Calendar of Events
Current Islamorada Events




- Sponsored Event
- Feb 24, 2023 - Feb 25, 2023 Key West
- Garden Club Midtown West Meander
- Website Key West Garden Club
- Key West Garden Club 305-294-3210 E-mail
- Facebook Instagram
- 5 flourishing private gardens are on display for nature enthusiasts to explore Friday & Saturday, Feb. 24-25. Tours by the Key West Garden Club from 10AM-3PM. The exclusive tours give examples of distinctive landscapes &plant-filled outdoor living areas.




- Sponsored Event
- Apr 15, 2023 - Apr 16, 2023 Key West
- NAS Key West Southernmost Air Spectacular
- Website Boca Chica Field, Key West
- Naval Air Station Key West FL 33040
- NAS Key West 305-293-2503 E-mail
- View video Facebook Twitter Instagram
- The Blue Angels & other military & civilian acts will fill the skies of the Florida Keys on April 15&16, at the NAS Key West Southernmost Air Spectacular air show at Boca Chica Field. This year’s show is celebrating 200 Years of the Navy in Key West.
- Buy tickets!




- Sponsored Event
- Feb 25, 2023 - Feb 25, 2023 Marathon
- 16th Annual Sombrero Beach Run
- Website Sombrero Beach
- Sombrero Beach Rd Marathon FL 33050
- 305-743-4582 E-mail
- #1 Running Event of its kind in the Florida Keys! 10/15K Run & 5K Run/Walk. Events happening all weekend – kickoff party Friday, Race Day entertainment, runners breakfast/lunch, drinks, ice-cold beer, custom t-shirts, raffles & fun planned all weekend!
- Buy tickets!




- Sponsored Event
- Dec 28, 2022 - Mar 18, 2023 Key West
- 63rd Annual Key West Home Tours
- Website
- 305-294-9501 E-mail
- Facebook Instagram
- The 63rd Annual Home Tours hosted by the Old Island Restoration Foundation offers a chance to peek into into some of the most beautiful 19th and 20th century residences on the island, learn fascinating history, and enjoy fine art collections and antiques.
- Jan 12, 2023 - Mar 16, 2023 Islamorada Arts & Culture
- Art Guild of the Purple Isles Annual Members' Judged Art Show
- Website
- The 57th annual members' judged art show for the guild continues through March 16 at Florida Keys History & Discovery Center. The show features 74 pieces of original art by 46 artists in nine different medium categories.
- Feb 7, 2023 - Feb 8, 2023 Islamorada Fishing
- Poor Girls Sailfish Tournament
- Website
- This regional charity competition raises money to spay and neuter feral cats in the Upper Keys. Trophies are awarded to the first-, second- and third-place teams, grand champion and runner-up grand champion anglers as well as for the largest dolphin fish, kingfish and tuna, among others. Events take place at the Islander Resort, mile marker 82.
- Feb 8, 2023 Islamorada Arts & Culture
- Florida Keys History & Discovery Center Lecture: Growing Up in the Keys
- Website
- Enjoy first-hand accounts from residents who grew up in the Keys. Len Rhodus, who grew up on Plantation Key, Ron Watson from Key Largo and Eddie Whiteman, raised on Islamorada’s Matecumbe islands are to reminisce. Doors open at 5, lecture from 6 to 7:30 p.m. at the center, located at the Islander Resort, mile marker 82. Tickets $10, advance registration required. Doors open at 5 p.m. with the lecture from 6 to 7:30 p.m. at the center, located at the Islander Resort, mile marker 82.
- Feb 16, 2023 Islamorada Arts & Culture
- Morada Way Third Thursday Art Walk in Islamorada
- Website
- The Morada Way Arts & Cultural District’s Third Thursday Art Walk in Islamorada is the organization’s landmark, monthly event. On the Third Thursday of each month, Keys-inspired fine artists, vendors, residents, and visitors congregate on Morada Way in Islamorada to celebrate the arts and culture in the Florida Keys. Enjoy a relaxing evening from 6-9 p.m. perusing local fine art, imbibing local craft beer and wine and listening to music, in the area between mile markers 81 and 82.
- Feb 18, 2023 Islamorada Arts & Culture
- Pops in the Park:
- Website
- “Who Let the Dogs Out?" is the theme for this month's free, outdoor concert from Keys Community Concert Band at Founders Park, mile marker 87, bayside, from 4 to 5 p.m. Saturday afternoon. Bring a blanket or lawn chair and pack a picnic basket for a family-friendly concert of animal-themed music. Bring your pooch to prance in the Puppy Parade. The Humane Animal Care Coalition will be there with adoptable pets.
- Feb 19, 2023 Islamorada
- Florida Keys Brewing Company 8th Anniversary Festival
- Website
- The Florida Keys Brewing tasting room and beer garden welcomes everyone for a family- and pet-friendly fun day with live music, food trucks, face painting, art vendors and special release local beers from noon to 10 p.m. The music lineup include Cortadito with traditional Cuban music from 1 to 3:30 p.m. and rock and roll with the Carousers from 5 to 9 p.m. 81611 Old Highway, Islamorada, in the Morada Way Arts and Cultural District between mile markers 81 and 82, oceanside.
- Feb 24, 2023 - Feb 25, 2023 Islamorada Fishing
- Backcountry Fly Championship Series
- Website
- Tournament anglers are to compete to catch the most inches of snook and redfish on fly in a challenge where 1 inch equals one point. Awards are to be given to the grand champion and runner-up, and to the anglers who catch the largest snook and redfish.