The Best Time to Skydive in the Florida Keys: A Month-by-Month Guide

Key Takeaways
The “best” time of year to skydive in the Florida Keys depends on what matters most to you. April and early May offer the strongest overall balance, while December through March offer cooler temperatures and lower rainfall. Summer brings more heat and afternoon showers, and also better value and fewer crowds on island. September and October are the quietest and often least expensive months, but they’re also the wettest and fall within peak hurricane season. Whenever you book, a morning jump gives you the best opportunity to get your skydive in before afternoon weather becomes a factor.

If you’re planning a skydive in the Florida Keys, the calendar matters more than you might think. Key West stays warm enough for skydiving year-round, but rainfall, temperatures, and tourism traffic change considerably from month to month. For the best skydiving weather, aim for April or early May. For the driest weather, look to the winter months. And if you’re considering September or October, build extra flexibility into your trip to account for Key West’s hurricane season.

When Should You Skydive in the Florida Keys?

Want quick info on the “best” time to visit the Keys? Use this guide:

• Best overall: April to early May
• Best for the driest weather: December through March
• Best balance of weather and value: April, May and early December
• Best for fewer crowds: September and October
• Best for a summer trip: May through July
• Best time of day: Morning
• Most weather flexibility needed: September and October

There is no traditional “skydiving season” in the Florida Keys. Skydive Key West operates year-round, so your ideal time to visit comes down to the experience you want and how much flexibility you have.

What Changes Month to Month in the Florida Keys?

Key West has a tropical climate, but it isn’t the same experience throughout the year. According to National Weather Service 1991–2020 climate normals, average daily highs range from 75.8°F in January to 90.6°F in August, while average monthly precipitation ranges from 1.53 inches in March to 7.24 inches in September.

These differences mean you’ll want to keep a few important things in mind when you’re planning a skydive:

• Weather
  Winter and spring tend to offer optimal skydiving weather as it’s drier and more comfortable. Summer is hotter and more humid, with more frequent showers. 

• Hurricane Season
  June through November is Atlantic hurricane season, with August through October typically seeing the greatest tropical activity. That doesn’t mean you can’t visit or jump during those months – it means your itinerary should leave room for changing conditions.

• Crowds
  Winter and early spring attract more visitors. Late summer and early fall are generally quieter.

• Cost
  Hotel and vacation prices tend to follow tourism demand, so the quieter months can offer better overall value. Skydive Key West’s published tandem pricing is constant, however; it doesn’t change across the year.

The Best Time to Skydive in the Florida Keys, Month by Month

January

Typical high: 75.8°F
Rainfall: 1.83 inches
Crowds: High
Price level: High

January is one of the coolest and driest times of year in Key West. It’s a great choice if you want comfortable temperatures for your vacation, although winter tourism means you’ll likely encounter more visitors and higher accommodation demand.

Verdict: Excellent weather, but expect peak-season crowds.

February

Typical high: 77.4°F
Rainfall: 1.54 inches
Crowds: High
Price level: High

February continues the dry, comfortable winter pattern. With some of the lowest rainfall of the year, it’s a particularly appealing month for outdoor activities.

Verdict: One of the best weather months if crowds aren’t a concern.

March

Typical high: 79.6°F
Rainfall: 1.53 inches
Crowds: Very high
Price level: High

March has the lowest average rainfall of any month in Key West, but spring travel can make the island considerably busier.

Verdict: Outstanding climate conditions, but not the quietest time to visit.

April

Typical high: 82.6°F
Rainfall: 2.07 inches
Crowds: Moderate-high
Price level: Moderate-high

April is a sweet spot between the cooler winter months and the hotter, wetter summer. Rainfall remains relatively low while temperatures are warm enough to feel unmistakably tropical.

Verdict: Our pick for the best overall month to skydive in the Florida Keys.

May

Typical high: 85.9°F
Rainfall: 3.12 inches
Crowds: Moderate
Price level: Moderate

May brings noticeably warmer weather, but it also gives you a chance to enjoy the Keys before summer rainfall reaches its highest levels. Crowds generally ease compared with the winter and spring peak.

Verdict: A strong choice for warm weather, fewer crowds and good overall value.

June

Typical high: 88.7°F
Rainfall: 4.23 inches
Crowds: Moderate
Price level: Moderate

June marks the beginning of hurricane season. Tropical activity isn’t typically at its peak yet, but summer heat and rainfall are becoming more prominent.

Verdict: A good option if you’re comfortable with heat and have a more flexible schedule.

July

Typical high: 90.2°F
Rainfall: 3.63 inches
Crowds: Moderate
Price level: Moderate

July is hot and humid, but the rainfall average is lower than June and August. Afternoon showers are part of the summer pattern, making an earlier jump reservation particularly appealing.

Verdict: A worthwhile summer month – especially if you plan your jump early in the day.

August

Typical high: 90.6°F
Rainfall: 5.37 inches
Crowds: Moderate-low
Price level: Low-moderate

August is the hottest month in the Key West climate normals and the beginning of the year’s wettest stretch. It’s also within the peak months of hurricane activity.

Verdict: Better for value and smaller crowds, but leave room for changing weather.

September

Typical high: 89.0°F
Rainfall: 7.24 inches
Crowds: Very low
Price level: Low

September is the month to approach with the most flexibility. It has the highest average rainfall of the year and falls directly within peak hurricane season. The upside is significant: fewer visitors and potentially lower accommodation costs.

Verdict: Great for a quieter, potentially less expensive trip – and also the possibility of a weather delay or cancellation.

October

Typical high: 85.8°F
Rainfall: 5.67 inches
Crowds: Low
Price level: Low-moderate

October is still wetter than most of the year, although temperatures begin to fall. Tropical weather remains an important consideration because October falls within the hurricane-season window.

Verdict: Good value for flexible travelers, but don’t build a tight schedule around one jump date.

November

Typical high: 81.0°F
Rainfall: 2.05 inches
Crowds: Moderate
Price level: Moderate

November is a major transition month. Rainfall drops sharply from October, temperatures become more comfortable and the end of hurricane season is on the horizon.

Verdict: One of the better choices for a skydiving trip during Key West’s shoulder season.

December

Typical high: 77.7°F
Rainfall: 2.16 inches
Crowds: High
Price level: High

December brings comfortable temperatures and relatively low rainfall. Demand increases as winter and holiday travel picks up, particularly later in the month.

Verdict: Excellent weather, especially in early December, before holiday crowds build.

The Three Best Times of Year to Plan Your Jump

If you have the flexibility to choose when you visit, these are the three windows we’d put at the top of the list:

1. Mid-April: Warm without the peak summer heat, relatively low rainfall and a shift away from the busiest winter travel period.

2. Early May: A little hotter, but still before the year’s wetter months really ramp up. It’s a particularly good compromise between weather and crowds.

3. Early December: Comfortable temperatures and low rainfall before the holiday season reaches full swing.

These aren’t the only good times to jump. They’re simply the windows we’d choose if the goal is to balance the overall Key West experience with favorable conditions for a skydive.

What’s the Best Time of Day to Skydive?

Morning is generally the best time of day to go skydiving in the Florida Keys.

That isn’t because afternoon jumps can’t happen. Weather conditions can be perfectly suitable later in the day. The advantage of a morning appointment is flexibility: during the warmer months, clouds and thunderstorms can develop or move through later in the day.

However, thunder showers can sometimes pass in 20 or 30 minutes, allowing operations to resume once conditions clear (if you’re willing to wait it out).

What Happens If Weather Cancels Your Skydive?

At Skydive Key West, if weather conditions don’t allow a jump, you will have the option to wait it out, reschedule for another day when the conditions are more favorable, or cancel altogether.

FAQ: Best Time to Skydive in Key West

When’s the best time to go skydiving in Key West, Florida?

April and early May offer one of the best combinations of warm temperatures, relatively low rainfall and manageable crowds. December through March are also excellent choices if your priority is drier, cooler weather.

What months should you avoid Key West?

There’s no month you automatically need to avoid. However, September and October require the most flexibility because they’re among the wettest months and fall within the peak of hurricane activity.

What are the best months to skydive?

April, May, and early December are our top choices for balancing weather, crowds and overall value. Winter is a strong option if minimizing rainfall is your priority.

When does skydiving season start and end?

Unlike most dropzones, there isn’t a traditional skydiving season at Skydive Key West. We operate 365 days a year, so you can plan a tandem skydive in any month!

Ready to Pick Your Perfect Jump Day?

There isn’t a single “best” time to skydive. The best date is the one that gives you the combination of weather, flexibility, and vacation experience you’re looking for.

Whether you want the warm, dry days of spring, a quieter summer getaway, or the budget-friendly pace of early fall, the Florida Keys give you plenty of opportunities to make the jump. Check out our Tandem Skydiving experience and book a date that works for your adventure! Blue skies.