Fall Fun & Festivals at Margaritaville Fort Myers Beach | Sept–Oct 2025
Fall Fun & Festivals at Margaritaville Fort Myers Beach | Sept–Oct 2025
Margaritaville Beach Resort Fort Myers Beach: Events & Fun for September & October 2025
Are you ready to plan your perfect escape to paradise? Margaritaville Beach Resort Fort Myers Beach is your ultimate destination for live music, entertainment, and island-inspired relaxation. With an exciting calendar full of festivals, themed weekends, and daily activities, there’s always something happening. Whether you’re a lifelong Parrothead or simply looking for unforgettable Fort Myers Beach events, here’s what’s on deck this September and October.
Celebrate Island Life: Fall Festival Highlights
September turns up the volume with the 11th Annual Island Hopper Songwriter Fest, ranked a top music festival by USA Today. From September 19 to 28, enjoy more than 60 free acoustic performances across Southwest Florida, including a Fort Myers Beach kickoff at Margaritaville on September 19 at 4 PM with performances by Claudia Hoyser, Danny Myrick, and more. Additional free shows continue through the weekend of September 26–28 featuring talents like Dave Pahanish, Essex County, Adam Craig, and The Reed Brothers. Guests booking stays in September can enjoy 20% off lodging with the “ISLAND” promo code.
Get ready for a lively beachside party October 3–5, celebrating Trop Rock music, featuring live bands, “boat drinks,” contests, and raffles benefiting the Alzheimer’s Association. The weekend includes DJ sets and concerts on the Sunset Terrace, plus chances to win Margaritaville stays and cruises. Dress in your best Parrothead attire for a chance to win fun prizes and enjoy a supportive community vibe.
Sandcastle Festival
If your visit lines up with this beloved beach tradition, don’t miss the astounding sand sculpting contests and displays along Fort Myers Beach—perfect for the whole family.
More Ways to Play Every Day
Beyond the festivals, Margaritaville Beach Resort offers daily and weekly entertainment sure to keep the island spirit alive:
Live Entertainment & Themed Nights at Lah De Dah Beach Bar & Grill: Enjoy live music daily, complemented by vibrant themed nights:
- Tuesday Trivia at 7 PM – Test your knowledge and win prizes in a fun, social atmosphere.
- Wednesday Karaoke starting at 8 PM – Sing your heart out or cheer on your friends with tropical beats.
- Thursday Bingo starting at 5 PM – Play for prizes while soaking in the beachfront vibe.
Fins Up! Beach Club Entertainment: Fins Up! Beach Club brings lively themed days throughout the week to keep guests entertained and coming back for more:
- Local Heroes Tuesdays: Every Tuesday, Fins Up! honors the hard work of military personnel, first responders, teachers, and healthcare workers with a special day just for them. Show your valid ID at the welcome cabana for free entry and enjoy a relaxing day poolside as a thank you for your service.
- 55+ & Fabulous Wednesdays: If you were born before 1970, Wednesday is your day to shine at Fins Up! Join fellow fun-lovers for a midweek party filled with music, socializing, and poolside vibes tailored just for the 55+ crowd.
Plus, live entertainment takes the stage Wednesday through Saturday to provide the perfect soundtrack to your poolside experience.
Important: Resort guests receive free access to Fins Up! Beach Club with wristbands included at check-in. For guests and visitors not staying at the resort, day passes are available for purchase, making all these fun events and amenities open to the public as well.
Wine Dinners at JWB Grill: Savor the flavors with monthly wine dinners featuring expertly paired menus and exceptional wines. Upcoming dates include:
Thursday, September 11 – “Napa vs. Paso Robles” wine experience starting at 6:30 PM.
Thursday, October 16 – “Copper Canes” wine experience starting at 6:30 PM
Thursday, November 20 – Far Niente wine experience starting at 6:30 PM.
Make your reservations today: https://qrco.de/jwbwine
Fitness & Wellness: Join water aerobics classes, boot camps on the beach, or calming morning yoga sessions to stay refreshed.
Family-Friendly Fun: From movie nights and trivia to arts and crafts like ceramic seashell bowl painting and airbrush tattoos, there’s something appealing for all ages.
Keep the glow of summer alive with our Endless Summer Escape spa special. For a limited time, indulge in any 50-minute service for just $109 + service charge and immerse yourself in pure tranquility. Whether you choose a luxurious massage, a radiant facial, or a rejuvenating body treatment (excluding Deluxe HydraFacial), each experience is designed to melt away stress, refresh your skin, and restore your inner glow.
Your visit also includes full-day access to the Fins Up Beach Club, a refreshing glass of champagne, and complimentary valet parking (based on availability). As the golden days fade into gentle breezes, give yourself the gift of relaxation and leave with that irresistible end-of-summer radiance.
Book now: https://qrco.de/spa-specials
Happy Hours to Unwind and Sip at Margaritaville:
Margaritaville Beach Resort Fort Myers Beach offers a variety of happy hour experiences across its restaurants and bars—perfect for relaxing after a day in the sun or kicking off an island evening.
- JWB Grill: Enjoy a sophisticated happy hour Sunday through Thursday from 4 PM to close (bar seating only). Specials include $4 off featured cocktails, call brand drinks, and wines by the glass. Pair your drinks with small plates like calamari, ceviche, tuna wontons, and meatball sliders.
- License to Chill Bar & Grill: Unwind Monday through Friday from 1 PM to 5 PM with great deals on $10 Margaritaville cocktails, frozen concoctions, appetizers, and $5 beer and seltzers—served with stunning Gulf views.
- Lah De Dah Beach Bar & Grill: Keep the party rolling daily from 8 PM to 11 PM with $10 frozen daiquiris, Margaritaville brand specialty drinks, and $5 Landshark draft beers—an ideal spot for tropical nightcaps.
- 5 O’Clock Somewhere Bar & Fins Up! Beach Club: While no standard daily happy hours, these venues host special events and extended parties. Check the resort calendar for the latest happenings to join the fun.
No matter which spot you choose, happy hour at Margaritaville Beach Resort is a tasty, relaxed way to enjoy island life.
Easy Valet Parking: The resort offers convenient public valet parking to let you focus on fun without the stress of finding a spot.
All Events Are Open to the Public
You don’t have to be a resort guest to enjoy the lively entertainment and culinary experiences. All events at Margaritaville Beach Resort are open to the public—so bring your friends and family for unforgettable island nights right here on Fort Myers Beach.
Plan Your Island Escape
With live music festivals, day-to-day fun, culinary delights, and a vibrant atmosphere, Margaritaville Beach Resort Fort Myers Beach is more than a place to stay—it’s your destination for island memories. Visit the official Entertainment Calendar to see up-to-date event listings and to book your next visit.
From parrot feathers to sandcastles, every guest finds their own slice of paradise this fall. What will your story be?
