Book direct and save up to 15% when you plan ahead. Learn More

A Group Of People With Fire
Scroll to Explore

5 Events You Won’t Want to Miss in Islamorada in 2023

Islamorada offers quiet beauty for travelers to escape to. While guests of the Islander Resort have onsite attractions and resort amenities like private cabanas, onsite swimming pools, and restaurants, it’s also fun and compelling to check out local events. Looking at a couple of ongoing gatherings, and some events on the calendar for later in the year here’s a brief guide to what travelers can look forward to in Islamorada in 2023. 


On the third Thursday of every month, artists from the Keys will gather with vendors and residents on Islamorada’s Morada Way for a free-to-attend art walk. This tradition dates back to 2011 and it continues to be a favorite among locals and travelers. From 6-9 pm on the Thursday of each art walk, Morada Way will be alive with late-night gallery openings, food on sale from local restaurants, live music, and opportunities to meet the artists. 

Morada Way. Islamorada, FL 



Islamorada Brewery & Distillery is a fantastic place to hang out and sample locally-made brews and spirits. Every Tuesday, it also comes to life with a super fun trivia night. It starts at 6 pm every week and offers travelers a great chance to hang out and interact with locals. The event will feature a food truck that will be open until 8 pm and one free beer per team player (21+). 

Islamorada Brewery & Distillery. Islamorada, FL 



Island Fest is one of Islamorada’s most reliable and eclectic annual traditions. A fundraising event for the Islamorada Chamber of Commerce, it’s been running for an astonishing 31 years. The two-day festival will feature live musical performances, a juried art show featuring works of sculpture, jewelry, paintings, and more from around the Keys, classic car exhibitions, and food provided by local chefs and vendors. 

Founders Park - April 1-2. Islamorada, FL 



Every year, runners come down to Islamorada in December for lasting warmth and another chance to run a great distance in competition with peers. The Islamorada Half Marathon is a two-day event that also features a 10K race, and the Beach N’ Beer Mile—combining a party atmosphere, beach setting, and still a little bit of movement. 

Islamorada Half Marathon - December 9-10. Islamorada, FL



Another December tradition, the Florida Keys Gold Cup Series begins every December and runs through January here in Islamorada. It comprises three events: the Islamorada Sailfish Tournament, Cheeca Lodge Presidential Sailfish Tournament, and the Islamorada Fishing Clubs’ Sailfish Tournament, the most recent of which just took place at the end of this past January.

Florida Keys Gold Cup Sailfish Championship. Islamorada, FL

Advanced Purchase

Be rewarded for planning ahead! Book 7 days prior to arrival and receive 15% off our best available rate Oceanside Resort.

Learn More

Sign Up for Our Newsletter