Fall Fun on Fort Myers Beach: Your Guide to the Biggest Events at Margaritaville
Kids are headed back to school, summer vacations are now memories, we all get back to our fall routines, and start to see the subtle breeze of change approach. All signs point to the inevitable winding down of summer. Things at Margaritaville Beach Resort Fort Myers Beach, however, are just starting to heat up!
There is so much to see and experience on Fort Myers Beach this fall, and there’s no better spot to make your headquarters for fun than Margaritaville.
Sizzle Dining at JWB Grill
Foodies from around southwest Florida give a collective gasp for the month we’ve all been waiting for – September - and Sizzle Dining.
JWB Grill, the best elevated casual dining spot on Fort Myers Beach, will once again be featured in Sizzle, with a show-stopping menu highlighting a petite filet, shrimp pasta, and our signature ceviche. Availability is limited, and reservations are strongly recommended to take advantage of this 3-course prix fixe menu for $49 per person (plus tax, gratuity, and beverages). Sizzle Dining runs September 1 – September 30, so be sure to reserve this special dining opportunity while you can.
JWB Sizzle dining menu & reservations
Labor Day Weekend / Jimmy Buffett Day
Labor Day Weekend is more than just celebrating the end of summer. At Margaritaville we kick off Labor Day Weekend on Friday, September 4th with Jimmy Buffet Day, our Day of Service. We celebrate just like Jimmy asked, by keeping the party going. This year, Margaritaville Beach Resort Fort Myers Beach has chosen to give back to local organization My Autism Connect.
There will be keepsake merchandise available in Margaritaville Shop, live music all weekend long, a great lineup of activities and games at Fins Up! Beach Club, and most importantly, an opportunity to give. Book your stay with our Keep the Party Going promotion and we will give $5 back to My Autism Connection.
Purchase a specialty drink in one of our limited-edition cups and we will give $1 back to My Autism Connection. Want to learn more about My Autism Connection and the people they serve? Visit their table On Friday, September 4th at Fins Up! Beach Club.
Start Making Your Jimmy Buffett Day Plans
Roar Offshore F1 Powerboat Races
Get ready to feel the roar as offshore powerboat racing returns to Fort Myers Beach in 2026 for the first time since 2021. Roar Offshore is back and it’s bringing high-speed super stock racing, waterfront excitement and an unforgettable race-day atmosphere back to the island.
Whether you are a longtime racing fan or experiencing offshore powerboat racing for the first time, this is one weekend you will not want to miss. Make Margaritaville your headquarters for racing fun and you’ll snag the best seat in the house to spectate. Stick around each evening because we’ve got a full calendar of amazing live music to help usher in the sunset.
Roar Offshore is packing the weekend schedule with tons of fun with pit parties, racer meet-n-greets, up-close photo ops with Super Stock racing boats, and more.
Want to learn more? Get all the 2026 Roar Offshore Boat Race Details
Margaritaville Beach Resort Fort Myers Beach is proud to be Title Sponsor of Roar Offshore 2026.
Nauti Nation
September keeps getting better as ‘America’s Least Exclusive Yacht Club’ comes to town. Nauti Nation is taking over Fort Myers Beach September 19-20, with the mission to bring together the crew that lives for the beaches, boats and bars. A portion of proceeds from the weekend benefit Birdwell Foundation.
Saturdays are for Sandbar Parties and that is exactly how Nauti Nation starts the weekend. Drop anchor in Big Carlos Pass for some sun and sand, then head to Lah De Dah Beach Bar at Margaritaville for an evening of live music with Todd Weatherill.
Get some rest and recharge because The Nauti Trail Bar Crawl is on tap for Sunday. Featured drinks, music, games and giveaways are planned as you make your way to the final stop back at Margaritaville.
Get Your Tickets to Participate in the 2026 Nauti Nation Fort Myers Beach Pub Crawl
Island Hopper Songwriter Fest
Live music is a cornerstone of the Margaritaville experience and Island Hopper is an amazing 10-day celebration of some of the best live music in southwest Florida.
Hop from one beautiful setting to another throughout the islands, beaches, and neighborhoods of Fort Myers, Florida as one of America’s most beloved live music festivals once again graces our shores. The festival boasts over 60+ free live performances from BMI’s best singer-songwriters, spanning genres from acoustic to folk, alt rock to country. The festival concludes on Fort Myers Beach September 25-27, and Margaritaville is once again home to the Opening Showcase for island jams on Friday, September 25th starting at 4pm. The grooves continue all weekend long at Margaritaville, with a full slate of incredibly talented singer-songwriters.
Checkout Margaritaville's Island Hopper Music Fest Schedule
ParrotPhest Trop Rock Weekend
If live music is your love language, and trop rock is your vibe, then ink your calendar for October 1-4, and set your GPS for ParrotPhest 2026, where we have an all-star lineup of trop rock talent weaving notes all around the resort.
It’s a weekend that is distinctly Margaritaville, exclusively southwest Florida, but all about making new friends and celebrating old ones all while raising funds for Alzheimer’s Association. At Margaritaville Fort Myers Beach we party with a purpose in coordination with the Southwest Florida and The Villages Parrothead Clubs with chances to win baskets, stays at Margaritaville properties across the United States, and maybe even a future stay in Fort Myers Beach if you show up in your feathered-best for our annual Parrot Pageant. We’ve created a trop rock weekend that’s all about beachy vibes, great tunes, and unforgettable fun.
Get Details and Make Reservations for an Amazing Trop Rock Weekend!
