Greg Fitzsimmons at Comedy Key West
When: November 18 - November 21, 2026
Where: Comedy Key West, 218 Whitehead St. Unit 5, Key West, FL 33040
Greg Fitzsimmons brings four nights of stand-up comedy to Comedy Key West, November 18–21, 2026, with performances at 8:00 PM each night.
A four-time Emmy Award-winning writer and veteran stand-up comedian, Fitzsimmons is the host of FitzDog Radio and co-host of the Sunday Papers and Childish podcasts. His extensive television and radio career includes appearances on The Joe Rogan Experience, The Howard Stern Show, The Adam Carolla Show, Late Show with David Letterman, The Tonight Show, Conan and Jimmy Kimmel Live. He also hosted his own SiriusXM program for more than a decade.
Comedy Key West is an intimate comedy club, and seating is first come, first served. Guests who purchase tickets together will be seated together, and arriving early is recommended for preferred seating.
There is a two-item minimum during the show. Love Seats accommodate two people, so one Love Seat counts as two tickets.
Shows may include adult themes, language and content. Guests must be at least 16 years old. Audience members are asked to keep conversations to a minimum during performances because of the intimate size of the room.
You might like these Events
Destroying David — Spotlight Series at Waterfront Playhouse
Destroying David Comes to Waterfront Playhouse Key West Destroying David comes to the Waterfront Playhouse in Key West as part of the theater’s Spotlight Series, with performances scheduled from Nove...
Key West Film Festival 2026
The Key West Film Festival returns November 18–22, 2026, for its 15th annual celebration of film, bringing five days of screenings, filmmakers and special programming to Old Town Key West. This year m...
Southernmost Turkey Trot 5K and Rooster Romp 2026
Southernmost Turkey Trot 5K & Rooster Romp 2026 – Thanksgiving Morning in Key West Kick off Thanksgiving Day in true island style at the Southernmost Turkey Trot 5K and Rooster Romp, happening Th...
Two-Hour Private Boat Charter – Best Time Ever Boat Charters
Best Time Ever Boat Charters, LLC.
Enjoy a private two-hour boat charter with Best Time Ever Boat Charters, offering a stylish, comfortable, and fast way to get on the water in the Florida Keys. This shorter private charter works well for groups looking for a flexible outing without committing to a full-day trip.
Book now!Key West Afternoon Sail, Snorkel, Kayak & Sunset Excursion
Danger Charters
Spend the afternoon on the water with Danger Charters on a Key West sail, snorkel, kayak, and sunset excursion. This trip combines classic sailing, shallow-water adventure, snorkeling, kayaking, and a sunset finish, making it a strong all-in-one option for visitors who want more than a simple boat ride.
Book now!
Key West Party Boat Fishing on FishMonster MAX
FishMonster Island Jane
Head out on a Key West party boat fishing trip aboard FishMonster MAX with Fish Monster Island Jane. This group fishing experience is a good fit for visitors who want an easy, affordable way to get on the water, fish with an experienced crew, and enjoy a classic Key West fishing adventure without booking a private charter.
Book now!