Windstar Cruises

Star Pride

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

Dec 20, 2026 · 7 nights

$3,846 oceanview · $549/night

Explora Journeys

Explora III

San Juan → Saint John's → Puerto Plata → Miami

Dec 28, 2026 · 8 nights

$7,385 suite · $923/night

5% above typical
SeaDream Yacht Club

SeaDream II

San Juan → Saint-Barthélemy → Jost Van Dyke → San Juan

Dec 19, 2026 · 8 nights

$6,856 oceanview · $857/night

1% above typical
Royal Caribbean International

Vision of the Seas

San Juan → Tortola → Basseterre, Saint Kitts → San Juan

Dec 6, 2026 · 7 nights

$758 oceanview · $108/night

8% above typical · Price trending up
Windstar Cruises

Star Pride

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

Dec 13, 2026 · 7 nights

$5,208 suite · $744/night

2% above typical · Price trending up
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
Royal Caribbean International

Vision of the Seas

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

Dec 27, 2026 · 7 nights

$1,428 interior · $204/night

8% above typical · Price trending up
Windstar Cruises

Star Pride

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

Dec 6, 2026 · 7 nights

$3,006 oceanview · $429/night

6% above typical · Price trending down
Royal Caribbean International

Rhapsody of the Seas

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

Dec 19, 2026 · 7 nights

$1,248 balcony · $178/night

3% above typical · Price trending up
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
Royal Caribbean International

Rhapsody of the Seas

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

Dec 5, 2026 · 7 nights

$1,799 suite · $257/night

1% above typical · Price trending up
Azamara Cruises

Azamara Journey

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

Dec 5, 2026 · 7 nights

$2,739 balcony · $391/night

5% above typical · Price trending up
Royal Caribbean International

Rhapsody of the Seas

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

Dec 26, 2026 · 7 nights

$2,294 suite · $328/night

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
Royal Caribbean International

Rhapsody of the Seas

San Juan → Tortola → Frederiksted, Saint Croix → San Juan

Dec 12, 2026 · 7 nights

$1,299 suite · $186/night

6% above typical · Price trending up
Celebrity Cruises

Celebrity Constellation

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

Dec 5, 2026 · 7 nights

$1,095 interior · $156/night

20% above typical
Royal Caribbean International

Vision of the Seas

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

Dec 13, 2026 · 7 nights

$673 interior · $96/night

7% above typical
Silversea Cruises

Silver Shadow

San Juan → Jost Van Dyke → Fort-de-France → San Juan

Dec 20, 2026 · 7 nights

$5,400 suite · $771/night

13% above typical
Royal Caribbean International

Vision of the Seas

San Juan → Tortola → Basseterre, Saint Kitts → San Juan

Dec 20, 2026 · 7 nights

$1,482 suite · $212/night

5% above typical · Price trending up
Celebrity Cruises

Celebrity Constellation

San Juan → Tortola → Saint George's → San Juan

Dec 12, 2026 · 7 nights

$986 oceanview · $141/night

18% above typical

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