Best Time To Visit Key West [+Off Season Events Too!]

Wan to know the best time to visit Key West, Florida?

Nestled just to the south of mainland Florida, there truly is never a bad time to visit this tropical paradise.

As you may already know, I have fallen in love with Key West for a number of reasons over my visits. The beautiful beaches, the crystal clear waters, and the vibrancy of this tiny island tick all of my travel must-haves.

Pair this with its pastel, conch-style architecture, its array of water sports, and the never-ending stream of bars and restaurants, and you can see why it’s heaven on earth.

With high temperatures all year round, Key West will appeal to people of all ages for a variety of reasons. Whether you’re an action gal or prefer a more chilled vacation, Key West has something for everyone.

In this article, I will take a look at all seasons and what Key West has to offer during these times. As I’ve said before, there is never really a bad time to visit Key West. However, this guide will hopefully help you choose the best time for you!

So let’s get started.

Snowbird Season

Snowbird Season key west

Due to its balmy winter temperatures, the term snowbird season has affectionately been coined to reference the visitors here who want to escape the cold weather in the winter months.

For this reason, you will find that peak season in Key West will generally fall between November and February, with snowbird season lasting until the end of April.

With November marking the end of hurricane season, the beautiful blue skies open up once again and the beginning of the heavy tourism months begin.

These winter months also offer very little rain, so expect the island to be a thriving mecca of vibrancy and activity.

Due to the calm weather and seas, the snowbird season is the perfect time to partake in the vast water sports on offer.

Situated in the heart of The Florida Keys National Park, Key West is the epicenter for snorkeling and marine life. With an array of sharks, rays, fish species, and wild dolphins, Key West is a superb choice for snorkeling during the winter months.

The snowbird season is also a key time to partake in some kayaking due to the calm ocean tides.

Due to the perfect mixture of low rain but warm temperatures, you can expect to see large numbers of tourists during these months. This inevitably bumps up prices due to the near non-existent hotel availability.

If you are looking for a more relaxed vacation, the winter months may not be the right time for you.

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Events To Look Out For During Snowbird Season

  • Key West Race Week – Exhilarating action with a 30-year history, this event is a big part of the Key West calendar
  • Key West Literary Seminar – An annual 4-day event bringing book lovers from around the world to this subtropical island
  • Key West Food & Wine Festival – Another January event showcasing a vast range of wines and inventive cuisines.

What I Love About Peak Season

  • Great Weather – A perfect blend of heat that’s not unbearable, low rain and calm seas, and out of hurricane season
  • Vibrancy – Due to the high level of visitors, this 8 square mile paradise comes alive during winter
  • Water sports – Due to the calm seas, the winter months are a great time for snorkeling, kayaking, and more

What’s Not To Love About Peak Season

  • High Volumes Of People – Due to its popularity, this small island is bursting at the seams during peak season
  • High Prices – High volumes of people equals high prices. If you are looking for a bargain, peak season might be the wrong choice
  • Low Availability – If you’re planning on visiting during the winter months, be sure to plan your trip in advance to avoid missing out

Summer Season

Summer Season key west

May through to late August mark the summer season of Key West. This is where it’s about to get seriously hot. If you can handle the heat, then the summer season is for you.

However, the summer season is not the island’s most popular for a reason. It also coincides with the start of rain and hurricane season. Completely unpredictable, prices reflect this and so you could grab a bargain.

That being said, early May could be the perfect balance between the hubbub of the tourist months, and the uncertainty of hurricane and rainy seasons. Early May is certainly my favorite time to visit.

The spring vacationers have started to depart, but there’s still an element of vibrancy in the air.

The weather conditions of early May are also pretty perfect. Dry, warm days and evenings without the humidity of high summer months.

Events To Look Out For During Summer Season

  • Conch Republic Independence Celebration – A lively annual event celebrating the eccentric good humor of Keys residents
  • Key West Pride Week – A four-day celebration in June celebrating love and diversity
  • The Hemingway Days Festival – A four-day celebration of Ernest Hemingway, his literary works, and his connection to Key West

What I Love About The Summer Season

  • Low Occupancy – During the summer months there are fewer visitors, so you have plenty of accommodation options
  • Low Prices – If you love to grab a bargain, summer season could be a great time to escape
  • High Heat – If you love the heat, then this is the perfect season to visit

What’s Not To Love About The Summer Season

  • Weather Unpredictability – During the summer season you can expect the unexpected. Torrential downpours, scorching temperatures, severe storms, and possible hurricanes! The summer months are not for the faint-hearted


off season key west

Marked as off-season, September and October are considered to be the wettest months at the heart of hurricane season.

There is no guarantee that a hurricane will occur, hurricanes can go years between episodes. However, if you do decide to travel during this time, it is worth being flexible with your travel plans and expecting the worst.

That being said, if you love to relax and watch the world go by at the heart of a downpour and thunderstorm, then you will not beat Key West for Instagram-worthy footage.

Key Events During Off-Season

  • Womenfest – A 5-day celebration to celebrate ALL women!
  • Fantasy Fest – A quirky 10-day fantasy celebration. Think eccentric costumes and lots of fun!

What I Love About Off-Season

  • The Mesmerizing Thunderstorms – If, like me, you like to watch a good thunderstorm, then these off-season months will showcase the best in the world
  • Restaurant Availability – Sample the best Key West has to offer with lots of availability due to a much smaller visitor volume

What’s Not To Love About Off-Season

  • Unpredictable Weather – If you’re not a fan of wind, rain, the risk of a thunderstorm; off- season may indeed put you off

My Overall Opinion

As you will be able to conclude, I am a huge fan of Key West and all it has to offer. Its rich and diverse history and culture, along with its quirky edge, gives the full package. Each and every single month has something to offer.

But for me, there really is Something About Ma(r)y!

Well, there you have it, the best time to visit Key West! Hopefully that helped, but if you want more info, we found you a video below.

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