No matter what time of year you visit Key West, there is always, ALWAYS something to do. This little island could really be renamed Key Fest for the amount of festivals that take place each month!
Here are a few of my own personal “Paradise Picks” for events and festivals that I like to plan my time around in Key West. Have questions? Book a consult or contact me here!
January
New Year’s Eve Shoe Drop Celebration 👠
The Southernmost City celebrates with a descending 6-foot red high heel shoe carrying drag queen Sushi at the Bourbon Street Pub/New Orleans House complex, 724 Duval St. Seconds before midnight, the high heel bearing a lavishly gowned and coiffed Sushi is to be lowered from the second-story balcony of the complex toward the cheering crowds below. As midnight strikes and the New Year officially begins, she will land and gleefully pop the cork on a ceremonial bottle of champagne.
New Year’s Eve: Conch Shell Drop at Sloppy Joe’s 🐚
The arrival of the New Year is to be heralded on the island’s Duval Street with the “drop” of a gigantic manmade conch shell, the symbol of the Florida Keys, to the flat roof of Sloppy Joe’s Bar, 201 Duval. Thousands of spectators gather on Duval for the annual gala, emceed by a rooftop host starting at 10 p.m. and featuring dancing in the street and a countdown to midnight recorded on a huge clock.
New Year’s Eve: Pirate Wench Drop at Schooner Wharf 🏴☠️
For piratical partiers, a New Year’s Eve salute to Key West’s rowdy seafaring roots is scheduled at the island’s Historic Seaport. At midnight, a winsome pirate wench is to descend from the top of the mast of the tall ship America 2.0 as cannon blasts welcome in the New Year. Scallywags in attendance can expect live music all day, dancing and festivities at the Schooner Wharf Bar, 202 William St.
Annual Florida Keys Seafood Festival 🦞
A family-friendly event with local fresh Keys seafood, drinks, marine-related crafts, youth activities, and live music. $5 admission per person; hours open from 11 a.m. – 8 p.m. on Saturday; 11 a.m. to 5 p.m. on Sunday, at Bayview Park, Truman Avenue and Jose Marti Drive.
Key West Food & Wine Festival 🍷
Top chefs and restaurateurs display culinary creativity and the Keys’ indigenous cuisine in a flavorful schedule of events for food lovers. Highlights include the lively “Old Town Uncorked,” neighborhood wine strolls, food and wine pairings, intriguing seminars, winemaker dinner series and a grand tasting.
February
💝 – Fall in love!
March
🍀 – Get lucky!
April
Annual Conch Republic Independence Celebration 🎉
With activities such as a lighthearted sea battle featuring tall ships, the Conch Republic’s 10-day birthday party showcases the independent and eccentric spirit that characterizes the Florida Keys.
Presented by Lazy Dog Adventures, the challenge includes a 12-mile Elite Race around the island and a 4-mile open race. Other events include a kick-off registration party, paddleboard clinics and races for kids.
May
Key West Songwriters’ Festival 🎶
The annual showcase of musical magic features America’s foremost performing songwriters, with concerts staged in intimate, audience-friendly island settings. The largest festival of its kind in the world celebrates over 20 years as both a tourist attraction and favourite of island locals. The festival revolves around five days and nights of big stars in intimate settings, introducing audiences to the faces, voices and stories behind the songs.
June
Key West Pride 🏳️🌈
Key West shows its Pride every day, and this is your chance to be a part of the celebration! The five-day schedule includes daytime pool and beach parties, late-night drag shows, on-the-water adventures ranging from snorkeling and kayaking to glass-bottom boat tours, a street fair, and pageants to select Mr., Miss and Ms. Key West Pride.
July
A wacky talent show, pie-eating and cooking contests and other tasty temptations await Key West visitors during the annual Key Lime Festival. Four days of culinary events for every taste are planned, including favorites from past years like the Key Lime Cocktail Sip & Stroll, and new favorites for Key Lime lovers like The Key Lime Pie Hop.
Key West Mermaid Festival 🧜🏼♀️
This fin-tastic five-day event will unite the Key West locals and tourists, our neighboring Keys, visiting mermaid communities, and mermaid enthusiasts from around the world, on our magical little island. Family friendly, with fun for all, join us as we raise awareness for our beautiful oceans and educate all humans to swim safely in mermaid tails. #TheTakeOverIsReel we like to say, and we look forward to getting salty with all of the captains and mermaids who work hard to make Key West and the Florida Keys a better place for all who live the island life and our visitors.
Come celebrate Mel Fisher’s historic find of the Atocha Mother Lode. Mel Fisher’s famous 90′ treasure salvage vessel JB Magruder will be on display at the dock behind Schooner Wharf Bar at the Historic Seaport. Sign up for a tour on board to see the latest treasure-finding technology that scours the ocean floor for centuries-old coins, gold bars, gold chains, emeralds and silver ingots. Meet and get autographs from the Golden Crew of the Atocha discovery along with the current treasure-hunting crew!
Sloppy Joe’s Bar in hosts its Annual Hemingway Look-Alike contest. Along with a street fair, running of the bulls and much more, this contest is one of many events in Key West to celebrate the birthday of Ernest Hemingway and honor his work as author and sportsman.
August
🎣 – Live like a local!
September
During a festival “crafted” for Labor Day weekend, attendees can sample nearly 200 beers and ales while also discovering the flavors of the continental United States’ southernmost city. The annual Key West BrewFest is highlighted by a lavish oceanside tasting festival, beer-focused brunches, pool parties featuring specialty beers, daytime tap takeovers and dinners pairing each course with brews that complement the cuisine.
October
Zombie Bike Ride 🧟♀️
We Cycle Bike Shop’s Zombie Bike Ride was created in 2009 by Marky Pierson of Wonderdog Studios and Evan Haskell and Chris Needham of WeCycle Bike Shop. The bike ride quickly grew from a couple hundred people to nearly 5,000 in 2013. The ride is a little over four miles long and takes a leisurely pace down US1 along the Atlantic Ocean, right at sunset. The Zombie Ride has grown to epic proportion with the help of thousands of fun-loving, bike-riding, costume-sporting, and rock-and-roll townspeople. A police escort leads the ride down US1, past the Zombie Beach Bash at Salute! On the Beach, and down to Duval Street where the ZombieFest continues.
Fantasy Fest is a 10-day festival of costumed parties in true Key West style. Over the years it has become the premier masking and costuming extravaganza, like nothing else you’ve ever seen. The festival has grown to encompass more than 60 parties, costumed marches, street fairs, and glamorous balls, as well as the show-stopping Fantasy Fest parade.
November
Race World Offshore Key West Championships 🚤
High-speed offshore powerboats are to compete in Key West, known internationally as one of the top venues for offshore powerboat racing. Three separate days of racing are scheduled during this week-long event for boat enthusiasts! Before and in between race days, are various social events including concerts and the opportunity for close views of raceboats and meeting crew members at the Truman Waterfront Race Village.
Lighting of the Bight: Key West Harbor Walk of Lights ✨
Gather on the Harbor Walk plaza at Greene and Elizabeth St. to best see the official lighting of the annual Key West “Harbor Walk of Lights” with more lights and creative displays than ever before, all continuing the “Maritime History of Key West” theme! The Key West “Harbor Walk of Lights” traditional main features will light up that night, including the Fishing Buoy Tree, a fresh pine Nautical Christmas Tree and the original Key West Lobster Trap Tree. Harbor Walk of Lights, lit nightly through New Year’s Eve, stretches along the Key West Historic Seaport and Key West Bight Marina.
December
The Lighted Bike Ride helps to gather the needed toys for the struggling, working families of Key West for the holidays. Families and individuals with lighted and decorated bikes ride through the streets for the community to see. Entry for the bike ride is an unwrapped toy or monetary donation for Holiday Helpers. Wesley House Family Services coordinates this bike ride – registration begins online in early October. The Lighted Bike Ride leaves Bayview Park at 7pm.
Key West City Hometown Holiday Parade 🎄
Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local flavor prevails with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade kicks off at Bayview Park’s Truman Avenue and White Street location. Catching tossed candy and seeing Santa are highlights for kids.
POSH – Paws Often Steal Hearts 🐕
Get fancy with a fascinator at Key West’s most elegant fundraiser for the Florida Keys SPCA. Food, drinks, live music and more in the gorgeous tropical gardens of the Audubon House.
Annual Rudolph Red Nosed 5K Run 🦌
Don your festive holiday running attire, affix your ruby-red nose, and join in the fun, starting and ending at the Southernmost Beach Café, 1405 Duval St. Race day check-in starts at 7am with 8am. start time. After the race, enjoy refreshments, fun, prizes and a huge silent auction.
Annual Schooner Wharf Bar Annual Lighted Boat Parade ⛵️
Lighted and decorated vessels from rowboats to tall ships proceed around Key West’s Historic Seaport and harbor areas. Festivities begin at 6 p.m. with parade following at 8 p.m. Holiday revellers can watch and applaud from bars, restaurants and resorts in and around the Historic Seaport as vessels of all shapes and sizes dazzle the crowd.
No need to gas-up the snowblower if you’re planning a holiday escape to the Conch Republic! Here, ‘Christmas chill’ means rockin’ your flops and kicking back island-style and one of the best ways to do that is hopping a ride on Old Town Trolley’s Holiday Lights & Sights Tour! The Southernmost City is all a twinkle, as the locals decorate their historic Key West homes in a splendid cascade of lights and other decorative touches to see who can outdo the other in a friendly, holiday-inspired competition.
*For New Year’s Eve festivities, please see January’s listing of events.
For an entire calendar of fishing, arts and culture events, click here!
Sherri in Paradise 