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Explora IV

7-night Eastern Caribbean Arc via Charlotte Amalie, Saint Thomas, Cayo Levantado & Ocean Cay

Apr 1, 2028 → Apr 8, 2028 • San Juan → Miami

Great balance

From $4,020

$574/night

Typical price

↓5% below typical

Explora IV

7-night Eastern Caribbean Arc via Cruz Bay, Saint John & Ocean Cay

Apr 15, 2028 → Apr 22, 2028 • San Juan → Miami

Great balance

From $4,020

$574/night

Typical price

↓5% below typical

Explora IV

7-night Eastern Caribbean Arc via Cruz Bay, Saint John & Pointe-à-Pitre

Apr 29, 2028 → May 6, 2028 • San Juan → Miami

5% below typical

From $4,020

$574/night

Typical price

↓5% below typical

Silversea Cruises

Silver Dawn • Silversea Cruises

11-night Eastern Caribbean Loop via Jost Van Dyke, Saint-Barthélemy & Basseterre, Saint Kitts

Jan 4, 2028 → Jan 15, 2028 • San Juan ↔

From $6,700

$609/night

Silversea Cruises

Silver Dawn • Silversea Cruises

11-night Southern Caribbean Loop via Jost Van Dyke, Saint-Barthélemy & Roseau

Jan 25, 2028 → Feb 5, 2028 • San Juan ↔

From $6,700

$609/night

Silversea Cruises

Silver Dawn • Silversea Cruises

10-night Eastern Caribbean Arc via Saint-Barthélemy, Roseau & Fort-de-France

Feb 22, 2028 → Mar 3, 2028 • San Juan → Miami

From $6,100

$610/night

Emerald Cruises

Emerald Kaia • Emerald Cruises

14-night Eastern Caribbean Arc via Jost Van Dyke, Spanish Town & Ponce

Feb 5, 2028 → Feb 19, 2028 • San Juan → Miami

From $13,030

$931/night

Typical price

↓3% below typical

Princess Cruises

Crown Princess • Princess Cruises

7-night Eastern Caribbean Loop via Saint Thomas, Basseterre, Saint Kitts & Roseau

Feb 14, 2027 → Feb 21, 2027 • San Juan ↔

3% below typical

From $889

$127/night

Typical price

↓3% below typical

Royal Caribbean International

Rhapsody of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg

Jun 27, 2026 → Jul 4, 2026 • San Juan ↔

Great balance

From $1,479

$211/night

Virgin Voyages

Valiant Lady • Virgin Voyages

8-night Eastern Caribbean Loop via Saint Thomas, Willemstad & Oranjestad

Nov 20, 2026 → Nov 28, 2026 • San Juan ↔

From $1,272

$159/night

Virgin Voyages

Valiant Lady • Virgin Voyages

5-night Bahamas Loop via Puerto Plata & Bimini

Apr 10, 2027 → Apr 15, 2027 • San Juan → Miami

3% below typical

From $677

$135/night

Typical price

↓3% below typical

Celebrity Cruises

Celebrity Constellation • Celebrity Cruises

7-night Southern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Roseau

Dec 19, 2026 → Dec 26, 2026 • San Juan ↔

↘ Trending down

From $749

$107/night

Typical price

↓3% below typical

Norwegian Cruise Line

Norwegian Prima • Norwegian Cruise Line

7-night Eastern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Bridgetown

Nov 27, 2027 → Dec 4, 2027 • San Juan ↔

Great balance

From $1,189

$170/night

Typical price

↓3% below typical

Explora Journeys

Explora I • Explora Journeys

16-night Eastern Caribbean Arc via Philipsburg, Saint John's & Little Bay

Jan 4, 2027 → Jan 20, 2027 • San Juan → Miami

From $9,410

$588/night

Typical price

↓2% below typical

Silversea Cruises

Silver Dawn • Silversea Cruises

10-night Eastern Caribbean Loop via Jost Van Dyke, Saint-Barthélemy & Basseterre, Saint Kitts

Feb 12, 2028 → Feb 22, 2028 • San Juan ↔

2% below typical

From $6,300

$630/night

Silversea Cruises

Silver Shadow • Silversea Cruises

10-night Eastern Caribbean Arc via Jost Van Dyke, Saint-Barthélemy & Little Bay

Jan 10, 2027 → Jan 20, 2027 • San Juan → Bridgetown

From $7,100

$710/night

Silversea Cruises

Silver Shadow • Silversea Cruises

10-night Eastern Caribbean Arc via Jost Van Dyke, Saint-Barthélemy & Little Bay

Feb 6, 2027 → Feb 16, 2027 • San Juan → Bridgetown

From $7,100

$710/night

Princess Cruises

Crown Princess • Princess Cruises

14-night Eastern Caribbean Loop via Saint Thomas & Basseterre, Saint Kitts

Mar 14, 2027 → Mar 28, 2027 • San Juan ↔

2% below typical

From $1,979

$141/night

Typical price

↓2% below typical

Norwegian Cruise Line

Norwegian Viva • Norwegian Cruise Line

7-night Southern Caribbean Loop via Basseterre, Saint Kitts & Castries

Dec 5, 2027 → Dec 12, 2027 • San Juan ↔

From $1,099

$157/night

Typical price

↓4% below typical

Royal Caribbean International

Rhapsody of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Tortola, Philipsburg & Saint John's

Sep 12, 2026 → Sep 19, 2026 • San Juan ↔

↘ Trending down

From $720

$103/night

Typical price

↓2% below typical

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