Exploring Key West In October - Top Tips, Activities & Events

Key West Parade

Key West remains one of the United State’s most popular destinations. It is the southernmost point of the country and the closest you can get to the Caribbean without leaving the continental U.S. With its all-year-round summer temperatures, soft sandy beaches, clear blue waters, pristine mangroves, and a ton of personality, Key West is a place to certainly put on your travel bucket list.

The month of October in Key West is one of the best times of the year to visit. During the entire month, the weather is comfortable, the water is crystal clear, and you can celebrate at Fantasy Fest towards the end of the month. Let’s explore other things you can do in Key West in October to have a wonderful time.

Our team at Night Kayak Key West is one of the most trusted local tour operators. We provide unique excursions to fill your itinerary during both days and evenings. Our knowledgeable tour guides take you through all the hidden nooks that you wouldn’t be able to discover on your own. Book your tour with us and experience the best the region has to offer.


Things To Do In Key West In October

Is October a good time to visit Key West? Oh yeah, baby! When planning a trip to Key West, it is worth considering the month of October. Here’s why:


Celebrate At The Bahama Village Goombay Festival

During October, you can enjoy one of Key West’s favorite celebrations, the Bahama Village Goombay Festival. At this popular festival, you can eat delicious food, shop from local vendors, and listen to local music in a family-friendly atmosphere that honors Bahamian heritage.

On October 20th, the opening ceremony kicks off the fun events and street fairs, which also marks the start of the famous annual Fantasy Fest.

Goombay Festival At Key West


Get Wild At The Numerous Events Of Annual Fantasy Fest

Key West’s annual Fantasy Fest has been compared to the grand parade of Rio de Janeiro’s Carnaval or New Orlean’s Madri Gras. This popular event is a 10-day October celebration in Florida filled with costumes, parades, pool parties, marching groups, neighborhood events, music, and much more.

Come and let your imagination and creativity flow. Although it is geared towards adults, there are also many family-friendly events and street fairs. Fantasy Fest is a perfect event for partying in one of the country’s most relaxed island atmospheres.

Fantasy Fest At Key West


Explore Nature At An October Night Kayak Guided Tour

In Key West, your vacation evenings can be filled with other fun exciting activities other than the party scene. With our local guides, you can enjoy a fully guided tour by knowledgeable captains where you may catch a glimpse of nocturnal marine life in a single or double-lighted glass bottom kayak. It is a magical adventure for the whole family.

You’ll be gliding through the narrow mangrove tunnels in the dark, where your guide will point out different wild species. It is also a great way to have a romantic October evening out with your sweetie. For 90 minutes, you will enjoy a safe and well-planned tour that departs from Marriott Beachside Marina.

Here are some things you should know about this adventurous marine evening tour:

  • For groups up to 18, a minimum of 6 participants

  • Guided tours in English

  • Complimentary garage parking

  • For people 4 years old and older

  • Weight capacity for single kayak 250lbs, double kayak 350lbs

  • Suggested clothing is shorts and T-shirts

  • Bug spray is not permitted to protect the ecosystem

  • Locked dock-box available to store valuables

  • No alcohol allowed

  • Full refund with a minimum 24-hour notice

Book your Night Kayaking Tour early to schedule the most convenient date on your trip!

Key West Night Kayaking


The Monroe County Sheriff’s Office Children’s Animal Farm

For a fun time with the entire family, visit animals at the Sheriff’s Office Animal Farm. You can see traditional farm animals as well as exotic animals. Take pictures with miniature horses, rabbits, pigs, sloths, lemurs, and alpacas. It is a place where you can see tropical birds of the region including peacocks.

The farm has been around since 1994 and has continued a tradition for local and vacationing families that come to see the animals. It’s a great way to unwind with nature and create a diverse itinerary during your visit.

Alcapas at Monroe County Sheriff’s Office Children’s Animal Farm


Key West Zombie Bike Ride

For an active exhilarating four-mile adventure, come to the Key West Zombie Bike Ride where you will feel like you’re in Michael Jackson’s Thriller video. This epic spectacle of bike-riding enthusiasts is police escorted and organized down Highway US1 to Duval Street. After the ride, you can enjoy all the festivities available at October ZombieFest.

It’s a day where thousands of people dress up in scary costumes and have a fun ride along some of Key West’s most popular spots. You won’t want to miss this unique ride in Key West!

Zombie Bike Ride


Other Things To Do In Key West

There’s a little bit of everything for all tastes when visiting Key West. This tropical paradise is perfect for nature and music lovers alike. The city is filled with opportunities to spend a day boating, fishing, snorkeling, and seeing North America’s only living coral reef.

Don’t miss other attractions such as:

  • Ernest Hemingway’s Home and Museum

  • Harry S. Truman Little White House

  • Fort East Martello Museum

  • West Martello Tower

  • Duval Street walking and shopping tour

  • Key West Butterfly and Nature Conservatory

  • Key West Sunset Celebration at Mallory Square

  • America’s Southernmost Point Buoy

  • Mel Fisher Maritime Museum

  • Historic North Roosevelt Blvd

For those that seek to see Key West marine life, sandbar trips are a unique way to experience the sea. For evening adventures on the water, consider two nights on an evening guided Key West tour with us at Night Kayak Key West.

Key West Sunset At Mallory Square


Tips When Visiting Key West

If you have never visited Key West, there are some tips you should keep in mind to make the most out of your trip.


Arriving To The Island

Although you can fly into Key West’s international airport, one of the best ways to arrive is by car. For a road trip experience you won’t forget, it is recommended that you fly into a South Florida city such as Miami or Fort Lauderdale and rent a vehicle.

You will be driving on the gorgeous Overseas Highway, which runs parallel to Henry Flagler’s rail lines. On this picturesque highway, you will go across the various quaint islands of the Florida Keys.

It is a great opportunity to stop in the small towns that you will find from Key Largo to Key West. It is a beautiful scenic drive that you can enjoy at 45 mph. From Miami, you can expect to drive for less than four hours to Key West.

Overseas Highway


Prepare For Key West’s Tropical Climate

When visiting this part of Florida, you must remember that the weather is warm throughout the year. You can expect to enjoy 75-degree weather in the winter and 90-degree weather in the summertime. Even winter evenings are a comfortable 60 degrees. Because of Key West’s subtropical climate, you can expect a rainy and hurricane season.

If you visit between June and November, you may experience rainy days. However, the good news is that the rain only lasts for a few minutes to less than one hour. You will be surprised at how quickly the sky clears up in Key West. This means that even during hurricane season, you will not have to worry about spending the whole day at the hotel.

Key West, Florida


How To Find The Best Key West Beaches

Key West is a paradise for beach bums. You will find popular beaches populated by tourists as well as hidden beaches that offer privacy. Unless you are visiting during spring break, you can rest assured that you will have plenty of options for finding a peaceful beach.

When visiting this tropical destination, you must keep in mind that peak season runs from November to March. It is when the whole country seeks to warm up down south to get away from cold winter days. You will find the area a bit more busy during these months, but you will still feel like you can enjoy a quiet tropical oasis.

A great way to see Key West and swim in its charming sandbars is to connect with us from Night Kayak Key West. We will take on private boat tours where you can go sandbar hopping and explore the natural beauty of the region.

Visit Key West Sandbars


Must Do In Key West – Not Just In October

Here are some quick tips to keep in mind when planning your Key West vacation:

  • Taste local seafood, Cuban, and Bahamian fare

  • Experience authentic Key lime pie

  • Eat breakfast at Blue Heaven

  • Ride on the Conch Train

  • Visit Eden House, Key West’s first hotel

  • Drink specials at the famous Green Parrot Bar

No matter how you choose to explore Key West in October, you are sure to have a great time. October is certainly one of the most exciting months to visit the paradise island. October is filled with activities for all types of travelers.

Key West Conch Train


Your Local October Tour Guides

Experience Key West in October as a local would. When you book a tour with us, you will connect to local guides that know the best parts of the island. We provide tourists with an intimate perspective of this paradise, allowing you to have an authentic experience.

Contact us today to book your October tour!

1 hour 30 minutes
Group Size
Up to 18

Night Kayak Guided Tour

Get a single or double glass-bottom kayak illuminated with lights and follow our tour guide on this one of a kind, unforgettable and simply magical adventure.

This slow paced, immersive, and very relaxing experience will allow you to see some cool, active at night marine life as you are gliding through crystal clear waters of Key West.

Guests will experience going through narrow mangrove tunnels at night, floating around shallow and calm waters as the tour guide will look for interesting critters for everyone to see.

3 hours
Group Size
1 to 6

Key West Sandbar Trip

Key West sandbars are our local well kept secret. This is where we take our families to hang out and relax on our days off. This is the perk of our island lifestyle. Now we want to share this experience with you.

Turquoise shallow waters, epic picture worthy sights all around you that look like a postcard - that is what you're signing up for!