When you imagine the Caribbean, you’re probably picturing turquoise waters, white sand beaches, and umbrella drinks in hand. And while it’s true that the Caribbean is warm and inviting year-round, some islands shine brighter at different times of the year.

Whether you’re planning a honeymoon, anniversary trip, or just need to escape the ordinary, here’s your island-by-island guide to the best time to go.

Aruba

Best Time to Visit: January to May

Why: Aruba sits outside the hurricane belt, so it’s a fantastic year-round destination—but winter and spring are ideal for dry weather and cooling trade winds.

Bonus Tip: August–October is great for deals, especially for couples looking to relax without crowds.

Bahamas

Best Time to Visit: Mid-December to mid-April

Why: It’s cooler, drier, and perfect for beach days. This is peak season for a reason.

Keep in Mind: Hurricane season (June–November) can be rainy, especially in September and October, but that’s also when you’ll find the best resort deals.

St. Lucia

Best Time to Visit: December to April

Why: Drier weather makes it perfect for exploring the Pitons or indulging in romantic resorts.

Pro Tip: May and June offer a sweet spot with lower prices and fewer crowds—perfect for honeymoons.

Jamaica

Best Time to Visit: November to mid-December or mid-January to April

Why: Avoid peak holiday crowds and enjoy sunny days, especially if you’re heading to Negril or Montego Bay.

Heads Up: May and October are rainier months—less ideal for outdoor adventures.

Turks & Caicos

Best Time to Visit: February to April

Why: It’s peak beach season, and Grace Bay will absolutely steal your heart.

Low-Key Season: June to November is quieter and more affordable but comes with the risk of storms.

Barbados

Best Time to Visit: December to early April

Why: Gorgeous weather, calm seas, and vibrant events like Crop Over in July.

Underrated Time: May and early June can be a gem for shoulder season travel.

Curaçao

Best Time to Visit: Anytime—especially January to September

Why: Located outside the hurricane belt, Curaçao offers reliable sunshine and color all year long.

Secret Season: Late spring is ideal—lower rates, fewer tourists, and postcard-perfect weather.

The U.S. Virgin Islands (St. Thomas, St. John, St. Croix)

Best Time to Visit: December to April

Why: Mild temperatures, great snorkeling visibility, and easy access for U.S. travelers.

Travel Smart: May and June are lovely and often overlooked by mainstream travelers.

 So, when should you go?

Choosing the best time to visit depends on your travel style. Want perfect weather? Go in peak season. Looking for quieter beaches and better rates? Consider shoulder season.

If you’re not sure which island (or season) is right for you, that’s where I come in. Whether you’re planning a honeymoon, a celebration trip, or just need some salty air in your soul, I’ll match you with the best island and perfect timing.