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Events in the Florida Keys

Event calendar provided with the courtesy of the Monroe County Tourist Development Council.

Events in Florida Keys for 2021

  • Jun 17, 2021 - Jul 10, 2021
  • 37th Annual Underwater Music Festival
  • Website 37th Annual Underwater Music Festival
  • 305-782-2411 E-mail
  • Facebook
  • Scheduled for the Saturday after July 4th, supported by US 1 Radio, Lubell Labs and Capt. Hooks Looe Key Adventure Strike Zone Charters. The festival emphasizes reef preservation, with the radio broadcast offering tips on ways divers & snorkelers can minimize impacts on the Keys' marine environment. Hundreds of boats converge at Looe Key, part of the continental United States' only living coral barrier reef, to enjoy this quirky event.
  • May 20 - June 07 Key West
  • Connections Project Mural: ‘A Mosaic of the Keys’
  • Website
  • The Connections Project mural, titled “A Mosaic of the Keys” is made up of individual 6-by-6-inch canvases that were decorated by local artists and creative residents, with the completed pieces arranged into the colorful mosaic. Art lovers can see the mural during a Keyswide “road show” tour, culminating at the Key West Art Center, 301 Front St.

  • June 01 - June 02 Key West
  • Rams Head presents: The Allman Betts Band with Special Guests, The River Kittens
  • Website
  • After a successful tour as The Devon Allman Project with special guest Duane Betts, the sons of Gregg Allman and Dickey Betts have joined forces to form The Allman Betts Band. Each evening of live music features new songs from their solo projects and classic Allman Brothers and Gregg Allman tunes. Tickets on sale starting April 14 at noon. Performances at Key West Theater, 512 Eaton St., begin at 8 p.m., doors open 7 p.m., patrons must be age 21 and over.

  • June 02 - June 05 Key West
  • Key West Pride
  • Website
  • Presented by the Key West Business Guild, events showcase the diversity and welcoming atmosphere that make the southernmost city a top vacation destination for LGBTQ visitors. The 2021 festival schedule includes pool parties at guesthouses and emporiums, drag shows by Key West’s top performers, a street fair on famed Duval Street, nighttime soirees at local clubs, a burlesque-style show with an LGBTQ flair and the lively "Rainbow Roast."

  • June 04 - June 06 Key Largo
  • Seventh Annual Skippers Dolphin Tournament
  • Email Website
  • This tournament is headquartered at Skippers Dockside Restaurant behind Key Largo’s Holiday Inn. Cash prizes of over $60,000 include a first-place prize of $20,000 as well as prizes for the top six teams and top lady and junior anglers.

  • June 04 - June 06 Big Pine Key
  • 28th Annual Original Big Pine & Lower Keys Dolphin Tournament
  • Website
  • The Lower Keys Chamber of Commerce presents this annual event where 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 open, ladies and youth divisions.

  • June 04 - June 04 Islamorada
  • Meet Wyland at History of Diving Museum
  • Email Website
  • Meet the world-renowned marine artist Wyland, from 5:30 - 7:30 p.m. Watch him paint, get an autographed gift and enjoy a tour of the museum, located at mile marker 82.9. Four Wyland original paintings, created on-site, are to be auctioned at 7:15 p.m. Tickets $75 per person.

  • June 05 - June 06 Key Largo
  • Coralpalooza 2021
  • Website
  • Presented by the Coral Restoration Foundation, Coralpalooza is slated as the world's largest coral restoration event! On World Oceans Day, join a celebration among ocean lovers to actively restore the planet’s third-largest barrier reef. Coralpalooza demonstrates the power of large scale, collaborative acton to save coral reefs. This year’s format, whether it is to be all digital, in-person or a hybrid of the two, is yet to be announced. Check online for updates.

  • June 06 - June 06 Key West
  • 11th Annual Key West Art Garden
  • Website
  • From 1-3 p.m., enjoy this year's exhibit of 30 unique pieces and talk to the artists who created them! Find out what their concept, was their process to create and how they are able to convey the sense of nature using natural or recycled materials. Art pieces are to be placed throughout the historic Key West Tropical Forest & Botanical Garden. Free admission.

  • June 07 - June 13 Key Largo
  • REEF presents: Fish Out of Water Virtual 5k Race
  • Website
  • The Key Largo-based Reef Environmental Education Foundation (REEF) is encouraging ocean enthusiasts everywhere to get moving in the name of conservation. Choose to run, walk, hike, bike or even swim, completing the 5K (3.1 miles) in one day or throughout the week. No matter how you participate, it’s a great way to get active in your community while making your miles count. Register before April 30, 2021 for the early bird discounted rate. Registration will remain open through May 28, 2021. All racers will receive a limited-edition race T-shirt, 2021 finishers medal, and bib. Premium registration levels also include a retro fanny pack and two custom vinyl stickers.

  • June 07 - June 11 Islamorada
  • 47th Annual Don Hawley Tarpon Fly Tournament
  • Website
  • Up to 25 of the world’s top fly-rod anglers endure a five-day test of patience and finesse, fishing Keys waters using fly tackle and 12-pound tippet. Named for the late fly fisherman and conservationist Don Hawley, the tournament benefits the Guides Trust Foundation, assisting professional fishing guides and supporting backcountry fishery conservation programs.

  • June 10 - June 10 Key West
  • Raul Malo Live at San Carlos Institute
  • Website
  • Celebrate the rich history of the San Carlos Institute, 516 Duval St., with a special performance by Grammy Award Winning Musician - Raul Malo of The Mavericks. The Evening will be emceed by Matt Asher, host of The Mattahser Show airing on PBS affiliates nationwide in October 2021. Doors open at 6:30 p.m., show begins at 7:30 p.m. Advance ticket purchases are $35, day of performance $45. Limited to 200 tickets.

  • June 11 - June 12 Marathon
  • 12th Annual Tah Dance!
  • Box Office 305-743-0994 Website
  • Enjoy an evening of dance with the Marathon Community Theatre's Dance Department along with community dance studios, dance groups and individual dancers. Show starts at 8 p.m., contact box office or buy tickets online.

  • June 11 - June 13 Islamorada
  • Ladies Let’s Go Fishing Screamin’ Reels Tournament
  • Email Website
  • Intended for novice anglers, this weekend is about learning and a non-intimidating, fun competition with the Ladies Let’s Go Fishing university organizers. Species include legal inshore and offshore fish. Charter a professional boat or fish on your own boat. This is a casual tournament with prizes for heaviest offshore fish, longest inshore fish and drawings for prizes of those who caught fish, plus bonus drawings. Dates and schedule subject to change.

  • June 12 - June 12 Key West
  • CFK Swim Around Key West
  • Email Website
  • CFK Swim Around Key West is a 12.5-mile endurance swim, open to individuals and relay teams, around the island of Key West through Atlantic Ocean and Gulf of Mexico waters. Organized by the College of the Florida Keys, it’s billed as the only sanctioned, insured and U.S. Coast Guard–permitted race around Key West. Associated events include shorter open-water swims and even "mermaid encounters."

  • June 15 - June 17 Islamorada
  • Ladies Tarpon Fly Tournament
  • Website
  • Connecting women worldwide through competition and conservation, this all-release invitational tournament represents a rich history of premier lady fly anglers who love the sport of saltwater fishing in the shallow waters of Islamorada and Florida Bay.

  • June 16 - June 20 Key West
  • I Love Stock Island Festival
  • Website
  • This five-day festival is to feature one-of-a-kind Stock Island-inspired activities and authentic immersive experience in local community, culture, and art. It's a great way to celebrate Father’s Day weekend with friends and family in the laidback atmosphere of Stock Island, just across the Cow Key Channel Bridge from Key West.

  • June 16 - June 16 Islamorada
  • Immerse Yourself! Lecture Series: The Future of Artificial Reefs
  • 305-664-9737 Email Website
  • The third Wednesday of each month enjoy a free presentation series, featuring a guest speaker covering topics from all aspects of the dive industry and marine environment. This month’s speaker is Joe Weatherby, founder of Artificial Reefs International. Presentation is to be provided via Zoom technology at 7 p.m. To request a spot please email to get your sign in information.

  • June 17 - June 17 Islamorada
  • Morada Way Art Walk
  • Website
  • Morada Way Arts & Culture District, located at 151 Morada Way between mile marker 81 and 82, is a non-profit in the heart of Islamorada with Morada Way Clay, Jessica Ann Art, Rum Brush, Limelight Studio/Gallery, & Partners. Check out Art Walk the third Thursday of each month. Enjoy a relaxing evening from 6-9 p.m. perusing local fine art, imbibing local craft beer and wine, listening to music, and seeing your favorite people! Event is socially distanced; artists and vendors, visitors asked to please wear masks.

  • June 18 - June 19 Key West
  • Key West Carnival
  • Website
  • Key West Carnival promises a weekend of authentic Caribbean entertainment, food, dance and merriment in keeping with Key West’s island heritage! Festivities include a costumed parade through the streets of Old Town, outdoor events at the Coffee Butler Amphitheater, Junkanoo bands and percussion bands and delightful foods from different Caribbean Islands. Grand Opening is set for 6 p.m. Friday, with daylong events Saturday from 7 a.m. to 7 p.m.

  • June 18 - June 20 Key West
  • VFW Fishing Tournament
  • Website
  • A family fun tournament, this event awards up to $3,000 for the heaviest dolphin. All proceeds benefit disabled and needy veterans in Monroe County. A new First Responder category has been added, for Police, Fire Fighters and Paramedics / EMTs to go along with other angler categories.

  • June 18 - June 18 Key West
  • Rams Head presents: Past II Present, A Toto Tribute Band
  • Website
  • Enjoy an evening of this optimum tribute band performing the music of Toto as well as music that members of Toto have written for other artists. Tickets on sale starting April 14 at noon. Performance at Key West Theater, 512 Eaton St., begins at 8 p.m., doors open 7 p.m., patrons must be age 21 and over.

  • June 19 - June 19 Key West
  • Truman's Tropical Fruit Festival
  • Website
  • Can you tell the difference between a haden and a kent mango? At the Tropical Fruit Festival, you’ll have the chance to taste all types of mangoes and other tropical fruits, sip tasty cocktails, watch cooking demos and much more. Learn about planting fruit trees and have the opportunity to purchase some to take home. From 9 a.m. to 1 p.m., on the grounds of the Harry S. Truman Little White House, Florida's only presidential museum, 111 Front St., this event includes fresh fruit, a tropical tree sale, local vendors, cocktails and kids’ activities.

  • June 21 - June 25 Islamorada
  • 58th Annual Gold Cup Tarpon Tournament
  • Website
  • This annual challenge appeals to “tarpon addicts,” and both experienced and novice anglers apply to compete in what is referred to locally as the “Wimbledon of tarpon fishing.” Headquartered at the Lorelei Restaurant and Marina, the all-release event is limited to 25 anglers by invitation only. Partial proceeds benefit the Guides Trust Foundation of the Florida Keys.

  • June 23 - June 27 Key West
  • Mango Fest Key West
  • Website
  • Experience all things Mango through shopping, education and demonstrations. Stroll virtually through a vendor village, enter a poetry contest, photo contest, see virtual culinary and cocktail demos, and more. Details to come for the 2021 event.

  • June 23 - June 24 Islamorada
  • IFC Captains Cup Dolphin Tournament
  • Website
  • Teams of up to four anglers compete for top prizes, and the total combined weight of three fish determines the winning team. If up to 25 boats register (the maximum number in field) first-prize cash winnings can reach $25,000.

  • June 25 - June 27 Big Pine Key
  • Inaugural Florida Keys PBA Charity Dolphin Tournament
  • Email Website
  • Headquartered at Ocean’s Edge Resort & Marina, Stock Island, this inaugural event is being organized by members of the S. Florida Police Benevolent Assoc. Anglers are invited for a weekend of fishing to support the Autism Society of the Keys and the Love Fund, Inc. Prizes based on number of entrants – 1st, 2nd, 3rd, 4th place, Top PBA Member, Top Female, Top Junior and Biggest Tuna.

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