Caribbean Cruise Planning: Islands, Weather, and Tips
The Lucy Team
We're the team behind Ask Lucy — travellers, food lovers, and language enthusiasts building an AI companion that helps you explore the world with confidence.
Eastern vs Western vs Southern Caribbean
Eastern Caribbean: St. Thomas, St. Maarten, Puerto Rico. More developed ports, duty-free shopping, beautiful beaches. Great for first-timers.
Western Caribbean: Cozumel, Grand Cayman, Jamaica, Belize. More cultural diversity, Mayan ruins, snorkeling. Good mix of beach and adventure.
Southern Caribbean: Aruba, Curacao, Bonaire, Barbados. Less crowded, more unique cultures, excellent diving. Longer sailings (9-14 days) from further south.
When to Go
Peak season is December through April — dry weather, cooler temperatures, and higher prices. Hurricane season runs June through November, with September and October being the highest risk months. Shoulder months (May-June, November) offer good weather and lower prices.
Tips for Caribbean Cruises
Bring reef-safe sunscreen — many islands ban harmful sunscreen chemicals.
Carry US dollars — accepted at most Caribbean ports.
Book snorkeling and diving independently for half the ship price.
Eat local food away from the port for authentic Caribbean cuisine at local prices.
Lucy helps at ports with Spanish, Dutch, French, or Creole menus and signs.