Festival ·
Swim for Alligator Lighthouse
Alligator Lighthouse · Islamorada
Dive into an unforgettable adventure during the Alligator Lighthouse Swim, an exhilarating open-water challenge.
Free
Things to Do in Islamorada, FL
Islamorada calls itself the sportfishing capital of the world and backs it up with charter docks at Bud N' Mary's and Whale Harbor, tarpon feeding at Robbie's and sandbar afternoons. The tiki bars and sunset restaurants along the Overseas Highway are the other reason to stop.
9 upcoming events · Updated September 2026 · events refreshed daily
This Weekend in Islamorada
Mon 7 – Thu 10- TODAY
Islander Resort Coastline Cleanup
3 pm · Islander Resort
- THU
Swim for Alligator Lighthouse
Alligator Lighthouse
- TODAY
Downtown Delray Restaurant Month
Downtown Delray Beach
- TODAY
School Girls, Or the African Mean Girls Play
The Hive Black Box Theater
- TODAY
Build a Better World: The Future Begins with You
Fort Lauderdale
- TODAY
Burgers & Buffet Tunes: A Tribute Show at Comedy Key West
12:30 pm · Comedy Key West
Things to Do in Islamorada
0 of 0
No things to do listed for Islamorada yet. Try a nearby town.
Events in Islamorada
9 of 9
Festivals & Markets 3
Festival ·
Son del Mundo Hispanic Heritage Event
Islamorada · Islamorada
Celebrate Hispanic culture and creativity at the lively Son del Mundo Hispanic Heritage Celebration.
Free
Festival · · 10 am
Florida Keys Farmers Market
Florida Keys Farmers Market · Islamorada
Spend your Sunday soaking up local flavor at the Florida Keys Farmers Market in Islamorada.
Free
Races & Runs 5
Race · · 7:45 am
Swim for Alligator Lighthouse
Islamorada
8 mi “The 8-mile swim to Alligator Lighthouse is a challenge. It’s not for the faint of heart" How it started When World Renowned Artist, Lighthouse Larry decided to swim, in his native town of…
$239
Race ·
Old Highway 5K Run/Walk
Coral Shores High School, Old Highway; 7:30 AM · Tavernier / Islamorada
5K Confirmed 2026. Flat, shaded out-and-back; shirts and medals to first 200.
Race ·
Islamorada Half Marathon & 10K + Rumrunner Run 5K/10K (12th annual)
Overseas Hwy, Islamorada · Islamorada
Half, 10K (Sun 7:00 AM); 5K, 10K (Sat 8:00 AM); beer mile Confirmed 2026. Largest Upper Keys race weekend. Info: islamoradarunning.com
Race · · 7 am
Islamorada Half Marathon & 10k, Rumrunner Run 5K/10K and Beach N' Beer Mile
Overseas Hwy · Islamorada
13.1 mi, 6.2 mi Welcome to the 12th annual Islamorada Half Marathon & 10K, Rumrunner Run 5K and Beach N’ Beer Mile! Our full weekend of road races and parties has become a bucket list event for people from all over…
$80
Race ·
USA Women's Half Marathon - Islamorada, Florida Keys
77522 Overseas Hwy (Islander Resort area) · Islamorada
Half (women-only) Confirmed 2027. Necklace finisher award, mimosas.
Community 1
Community · · 3 pm
Islander Resort Coastline Cleanup
Islander Resort · Islamorada
Give back to the beautiful shores of Islamorada during the Islander Resort Coastline Cleanup.
Free
Where to Eat in Islamorada
0 of 0
No restaurants listed for Islamorada yet. Try a nearby town.
FAQ: Islamorada
What is there to do in Islamorada this weekend?
Events in Islamorada include Islander Resort Coastline Cleanup (Sep 7, Islander Resort), Swim for Alligator Lighthouse (Sep 10–12, Alligator Lighthouse) and Downtown Delray Restaurant Month (Sep 1–30, Downtown Delray Beach). The weekend strip at the top of this page is refreshed daily.
What towns are near Islamorada?
The closest towns to Islamorada are Key Largo (16 mi), Marathon (32 mi), Homestead (39 mi), Big Pine Key (49 mi), Coconut Grove (59 mi) and Coral Gables (59 mi). Each has its own guide on this site.