Princess Cruises

Emerald Princess

San Juan → Saint Thomas → Castries → Bridgetown

Nov 21, 2027 · 5 nights

$1,239 suite · $248/night

11% below typical · 3-month low
Princess Cruises

Emerald Princess

San Juan → Tortola → Castries → San Juan

Nov 28, 2027 · 14 nights

$1,848 balcony · $132/night

11% below typical · 3-month low
Princess Cruises

Emerald Princess

San Juan → Philipsburg → Bridgetown → San Juan

Jan 2, 2028 · 7 nights

$1,249 suite · $178/night

11% below typical · 3-month low
Princess Cruises

Emerald Princess

San Juan → Tortola → Castries → San Juan

Jan 9, 2028 · 14 nights

$1,293 interior · $92/night

10% below typical · 3-month low
Princess Cruises

Emerald Princess

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

Jan 16, 2028 · 14 nights

$1,758 balcony · $126/night

11% below typical · 3-month low
Princess Cruises

Emerald Princess

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

Jan 30, 2028 · 14 nights

$1,968 balcony · $141/night

11% below typical · 3-month low
Princess Cruises

Emerald Princess

San Juan → Tortola → Castries → San Juan

Feb 20, 2028 · 14 nights

$1,533 interior · $110/night

14% below typical · Price trending down
Windstar Cruises

Star Legend

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

Feb 14, 2028 · 7 nights

$3,493 balcony · $499/night

11% below typical · 3-month low
Royal Caribbean International

Rhapsody of the Seas

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

Nov 7, 2026 · 7 nights

$1,348 suite · $193/night

9% below typical · Price trending down
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
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
Windstar Cruises

Star Pride

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

Jan 10, 2027 · 7 nights

$3,703 oceanview · $529/night

8% below typical · Price trending down
Royal Caribbean International

Grandeur of the Seas

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

May 22, 2027 · 7 nights

$633 interior · $90/night

14% below typical
Royal Caribbean International

Grandeur of the Seas

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

Jul 3, 2027 · 7 nights

$854 interior · $122/night

14% below typical · Price trending down
Norwegian Cruise Line

Norwegian Prima

San Juan → Tortola → Saint Thomas → San Juan

Nov 20, 2027 · 7 nights

$2,559 suite · $366/night

35% below typical · 3-month low
Norwegian Cruise Line

Norwegian Prima

San Juan → Tortola → Saint Thomas → San Juan

Dec 18, 2027 · 7 nights

$3,119 suite · $446/night

42% below typical · 3-month low
Princess Cruises

Emerald Princess

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

Dec 19, 2027 · 14 nights

$2,128 balcony · $152/night

6% below typical · 3-month low
Explora Journeys

Explora IV

San Juan → Saint-Barthélemy → Ocean Cay → Miami

Jan 22, 2028 · 7 nights

$3,640 suite · $520/night

9% below typical · Price trending down
Princess Cruises

Emerald Princess

San Juan → Saint Thomas → Castries → San Juan

Jan 23, 2028 · 14 nights

$1,238 interior · $88/night

12% below typical · 3-month low
Norwegian Cruise Line

Norwegian Prima

San Juan → Tortola → Saint Thomas → San Juan

Jan 29, 2028 · 7 nights

$2,459 suite · $351/night

28% below typical · 3-month low

Browse by departure port