Oceania Sirena • Oceania Cruises

14-night Southern Caribbean Loop via Oranjestad, Willemstad & Kralendijk

Dec 22, 2027 → Jan 5, 2028 • Miami ↔

Crown Princess • Princess Cruises

14-night Southern Caribbean Loop via Philipsburg, Fort-de-France & Roseau

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

Seven Seas Grandeur • Regent Seven Seas Cruises

10-night Southern Caribbean Loop via Saint George's, Kingstown & Castries

Feb 14, 2028 → Feb 24, 2028 • Bridgetown ↔

Arvia • P&O Cruises

14-night Southern Caribbean Loop via Philipsburg, Tortola & Roseau

Dec 6, 2027 → Dec 20, 2027 • Basseterre, Saint Kitts ↔

Emerald Princess • Princess Cruises

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

Jan 23, 2028 → Jan 30, 2028 • San Juan ↔

Emerald Princess • Princess Cruises

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

Feb 6, 2028 → Feb 13, 2028 • San Juan ↔

Seven Seas Grandeur • Regent Seven Seas Cruises

10-night Southern Caribbean Loop via Saint George's, Oranjestad & Willemstad

Feb 4, 2028 → Feb 14, 2028 • Bridgetown ↔

Queen Mary 2 • Cunard Line

20-night Southern Caribbean Arc via New York, Basseterre, Saint Kitts & Castries

Dec 14, 2027 → Jan 3, 2028 • Southampton → New York

Crown Princess • Princess Cruises

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

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

Queen Mary 2 • Cunard Line

14-night Southern Caribbean Arc via Saint Thomas, Bridgetown & Castries

Nov 24, 2028 → Dec 8, 2028 • New York ↔

Queen Mary 2 • Cunard Line

21-night Southern Caribbean Arc via New York, Saint Thomas & Bridgetown

Nov 17, 2028 → Dec 8, 2028 • Southampton → New York

Queen Mary 2 • Cunard Line

28-night Southern Caribbean Loop via New York, Saint Thomas & Bridgetown

Nov 17, 2028 → Dec 15, 2028 • Southampton ↔

Valiant Lady • Virgin Voyages

8-night Southern Caribbean Loop via Saint Thomas, Bridgetown & Kingstown

Mar 19, 2027 → Mar 27, 2027 • San Juan ↔

Valiant Lady • Virgin Voyages

7-night Southern Caribbean Loop via Road Town, Tortola, Castries & Bridgetown

Feb 20, 2027 → Feb 27, 2027 • San Juan ↔

Queen Mary 2 • Cunard Line

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

Dec 21, 2027 → Jan 3, 2028 • New York ↔

Oceania Sonata • Oceania Cruises

14-night Southern Caribbean Arc: Charlotte Amalie, Saint Thomas, Cruz Bay, Saint John & Roseau

Feb 22, 2029 → Mar 8, 2029 • Miami ↔

Mar 2, 2029 → Mar 13, 2029 • Miami ↔

Mar 20, 2029 → Mar 31, 2029 • Miami ↔

Dec 5, 2028 → Dec 16, 2028 • Miami ↔

Carnival Firenze • Carnival Cruise Line

14-night Southern Caribbean Arc: Philipsburg, Antigua & Castries

Feb 20, 2028 → Mar 5, 2028 • Port Canaveral ↔