Seven Seas Grandeur • Regent Seven Seas Cruises

10-night Eastern Caribbean Loop via San Juan, Saint-Barthélemy & Philipsburg

Nov 29, 2026 → Dec 9, 2026 • Miami ↔

MSC World America • MSC Cruises

14-night Western Caribbean Loop via Puerto Plata, Ocean Cay & Cozumel

Sep 5, 2026 → Sep 19, 2026 • Miami ↔

MSC World America • MSC Cruises

14-night Western Caribbean Loop via Puerto Plata, Ocean Cay & Cozumel

Oct 30, 2027 → Nov 13, 2027 • Miami ↔

Silver Ray • Silversea Cruises

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

Jan 5, 2027 → Jan 16, 2027 • Miami ↔

MSC World America • MSC Cruises

14-night Western Caribbean Loop via Puerto Plata, Ocean Cay & Cozumel

Nov 28, 2026 → Dec 12, 2026 • Miami ↔

Valiant Lady • Virgin Voyages

7-night ABC Islands Loop via Willemstad & Cruz Bay, Saint John

Mar 27, 2027 → Apr 3, 2027 • San Juan ↔

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 Ray • Silversea Cruises

8-night Southern Caribbean Arc via Castries, Saint George's & Port Elizabeth, Bequia

Dec 18, 2027 → Dec 26, 2027 • Bridgetown → San Juan

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 ↔

Sky Princess • Princess Cruises

9-night Eastern Caribbean Loop via Grand Turk Island, Puerto Plata & Princess Cays

Nov 20, 2026 → Nov 29, 2026 • 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 ↔

Sun Princess • Princess Cruises

14-night Eastern Caribbean Loop via Grand Turk Island, San Juan & Cozumel

Mar 14, 2027 → Mar 28, 2027 • Fort Lauderdale ↔