Calendar of Events



Oct 7-9. Key Largo, 5th Annual Downtown Key Largo Songfest.
Oct 9-12. Islamorada Fall All – Tackle Bonefish & Permit Championship
Oct 12-16. Key Largo, Humphrey Bogart Film Festival. Online info
Oct 15-16. Key West, Stand Up Paddle Invitation.
Oct 15-May 15. Stone Crab Season.
Oct 22. Marathon, 6th Annual Stone Crab Eating Contest. 305-743-4353
Oct 21-22. Key West, Goombay Fantasy Fest World Famous Street Festival.
Oct 23. Key West, Halloween Half Marathon & 5KRun.
Oct 21-30. Key West, 37th Annual Fantasy Fest. 305-296-1817


Nov 6-13. Key West World Championship Race. High speed offshore power- boat race. 305-296-6166
Nov 10-12. Islamorada, Cheeca Lodge & Spa All-American Backcountry Tournament.
Nov 12. 8th Annual Key Largo Bridge Run. 305-451-1642
Nov 12. Marathon, 19th Annual Taste of the Islands.
Nov 16-20. 5th Annual Key West Film Festival. 941-527-9385
Nov 23-27. Key West International Sand Art Competition.
Nov 26. Big Pine & the Lower Keys Island Art Festival. 305-872-2411


Dec 2. Islamorada, Florida Keys Holiday Festival. 305-664-4503
Dec 3. Key West Holiday Parade. Starts at 7pm. 305-809-3881
Dec 10. Key West, Schooner Wharf Bar 24th Annual Lighted Boat Parade. 305-292-3302
Dec 10. Marathon, Boot Key Harbor Lighted Christmas Boat Parade. 305-849-0285
Dec 11. Key Colony Beach Lighted Boat Parade. 305-743-7214
Dec 17. Lower Keys Lighted Boat Parade. 305-923-5370
Dec 17. Key Largo Holiday Lighted Boat Parade. 305-394-3736
Dec 31. Key West, New Year’s Eve Shoe Drop Celebration. 305-304-2643


Jan 3. Key Largo, Orange Bowl Swimming Classic. 305-453-7946
Jan 6-7. Key Largo, Brew on the Bay. 305-304-0554
Jan 5-15. Key Largo & Islamorada Food & Wine Festival. 305-394-3736
Jan 7-9. Marathon, The Florida Keys Celtic Festival. 941-625-8544
Jan 13-14. Key West, 57th Annual House & Garden Tours. 305-294-9501
Jan 15. Key West Half Marathon & 5K Run. 305-240-0727
Jan 14. Islamorada, Art Under the Oaks – 34th Annual. 305-664-0888
Jan 14-15. 12th Annual Big Pine Key Nautical Flea Market. 305-872-2411
Jan 14-15. Key West, 12th Annual Florida Keys Seafood Festival.
Bay View Park, 11am-8pm on Saturday, 11am-5pm on Sunday. 305-872-9026
Jan 22-Feb 3. Key West, Conch Republic Cup, Key West Cuba Race Week.
Jan 15-20. Key West, Quantum Race Week.
Jan 25-29. Key West’s Food & Wine Festival. 800-474-4319


Feb 2-4. Key West, Cuda Bowl. Hurricane Hole Marina. 305-744-0903 Feb 4-5. Marathon Community Park, Annual Pigeon Key Art Festival. 440-477-7203
Feb 18. Marathon, Inaugural American Legion Riders Coral Head Music Festival. Noon – 11pm. Marathon Community Park Amphitheater. Feb 25-26. Key West, Old Island Days Art Festival. 305-294-1243


Mar 26. Key West, Happy Birthday Tennessee Williams! Celebrate the 104th birthday of Tennessee Williams and his life in Key West.
Visit website for details of the months events at
Mar 4. Key West, 55th Annual Conch Shell Blowing Contest. 305-294-9501
Mar 3-5. Marathon, 10th Annual Sombrero Beach Run. Awards are given to the overall finishers in the 10k run, 5k run, and 5k walk. 305-743-4582 or 305-289-9868
Mar 11-12. Annual Original Marathon Seafood Festival. 305-743-5417
Mar 13-16. March Merkin Permit Tournament. Key West Harbour Yacht Club, Key West, FL