Silver Shadow • Silversea Cruises

7-night Eastern Caribbean Loop via Little Bay, Saint John's & Saint-Barthélemy

Jan 30, 2027 → Feb 6, 2027 • San Juan ↔

Silver Dawn • Silversea Cruises

10-night Eastern Caribbean Loop via Jost Van Dyke, Saint-Barthélemy & Basseterre, Saint Kitts

Jan 15, 2028 → Jan 25, 2028 • San Juan ↔

Silver Dawn • Silversea Cruises

10-night Eastern Caribbean Loop via Jost Van Dyke, Saint-Barthélemy & Basseterre, Saint Kitts

Feb 12, 2028 → Feb 22, 2028 • San Juan ↔

Emerald Kaia • Emerald Cruises

9-night Eastern Caribbean Arc: Saint-John, Ponce & Grand Turk Island

Feb 20, 2029 → Mar 1, 2029 • San Juan → Miami

SeaDream I • SeaDream Yacht Club

7-night Eastern Caribbean Arc: Salinas & Jost Van Dyke

Mar 10, 2029 → Mar 17, 2029 • San Juan ↔

SeaDream I • SeaDream Yacht Club

7-night Bahamas One-Way: Samana & San Salvador Island

Mar 24, 2029 → Mar 31, 2029 • San Juan → Freeport, Grand Bahama

Norwegian Prima • Norwegian Cruise Line

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

Nov 27, 2027 → Dec 4, 2027 • San Juan ↔

Emerald Kaia • Emerald Cruises

7-night Eastern Caribbean Loop via Philipsburg, Saint John's & South Friars Bay

Dec 27, 2027 → Jan 3, 2028 • San Juan ↔

Crown Princess • Princess Cruises

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

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

Azamara Journey • Azamara Cruises

7-night Southern Caribbean Arc via Spanish Town, Antigua & Saint-Pierre

Nov 21, 2026 → Nov 28, 2026 • San Juan → Bridgetown

Azamara Journey • Azamara Cruises

10-night Eastern Caribbean Arc via Saint Thomas, Spanish Town & Antigua

Dec 18, 2026 → Dec 28, 2026 • San Juan → Bridgetown

Viking Sea • Viking Cruises

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

Nov 5, 2026 → Nov 15, 2026 • San Juan ↔

Viking Sea • Viking Cruises

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

Nov 15, 2026 → Nov 25, 2026 • San Juan ↔

Viking Sea • Viking Cruises

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

Nov 25, 2026 → Dec 5, 2026 • San Juan ↔

Crystal Symphony • Crystal Cruises

3-night Eastern Caribbean Arc via Marigot & Roseau

Sep 14, 2026 → Sep 17, 2026 • San Juan → Bridgetown

Crystal Symphony • Crystal Cruises

7-night Eastern Caribbean Arc via Jost Van Dyke & Antigua

Nov 4, 2026 → Nov 11, 2026 • San Juan → Fort Lauderdale

Crystal Serenity • Crystal Cruises

5-night ABC Islands One-Way via Jost Van Dyke & Oranjestad

Nov 27, 2026 → Dec 2, 2026 • San Juan → Cartagena

Viking Sea • Viking Cruises

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

Dec 5, 2026 → Dec 15, 2026 • San Juan ↔

Crystal Symphony • Crystal Cruises

7-night Eastern Caribbean Arc via Jost Van Dyke & Cruz Bay, Saint John

Dec 13, 2026 → Dec 20, 2026 • San Juan → Fort Lauderdale

Viking Sea • Viking Cruises

21-night Amazon River Loop via Bridgetown, Kourou / Îles du Salut & Santarém

Dec 15, 2026 → Jan 5, 2027 • San Juan ↔