Things to do in Key West in The Fall 2021 [Guide]

It’s that time of year again. Pumpkin spice is flowing, leaves are falling, and temperatures are dipping. Here in Key West, dipping temperatures mean that the high is now only 79 degrees so, at the most, you might want to pack a light sweater.

Even though we may not be dipping our toes in the water, there are still plenty of activities to do this fall in Key West. It’s still a great place for fall retreats, fall breaks, or just a little getaway for you and friends or family.

Let’s run through some top things to do in Key West this fall.

The Key West Film Festival

It’s time for cinephiles to unite for the 10th annual Key West Film Festival. Movies and special events will be played in special areas all sound Key West such as the Key West Theater and the San Carlos Institute.

This year, the event will take place at the outdoor venue of the Coffee Butler Amphitheater. Lasting four days from November 17-21, there will also be special guests and special screenings.

The Fantasy Fest

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. Held from October 22-31st.

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.

Offshore Racing World Champions

Power boats from all over the world come with teams and engage in high-speed races around the Key West Harbor.

Race World Offshore is the premier Offshore Racing Sanctioning body in the United States and our team is dedicated to producing an unforgettable week from November 7th-14th.

The Super Boat International races are a longstanding tradition on the island and are known as the Indianapolis 500 of power boat racing!

Key West Farmers Market  

Shop small and local at the weekly Farmers Market featuring fresh produce grown in Homestead, gorgeous orchids & native plants, artisan selection of meats and cheeses, pickles, honey, nuts & dried fruits, natural soaps and so much more.

Held every Thursday from 3pm til sunset at Truman Waterfront Park- rain or shine. You’re guaranteed to find Key West crafts, gifts and the perfect souvenir to take home.

Join us on Thursday, October 28th for a special Trick or Treats at the Waterfront Market starting at 8pm. Several of our vendors will be decorated and offering treats - or tricks - to all our great customers.

Pro-tip: Bring a blanket or chairs to enjoy the park and treats. Costumes encouraged!

Wrapping Up

We look forward to seeing you in Key West. As part of the health guidelines, masks are mandatory and social distancing must be practiced in all areas. Help us keep Key West a safe place.

If you want to visit Key West this month, now is the time to book. We have a special partnership with Aztec Airways, offering cheap flights from Fort Lauderdale to Key West via air taxi at a private terminal! Contact us today for more information.