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    5. Key West Food Tour with Hemingway History
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    Key West Food Tour with Hemingway History

    Taste Key West favorites and trace Hemingway’s footsteps on a guided 2-hour stroll

    From$98/ person

    Duration

    2 hours

    Includes

    Guided walking tour, food tastings

    Highlights

    Stroll through Key West following Ernest Hemingway’s footsteps while sampling local flavors. Your guide shares lively stories at the writer’s favorite haunts and historic sites.

    1. Visit Hemingway House, Sloppy Joe’s, and other landmarks
    2. Sample chicken Caesar wrap, bean salad, and key lime pie
    3. Hear engaging tales of Hemingway’s life and Key West history
    4. Explore the harbor where the author kept his boat Pilar
    5. Walk at a moderate pace suitable for most fitness levels

    What's Included

    1. Guided 2-hour walking tour
    2. Three food tastings
    3. Ponchos provided in rain

    Things to know

    Tour operates rain or shine; bring water, sunscreen, hat, and comfortable walking shoes. Please arrive 15 minutes before start outside the Hemingway House gate.

    FAQs

    Q: Where and when does the tour meet?

    A: You’ll meet your tour guide at the front gate of the Ernest Hemingway Home and Museum in Key West. The tour start time is listed as 9:00 a.m. for the Food & Walking Tour.

    Q: What will we see during the tour?

    A: The guide will take you to the places where Ernest Hemingway lived, worked and played in Key West, including his first apartment, the location of his boat “Pilar”, the bookstore that sold his books, places he watched/refereed boxing matches, where he fished and chartered boats, and his frequent bar haunt Sloppy Joe’s Bar.

    Q: What is included in terms of food and refreshments?

    A: The tour includes three food tastings: a grilled chicken Caesar wrap, a bean salad with a mango-poppy dressing, and a slice of Key Lime pie.

    Q: What should I bring and what level of fitness is required?

    A: You should bring water, sunscreen, a hat and wear comfortable clothes and walking shoes. The tour is moderately paced and suitable for most fitness levels.

    Q: Is parking available near the meeting point?

    A: Yes. There are several paid parking lots and garages within a short walk of the Hemingway House.

    Experience provided by Hemingway in Key West Tours
    Experience provided by Hemingway in Key West Tours

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

    Reference #HPRVDY

    Adult

    $98

    Ages 13+ • Includes food and drink

    0

    Child

    $69

    Ages 6-12 • Includes food and drink

    0

    Small Child

    $0

    Ages 5 and under

    0

    Why book through Greetwell?

    • Greetwell Approved

      This experience meets our quality and safety standards

    • Includes Concierge Support

      Our team is here to help with questions, timing, or special requests

    • Flexible Cancellation

      Plans change? Most experiences offer flexible cancellation

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    Cancellation policy

    Receive a full refund with at least 24 hours' notice or if the operator cancels due to weather or unforeseen circumstances. No-shows are charged the full price. Exclusions apply to private tour cancellations.

    Meeting location

    The Hemingway House, 907 Whitehead St, Key West, FL 33040

    4.9 stars• 30 reviews

    Review summary

    4.9
    Excellent
    30 reviews•Google Maps

    This tour company has clearly hit on something special, particularly with their Jimmy Buffett walking tour that seems to steal the show. Guide Caleb gets mentioned repeatedly and for good reason: reviewers consistently praise his deep knowledge, engaging personality, and ability to make the experience fun through trivia, music, and even some groan-worthy jokes. Whether you're a hardcore Parrothead or just casually familiar with Buffett's music, people say the tour brings his story to life by visiting the actual spots that inspired his songs. The inclusion of key lime pie and margaritas along the way doesn't hurt either. Jessica also earns praise for her guiding skills, impressing even self-described Buffett experts. The Hemingway-focused tours get equally enthusiastic responses, with guides described as knowledgeable storytellers who share details you'd miss on a self-guided visit. The famous six-toed cats are a highlight for many visitors. Groups of all ages seem to enjoy these experiences, and the company apparently runs tours even for just two people, which one couple especially appreciated. A few practical notes: arrive early since parking can be tricky, and at least one reviewer mentioned cash-only payment. The food served on tours consistently gets compliments. Overall, this appears to be one of those experiences that becomes a trip highlight, whether you're diving deep into literary history or living that laid-back Margaritaville lifestyle.

    What people are saying

    Review 1 of 5
    5/5

    We had the most wonderful Hemingway tour with Caleb! My husband and I came down for his 40th birthday for the full Hemingway Experience in Key West and were so excited for this walking tour! Caleb was so knowledgeable, friendly, and made the entire experience absolutely fantastic and memorable! We especially appreciate the tour still running even though it was just us two - we can’t wait to come back!!

    Photo of Caitlin Fort

    Caitlin Fort

    March 25, 2025

    Review 1 of 1
    5/5

    We had the most wonderful Hemingway tour with Caleb! My husband and I came down for his 40th birthday for the full Hemingway Experience in Key West and were so excited for this walking tour! Caleb was so knowledgeable, friendly, and made the entire experience absolutely fantastic and memorable! We especially appreciate the tour still running even though it was just us two - we can’t wait to come back!!

    Photo of Caitlin Fort

    Caitlin Fort

    March 25, 2025

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