Rotterdam • Holland America

21-night Western Caribbean Loop via Half Moon Cay, Falmouth & Cozumel

Dec 12, 2026 → Jan 2, 2027 • Fort Lauderdale ↔

Rotterdam • Holland America

21-night Eastern Caribbean Loop via Philipsburg, Basseterre, Saint Kitts & Cozumel

Dec 22, 2026 → Jan 12, 2027 • Fort Lauderdale ↔

Vision of the Seas • Royal Caribbean International

7-night Southern Caribbean Loop via Bridgetown, Saint George's & Castries

Feb 27, 2028 → Mar 5, 2028 • 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 ↔

Valiant Lady • Virgin Voyages

7-night Eastern Caribbean Loop via Philipsburg, Bridgetown & Castries

Mar 6, 2027 → Mar 13, 2027 • San Juan ↔

Valiant Lady • Virgin Voyages

6-night Eastern Caribbean Loop via Road Town, Tortola & Basseterre, Saint Kitts

Mar 13, 2027 → Mar 19, 2027 • San Juan ↔

Explora II • Explora Journeys

7-night Southern Caribbean Loop via Port Elizabeth, Bequia, Castries & Bridgetown

Jan 16, 2028 → Jan 23, 2028 • 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 ↔

Norwegian Prima • Norwegian Cruise Line

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

Jan 1, 2028 → Jan 8, 2028 • San Juan ↔

Valiant Lady • Virgin Voyages

7-night Southern Caribbean Loop via Philipsburg, Bridgetown & Castries

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

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 ↔

Celebrity Ascent • Celebrity Cruises

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

Mar 19, 2027 → Mar 29, 2027 • Fort Lauderdale ↔

Mar 2, 2029 → Mar 13, 2029 • Miami ↔

Mar 20, 2029 → Mar 31, 2029 • Miami ↔

Norwegian Prima • Norwegian Cruise Line

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

Mar 25, 2028 → Apr 1, 2028 • San Juan ↔

Norwegian Prima • Norwegian Cruise Line

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

Apr 8, 2028 → Apr 15, 2028 • San Juan ↔

Seabourn Ovation • Seabourn

7-night Eastern Caribbean Arc via Castries, Little Bay & South Friars Bay

Jan 23, 2027 → Jan 30, 2027 • Bridgetown → Philipsburg

Oceania Marina • Oceania Cruises

12-night Eastern Caribbean Loop via Oranjestad, Willemstad & Kingstown

Feb 1, 2027 → Feb 13, 2027 • Miami ↔

Oceania Sirena • Oceania Cruises

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

Nov 28, 2027 → Dec 10, 2027 • Miami ↔

Oceania Sonata • Oceania Cruises

23-night Western Caribbean Arc: Progreso, Cozumel & Roatán

Dec 19, 2028 → Jan 11, 2029 • Miami ↔