• Bougie Afternoon Tea Party

    Hellings Curry Museum 319 Duval Street, Key West, FL, United States

    Mark your calendars for the second annual Key West Woman's Club Bougie Afternoon Tea Party on January 17th! This delightful event will benefit Take Stock In Children, with a $25,000 Monroe County scholarship to be awarded. Live Music Fun Contest & Prizes Specialty Cocktails Beautiful Decor Finger Sandwiches Petite Quiches Scones & Clotted Cream Mini...

    $150
  • School of Rock presented by the Key West Film Society

    Tropic Cinema 416 Eaton Street, Key West, FL, United States

    Movies Under the Stars: School of Rock Get ready to rock with a high-energy, family-friendly screening of the 2003 comedy School of Rock! Follow a down-on-his-luck guitarist who poses as a substitute teacher and turns a class of straight-A students into a mind-blowing rock band. Packed with laughs, heart, and unforgettable music, this feel-good film...

    Free
  • Glow Hours at Hugh’s Views

    Glow Hours at Hugh’s Views

    The Studios of Key West 533 Eaton Street, Key West, FL, United States

    Our Hugh’s View roof terrace offers the best views in town, and an ideal spot to catch the sunset and a drink with friends. The bar is open, admission is free, and everyone looks great in the golden twilight. Free and open to the public on Monday's and Tuesdays from 6pm-8pm

    Free
  • Trivia Night Mondays at Key West Cooking School

    Key West Cooking School 291 Front Street, Key West, FL, United States

    Test Your Knowledge & Tastebuds every Monday from 6:00 to 8:30 PM for a sizzling evening of fun, food, and friendly competition at Trivia Night at the Key West Cooking School! Gather your team or come solo and make new friends as we challenge your brain with a mix of pop culture, history, food facts,...

    Free
  • The Heart-Starters “A Swingin’ Night with The Heart-Starters”

    Harry S. Truman Little White House 111 Front Street, FL, United States

    The Key West Harry S. Truman Foundation presensts The Heart-Starters “A Swingin’ Night with The Heart-Starters” Live on the North Lawn 5:15 pm Gates open for cocktails 6:00 pm Performance starts 6:45 pm Intermission 7:00 pm Second Half 8:00 pm End The Heart-Starters: Truman Era Tribute Band – The Heart-Starters are True to Truman. Join...

    $40 – $240
  • Glow Hours at Hugh’s Views

    Glow Hours at Hugh’s Views

    The Studios of Key West 533 Eaton Street, Key West, FL, United States

    Our Hugh’s View roof terrace offers the best views in town, and an ideal spot to catch the sunset and a drink with friends. The bar is open, admission is free, and everyone looks great in the golden twilight. Free and open to the public on Monday's and Tuesdays from 6pm-8pm

    Free
  • 66th Annual Home Tours presented by Old Island Restoration Foundation

    Various Key West, FL, United States

    66th Annual Home Tours presented by Old Island Restoration Foundation! Our 66th Home Tours will bring you joy and excitement to local homes that are opened for your viewing pleasure. Strolling through Key West, do you ever wonder what lies behind a beautiful, historic, intriguing, and private door? Each month features different homes, so enjoy...

    $45 – $55
  • “Remember the First Ladies” at America250

    Harry S. Truman Little White House 111 Front Street, FL, United States

    Friday, January 23, 2026 – Save the Date! Join us on the lawn at the Harry S. Truman Little White House to discusses the book, Remember the First Ladies: The Legacies of America’s History-Making Women , with the authors, Anita McBride, Diana B. Carlin, & Nancy Kegan Smith and moderator Dr. Kurt Graham. Remember the...

    $40 – $60
  • 66th Annual Old Island Restoration Foundation Home Tours

    Various Key West, FL, United States

    66th Annual Home Tours presented by Old Island Restoration Foundation! Our 66th Home Tours will bring you joy and excitement to local homes that are opened for your viewing pleasure. Strolling through Key West, do you ever wonder what lies behind a beautiful, historic, intriguing, and private door? Each month features different homes, so enjoy...