Best Time to Visit Key West

Back to Blogs

Best Time to Visit Key West: A Private Jet Traveler's Guide

Key West, the southernmost point of the continental United States, is a unique blend of natural beauty, cultural vibrancy, and relaxed island living. For those contemplating private flights to Key West to this Floridian paradise, understanding the nuances of its seasonal weather and tourist trends is crucial.

Odyssey Airways is here to guide you through the best time to visit Key West, ensuring your trip is as perfect as the journey there.

Winter Delight: January to March

The winter months are arguably the best time to visit Key West. With average temperatures hovering around a comfortable 70°F, it's a great escape from colder northern climates. These months are ideal for outdoor activities like sailing, fishing, and exploring historical sites. Key events like the Key West Literary Seminar in January and the Food and Wine Festival are major draws.

For those looking to avoid the winter crowds and still enjoy mild Key West weather, late January and February are your best bet. Odyssey Airways offers the privacy and comfort of private charter flights, ensuring a peaceful start to your island adventure.

Spring Serenity: April to June

April through June marks a sweet spot in Key West. The weather is remarkable, and the island is less crowded, making it a great time for a tranquil getaway. This period is perfect for witnessing the island's natural beauty in full bloom, enjoying strolls down Duval Street or Mallory Square and participating in events like the Key West Fishing Tournament in April. Our complete guide to Key West outlines all the key features of this great island paradise.

Traveling on a private jet charter with Odyssey Airways during this time means experiencing unmatched flexibility and comfort, allowing you to fully immerse in the island’s springtime charm.

Rainy Season Insights: July to September

The rainy season in Key West occurs in the summer months between July and September, and travelers may easily consider these months as the worst time to visit Key West. This period sees higher humidity and frequent, though usually brief, afternoon showers. Despite the rain, the island's summer vibrancy doesn't fade, with events like Hemingway Days in July and Lobsterfest in August.

Odyssey Airways' private jets provide a respite from unpredictable weather, ensuring a hassle-free journey to and from the island, rain or shine.

Avoiding the Crowds: Fall

Visitors seeking a more intimate experience can consider October to December as the least crowded period in Key West, making it ideal. The weather is still warm and inviting, and the island’s pace slows down. Fantasy Fest in October is a notable exception, bringing a surge of visitors.

Worst Times for Crowds

The peak tourist season in the Florida Keys runs from December through March, with the highest influx around holidays and spring break. If avoiding crowds is a priority, steer clear of these months, particularly around major events and festivals.

Best Time to Visit Key West
No items found.


Key West is a year-round destination, each season offering its own unique allure. Odyssey Airways ensures your charter flights into Key West International Airport aligns perfectly with your travel preferences, whether it’s in the quiet fall months or the lively summer season. Experience the ultimate in luxury and convenience with private jet travel, making your trip to Key West memorable, regardless of when you choose to visit.


Discover the most common questions.

Contact us for more information
Are there any specific dress codes or attire requirements when flying private?

When flying privately, there is no specific dress code to adhere to. The beauty of private air travel lies in the freedom to dress in a manner that makes you feel comfortable and at ease. Whether you prefer to dress casually, in business attire, or anything in between, the choice is entirely yours. At Odyssey Airways, we value your comfort and individuality, allowing you to embrace your personal style while enjoying the luxury and convenience of flying private. Sit back, relax, and travel in the attire that suits you best.

Can I bring my own personal items or decorations to customize the interior of a private jet?

Private jet travel often becomes a memorable backdrop for special celebrations like birthdays or anniversaries. At Odyssey Airways, we are delighted to enhance your experience by assisting with temporary decorations for your flight. Our attentive flight crew will ensure that these decorations do not interfere with the safe operation of the aircraft, as safety is our top priority. Your comfort and satisfaction remain of utmost importance to us, and we take pride in creating an unforgettable ambiance for your milestone moments in the sky. Let us help make your celebration even more extraordinary on board with Odyssey Airways.

Can I bring my own food and drinks on a private jet?

You are welcome to bring your own food and non-alcoholic beverages on your private jet rental. Our dedicated Odyssey team will ensure that any alcoholic beverages you desire for your private jet charter are stocked on the aircraft. Additionally, we can cater to your specific culinary preferences and accommodate any food requests you may have. Please note that Federal Regulations prohibit passengers from carrying alcoholic beverages on board for consumption. However, you are permitted to transport special wines or beverages for your personal enjoyment at your destination, such as for a special occasion or dinner. Let us assist in creating a delightful dining experience during your private jet journey with Odyssey Airways.

How do you get on empty leg flights?

The best way to take advantage of empty legs will be to sign up for our empty leg mailing list. You get exclusive access and be the first to know when an empty leg is generated and available book a deal on a private jet charter.

Quote your flight quickly!

Quote my flight