Silver Shadow • Silversea Cruises

7-night Eastern Caribbean Loop via Basseterre, Saint Kitts & Terre-de-Haut

Dec 27, 2026 → Jan 3, 2027 • San Juan ↔

Silver Dawn • Silversea Cruises

7-night Eastern Caribbean Loop via Philipsburg & Roseau

Dec 28, 2027 → Jan 4, 2028 • San Juan ↔

Sun Princess • Princess Cruises

7-night Eastern Caribbean Loop via Princess Cays & Puerto Plata

Nov 27, 2027 → Dec 4, 2027 • Fort Lauderdale ↔

MSC World America • MSC Cruises

14-night Miami → Puerto Plata → San Juan → Ocean Cay + 6 more

Sep 16, 2028 → Sep 30, 2028 • Miami ↔

Silver Ray • Silversea Cruises

8-night Eastern Caribbean Arc via Cruz Bay, Saint John & Fort-de-France

Dec 26, 2027 → Jan 3, 2028 • San Juan → Miami

Sun Princess • Princess Cruises

14-night Eastern Caribbean Loop via Princess Cays, Puerto Plata & Cozumel

Nov 27, 2027 → Dec 11, 2027 • Fort Lauderdale ↔

Silver Nova • Silversea Cruises

8-night Eastern Caribbean Arc via Charlestown & Roseau

Dec 29, 2026 → Jan 6, 2027 • San Juan → Miami

Silver Ray • Silversea Cruises

11-night Eastern Caribbean Loop via San Juan, Basseterre, Saint Kitts & Deshaies

Jan 5, 2027 → Jan 16, 2027 • Miami ↔

Enchanted Princess • Princess Cruises

11-night Eastern Caribbean Loop via Basseterre, Saint Kitts, Roseau & Bridgetown

Dec 24, 2027 → Jan 4, 2028 • Fort Lauderdale ↔

Silver Dawn • Silversea Cruises

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

Dec 21, 2027 → Dec 28, 2027 • San Juan ↔

Silver Dawn • Silversea Cruises

7-night Eastern Caribbean Loop via Saint-Barthélemy, Saint John's & Fort-de-France

Feb 5, 2028 → Feb 12, 2028 • San Juan ↔

Regal Princess • Princess Cruises

14-night Eastern Caribbean Loop via Puerto Plata, San Juan & Cozumel

Sep 12, 2026 → Sep 26, 2026 • Fort Lauderdale ↔

Silver Nova • Silversea Cruises

12-night Eastern Caribbean Arc via San Juan, Saint-Barthélemy & Basseterre, Saint Kitts

Jan 6, 2027 → Jan 18, 2027 • Miami → Bridgetown

Silver Shadow • Silversea Cruises

7-night Eastern Caribbean Loop via Saint-Barthélemy, Basseterre, Saint Kitts & Little Bay

Feb 26, 2027 → Mar 5, 2027 • San Juan ↔

Sun Princess • Princess Cruises

14-night Eastern Caribbean Loop via Princess Cays, Puerto Plata & Cozumel

Jan 8, 2028 → Jan 22, 2028 • Fort Lauderdale ↔

Crown Princess • Princess Cruises

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

Jan 3, 2027 → Jan 17, 2027 • San Juan ↔

Emerald Princess • Princess Cruises

7-night Eastern Caribbean Loop via San Juan, Saint Thomas & Philipsburg

Dec 31, 2027 → Jan 7, 2028 • Bridgetown ↔

Sky Princess • Princess Cruises

8-night Eastern Caribbean Loop via Princess Cays & San Juan

Dec 27, 2026 → Jan 4, 2027 • Port Canaveral ↔

MSC World America • MSC Cruises

7-night Eastern Caribbean Loop via Puerto Plata & Ocean Cay

Sep 4, 2027 → Sep 11, 2027 • Miami ↔

Silver Shadow • Silversea Cruises

7-night Eastern Caribbean Loop via Saint-Barthélemy, Saint John's & Little Bay

Jan 3, 2027 → Jan 10, 2027 • San Juan ↔