• Happy Hour at the Harry S. Truman Little White House

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

    Join us for a special evening at the historic Truman Little White House, where history meets hospitality in the heart of Key West. "Happy Hour at Harry’s" is an exclusive event designed to showcase the charming and iconic spaces of the Truman Little White House, while offering a unique opportunity to learn more about becoming...

    $25
  • Valentine’s Day aboard Sunset Sail Key West

    Sunset Sail Key West 7001 Shrimp Road, Key West, United States

    Set sail on a romantic evening you’ll never forget aboard the luxurious Sunset Sail Key West, the perfect way to celebrate love this Valentine’s Day. As the sun begins its descent over the turquoise waters of the Gulf of Mexico, you and your special someone will embark on an unforgettable cruise, complete with breathtaking views,...

    $45 – $109
  • Movies Under the Stars: Princess Diaries

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

    Tropic Cinema in partnership with the Monroe County Public Library launches its “Movies Under the Stars” series starting November 16 with the screening of the Disney classic and audience favorite Mary Poppins. Tropic Cinema in conjunction with the library has been hosting the family friendly series for three years now. The movies are shown outdoors...

    Free
  • Presidential Families Weekend Forum 2025

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

    Descendants who can trace their lineage directly to one or more of the 46 U.S. presidents will come together to share unique stories, personal anecdotes, and valuable historical insights about how their ancestors wielded the immense power of the presidency to shape and influence the course of U.S. history and government. This fascinating forum, presented...

    $40 – $60
  • An Evening with Freedy Johnston

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

    Come out for a rare opportunity with Freedy Johnston, celebrated singer-songwriter and masterful storyteller, as he performs in the intimate Carper Theater at the Tropic Cinema. Known for hits like Bad Reputation, This Perfect World, The Lucky One, and Evie’s Tears, Freedy Johnston’s evocative voice and timeless songs have earned him a loyal following across...

    $25
  • Jazz in the Gardens

    Jazz in the Gardens
    The Gardens Hotel 526 Angela Street, Key West, FL, United States

    Whether you are trying to unwind after a day of exploring Key West or prepping for a night out on nearby Duval Street, d'vine Wine Gallery at the Gardens Hotel is the perfect place to enjoy a glass of wine while listening to some great live music. The Gallery hosts live music performances Sunday evenings...

  • Give ‘Em Hell Harry

    Give ‘Em Hell Harry
    Harry S. Truman Little White House 111 Front Street, FL, United States

    Give ‘Em Hell, Harry! Starring Clifton Truman Daniel Grandson of President Harry S. Truman Give ‘Em Hell, Harry!, by Samuel Gallu, is a faithful and often humorous portrayal of President Harry S. Truman’s life and presidency. It spans his childhood, his “political apprenticeship” as a judge in Jackson County, MO, his years in the U.S....

    $80 – $240
  • Give ‘Em Hell Harry

    Give ‘Em Hell Harry
    Harry S. Truman Little White House 111 Front Street, FL, United States

    Give ‘Em Hell, Harry! Starring Clifton Truman Daniel Grandson of President Harry S. Truman Give ‘Em Hell, Harry!, by Samuel Gallu, is a faithful and often humorous portrayal of President Harry S. Truman’s life and presidency. It spans his childhood, his “political apprenticeship” as a judge in Jackson County, MO, his years in the U.S....

    $80 – $240
  • 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
  • Jazz in the Gardens

    Jazz in the Gardens
    The Gardens Hotel 526 Angela Street, Key West, FL, United States

    Whether you are trying to unwind after a day of exploring Key West or prepping for a night out on nearby Duval Street, d'vine Wine Gallery at the Gardens Hotel is the perfect place to enjoy a glass of wine while listening to some great live music. The Gallery hosts live music performances Sunday evenings...