While seasons matter when you’re planning a vacation in most places around the world, any time of the year is a great time to visit Key West. In the fall, the island cools off just a bit and beckons people from all walks of life to come experience its majesty. If you’re planning a vacation to the southernmost city in the fall, this guide will provide you with all you need to know.
Outdoor and Water Activities
Forget the heat of summer, fall in Key West means cooler ocean breezes and refreshing water temperatures. Enjoy the outdoors with these activities.
In the fall, touring the island by bike is a great option. The air is lighter than the humid months of summer, making it easy to ride without getting overheated. There are numerous companies providing bike tours of the island, both guided and self-guided. One of the most popular bike tours, Lloyds Tropical Bike Tour, is an off-the-beaten-path adventure. Hop on a bike and follow this well-known Conch around the island while you sample local produce right off the trees! During the fall, it could be anything from a ripe coconut (that Lloyd will crack open right before your eyes) to something you’ve never tasted before like sapodilla or a sugar apple.
One of the most alluring aspects of Key West is the magnificent crystal waters that surround the island and the vibrant world that exists beneath them. Snorkeling the reefs in Key West provides an unforgettable experience for people of all ages and numerous water sports companies offer tours throughout the year. In the fall, the seas here are just a bit cooler, but still warmer than most other places around the country! With water temperatures averaging 86 degrees in September, 82 in October and 76 in November, the Gulf of Mexico and Atlantic Ocean are comfortable and enticing to visitors from all over the world.
Whether you’d like to soar above the island on a parasail, discover why everyone loves a Key West sunset cruise or visit the reef without getting wet on a Glass Bottom Boat, you can do it all in Key West. And the beautiful part is, enjoying the island’s multitude of watersports in the fall means you’ve avoided the rainy summer months and haven’t yet hit the winter cool down.
Fury Water Adventures, a local Key West watersports company, offers special trips during the fall including:
Located 70 miles west of Key West in the middle of the Gulf of Mexico, the Dry Tortugas National Park is a once-in-a-lifetime adventure for beach goers, nature lovers and photographers alike. In the fall, the milder temperatures make it comfortable to explore the many outdoor wonders of this unique destination. Take a tour of Fort Jefferson and learn about its military history, go snorkeling in the clear blue waters of the Gulf of Mexico, or relax with a leisurely stroll along the beaches of Garden Key. It’s also a great time of year for an overnight camping trip.
No matter the time of year, you can’t miss the nightly sunset celebration at Mallory Square. Stroll along the water, sip a tropical beverage and be transported to a Key West state of mind as the sun dips below the horizon. During the fall, you’ll want to get there by 4:30 p.m. to have time to enjoy the street performers, live entertainment and of course, the main event.
The weather may still be warm during the fall in Key West, but that doesn’t mean there aren’t a few cool breezes to be felt at the island’s most haunted places. Join Ghosts & Gravestones aboard the Trolley of the Doomed to learn about sacred sites like the Grotto of Our Lady of Lourdes, the African Slave Cemetery and Captain Tony’s Saloon. Drive past the Artist’s House where Eugene lived and where a servant gave him a one-of-a-kind handmade doll he named Robert. Your Ghost Hosts will keep the haunts coming as they share eerie stories about the darker side of Key West.
Beautiful Gardens at the Museums
Many of Key West’s most popular museums feature historical sites both inside and out. Wander through the gardens and green spaces for the full museum experience done the Key West way.
Because much of the allure of the historic Ernest Hemingway House and Museum comes from its magnificent gardens and the pool area, visiting in the fall is much more pleasant than when the Florida heat is at its peak. During the fall, you will be treated to a view of many of the property’s beautiful flowers and landscaping. You may even be more likely to spot the famed polydactyl (six-toed) cats that make the Hemingway House their home. After a tour of this historic home, it’ll be easy to see how the famous writer was inspired by his Key West surroundings. Tours are offered daily from 9 a.m. to 5 p.m. and are about 30 minutes long.
Located in the Truman Annex on Front Street, the Truman Little White House holds a unique place in American history and is a must-visit during your vacation to Key West. Originally serving as the naval station’s command headquarters during several wars, this historic structure became President Truman’s winter home in 1948. The president became so enamored with it and the island that he ended up staying for 175 days. During that time, Truman ran the government from what became the Little White House. Today, visitors can see many of the Truman family’s belongings, furniture, historical documents and rooms where numerous landmark events took place.
The cooler temperatures of fall make it an ideal time to tour the lush botanical gardens that surround the house. You’ll also find that tours during this time of year are usually less crowded. They take place daily from 9 a.m. to 4:30 p.m. and last about 20 minutes.
The Audubon House & Tropical Gardens showcases the work of John James Audubon and commemorates the artist’s visit to Key West in 1932 when he drew 18 new birds for his “Birds of America” folio. The house, which was built in 1846, belonged to Captain John Geiger and was occupied by his family for close to 110 years. After, it was purchased by Frances and Mitchell Wolfson, who immediately began restoration including adding electricity and antique furnishings that date back to the first half of the 19th century. Once finished, the Audubon House was opened to the public in 1960.
Fall is the ideal time to explore the grounds and gardens of this historic structure as well as to discover the artwork of Audubon that graces the walls of the house museum. During this time of year, the house and gardens are open from 9:30 a.m. to 4:15 p.m.
Al Fresco Dining & Live Entertainment
During the months of fall, the best way to dine in Key West is al fresco and with a waterfront view. Luckily, the island has its share of ideal spots to do just that!
Enjoy refreshing sea breezes and picturesque views at this longstanding waterfront restaurant. Fresh seafood and live turtle races too!
Watch the boats sailing into the dock as you dine on the freshest oysters and seafood on the island. Fall is still the best time of year to eat oysters and if you’re a fan, Half Shell Raw Bar is shucking them fresh to order!
This place is not just overlooking the water, it’s floating on it! Enjoy the views and the authentic Thai cuisine during your Key West adventure.
This restaurant serves up elegant waterfront dining where you can indulge on succulent Key West lobster during the fall season. Everything here is made to order and mostly locally sourced produce, seafood and meats.
A hidden gem tucked away on Stock Island, you’ll love sitting outside at this open-air, laid back restaurant that serves fresh seafood. This is also a great place for a hearty breakfast with amazing views.
No need to change out of your flip flops and beach cover ups before dinner at Salute!. Just head over to this Higgs Beach café for spectacular ocean views and delightful fall weather. Fewer travelers visit Key West in September and early October, so you won’t have to wait long to dig into mussels, pink shrimp and other specialties.
Annual Events & Festivals
There’s always something happening in Key West and the fall season is no exception. If you find yourself traveling to the island from September to November or you’re a local Conch, join in on the fun of these events and festivals.
September 2 – September 6, 2021
In its 8th year, this event attracts thousands of beer connoisseurs. Includes beer dinners, brunches, happy hours, pool parties and a signature tasting event.
October 22-23, 2021
Held in Key West’s historic Bahama Village, you’ll enjoy island-style food, arts and crafts, live entertainment and more.
October 22-31, 2021
This is the biggest and most famous event held in the fall. Fantasy Fest is an adult-only, 10-day party that’s been going on for more than 25 years and features parades, parties, costumes, lots of revelry and libations. To combat the usual slow down of tourism in the month of October, Fantasy Fest was created in 1978 by several local business people and members of the Tourist Development Association. Nearly empty streets, restaurants and hotels were transformed into one of the busiest times of the year for the city with the birth of this one event.
November 7-14, 2021
Power boats from all over the world come with teams and engage in high-speed races around the Key West Harbor. The Super Boar International races are a longstanding tradition on the island and are known as the Indianapolis 500 of power boat racing!