Events at Sea in Caribbean

Turquoise water, short hops between islands.

Turquoise water, short hops between islands and warm evenings on deck. Caribbean sailings leave mostly from Florida and Texas, and run from three nights to two weeks.

2 Upcoming Events

Refine in Explore
Placeholder cover image for Family Tide Week

Family Tide Week

  • Jun 7–14, 2027 · 7 nights
  • Galveston → Western Caribbean
  • Pelican Star
Placeholder cover image for Neon Nights at Sea

Neon Nights at Sea

  • Dec 11–18, 2026 · 7 nights
  • Miami → Eastern Caribbean
  • MV Aurora Lark

Questions, answered

When is the best time to sail the Caribbean?

The dry season runs from about December to April. Hurricane season is June to November, so itineraries then can change, and prices are often lower.

How long are Caribbean sailings?

Most are three to seven nights. Longer loops reach the southern islands.

Which ports do Caribbean events leave from?

Mostly Miami, Fort Lauderdale, Port Canaveral and Galveston, with some from San Juan.