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Departures Itineraries
Azamara Cruises

Azamara Journey

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

Nov 7, 2026 · 7 nights

$1,839 balcony · $263/night

8% below typical · 3-month low
Azamara Cruises

Azamara Journey

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

Dec 5, 2026 · 13 nights

$7,129 suite · $548/night

9% below typical · 3-month low
Holland America

Volendam

Fort Lauderdale → Key West → Half Moon Cay → Fort Lauderdale

Dec 22, 2026 · 14 nights

$1,549 oceanview · $111/night

16% below typical · 3-month low
Virgin Voyages

Valiant Lady

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

Jan 16, 2027 · 7 nights

$1,183 oceanview · $169/night

15% below typical · Price trending down
Explora Journeys

Explora I

San Juan → Saint-Barthélemy → Boca da Valeria → Manaus

Feb 5, 2027 · 12 nights

$7,680 suite · $640/night

6% below typical · 3-month low
Holland America

Zuiderdam

Miami → Half Moon Cay → Falmouth → Miami

Feb 14, 2027 · 20 nights

$2,799 oceanview · $140/night

10% below typical · 3-month low
P&O Cruises

Britannia

Bridgetown → Philipsburg → Curaçao → Bridgetown

Mar 6, 2027 · 14 nights

$2,215 interior · $158/night

8% below typical · 3-month low
Windstar Cruises

Wind Surf

Philipsburg → Jeju → Saint-Barthélemy → Philipsburg

Mar 6, 2027 · 7 nights

$3,097 oceanview · $442/night

9% below typical · 3-month low
Windstar Cruises

Wind Surf

Philipsburg → Jeju → Saint-Barthélemy → Philipsburg

Mar 20, 2027 · 7 nights

$4,287 suite · $612/night

27% below typical · 3-month low
Explora Journeys

Explora II

San Juan → Port Elizabeth, Bequia → Castries → San Juan

Jan 16, 2028 · 7 nights

$3,920 suite · $560/night

7% below typical · 3-month low
Princess Cruises

Emerald Princess

San Juan → Tortola → Bridgetown → San Juan

Feb 6, 2028 · 7 nights

$644 interior · $92/night

16% below typical · 3-month low
Regent Seven Seas Cruises

Seven Seas Prestige

Panama City → Cartagena → Charlotte Amalie, Saint Thomas → Miami

Mar 14, 2028 · 12 nights

$7,199 suite · $600/night

6% below typical · 3-month low
Viking Cruises

Viking Sky

San Juan → Saint Thomas → Frederiksted, Saint Croix → San Juan

Dec 24, 2028 · 10 nights

$3,799 balcony · $380/night

5% below typical · 3-month low
Explora Journeys

Explora I

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

Feb 5, 2027 · 24 nights

$17,360 suite · $723/night

6% below typical · Price trending down
Princess Cruises

Island Princess

Fort Lauderdale → Philipsburg → Curaçao → Fort Lauderdale

Nov 15, 2027 · 14 nights

$1,319 interior · $94/night

11% below typical · 3-month low
Princess Cruises

Emerald Princess

San Juan → Saint Thomas → Bridgetown → San Juan

Jan 23, 2028 · 7 nights

$924 balcony · $132/night

12% below typical · 3-month low
Princess Cruises

Emerald Princess

San Juan → Tortola → Bridgetown → San Juan

Mar 19, 2028 · 7 nights

$979 interior · $140/night

13% below typical · 3-month low
Norwegian Cruise Line

Norwegian Breakaway

Boston → Saint Thomas → Georgetown, Grand Cayman → New Orleans

Nov 8, 2026 · 14 nights

$869 interior · $62/night

28% below typical · Price trending down
Princess Cruises

Caribbean Princess

Fort Lauderdale → Oranjestad → Celebration Key → Fort Lauderdale

Nov 23, 2026 · 12 nights

$699 interior · $58/night

13% below typical · 3-month low
Virgin Voyages

Valiant Lady

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

Dec 26, 2026 · 7 nights

$1,813 balcony · $259/night

19% below typical · Price trending down

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