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  • 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...

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    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...

    Free

  • Passport to the World Wine Tasting

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

    Join us at The Gardens Hotel's d'vine wine gallery for an intimate journey through the vineyards of the world! In this immersive wine class, "Passport to the World," you'll explore...

    $35.00

  • 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...

    Free

  • 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...

    $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...

    $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...

    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...

    $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...

    $25