Quick answer: Fort Myers, Florida has 3 verified upcoming comedy shows at 2 venues from November 20, 2026 to December 30, 2026. Standouts: Jeff Dunham and Jim Gaffigan at Hertz Arena in Estero, plus An Idiot’s Guide to Wine at The Venue at Millennial in downtown Fort Myers.
Updated November 4, 2026
Fort Myers comedy shows are lining up for the busy season. Nationally, the midterms are finally over, which means no more campaign ads between every inning, quarter and weather report. Whoever you voted for, everybody can agree the commercials were the worst part.
Locally, Fort Myers, Florida has its own election story: Byron Donalds, the congressman from right here in Southwest Florida, is Florida’s next governor, according to NBC News projections. And the other annual tradition is underway. The snowbirds are back, the license plates are from Ohio and Michigan again, and the dinner reservations just got harder.
What’s the mood in Fort Myers right now?
This is the good part of the year. The humidity backs off, the Everblades are back on the ice at Hertz Arena, and the Edison and Ford Winter Estates starts Holiday Nights on November 27, the day after the 47th Fort Myers Turkey Trot. Everybody wants to be outside, and then everybody wants a plan for the night.
The comedy calendar here is small but strong. Two arena-sized names in December and a wine comedy show downtown. If your relatives are visiting for the holidays, that’s three nights you don’t have to plan.
What comedy shows are coming up in Fort Myers?
Every date and time below comes from structured ComedyCalendar.com event data, and every link goes to a ComedyCalendar.com event page. Times are Eastern.
| Date | Time | Comedian | Venue | Neighborhood or Area |
|---|---|---|---|---|
| Fri, Nov 20, 2026 | 6:00 PM ET | An Idiot’s Guide to Wine
|
The Venue at Millennial | Downtown Fort Myers, Royal Palm Avenue |
| Sat, Dec 12, 2026 | 5:00 PM ET | Jeff Dunham
|
Hertz Arena | Estero, Everblades Parkway |
| Wed, Dec 30, 2026 | 7:00 PM ET | Jim Gaffigan
|
Hertz Arena | Estero, Everblades Parkway |
An Idiot’s Guide to Wine
Friday, November 20 at 6:00 PM ET
The Venue at Millennial in Fort Myers
An Idiot’s Guide to Wine at The Venue at Millennial is a comedy show about wine for people who just point at the menu. Two shows that Friday at 6 and 9 PM, and it comes back Saturday, January 23 with the same two times. Easy girls’ night.
Jeff Dunham
Saturday, December 12 at 5:00 PM ET
Hertz Arena in Estero
Jeff Dunham brings Inappropriate Contact to Hertz Arena on a Saturday at 5 PM. Walter, Peanut, Achmed, the whole crew. An early arena show means dinner after, and the grandparents in town for the season will love it.
Jim Gaffigan
Wednesday, December 30 at 7:00 PM ET
Hertz Arena in Estero
Jim Gaffigan brings Everything is Wonderful! to Hertz Arena on December 30. The dead zone between Christmas and New Year’s is the perfect time for an hour of jokes about food and family, since you just spent a week with both.
Where to see stand-up in Fort Myers
The Venue at Millennial at 1811 Royal Palm Ave. is in downtown Fort Myers and hosts An Idiot’s Guide to Wine on November 20 and January 23.
Hertz Arena at 11000 Everblades Parkway in Estero is home of the Florida Everblades, and it has Jeff Dunham on December 12 and Jim Gaffigan on December 30.
Fort Myers comedy FAQ
Which big-name comedians are coming to Fort Myers?
Jeff Dunham plays Hertz Arena on Saturday, December 12 at 5:00 PM ET, and Jim Gaffigan plays Hertz Arena on Wednesday, December 30 at 7:00 PM ET.
Is there a comedy show in Fort Myers between Christmas and New Year’s?
Yes. Jim Gaffigan brings Everything is Wonderful! to Hertz Arena in Estero on December 30.
What’s a good comedy date night in Fort Myers?
An Idiot’s Guide to Wine at The Venue at Millennial pairs comedy with wine downtown, with 6 PM and 9 PM shows on Friday, November 20 and Saturday, January 23.
Find more Fort Myers comedy
Season is just getting started, and more shows get added as the snowbirds roll in. For the full, always-updated list, check the Fort Myers comedy shows page, or browse every show around the state on the Florida comedy shows page. Pick a night and send it to the group chat.
