• Little White House Tours and Presidential Holiday Card Presentation

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

    Tuesday, December 23rd, 2025, 6-8pm Join us for a festive evening at the Key West Harry S. Truman Little White House. You will start with a cup of eggnog or a hot toddy and some holiday cookies. Then you will take a tour of the house to see all the beautiful, traditional holiday decorations and...

    $25 – $35
  • Christmas Day Brunch Aboard Schooner America 2.0

    Classic Harbor Line 202R William Street, Key Weset, FL, United States

    Enjoy Christmas morning the Key West way – sailing! Enjoy the vibrant colors of Key West as you sip champagne, dine on a delicious brunch, and glide through crystal clear surrounding waters on one of Key West’s premiere holiday cruises. This Christmas brunch Key West-style features complimentary mimosas, bloody marys, champagne, wine, beer, soft drinks,...

    $168
  • Truman Waterfront Farmers Market

    Truman Waterfront Farmers Market

    Truman Waterfront Park Southard Street, Key West, FL, United States

    Join us every Thursday from 2 pm to 7 pm at the Truman Waterfront for fresh produce grown in Homestead, gorgeous orchids & native plants, artisan selection of meats and cheeses, pickles, honey, nuts & dried fruits, natural soaps and so much more. You’ll find Key West crafts, gifts and the perfect souvenir to take...

    Free
  • 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...

    $45 – $55
  • Little White House – Tours and Presidential Holiday Card Presentation

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

    Tuesday, December 26th, 2025, 6-8pm Join us for a festive evening at the Key West Harry S. Truman Little White House. You will start with a cup of eggnog or a hot toddy and some holiday cookies. Then you will take a tour of the house to see all the beautiful, traditional holiday decorations and...

    $25 – $35
  • 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...

    $45 – $55
  • Sheriff’s Animal Farm Open House

    Sheriff’s Animal Farm Open House

    The Monroe County Sheriff's Office Children's Animal Farm 5501 College Road, Key West, FL, United States

    Make sure to visit the family-friendly Monroe County Sheriff's Animal Farm, open on the second and fourth Sundays of each month from 1 to 3 p.m. Visits are free of charge, but donations are always welcomed. The farm started as a haven for homeless animals. The first residents were Muscovy ducks and a group of...

    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
  • 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