Walk Key West’s Hemingway haunts with three food tastings
2 hours
Guide, walking tour, tastings
Meet your guide at the front gate of The Hemingway Home and Museum and follow Hemingway’s Key West footsteps. Walk to places where he lived, worked, and spent time, with tastings along the way.
Please arrive 15 minutes before your tour start time. Tours run rain or shine. Gratuities are appreciated; standard tips for excellent service are 20%.
Full refund with 24 hours notice of cancellation. No-shows will be charged the full price. Full refund if the operator cancels due to weather or other unforeseen circumstances. Exclusions apply to Private Tour Cancellations.
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.
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.
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.
Outside the front gate of the Hemingway House ( 907 Whitehead St.)
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.
Had a great time!!! Our tour guide JP was very entertaining and knowledgeable about Jimmy Buffett and the places he frequently visited and stayed. Definitely recommend if you are a Parrothead. Like it states when you book the tour, it is a lot of walking, but JP always made sure we stayed together and didnt get separated.
Karl Seghorn
January 9, 2026
Had a great time!!! Our tour guide JP was very entertaining and knowledgeable about Jimmy Buffett and the places he frequently visited and stayed. Definitely recommend if you are a Parrothead. Like it states when you book the tour, it is a lot of walking, but JP always made sure we stayed together and didnt get separated.
Karl Seghorn
January 9, 2026