
34th Kelly McGillis Classic
January 20 - 26, 2026
EXPRESS ITINERARY – Kelly McGillis Classic #34
January 20 – 26, 2026
(for those teams or individals arriving to the island before Tuesday, please contact the IWFFA office and we will be happy
to include you in our pre-tournament activities, to show you a variety of places and venues and activities)
Day 1 – Tuesday – January 20, 2026
TUE – Bike Tour Stock Island & Key West 10AM – 12PM – South & Duval – Free (We cycle opens 9 -5am) 5160 US 1
TUE – Flag Football Clinic – Bernstein Park 1 -2:30PM – 6751 – 5TH AVE – Free
TUE – Kayak Tour @ Lazy Dog 3 – 4:30PM – 5114 Overseas – Stock Island – Free
TUE – Dinner – EL MOCHO Restaurant 6 -7:30PM – 5708 Maloney Ave – $
TUE – Arm Wrestling Contest-Beards & Brew 8:30PM – late – 5450 MacDonald Ave #6 – BEARDS & BREWS – $
Day 2 – Wednesday – January 21, 2026
WED – WEOW RADIO 92.7 FM !! 7AM-8AM Radio Interview with Kelly McGillis & Afghan Flag Football Players
WED – Flag Football Clinic 9AM-10:30 WICKER FIELD – 3155 Flagler- FREE
WED – Save the Drunken Sailor 11am – 1PM Higgs Beach – 1000 Atlantic – FREE
WED – Officiating Clinic 2 – 3PM WICKER FIELD – 3155 Flagler – Register
WED – KICK BALL! 3-4PM Wicker Field-3155 Flagler- FREE
WED – Tournament Dinner 8PM – 9PM Brady’s Pub – 1900 Flagler – $
WED – TOILET RELAY RACE 9PM Brady’s Pub – 1900 Flagler – FREE
Day 3 – Thursday – January 22, 2026
THUR – Coaching Flag Football for the Beginner 9:00AM – 10:00 – Wicker Field-3155 Flagler- Register
THUR – Officiating Review & Test / Certification 10:00AM – 10:30 AM – Wicker Field-3155 Flagler – FREE
THUR – Flag Football Scrimmage (sign up) 10:30 – 12:00PM – Wicker Field-3155 Flagler- FREE
THUR – Women Speaker Series 1-3PM – Key West Library – 700 Fleming- FREE
THUR – Opening Ceremonies 4:30 – 6PM – Half Shell Raw Bar – 231 Margaret – FREE
THUR – Kelly’s Players Parade 6PM – 7PM – Begins Half Shell Raw Bar – 231 Margaret- FREE
THUR – Tournament Teams Registration 8 – 11PM – Bourbon St. Pub – 724 Duval- Free
Day 4 – Friday – January 23, 2026
FRI – Tournament Games Begins 10AM-5PM – Wicker Field – 3155 Flagler- FREE
FRI – Spirit of Independence Sunset Sail 4:30 PM – 6:30PM- 202 William – discounts to all our teams
FRI – Women’s Drag King Contest & Dance 8PM – till late @ Sidebar – 504 Angela – $
Day 5 – Saturday – January 24, 2026
SAT – Tournament Games Continues 8AM – 6PM – Wicker Field – 3155 Flagler- FREE
SAT – Girls Night Out- FREE 4:30PM – 7:30PM – Trolly Pick Up @ Wicker Field Parking Lot
Angelas Pizzeria 208 Duval & Key Lime Pie Co. 511 Greene
SAT – Pool Party – Shooterz Pool Hall 6 – 8 PM – 3102 Flagler – w. D.J. Ja Maree
SAT – Women’s Party Ms. IWFFA Contest 9 PM till late – KAYA Muli – Bar Complex – 618 Duval – $
DAY 6 – SUNDAY – JANUARY 25, 2026
SUN – Tournament Play-Offs & Championships 8AM – 7PM – Wicker Field – 3155 Flagler- FREE
SUN – Juniors & Girls Awards Time Approx 3PM – Wicker Field – 3155 Flagler- FREE
SUN – Women’s Awards Dinner 8PM – El SIBONEY – 5501 5th St. – Stock Island- $
Day 7 – January 26, 2026 – Monday
MON – Breakfast El Mocho Restaurant 9AM-10AM – 5708 Maloney Ave – Stock Island
MON – Flag Football Trainers Clinic 10AM-11:00 – BERNSTEIN PARK – 6751 – 5TH AVE – Stock Island
MON – Punch Ball 11AM – 12AM – BERNSTEIN PARK – 6751 – 5TH AVE – Stock Island
MON – Flag Football Conference 12AM-1PM – BERNSTEIN PARK – 6751 – 5TH AVE – Stock Island
MON – Hurricane Hole Restaurant Lunch 1:30PM 5110 Overseas Hwy– $ – Stock Island
MON – Botanical Garden 3PM – 4PM – 5210 College Rd – Stock Island
We hope you had a fantastic Kelly McGillis Classic Experience! It’s not just about the games, unity, fun, making new friends and of course….. GREAT FLAG FOOTBALL. Hope to see you next year at the 35th Kelly McGillis Classic January 20 – 26, 2026