Valiant Lady • Virgin Voyages

8-night ABC Islands Loop via Oranjestad, Willemstad & Kralendijk

Jan 29, 2027 → Feb 6, 2027 • San Juan ↔

Valiant Lady • Virgin Voyages

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

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

Vision of the Seas • Royal Caribbean International

7-night ABC Islands Loop via Charlotte Amalie, Saint Thomas & Kralendijk

Feb 20, 2028 → Feb 27, 2028 • San Juan ↔

Star of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Coco Cay & Charlotte Amalie, Saint Thomas

Jun 13, 2027 → Jun 20, 2027 • Port Canaveral ↔

Resilient Lady • Virgin Voyages

8-night Eastern Caribbean Loop via Puerto Plata & San Juan

Dec 19, 2026 → Dec 27, 2026 • Miami ↔

Britannia • P&O Cruises

14-night Southern Caribbean Loop via Philipsburg, Antigua & Basseterre, Saint Kitts

Feb 6, 2027 → Feb 20, 2027 • Bridgetown ↔

Queen Elizabeth • Cunard Line

26-night Transatlantic Crossing via Saint Thomas, Basseterre, Saint Kitts & Kingstown

Dec 23, 2027 → Jan 18, 2028 • Miami → Southampton

Rhapsody of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg

Jan 15, 2028 → Jan 22, 2028 • San Juan ↔

Iona • P&O Cruises

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

Dec 25, 2027 → Jan 8, 2028 • Bridgetown ↔

Iona • P&O Cruises

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

Nov 26, 2027 → Dec 10, 2027 • Bridgetown ↔

Iona • P&O Cruises

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

Nov 27, 2027 → Dec 11, 2027 • Bridgetown ↔

Feb 7, 2029 → Feb 16, 2029 • Miami ↔

Rhapsody of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg

Apr 15, 2028 → Apr 22, 2028 • San Juan ↔

Carnival Magic • Carnival Cruise Line

8-night Eastern Caribbean Loop via Half Moon Cay & San Juan

Mar 11, 2028 → Mar 19, 2028 • Miami ↔

Disney Dream • Disney Cruise Line

7-night Eastern Caribbean Loop via Philipsburg & Disney Castaway Cay

Feb 19, 2027 → Feb 26, 2027 • Fort Lauderdale ↔

Disney Destiny • Disney Cruise Line

7-night Eastern Caribbean Loop via Lighthouse Point, Florida & San Juan

Dec 12, 2026 → Dec 19, 2026 • Fort Lauderdale ↔

Oceania Allura • Oceania Cruises

10-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Saint-Barthélemy & Philipsburg

Dec 2, 2026 → Dec 12, 2026 • Miami ↔

Grandeur of the Seas • Royal Caribbean International

7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg

May 29, 2027 → Jun 5, 2027 • San Juan ↔

Arvia • P&O Cruises

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

Dec 17, 2027 → Dec 31, 2027 • Bridgetown ↔

Seabourn Ovation • Seabourn

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

Feb 13, 2027 → Feb 27, 2027 • Bridgetown ↔