What’s Up
So you’ve reached your final Florida destination, now what? Well, hold tight because this is one Florida destination where the fun never stops! In fact, there are probably more events and festivals going on in the Florida Keys & Key West than in any other Florida destination. Here’s a quick list of fun Keys’ happenings that you won’t want to miss! However be aware that due to COVID-19, we recommend that you check ahead.
Please confirm details with event organizers or venues in case of changes or cancellations.
ONGOING
Daily
Mini Golf
Ramrod Key: Come play the southernmost mini-golf course in the Florida Keys. This kid-friendly 18-hole course is a perfect family adventure. It boasts a fun caveman theme with two giant waterfalls and four fountains. And get this: If you’re 21+, you and your friends can have a cocktail or glass of wine while you putter around. Happens daily from 10 am – 10 pm at Boondocks Grille & Draft House at 27205 Overseas Hwy (MM 27.5) on Ramrod Key. Be sure to check out their special party packages and tournaments. Info: 305-872-4094; boondocksus.com.
Daily
Miniature Golf
Marathon: The Keys’ newest and largest mini- golf attraction is a full size 18 hole course that challenges the best of the best. A fun tropical theme, lush landscaping and an amazing local coral rock waterfall makes it one of the Middle Keys’ “Must See” destinations. Top it all off with a variety of snacks, slushies, frozen daiquiris or cold beers and you’ve got yourself a great day — not at the beach! Special event packages and tournaments, too! Open daily 10am – 10pm at Porky’s Bayside, 1410 Overseas Hwy in Marathon. Info: 305-731-7592; porkysbaysidebbq.com
Daily
Green Pineapple Key West Yoga
Key West: Whether you’re a beginner or a seasoned practitioner, this Hatha-based yoga studio offers daily classes designed for every skill level. Based on the foundations of traditional yoga practices, categories include Vinyasa, Yin, Restorative, Gentle, Breath and Mindful Movement, Pilates, and Meditation. The Green Pineapple Yoga Shala also offers workshops to feed your body, mind, and soul. Private or Group Classes are also available. Come early or stay after class for fresh juice, tea, or a super healthy Zen bite in the plant-based Wellness Cafe. Find it nestled inside The Green Pineapple Wellness Center, 1130 Duval Street, Key West. Info: 305-509-7378; greenpineapplewellness.com.
Nightly
Key West Sunset Celebration
Key West: Each evening, about two hours before sunset, flocks of people gather at Key West’s Mallory Square and on the pier behind the Opal Resort & Marina on Front Street to watch the sun slowly sink into the Gulf of Mexico and to revel in the colorful street performers, local artists, psychics and food vendors who have made Key West’s Sunset Celebration a world-famous, multicultural happening.
Nightly
Snook’s Bayside Sunset Celebration
Key Largo: Kick back with a rum punch on Snook’s 5,000-square-foot waterfront patio, listen to some great live music, and enjoy an unobstructed panoramic view of the sun sinking into the Florida Bay. You can also get Happy Hour prices from 4 – 6 pm on various libations and appetizers. The nightly event is ceremoniously marked by the “Sunset Horn” bellowing just before the fiery ball disappears into the horizon. The celebration continues well after dark with live entertainment and dancing under the palms. Takes place at Snooks Bayside & Grand Tiki at MM 99.8, Southbound Lane behind the Sandal Factory Outlet in Key Largo. Info: 305-453-5004; snooks.com.
Nightly
Aquaplex
Key West: With three reimagined venues all under one roof, Key West’s state-of-the-art entertainment complex is where it’s all happening. This world-class dance club, with high-tech lighting and an industrial vibe, also boasts a lovely outdoor garden bar called the Back Bar, replete with Aqua Belle, a fusion food truck serving breakfast, lunch, dinner, and late-night bites. There’s also 22&Co, heralded as the best drag bar in the Keys. But the crowning jewel of it all is the Birdcage Cabaret featuring the world-renowned female impressionist and singer Christopher Peterson, backed by The Aquanettes, an outrageous troupe of talented drag queens who sing and dance the night away. This is THE place to go for “not-to-be-missed” entertainment. Find it all at 711 Duval St. Info: 305-294-0555; aquakeywest.com.
Weekly
Every Monday & Tuesday
Glow Hours: Rooftop Happy Hour on Hugh’s View
Key West: For a headier Happy Hour, head up to Hugh’s View, where the bar is open, there is free admission, and everyone looks great in the golden twilight. Hugh’s View sits on the roof of The Studios of Key West. It offers panoramic vistas across the rooftops of Old Town, from the Gulf of Mexico on one side to the Atlantic on the other. Takes place from 6 – 8 pm at The Studios of Key West, 533 Eaton St. Info: tskw.org.
Every Thursday
Key West Waterfront Farmers Market
Key West: This traditional farmer’s market includes produce, seasonal fruits, cheese, pickles, nuts, honey, seafood, fresh bread, hot sauces, and more. You can also shop for local arts & crafts, flea market goods, jewelry, clothing/t-shirts, cigars, and CBD. Takes place from 2 pm – 7 pm at the Truman Waterfront (end of Southard St). FYI: Bring your own bags. Info: 305-731-3385; keysartisanmarket.com.
Every Saturday
Open-Air Market
Ramrod Key: Forget about driving miles to find local Florida Keys art, handmade jewelry, one-of-a-kind creations, fresh organic produce, greens, and flowers. You’ll find all that and more right at Boondocks. Takes place from 9 am – 2 pm in the parking lot of Boondocks Plaza, 27205 Overseas Hwy (MM 27.5) on Ramrod Key. Info: 305-872-4094; boondocksus.com.
Every Sunday
Jazz in The Gardens
Key West: Enjoy hot jazz amidst lush flora and fauna during this free hang that draws Key West’s top jazz cognoscenti. Full bar, champagne, and fabulous wines. Takes place from 5:30 – 8 pm at the Gardens Hotel, 526 Angel St, Key West. Info: 305-294-2661; gardenshotel.com.
Every Sunday
Key West Artisan Market
Key West: Shop a curated outdoor market offering fine crafts and art from talented Florida Keys makers, a wide variety of food and libations, and local musicians and authors. Takes place from 10 am – 2 pm at Higgs Beach, 1801 White St. Info: 305-731-3385; kwartisanmarket.com.
MONTHLY
Third Wednesday
Immerse Yourself!
Islamorada: This free monthly presentation occurs on-site at the History of Diving Museum or virtually so you can tune in from wherever you are. Experts cover maritime history, archeology, diving, and marine science topics. Coming up: Salvaging the Deep, Hunting the Invasive Lionfish, and Diving Into Volcanoes. The on-site presentation takes place at 7 pm at the History of Diving Museum, 82990 Overseas Hwy. To learn about each month’s presentation, call 305-664-9737 or hit divingmuseum.org.
First Friday
First Fridays on Fleming
Key West: “The Fabulous 500 Block of Fleming Street” showcases boutiques, galleries, and eateries with all kinds of cool events, including jewelry trunk shows, art openings, book signings, tastings, and libations. It takes place from 6 – 9 pm. Info:305-304-9001; shoplocalkeywest.com.
First Saturday
Market on the Green
Key West: Shop some amazing local arts at this fun artisan market. Takes place from 10 am – 2 pm at the Sunset Green Event Lawn between the Gates Key West Hotel and 24 North Hotel, 3852 N Roosevelt Blvd. Info: 305-400-4117; thekeyscollection.com.
Third Saturday
Native Plant Sale
Key West: Peruse over 2,000 native, rare, and endangered plants from the Keys, Cuba, and the Western Caribbean at this terrific monthly plant sale. Takes place from 9 am to noon at the Key West Tropical Forest and Botanical Garden, 5210 College Rd. Info: 305-296-1504; keywest.garden.
SPECIAL EVENTS
Now – December 31
Aquanauts to Astronauts
Islamorada: This limited-time featured exhibit examines the connections between space and underwater exploration. The exhibition features stories and artifacts from NASA, including how they use diving to train future astronauts. Takes place daily from 9 am – to 5 pm at The History of Diving Museum, 82990 Overseas Hwy. Info: 305-664-9737; divingmuseum.org.
April 19 – 28
42nd Annual Conch Republic Independence Celebration
Key West: This raucous annual event commemorates the founding of our Conch Republic. The celebration includes a ton of fun events, including a big Kick-Off Party, Conch Republic Music Party, Boat Parade, Art & Craft Fair, Pirates’ Ball, Red Ribbon Bed Races, a wacky “Drag Queen” Race, and much more. Info: 305-296-0213; conchrepublic.com.
April 19
Conch Republic Independence Celebration: Kick-Off Party
Key West: Enjoy great live music, a fun Conch Shell Blowing Contest and stories about how Key West’s Conch Republic was born. Festivities kick off at 7 pm at Schooner Wharf Bar in Key West’s Historic Seaport at the foot of Williams St. Info: 305-292-3302; schoonerwharf.com.
April 25
Conch Republic Independence Celebration: Post Parade Party
Key West: Follow the Conch Republic’s annual parade back to the Historic Seaport for a party that rocks the docks. Takes place at Schooner Wharf Bar in Key West’s Historic Seaport at the foot of Williams St. Info: 305-292-3302; schoonerwharf.com.
April 26
Conch Republic Independence Celebration: Great Battle Victory Party & Surrender Ceremony
Key West: Celebrate the Conch Republic’s raucous sea battle victory over the US Coast Guard. Kicks off at 9pm at Schooner Wharf Bar in Key West’s Historic Seaport at the foot of Williams St. Info: 305-292-3302; schoonerwharf.com.
April 27
Conch Republic Independence Celebration: Pirates’ Ball & Costume Contest
Key West: Arghh – don your best pirate threads and get ready for the biggest pirate bash in the Keys. Prizes for best costume. The fun starts at 7pm at Schooner Wharf Bar in Key West’s Historic Seaport at the foot of Williams St. Info: 305-292-3302; schoonerwharf.com.
April 26 – 28
47 Mile Offshore Grand Prix
Marathon: Race World Offshore returns to Marathon with exciting offshore racing that showcases the world’s best and fastest boats. Race boats will navigate a new course in the Gulf of Mexico, close to shore, alongside the recently renovated Old 7 Mile Bridge. You can get a great view of the action from the Old 7 Mile Bridge. Info: 305-800-RACE; raceworldoffshore.com.
April 28
Wreckers Cup Race Series
Key West: Catch the last leg of the spirited 7-mile race to Sand Key, where bragging rights are the top prize. The race kicks off at 1 pm, followed by an Awards Party & Ceremony at 7 pm at Schooner Wharf Bar, 200 Williams St in Key West’s Historic Seaport. Info: 305-292-3302; schoonerwharf.com.
May 5
Cinco de Mayo Celebration
Key West: Grab your salt shaker and party with Margarita during this fun, annual celebration that includes live Salsa music, a Taco Eating & Hot Pepper Eating Contest, and prizes for Best Mexican Hat. The action starts at 7 pm at the Schooner Wharf Bar in Key West’s Historic Seaport at the foot of Williams St. Info: 305-292-3302; schoonerwharf.com.
May 26
33rd Annual Schooner Wharf Bar Minimal Regatta
Key West: Known as “the only boat race you can view from start to finish from shore,” this wacky regatta is also a race to stay afloat. Savvy sailors use minimal materials, including plywood and duct tape, to build their tiny vessels. Races begin at Noon at Schooner Wharf Bar, 202 William St in Key West’s Historic Seaport. Info: 305-292-3302; schoonerwharf.com.
June 1
17th Annual Pride Follies
Key West: A precursor to Key West’s famous Pride Week, this original variety show includes an array of unforgettable comedy, singing, and dancing. Acclaimed performer Destiny Montgomery, Fantasy Fest Queen 2017, returns to direct another outrageous production. Full bar service. Doors open at 7 pm; Showtime at 8 pm. FYI: This show always sells out, so get your tickets early. Takes place at the Key West Theater, 512 Eaton St. An After Party follows at Mangoes, 700 Duval St. Info and tickets: 305-985-0433; keywesttheater.com.
June 5 – 9
Key West Pride
Key West: Key West shows its Pride daily, and this is your chance to participate in 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 “70’s Disco” Street Fair, wine tastings, a parade, and more. Complete schedule at gaykeywestfl.com. Info: 305-294-4603.
June 5
Key West Pride Kick-Off Disco Party
Key West: Don your best “Saturday Night Fever” disco garb and go downtown for this throwback party where everyone shines. It takes place from 5:30 – 7:30 pm at Hard Rock Cafe, 313 Duval St. A complete schedule is available at gaykeywestfl.com. Info: 305-294-4603.
June 7 – 9
41st Annual Lower Keys Chamber Dolphin Tournament
Lower Keys: Anglers contend for over $35,000 in cash prizes and awards. A special cash prize of $20,000 is awarded for the largest dolphin over 50 pounds. Additional prizes await winners in the open ladies and youth divisions. You can register for the tournament and enjoy appetizers and a cash bar on Friday starting at 5 pm at KOA Sugarloaf Key, 251 State Rd 939 FL 20. Info: 305-872-2411; lowerkeyschamber.com.
June 7
Key West Pride 70’s Retro Disco Party
Key West: Get ready to boogie the night away at Mangoes’ exclusive Ricky Ricardo Room. Prizes for best 70s-themed attire. FYI: Space is limited, and tickets are going fast. Grab ’em while you can. The party starts at 9 pm at Mangoes, 700 Duval St. A complete schedule is available at gaykeywestfl.com. Info: 305-294-4603.
June 8
Key West Pride’s “We Are Family” Street Fair & Disco Party
Key West: This year’s blockbuster Street Fair is more festive than ever, with vendors galore and a drag show to boot. It’s also a perfect opportunity to break out your favorite pride-themed outfit and strut your stuff! Takes place from 4 – 8 pm on the 700 – 900 block of Duval St, followed by a raucous disco party led by DJ Mr. Enjoy. Complete schedule at gaykeywestfl.com. Info: 305-294-4603.
June 9
Key West Pride Drunken’ Drag Brunch
Key West: Celebrate “Sunday Funday,” Key West style, at this wild Drag Brunch Show, which has been voted as one of the Top 10 Drag Brunch Shows in the USA by the Miami Herald. FYI: After the show, stick around for the After Party, where you can get your picture taken with the beautiful drag queens and dance the day away to DJ Jeff’s tunes. This 21+ event kicks off at Noon at Mangoes, 700 Duval St. Complete schedule at gaykeywestfl.com. Info: 305-294-4603.
June 9
Disco Tea Dance: Key West Pride Edition
Key West: Key West’s legendary Sunday Tea Dance rocks poolside with great music from local radio star DJ Rude Girl. Starts at 4 pm at La Te Da, 1125 Duval St. Complete schedule at gaykeywestfl.com. Info: 305-294-4603.
June 9
Key West Pride Parade
Key West: This annual “out-and-proud” Pride Parade celebrates the 70’s Disco Era and tops off a week-long celebration. Kicks off at 5 pm from Quay Road at the Truman Waterfront. The parade then proceeds to Whitehead St, takes a left onto Front St, then right onto Duval. The parade finally ends on United St (ultimately Tea Dance). Complete schedule at gaykeywestfl.com. Info: 305-294-4603.
July 3 – 7
Annual Key Lime Festival
Key West: Enjoy five days of fun Key Lime culinary events for every taste. The long limey holiday weekend includes a full menu of activities, including a Key Lime Sip & Stroll, Key Lime Pie Hop, a gravity-defying Key Lime Pie Drop from the top of the Key West Lighthouse, and the World Famous Key Lime Pie Eating Championship. It’s one tasty, lip-smacking 5-day fest! Complete event schedule at keylimefestival.com.
July 4
Independence Day Celebration
Keys-Wide: There are lots of 4th of July happenings going on all over the Keys, so here’s a quick view of what’s happening:
Key Largo: Celebrate Independence Day with an annual 4th of July Parade, which rolls out at 9:45 am from MM 98 -100, followed by a picnic. Enjoy a fireworks display at 10 pm on Blackwater Sound, MM 104, Bayside.
Marathon: The holiday parade begins at 10 am on Sombrero Blvd. (MM 50, Oceanside), followed by free day-long festivities at Sombrero Beach, culminating with a massive fireworks display at 9 pm.
Big Pine & The Lower Keys: The celebration starts at 5 pm at Big Pine Community Park with music, food, and fun, followed by a fireworks extravaganza after sunset. Key West: Fireworks light up the Atlantic at 9 pm off the White St Pier.
July 4
Annual Hospice & VNA July 4th Picnic
Key West: This annual family-friendly, beachside picnic is also a fundraiser for Monroe County’s Hospice with an endless supply of hot dogs and hamburgers, top entertainment, a silent auction, children’s activities and a giant fireworks display off of the White Street Pier by Higgs Beach. VIP seating on the beach is available. Festivities start at 5 pm on the lawn and beach of the historic Casa Marina Resort, 1500 Reynolds St. Info: 305-294-8812.
July 12 – 13
40th Annual Underwater Music Festival
Big Pine & The Lower Keys: The big 40th anniversary of this quirky underwater concert for divers, snorkelers, and the occasional mermaid is guaranteed to be bigger and better than ever! The annual shindig, which promotes reef preservation, kicks off on Friday from 6 – 8 pm with live music, light bites, and beverages at Mote Marine, 24244 Overseas Hwy on Summerland Key. The submerged songfest, also broadcast on US 104.1 FM, takes place on Saturday at Looe Key Reef in the Florida Keys National Marine Sanctuary, approximately 5 miles south of Big Pine Key. Transportation is available from local dive shops. Info: 305-872-2411; lowerkeyschamber.com.
July 12 – 13
4th Annual Florida Keys Brew-BQ & Craft Beer Festival
Marathon: Mouth-watering BBQ and tons of delicious craft beers for washing it down are the stars of this annual shindig sponsored by the Marathon Chamber. Highlights include an amateur BBQ cooking competition, vendors, boats, live music, kids’ games, and more. It takes place on F from 5 – 9 pm, on Sa from 11am – 8 pm, and on Su from Noon – 5 pm at Marathon Community Park, 3911 Overseas Hwy (MM 49), Marathon. Info: 305-743-5417; keysbrewbq.com.
July TBD
Mel Fisher Days Celebration
Key West: This annual charity event tributes the rum-and-coke drinking, gold chain-adorned Keys character remembered as “the world’s greatest treasure hunter” whose discovery of the Nuestra Señora de Atocha shipwreck and whose life and motto, “Today’s the Day,” inspired people worldwide to follow their dreams. The event includes live music, Mel Fisher trivia games, a 50/50 raffle, the ever-popular “X Marks the Spot Cupcake” game of chance where one lucky winner scores a piece of authentic treasure, a vast online silent auction, a live on-stage auction for a piece from the “Taffi’s Treasures” jewelry line, and presentation of the annual Mel Fisher Lifetime Achievement Award. Festivities start at 4 pm at Schooner Wharf Bar, 202 William St in Key West’s Historic Seaport. Info: 305-292-3302; schoonerwharf.com.
July 16 – 21
Hemingway Days
Key West: Writers, anglers, and fans of the late author Ernest Hemingway’s work converge on Key West for the annual Hemingway Days celebration. The festival honors the legacy of the American literary giant who lived and wrote on the island for most of the 1930s. This celebration includes a three-day Marlin Tournament, the raucous Hemingway® Look-Alike Contest, the wacky Running of the Bulls down Duval St, and a 5K run that salutes his sporting interests. Info: 305-294-0320; fla-keys.com.
July 20
Hemingway 5K Sunset Run/Walk & Paddle-Board Race
Key West: Fitness walkers and paddle board enthusiasts test their skills and celebrate Hemingway’s sporting lifestyle in Key West’s hottest race (literally). The 3-mile ocean course Paddle Board Race kicks off on Sa at 5:30 pm from Higgs Beach, followed by the 5K Run/Walk at 7:30 pm at Key West’s Southernmost Point. Register between 3 – 7 pm on the beach outside the Southernmost Cafe, 1405 Duval St. Stick around after the race for a great awards beach party from 8 – 10:00 pm with live music, free food, libations, and raffles. Info: 305-240-0727; keywesthalfmarathon.com.
July 24 – 25
Lobster Mini-Season
Florida Keys: Every Lobster mini-season, the coastal areas of Florida are flooded with lobster hunters trying to get their share of this year’s bounty. There are two Florida Lobster Seasons, the two-day mini-season and the 8-month regular lobster season. The Lobster Mini-Season is always the last consecutive W and Th in July.
COMING SOON
August 7 – 11
Tropical Heat
Key West: This All-Male-All-Adult fever-pitched festival includes more than a dozen intriguingly decadent events ranging from drag shows to themed pool parties and gatherings at island clubs. Not for the faint-hearted! Info: 305-294-4603; gaykeywestfl.com.
September 4 – 8
Key West Womenfest
Key West: This blockbuster four-day festival celebrates freedom and diversity and is a magnet for thousands of women from around the world who come to Key West for non-stop fun, parties, live performances, and lots of activities. Info: 305-294-4603; gaykeywestfl.com.
October 18 – 27
Key West Fantasy Fest:
“It’s A 90’s Neon Cosmic Carnivale”
Key West: This outrageous ten-day costuming and masking celebration showcases flamboyant masquerade competitions (including one for pets!), a Headdress Ball, exuberant promenades, street fairs, and a grand parade that stars marching groups, island-style bands, and lavish floats. A complete schedule of events at Fantasyfest.com.
OTHER FLORIDA
HAPPENINGS
MONTHLY
Every Third Friday
Music Walk
Fort Meyers: The streets of the Historic River District come alive for this terrific one-night-only concert. Enjoy great music from a wide variety of performers. Free to attend and it’s fun for all ages. Info: myriverdistrict.com.
May 26
Annual International Cuban Sandwich Festival
Tampa: Bite into the “official sandwich of Tampa Bay,” handcrafted by Florida Cuban sandwich artisans, and enjoy live entertainment, Cuban art, culture, and the world’s biggest Cuban sandwich contest. Takes place from Noon – 6 pm at Centennial Park,1800 E 8th Ave in historic Ybor City. Info: 813-319- 5850; CubanSandwichFestival. com.
August 23 – 24
Annual Coke Zero Sugar 400
Daytona: One of NASCAR’s most anticipated events brings together NASCAR racing under the lights at the world’s only motorsports stadium, with pageantry and patriotism to make for an unforgettable July 4th weekend. This fan-favorite event includes some of the most exciting racing of the season as drivers battle three-wide for a coveted DAYTONA victory. The race is followed by a spectacular fireworks display! Takes place at 7 pm at the Daytona International Speedway, 1801 W International Speedway Blvd, Daytona Beach. Info: 800-748-7467; DaytonaInternationalSpeedway.com.
