Windstar Cruises

Star Pride

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

Dec 27, 2026 · 7 nights

$3,563 oceanview · $509/night

24% below typical · 3-month low
Norwegian Cruise Line

Norwegian Prima

San Juan → Philipsburg → Tortola → San Juan

Dec 27, 2026 · 7 nights

$1,419 interior · $203/night

26% below typical · 3-month low
Virgin Voyages

Valiant Lady

San Juan → Oranjestad → Basseterre, Saint Kitts → San Juan

Dec 5, 2026 · 7 nights

$763 interior · $109/night

31% below typical · 3-month low
Virgin Voyages

Valiant Lady

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

Dec 12, 2026 · 7 nights

$973 oceanview · $139/night

26% below typical · 3-month low
Virgin Voyages

Valiant Lady

San Juan → Basseterre, Saint Kitts → Willemstad → San Juan

Dec 19, 2026 · 7 nights

$1,043 balcony · $149/night

25% below typical · 3-month low
Explora Journeys

Explora III

San Juan → Road Bay → Grand Turk Island → Miami

Dec 13, 2026 · 7 nights

$3,965 suite · $566/night

6% below typical · 3-month low
Celebrity Cruises

Celebrity Constellation

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

Dec 26, 2026 · 7 nights

$1,024 interior · $146/night

16% below typical · 3-month low
Norwegian Cruise Line

Norwegian Prima

San Juan → Philipsburg → Saint Thomas → San Juan

Dec 13, 2026 · 7 nights

$869 oceanview · $124/night

11% below typical
Princess Cruises

Crown Princess

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

Dec 27, 2026 · 14 nights

$1,946 interior · $139/night

10% below typical · Price trending down
Explora Journeys

Explora I

San Juan → Basseterre, Saint Kitts → Road Bay → Miami

Dec 20, 2026 · 7 nights

$5,600 suite · $800/night

6% below typical · 3-month low
Princess Cruises

Crown Princess

San Juan → Saint Thomas → Bridgetown → San Juan

Dec 27, 2026 · 7 nights

$1,101 oceanview · $157/night

17% below typical · 3-month low
Windstar Cruises

Star Pride

San Juan → Saint-Barthélemy → Marmaris → San Juan

Dec 27, 2026 · 14 nights

$6,534 oceanview · $467/night

9% below typical · 3-month low
Norwegian Cruise Line

Norwegian Prima

San Juan → Philipsburg → Tortola → San Juan

Dec 6, 2026 · 7 nights

$1,559 suite · $223/night

28% below typical
Norwegian Cruise Line

Norwegian Prima

San Juan → Oranjestad → Tortola → San Juan

Dec 20, 2026 · 7 nights

$1,459 suite · $208/night

44% below typical · 3-month low
Explora Journeys

Explora III

San Juan → Road Bay → Charlotte Amalie, Saint Thomas → San Juan

Dec 13, 2026 · 15 nights

$10,255 suite · $684/night

7% below typical · Price trending down
Virgin Voyages

Valiant Lady

San Juan → Philipsburg → Saint John's → San Juan

Dec 26, 2026 · 7 nights

$1,673 balcony · $239/night

25% below typical · 3-month low
Explora Journeys

Explora I

San Juan → Basseterre, Saint Kitts → Jeju → San Juan

Dec 20, 2026 · 15 nights

$12,280 suite · $819/night

1% below typical
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

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