Weather In October

October in Key West is fantastic because the weather is warm but not oppressively hot, and the tourist crowds have significantly thinned out. It's a time when locals savor the island, and you can enjoy discounts, pleasant evenings, and warm ocean waters.

Dress in layers and bring appropriate clothing to stay warm and dry, as temperatures can vary.

Yes, October is a transitional period, and the ocean and weather can be unpredictable. You should stay informed about weather forecasts, have safety equipment, communication devices, navigation tools, and extra supplies on hand, and be vigilant for signs of changing weather.

October is my favorite time of year in Key West!

Not just because of the world’s famous “fantasy fest” or that you can wear virtually any costume that a creative mind can conceive and walk down the street in broad daylight and no one will notice… but one simple, unique thing… the weather.

Don’t let anybody tell you that Key West isn’t a tropical paradise. But when you throw around the word “tropical” if you live in northern latitudes, it’s actually quite desirable. But if you’ve ever spent August in Key West, the weather is nothing less than a human rights violations… I mean, it’s HOT!! I have found that everything is just constantly wet. The humidity causes all of the air-conditioned businesses to sweat through their windows. You are constantly wet, either from showering, swimming, or just plain sweating… as an adventure, outfitter, and tour guide, it’s survivable, because we live and work on the water, and at any given time, we can just take a dip into the ocean and get a temporary reprieve from our very Caribbean climate.

Once September and October is reached the days are still warm, but not oppressively hot. At about 5 o’clock, the evenings start to become very enjoyable and you get an occasional cool breeze. But the ocean itself, is still very warm and inviting. But what makes this so special? There is nobody here! The tourists have all returned, the kids are back in school, and the cities’ occupancy dips below 25%, and the locals savor this time of year! The hotel prices plummet, restaurants offer two for one discounts all over the place, there’s no traffic, Duval Street seems navigable by foot and Harkins back to the old days of Key West when this was just a music-centric town, with a fishing problem…

Surviving and Thriving on the Ocean in Key West, Florida in October is a bit of a finesse, play, or a dance, if you will.

When stepping out of our little town, and out into our amazing oceanographic wonderland, you have to take a few things into consideration because the atmosphere and ocean is still in a state of flux because of the change of season. This is when Poseidon starts to get a bit grouchy when venturing out into the ocean around Key West, Florida in October. It’s crucial to adopt a survival mindset. Mother Nature can be unpredictable, and the sea is no exception. To ensure your safety and make the most of your adventure, here’s a breakdown of how to prepare for the ocean’s weather during this time of the year.

Stay Informed:

Keep a close eye on weather forecasts and marine weather updates. In October, Key West can experience tropical storms or sudden weather changes. Be prepared to adapt your plans if necessary.

Safety Equipment:

Prioritize safety equipment. Ensure your boat or charter has life jackets, a first-aid kit, fire extinguishers, and emergency flares. Consider investing in an Emergency Position Indicating Radio Beacon (EPIRB) for added safety.


Bring reliable communication devices, such as a marine VHF radio or satellite phone. Being able to reach out for help in case of emergencies is essential.

Navigation Tools:

Have accurate navigation tools on hand, including GPS and nautical charts. Knowing your exact location and potential hazards is crucial.

Water and Food:

Always carry more than enough water and non-perishable food for your trip, in case it extends longer than anticipated.


Dress in layers and bring appropriate clothing. Even in October, temperatures can vary, and it’s vital to stay warm and dry.

Survival Gear:

Consider adding survival gear to your kit, such as a multi-tool, a flashlight, and a waterproof lighter. These tools can be invaluable in emergencies.

Float Plan:

Before setting out, share a detailed float plan with a trusted friend or family member. Include your departure and arrival times, your planned route, and your emergency contacts.

Watch for Signs:

Keep an eye out for signs of changing weather, like dark clouds, sudden wind shifts, or a drop in temperature. These can signal incoming storms.

Radar and Weather Apps:

Use technology to your advantage. Radar apps and weather-tracking tools on smartphones can provide real-time updates while on the water.

Emergency Drills:

Familiarize yourself and your crew with emergency procedures, including man-overboard drills and what to do in case of capsizing.

Check Equipment:

Regularly inspect your boat or charter for any maintenance issues. Don’t leave anything to chance.

Local Knowledge:

If you’re not familiar with the area, consider hiring a local guide. They know the waters, potential hazards, and weather patterns intimately.

In a survivalist mindset, being over-prepared is better than being caught off guard. By following these steps and keeping safety at the forefront of your plans, you’ll be ready to tackle the ever-changing weather conditions on the ocean around Key West, Florida in October, ensuring a safe and enjoyable adventure. Of course, as a premier adventure outfitters, we have all of these things taken care of for you. We do it all with a little bit of sleight-of-hand. All of the things that I have mentioned have been expertly camouflaged into a super high-end luxury sailing catamaran yacht charter experience!

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