Enjoying All Key West Has to Offer in The Fall! 2023 Edition

When we think of the fall, leaves changing colors and chilly temperatures often come to mind. However, if you’re lucky enough to be in Key West, Florida during this season, you’ll experience the fall in a unique way. While the leaves of palm trees don’t change color, Key West has its own set of enchanting activities that capture the spirit of the season. From outdoor adventures to cultural experiences, here are some must-do activities to make the most of your fall getaway in Key West!

Sunset Sailing

Key West is renowned for its breathtaking sunsets, and there’s no better way to soak in the fall colors of the sky than by taking a sunset sailing trip. Whether you opt for a private charter with Sebago Watersports or a group excursion, you’ll be treated to a mesmerizing display of oranges, pinks, and purples as the sun dips below the horizon. Sip on a tropical cocktail and relish the serenity of the ocean while feeling the gentle autumn breeze.

Kayaking and Paddleboarding

Fall is an ideal time to explore the pristine waters around Key West. With cooler temperatures and calmer seas, kayaking and paddleboarding become even more enjoyable. Rent equipment or join a guided tour to paddle through the mangrove forests, spot marine life, and take in the lush greenery that surrounds you. Don’t forget your camera – you’ll want to capture the vibrant foliage and clear waters.

For example, with Clearly Unique Charters, you’ll be blown away by the front-row seat and view of the underwater world. Tours combine kayaking and snorkeling aboard completely clear and glass bottom, two person kayaks. Glass bottom viewing allows you to see the fascinating world of the mangrove island above the water and the diverse eco-system of the ocean floor. On kayak tours, you can explore Key West’s beautiful, peaceful and diverse backcountry.

Key West Fantasy Fest!

Key West has a vibrant cultural scene, and fall is no exception. Check the local event calendar for festivals, concerts, and art exhibitions happening during your visit. The annual Fantasy Fest, typically held in late October, is a wild and colorful celebration featuring extravagant costumes, parades, and live entertainment. Check out the full schedule of events here!

Culinary Delights

Savoring delicious food is a must during any trip, and Key West offers a variety of culinary delights. Fall is the perfect time to enjoy fresh seafood and tropical flavors. Try the local seafood shacks for conch fritters, key lime pie, and mouthwatering fish tacos. Don’t forget to pair your meals with a cold local craft beer or a refreshing coconut cocktail. Check out fabulous spots at the Key West Historic Seaport like Conch Republic Seafood Co, Schooner Wharf Bar, Half Shell Raw Bar, B.O’s Fish Wagon, and a number of other spots with delicious local bites and a wonderful atmosphere to go with it.

half shell raw bar

Lighting of the Bight – Harborwalk of Lights!

harborwalk of lights

Gather on the Harbor Walk plaza at Greene and Elizabeth St. to best see the official lighting of the 2023 Key West “Harbor Walk of Lights” with lights and creative displays reflecting the “Maritime History of Key West.” The Key West “Harbor Walk of Lights” stays lit nightly through New Year’s Eve, stretching along the Key West Historic Seaport and Key West Bight Marina.


In sum, from sunset sailing to seasonal festivals like the Bight Before Christmas Harborwalk of Lights, Key West offers a one-of-a-kind fall experience that will leave you with lasting memories. So, pack your bags, soak up the autumn sun, and make the most of your fall getaway in this tropical paradise.

For more information on the fantastic and unique shops, restaurants, museums, and watersports activities available at the Key West Historic Seaport all year round, visit www.KeyWestHistoricSeaport.com!

Key West Historic Seaport and Bight Marina

Your Gateway to Everything Key West!

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