov 26, 2028 · 14 nights

$1,604 · $115/night

Princess Cruises

Caribbean Princess

San Juan → Saint Thomas → Castries → San Juan

Dec 3, 2028 · 14 nights

$1,504 · $107/night

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