My wife and I have started planning our 2027 calendar, and one thing is certain: We won’t be sitting around wondering what to do. One of her superpowers is finding fun and interesting events for us to attend—and they’re often free! From outdoor festivals and live music to art shows and sporting events, Southwest Florida has plenty going on during the winter season.
Here are some events that we’ve put on our radar. We probably won’t do all of them…but I hope we do.
DECEMBER
Bonita Springs Holiday in the Park — Early December | Riverside Park, Bonita Springs | Free
Who says you need to travel north to enjoy a little winter magic? This annual celebration brings holiday lights, live entertainment, seasonal activities, and even a chance to experience “snow” in Florida. It is a fun way to get into the holiday spirit without spending much.
JANUARY
Florida Everblades Hockey Game — January 8 | Hertz Arena, Estero | $30-$100
I am not a huge hockey fan but enjoy watching it in person. We attended our first Blades game last year at Hertz Arena and loved it. Apparently, they have a bit of a cult following. Super fun atmosphere. (The Blades’ season started in October. They have 36 home games this year.)
Southern Fried Swamp Jam — January 16 | Seminole Casino Hotel, Immokalee | Free admission. VIP Tickets available.
We went to a concert at Seminole Casino last year, and it was great. Outdoors, free, and with food trucks nearby. (Bring your chairs!) This year’s lineup includes 38 Special, The Outlaws, Confederate Railroad, and a Creedence Clearwater Revival tribute band. It’s a 21-and-over event.
NOIS Saxophone Quartet — January 20 | FGCU, Estero | $15
I wrote last month about FGCU and everything it has to offer, including concerts through its Bower School of Music and Arts. The NOIS Saxophone Quartet performs a mix of classical music, contemporary works, and jazz-inspired pieces. This one sounds like a great way to enjoy an evening of live music close to home.
Nash to Naples Songwriter Fest — January 23 | Cambier Park, Naples | Approximately $75
If you’re into country music and hearing the stories behind the songs, this is a great event. We’ve attended twice. It’s not cheap, but the proceeds go to a good cause. This outdoor concert brings Nashville songwriters to Naples to perform their music and to share the stories behind it.
FEBRUARY
Fort Myers Greek Fest — February 19–21 | Annunciation Greek Orthodox Church, Fort Myers | Check admission details
We like events that let us experience another culture while enjoying a good meal and live entertainment. We haven’t been to this one yet, but we’re putting it on the calendar. Two gyros, please.
Coconut Point Art Festival — February 20–21 | Coconut Point, Estero | Free admission
We don’t have to go far for this one. Coconut Point turns into an outdoor gallery, with more than 200 artists displaying everything from paintings and photography to sculpture and jewelry. We can browse the art, enjoy the outdoor atmosphere, and finish with lunch or dinner at one of the nearby restaurants.
Bonita Brew Fest — February 20 | Riverside Park, Bonita Springs | Approximately $25
If you like sipping a craft beer or a cider, you might want to check this one out. It includes food trucks and live music. It’s a chance to sample different brews and spend a few hours outdoors with friends. Admission includes tasting samples; food is extra.
MARCH
Fort Myers Beach Lions Club Shrimp Festival — March 13–14 | Fort Myers Beach | Check event details
Fort Myers Beach has rebounded nicely since Hurricane Ian, and we love finding excuses to go there. Hanging out at the beach and eating fresh shrimp sounds like a pretty good reason. We have not yet attended their Shrimp Festival but plan to check it out this year.
Naples St. Patrick’s Day Parade — Date to be confirmed | Downtown Naples | Free
You don’t have to be Irish to enjoy a St. Patrick’s Day parade! We’re keeping an eye out for the confirmed date for this annual celebration, which brings marching bands, floats, and plenty of Irish spirit to downtown Naples.
That’s our current calendar for 2027. For us, it’s a good mix of things we have done in the past and new events to check out. And if my wife keeps working her magic, we’ll probably add a few more fun things to the calendar before January even arrives!
