Key West In September - 7 Fun Things To Do In The Off-Season

Things To Do In Key West In September

If you’ve always wanted to visit Key West, but don’t relish the idea of sharing a stroll on the historic seaport with droves of other guests, then consider coming to Key West in September. Key West is the southernmost city in the continental United States and though it’s often bustling with visitors throughout the year, you’ll find a break in the crowds during September.

The Conch Republic may be in the midst of hurricane season during September, but you’re less likely to see a hurricane than you are occasional tropical storms throughout the season. Whether you’re coming for the Labor Day weekend or indulging in a longer stay, September is a wonderful time of year to explore Key West.


1) Thrill Seekers Unite On The Waters Of Key West

One of the best activities to take part in when visiting Key West is to hop in a kayak and explore the crystal clear waters to seek out tropical fish and other stunning marine life. At Key West Paddle, we take pride in showcasing why Key West is a top destination for nighttime exploration.

Our nighttime kayak tour lets you hop into an LED-lit, glass-bottomed kayak and explore the mangroves of Key West after the sun goes down. Not only will you get away from the crowds in town, but you’ll see countless marine creatures come to life in the tunnels and shorelines of Key West’s mangrove forests.

Join us as we unveil the enchanting allure of Key West after dark, offering visitors an unforgettable experience year-round. Contact us before your trip so we can help you plan the most unforgettable night excursion of your life!

Key West As A Top Destination For Nighttime Exploration

2) Attend Some Of Key West’s Annual Events This September

There are a couple of events that take place here in Key West every September, and if you plan on visiting this fall, then you don’t want to miss these exciting outings.


Key West Brewfest

If you’re looking for a fun event that will also help you explore Key West in a new way, then consider a visit to the annual Key West Brewfest! There are beer pairing dinners, pool parties throughout Key West, tap takeovers, and ends with a massive beer-tasting event that includes about 150 well-known and locally brewed beers to try.

Visit And Have Fun At Key West Brewfest

Key West’s Womenfest  

If you’re visiting Key West this September you’ll find the Annual Womenfest Celebration from the 4th to the 8th in 2024. There will be women-only events happening all five days, including burlesque shows, pool parties, cornhole tournaments, sunset sails and much more!

Join us at Key West Womenfest, where you can engage in a diverse array of activities, socialize, embrace your true self, bask in the sun, and revel in unforgettable parties and dancing throughout the night.

Pool Parties Celebration Of Womanhood At Key West

3) Indulge In A Day Of Snorkeling In Key West

Your visit to Key West wouldn’t be complete without a snorkeling excursion off the shores of either Higgs Beach or Smathers Beach. These two locations are known for some of the best snorkeling spots in Key West, so you don’t want to miss out on an unforgettable experience. Higgs Beach is home to a pier that allows you to step down easily into deeper waters to explore the creatures both large and small that call these waters home.

You’re likely to see Moray eels, stingrays, and countless tiny tropical fish amongst the coral reef as you snorkel off the shore at Higgs Beach. Heading out into deeper waters will lead you to one of the only underwater sculpture exhibits in the world! Head over to Smathers Beach if you’d like to indulge in some relaxing shallow water.

If you have time to visit a farther location, catch the ferry to Dry Tortugas National Park for an unforgettable snorkeling experience along this secluded island paradise. The Dry Tortugas National Park has many trails and picnic spots to indulge in as well, but you may also want to dive into some Key West history by exploring the old military fort on the island while you’re there.

Snorkel and See Coral Reef At Higgs Beach Key West

4) The Cuisine Is Always In Season When You Visit Key West

If you’re coming to the Florida Keys in the low season, one thing you can always count on is the tasty cuisine throughout Key West. While you can almost always find a delectable Key Lime Pie on the menu, there are so many other flavors to experience during your time in Key West.

Here are just a few of our favorite places and some of the menu options available:


Blue Heaven

Do not miss your chance to eat at this whimsical restaurant in Key West. The decor is sprinkled with colorful coconuts and nautical themes as chickens and cats graze the area for added entertainment. Some of the best dishes on the menu at Blue Heaven include:

  • Key Lime Pie

  • Scallops provencale

  • Miso-marinated eggplant salad

Enjoy the outdoor dining at this establishment to take in all the beautiful art and the roaming animals while you dine in the fresh air.

Key West Delicious And Iconic Dessert Key Lime Pie

Hot Tin Roof Restaurant

This elegant location is right along the water at Ocean Key Resort & Spa, so the ocean views become a part of your culinary experience. You’ll find Caribbean and Cuban cuisines on the menu that are fully rooted in the culture and history of Key West. Some of our favorites include:

  • Crab Benedict

  • Tuna tacos in wonton shells

  • Crispy chicken cheddar waffles

There are tons of packages to enjoy at the Hot Tin Roof Restaurant, including romance packages at sunset and so much more. Be sure to call ahead and reserve a table for the best experience!

Tuna Tacos - One Of Key West Favorite Cuisines

5) Key West’s Rich History And Culture Never Go Out Of Season

If you’re looking for ways to experience Key West in the off-season but want a different excursion than sitting on the beach, then consider an evening at the Key West Theater or a trip down memory lane at the Key West Museum of Art & History. Each location is a must-visit, especially if you’re looking for something to fill your time with family and friends.

The Key West Theater is always hosting live events with live music, comedians, and other performers from around the world and locally. If you head over to the Key West Museum of Art & History you can enjoy an afternoon full of education on the history of Key West, from devastating hurricanes to plundering pirates and shipwrecks of old.

Trip Down Memory Lane At The Key West Theater

6) The Many Things To Do In Key West During Your Stay

There are some places and activities in Key West that never end, and we have a comprehensive list of all the things you won’t want to miss while you’re in town.


Discover Duval Street And Mallory Square

If you love to drink or party, then an evening on Duval Street should be at the top of your list. There are countless bars, restaurants, and other establishments brimming with entertainment from live music and dancing to comedians and more. Not far from Duval Street, you’ll find the Old Town Trolley Tour that will take you all around town to different stops at popular attractions. Just before sunset, hop off at Mallory Square to watch the sun go down during the Sunset Celebration. There are always live performers, street vendors, good food, and even dancing.

Countless Bars And Restaurants At Duval Street Key West

Visit Stock Island

If you’re searching for a more peaceful experience then head to Stock Island where you can spend some time at the Key West Tropical Forest & Botanical Garden. Meander down pathways and through exhibits of natural beauty with all the stunning tropical flora and fauna that call Key West and the Florida Keys home.

Peaceful Experience At Stock Island Key West

Explore The Key West Lighthouse

You can also spend some time exploring the Key West Lighthouse and quarters where keepers and their families once kept the shorelines of Key West safe from impending shipwrecks. Climb the stairs to the top to capture a breathtaking view or look through old belongings to give you an idea of what life was like for a lighthouse keeper years ago.

Explore The Key West Lighthouse

Take A Photo At The Southernmost Point Buoy

One last thing you won’t want to miss in Key West is a photo at the Southernmost Point Buoy. This colorful staple is visited by hundreds of people every day and it marks the southernmost point in the United States. Make sure to have your camera and grab the selfie of a lifetime while you’re here!

Take A Photo At The Southernmost Point Buoy

7) Stay In Style

One of the benefits of coming to Key West in September is the resorts and fancy hotels at your disposal. Not only will there be fewer guests to contend with, but you might just get an amazing room rate too!

Many of the hotels and resorts in Key West offer spa services, private beach access, pools, and restaurants to enjoy, so you really can’t go wrong with where you choose to stay. Here are just a few of our favorites:

  • Sunset Key Cottages

  • Ocean Key Resort & Spa

  • Hyatt Centric Resort & Spa

Call ahead to ask about packages and amenities and shop around for the best deals during your stay!

Key West Resort And Spa

See The Best Sites In Key West

As you explore the stunning sights of Key West in September, embarking on a kayak tour with Key West Paddle is an absolute must. We give you all the gear you need to have a safe trip, and our expert guides know all the best spots to lead you to see the amazing marine life and nightlife of the enchanting mangrove forests.

Glide through the crystal-clear waters, marvel at the diverse ecosystem, and create unforgettable memories as you discover the best sites Key West has to offer.

Our night kayak tours promise an extraordinary experience that will leave you in awe of the natural wonders that surround this tropical paradise.

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!