Varadero in July

November through April gives you the sweet spot - dry weather, comfortable temperatures, and steady trade winds that keep humidity bearable. December and January see the most crowds and highest prices, especially around Christmas and New Year's. February and March offer the best balance of good weather and reasonable rates. April starts getting warmer but still pleasant. May through October brings rain, humidity, and hurricane season. But here's the upside: summer rates drop significantly, and afternoon thunderstorms usually clear quickly. Hurricane season runs June through November, with September and October seeing the highest risk. The water stays warm year-round (78-84°F), so swimming is always an option. Avoid March if you can - that's spring break season, and the peninsula gets overrun with college groups. November offers the best value - post-hurricane season but before peak winter rates kick in.