Valiant Lady • Virgin Voyages

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

Feb 20, 2027 → Feb 27, 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 ↔

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 ↔

Mar 2, 2029 → Mar 13, 2029 • Miami ↔

Mar 20, 2029 → Mar 31, 2029 • Miami ↔

Oceania Sirena • Oceania Cruises

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

Nov 28, 2027 → Dec 10, 2027 • Miami ↔

Dec 5, 2028 → Dec 16, 2028 • Miami ↔

Vision of the Seas • Royal Caribbean International

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

Mar 26, 2028 → Apr 2, 2028 • San Juan ↔

Carnival Firenze • Carnival Cruise Line

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

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

Volendam • Holland America

14-night Southern Caribbean Loop via Key West, Oranjestad & Charlotteville

Dec 22, 2026 → Jan 5, 2027 • Fort Lauderdale ↔

Scarlet Lady • Virgin Voyages

6-night Southern Caribbean Loop via Kingstown & Bridgetown

Jan 2, 2028 → Jan 8, 2028 • San Juan ↔

Vision of the Seas • Royal Caribbean International

7-night Southern Caribbean Loop via Bridgetown, Roseau & Kingstown

Feb 13, 2028 → Feb 20, 2028 • San Juan ↔

Scarlet Lady • Virgin Voyages

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

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

Iona • P&O Cruises

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

Dec 4, 2027 → Dec 18, 2027 • Antigua ↔

Oceania Sonata • Oceania Cruises

29-night Southern Caribbean Arc via Oranjestad, Willemstad & Panama Canal

Dec 6, 2027 → Jan 4, 2028 • Miami → Los Angeles

Carnival Pride • Carnival Cruise Line

12-night Southern Caribbean Loop via Philipsburg, Fort-de-France & Bridgetown

Nov 28, 2027 → Dec 10, 2027 • Baltimore ↔

Britannia • P&O Cruises

14-night Southern Caribbean Loop via Oranjestad, Curaçao & Kingstown

Dec 12, 2026 → Dec 26, 2026 • Bridgetown ↔

MSC Seaview • MSC Cruises

7-night Southern Caribbean Loop via Pointe-à-Pitre, Castries & Bridgetown

Feb 6, 2027 → Feb 13, 2027 • Fort-de-France ↔