What's Up

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!

Because event updates are happening daily due to COVID-19, we recommend that you check for late breaking news on individual event websites.  Thank you!


Jazz at Tavern N’ Town

Key West: Some of Key West’s top talent including “Island Chanteuse” Carmen Rodriquez and Michael Thomas perform nightly from 5-7pm during Key West’s best Happy Hour. Takes place at Marriott Beachside Resort, 3841 N. Roosevelt Blvd. Info: 305-296-8100; tavernntown.com.

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 Margaritaville Resort & Marina 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. Experience it nightly at the end of upper Duval Street.

Every Tuesday
Mario Sanchez Original Works & Lecture

Key West: Owner of Key West’s renowned Gallery on Greene, Nance Frank has curated multiple exhibits of famed Cuban artist, Mario Sanchez with catalogues for his exhibit presented by The American Folk-Art Museum, The Museum of the City of New York as well as Cuba’s National Museum. Her weekly presentation about Sanchez’s life and work is absolutely fascinating. Takes place at 2pm every Tues at the Gallery on Greene, 606 Greene St, Key West. 305-304-2323; galleryongreene.com.

Wednesday – Saturday
Cabaret in The Gardens

Key West: Key West’s Gardens Hotel is one of the most beautiful boutique hotels on the island and every Weds through Sat from 5 – 7pm, you can enjoy wonderful, live piano music in the Hotel’s intimate Cabaret. Full bar and stellar wines are the coup de gras. Find at 525 Angela St, Key West. Info: 305-294-2661; gardenshotel.com.

Every Saturday & Sunday
Big Pine Flea Market

Big Pine Key: Discover all kinds of great finds at unbeatable prices at this long-time Lower Keys Flea Market that showcases an eclectic mix of both used and new merchandise, as well as locally made soaps, tools and tarps, fishing supplies, watches and jewelry, fresh seafood and produce, homemade ice cream, weekend Fish Fry and inflatable bounce houses and rides. Open from 8am – 2pm every Sat and Sun through July. Free admission and parking. Find it at 30250 Overseas Hwy, Oceanside on Big Pine Key. Info: 305-872-4103; bigpinefleamarket.com.

Every Sunday
Jazz in The Gardens

Key West: Enjoy some terrific 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 – 8pm at the Gardens Hotel, 526 Angel St, Key West. Info: 305-294-2661; gardenshotel.com.

First Thursday Art & Shopping Walk

Key West: Each month, The Studios of Key West (TSKW), along with many other neighboring galleries in the 500 Block of Fleming St, host special exhibitions from 6 – 9pm. More info: : 305-296-0458; tskw.org.

Third Thursday Morada Way Art Walk

Islamorada: Fine arts, live music, and “culinary art” are the hallmarks of this festive monthly event that showcases both national and local artisans in galleries along the Morada Way Arts & Cultural District. Takes place from 6 – 9pm on Old Hwy, MM 81.5, Oceanside, Islamorada. Info: 305-393-6012; moradaway.org.

Every 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. It takes place from 9am-Noon at the Key West Tropical Forest and Botanical Garden, 5210 College Rd. Info: 305-296-1504; keywest.garden.

First Friday MM 104 Block Party

Key Largo: Stroll among artists, shop for gifts, enjoy street bites from local eateries, and more during this fun monthly Block Party. Takes place on the First Friday of every month from 6 – 10pm, rain or shine along the Overseas Highway at mile marker 104 in Key Largo. Info: keylargofirstfriday.com.

Second Saturday Art Stroll

Stock Island: The Stock Island Arts District throws open its doors on the second Saturday of each month, where you can leisurely stroll about the many art galleries, working studios, and eclectic shops. Look for the festive pink “Art District” banners flying at each participating location. Takes place from 11am – 4pm on Feb 8, March 14 and April 11. Info: 305-731-5780; ILoveStockIsland.org.

Now – July 31
10th Annual Key West ART in the Garden

Key West: Meander over Garden boardwalks and down pathways through dap-pled shade cast by fresh greenscape, colorful blossoms and winged creatures of nature and spot … sculpture! Nature has been benign in recent months with spring rains bringing renewal and the return of ART in the GARDEN with artistic expressions emphasizing harmony with nature. Created by local artists, these works ac-cent the natural beauty of the garden and feature earth-friendly themes, including recycled and natural materials. Takes place daily from 10am – 4pm at the Key West Tropical Forest & Botanical Garden, 5210 College Road, Key West. Info: 305-296-1504; keywest.garden.

July 10 – 12
36th Annual Underwater Music Festival

Big Pine & The Lower Keys: A quirky concert broadcast underwater for divers, snorkelers and the occasional mermaid emphasizes reef preservation. The submerged songfest is held at Looe Key Reef in the Florida Keys National Marine Sanctuary, approximately 5 miles south of Big Pine Key. Transportation available from local dive shops. Info: 305-872-2411; lowerkeyschamber.com.

July 10 – 12
27th Annual Big Pine & Lower Keys Dolphin Tournament

Lower Keys: Presented by The Lower Keys Chamber of Commerce, this premiere fishing tournament event, attracts top anglers who contend for more than $40,000 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. Info: 305-872-2411; lowerkeyschamber.com.

July 21 – 26
40th Annual 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, virtual symposium presentations, poetry readings, a street fair,celebrating Key West’s lively spirit, a commemoration of the 121st anniversary of the author’s July 21 birth and a 5k run that salutes his sporting interests. However, representatives of the Hemingway Look-Alike Society and Sloppy Joe’s Bar have announced that the 40th annual Hemingway® Look-Alike Contest is canceled this year because of the global COVID-19 pandemic. The next Hemingway Look-Alike Contest is scheduled July 22-24, 2021. info: 305-294-0320; fla-keys.com.

July 25
31st Annual Hemingway 5K Sunset Run/Walk & Paddleboard Race

Key West: Fitness walkers and paddle board enthusiasts can 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 at 5:30pm at the Southernmost Beach followed by the 5K Run/Walk at 7:30pm at Key West’s Southernmost Point. Cool off after the race with an ocean dip and cold libations. Register between 3 – 7pm on the beach outside the Southernmost Cafe, 1405 Duval St. Info: 305-240-0727; keywesthalfmarathon.com.

July 29 – 30
Mini-Lobster Season

Every Mini Lobster 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 2 day mini season and the 8 month regular lobster season. The mini lobster season is always the last consecutive Wednesday and Thursday in July.

August 6 – 9
24th Annual Key West Lobsterfest

Key West: It’s a weekend of “Lobstermania” when approximately 10,000 pounds of succulent, locally caught lobster is grilled, sautéed, stuffed and deliciously prepared to celebrate the bounty of the Keys lobster season. Lots of activities all weekend long.Info: 305-998-8599; keywestlobsterfest.com.

CANCELED  August 12 – 16
Tropical Heat

Key West: This All-Male-All-Adult fever-pitched festival includes more than a dozen intriguing-ly decadent events ranging from drag shows to themed pool parties and gatherings at island clubs. Not for the faint-hearted! Info: 305-294-4603; tropicalheatkw.com.

CANCELED  September 2 – 6

Key West: This blockbuster four day festival celebrates freedom and diversity and is a mag-net for thousands of women from around the world who come to Key West for non-stop fun, parties, live performances and tons of activities. Info: 305-294-4603; womenfest.com.

September 3 – 7
10th Annual Key West Brewfest

Key West: More than 150 beers and craft brews are on tap at this “tasty” annual event that includes beer dinners, beer brunches, Happy Hour parties, pool parties, late-night parties, seminars and the Signature Tasting Festival Event on Sat, August 31st. Info: 800-354-4455; keywestbrewfest.com.

October 1 – 4
Reef Fest

Key West: The annual celebration of marine conservation includes ocean adventures like
of kayaking, snorkeling and diving, all alongside marine life experts. Afternoons feature free seminars from renowned experts in a variety of marine topics. Evenings boast food, drinks and fun with friends old and new. All events are open to the public. Info: 305-852-0030; reef.org.

October 7 – 11
Key West Songwriters Festival

Key West: Audiences can rock, sway and sing along to some of America’s hottest contempo-rary hits and classics at the annual Key West Songwriters Festival, the largest festival of its kind. Since 1997 BMI has been a presenting sponsor of the festival and has helped it grow into both a tourist attraction and favorite of island locals. The festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories be-hind the songs. Info: keywestsongwritersfestival.com.

October 9 – 11
Phil Peterson’s Florida Keys Poker Run

Florida Keys: Motorcyclists from throughout the United States travel down one of America’s most scenic highways to raise money for charity. Riders traverse the Overseas Highway (US Highway 1), the roadway from mainland to the Lower Florida Keys, that features dozens of bridges and long vistas of breathtaking open water. Bikers have a great ride and a fun time, while helping charity organizations. Info: petersonsharley.com.

October 15 – 18
Key Largo Original Music Fest

Key Largo: Four days of multiple musical happenings set the stage, during this eclectic music festival which showcases hit songwriters from Nashville and beyond, as well as an elite group of local and national singers and bands who perform everything from Rock to Country to Blues and more. The festival kicks off on Thurs, May 18 at Sundowners Water-front Restaurant, MM 104, Bayside and continues all weekend long with multiple stages at neighboring Cactus Jacks and Señor Frijoles. For a full schedule of events call 305-394-37; keylargooriginalmusicfest.com

CANCELED  October 16 – 25
Fantasy Fest®: Roaring 2020’s &
Future Fictions

Key West: This outrageous 10-day costuming and masking celebration features flamboyant masquerade competitions, exuberant promenades, street fairs and a grand parade that stars marching groups, island-style bands and lavish floats. More info: 305-295-9112;  FantasyFest.com.

October 18
10th Annual Zombie Bike Ride

Key West: This costumed, rock n’ Roll bike ride typically draws several thousand men, women and children – and even a few pets. Garbed in ragged costumes and frightening face and body makeup, they pedal along the island city’s Atlantic Ocean shore in a deliciously scary spectacle. The goulash event starts at 2pm when “Zombieland” opens at Fort East Martello Museum, a reputedly haunted historic site overlooking the Atlantic Ocean at 3501 S. Roosevelt Blvd. Info: zombiebikeride.com.

November 8 – 15
Race World Offshore Key West Championship Races

Key West: High speed offshore powerboats race in Key West Harbor and surrounding waters in this annual challenge, known internationally as the Indianapolis 500 of powerboat racing. A portion of the 6.5-mile course runs through Key West Harbor where racers can achieve speeds above 140 mph and provide fans with breathtaking displays of skill and power. Info: 305-296-6166.

November 15
23rd Annual Taste of The Islands

Marathon: This award-winning event draws several thousand attendees and features local restaurants, live entertainment, vendors and artists, a tribute to veterans, fashion show, kids activities plus live and Chinese auctions. Takes place from 11am – 5pm at Marathon Community Park, MM 49, oceanside, Marathon. Info: 305-923-9976.


September 18 – 27
Island Hoppers Songwriter Fest

Captiva Island/Downtown Fort Myers/Fort Myers Beach: Southwest Florida’s highly anticipated 10-day music festival draws some of country music’s greatest singer-songwriters from Nashville and nationwide. Enjoy more than 80 artists and over 100+ shows (most of which are free) in small intimate venues Info: island-hopper.fortmyers-sanibel.com.

October 3 – 4
26th Annual Downtown Sarasota Crafts Festival

Sarasota: Shop a variety of fine crafts, including jewelry, pottery, ceramics, photography, painting and more. And don’t forget to check out the Green Market. Takes place downtown Sarasota from 10am – 5 pm. Info: ArtFestival.com.

October 15 – 18

Daytona: Motorcycle enthusiasts converge on beautiful Daytona Beach for four days of beautiful Florida weather, live music, and motorcycle racing at Daytona International Speedway. It’s also a terrific opportunity to tool around miles of scenic rides along famous A1A. You can find the Welcome Center directly across from Daytona International Speedway at the corner of Checkered Flag Blvd and Daytona Blvd. Info: biketoberfest.org.