Azamara Cruises

Azamara Journey

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

Nov 7, 2026 · 7 nights

$1,159 interior · $166/night

8% below typical · 3-month low
Virgin Voyages

Valiant Lady

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

Nov 7, 2026 · 7 nights

$1,183 balcony · $169/night

32% below typical · 3-month low
Virgin Voyages

Valiant Lady

San Juan → Road Town → Basseterre, Saint Kitts → San Juan

Nov 14, 2026 · 6 nights

$894 balcony · $149/night

32% below typical · 3-month low
Virgin Voyages

Valiant Lady

San Juan → Saint Thomas → Philipsburg → San Juan

Nov 20, 2026 · 8 nights

$952 interior · $119/night

Azamara Cruises

Azamara Journey

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

Nov 21, 2026 · 14 nights

$4,889 balcony · $349/night

Azamara Cruises

Azamara Journey

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

Nov 21, 2026 · 7 nights

$1,169 oceanview · $167/night

15% below typical · 3-month low
Windstar Cruises

Star Pride

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

Nov 22, 2026 · 14 nights

$6,744 balcony · $482/night

Windstar Cruises

Star Pride

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

Nov 22, 2026 · 7 nights

$2,691 oceanview · $384/night

Virgin Voyages

Valiant Lady

San Juan → Saint Thomas → Philipsburg → San Juan

Nov 28, 2026 · 7 nights

$833 oceanview · $119/night

34% below typical · 3-month low
Explora Journeys

Explora III

San Juan → Road Town → Terre-de-Haut (Les Saintes) → San Juan

Nov 29, 2026 · 14 nights

$8,220 suite · $587/night

13% below typical · 3-month low
Windstar Cruises

Star Pride

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

Nov 29, 2026 · 7 nights

$2,618 oceanview · $374/night

14% 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
Norwegian Cruise Line

Norwegian Prima

San Juan → Philipsburg → Tortola → San Juan

Dec 6, 2026 · 7 nights

$1,559 suite · $223/night

28% below typical
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
Norwegian Cruise Line

Norwegian Prima

San Juan → Philipsburg → Saint Thomas → San Juan

Dec 13, 2026 · 7 nights

$869 oceanview · $124/night

11% below typical
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
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 I

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

Dec 20, 2026 · 15 nights

$12,280 suite · $819/night

1% below typical
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
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

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