Hemingway Food and Walking Tour in Key West

The apartment where he finished "A Farewell to Arms," the boat he kept, the bar where he drank.

A guided walking tour of Key West that traces Ernest Hemingway's life through the actual places he lived, worked and played (his first apartment, where his boat the Pilar was kept, boxing venues he frequented, and Sloppy Joe's bar) with three food tastings (grilled chicken caesar wrap, bean salad with mango poppy dressing, and key lime pie) woven through the route. The tour runs two hours with a live English-speaking guide and covers the bookstore where his books were sold, the Key West Harbor where he fished and chartered boats, and numerous other historical sites he frequented.

Step-by-step itinerary

Hemingway sites and food tasting

• Meet guide at Hemingway House
• Visit Hemingway's boxing match locations
• See where Hemingway kept his boat Pilar
• Stop at bookstore selling Hemingway's books
• Visit Hemingway's first Key West apartment
• Enjoy lunch and key lime pie
• Visit train, fishing, and boat charting sites
• Visit Sloppy Joe's bars
• See other Hemingway historical sites

The experience

You meet your guide outside the Hemingway House and walk from there through the neighborhoods and landmarks that shaped his years in Key West. The route takes in the boxing venues where he watched and refereed matches, the dock where he kept the Pilar, the bookstore that sold his work, and the first apartment where he finished writing one of his most famous novels. The walking unfolds at a moderate pace across two hours, moving between the old town streets and the harbor.

Food comes woven into the route rather than bundled at the end. You'll have a grilled chicken caesar wrap and a bean salad with the famous mango poppy dressing at stops along the way, then a slice of key lime pie before heading to the harbor. That sequence lets you taste the local food culture while the guide connects each place to Hemingway's actual life there, where he fished, where he took the train, where he chartered boats.

The tour ends at Sloppy Joe's, the original bar and its successor location, where Hemingway spent considerable time. By then you've walked the real geography of his Key West rather than read about it, and the guide has placed each stop in the context of what he actually did there. Public transportation options are nearby if you need them after the tour finishes.

What’s included

• Three food tastings (grilled chicken caesar wrap, bean salad with mango poppy dressing, and key lime pie).
• a live English-speaking guide for the full two-hour walk.
• access to the real locations where Hemingway lived, worked and spent his time in Key West, including his first apartment, the bookstore where his books were sold, the dock where he kept his boat the Pilar, boxing venues, the Key West Harbor, and Sloppy Joe's bar.

Before you book

Days and timesEvery dayDeparts at 09:30

Book up toStart time

AgesAdult (13 and older) · Child (6 to 12 years) · Infant (under 6): free

GroupUp to 15

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends at a different place from where it starts.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated yesterday

Good to know

Moderate physical effortPublic transport nearbyNot recommended with heart problems

Operated by Hemingway in Key West Tours

Is this one for you?The tour covers two hours of walking at a moderate pace through Key West's streets and harbor, so it suits travelers who are comfortable on their feet and want to move through the actual geography of Hemingway's life rather than stay in one place. If you prefer shorter walks or have cardiovascular concerns, this route will feel demanding.

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Top questions

Can children come?

Yes. Ticket types: Child (6 to 12 years); Infant (under 6): free.

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

What food do I get to eat on the Hemingway walking tour in Key West?

Three tastings are included: a grilled chicken caesar wrap, a bean salad with mango poppy dressing, and a slice of key lime pie. They're served at different points along the route rather than all at once.

Where does the Hemingway tour start and what is the first place you visit?

You meet your guide outside the front gate of the Hemingway House, which is where the tour begins. From there you walk to the real places he lived and worked throughout Key West.

Does the tour include Sloppy Joe's bar?

Yes. Sloppy Joe's is the final stop on the tour. You visit both the original bar and its second location, where Hemingway spent a lot of time drinking.

How long is the walking tour and how much walking is involved?

The tour runs two hours total. It covers multiple neighborhoods and sites across Key West at a moderate walking pace, so you should have at least a moderate level of physical fitness to comfortably complete it.

What was Hemingway's boat and where do you see it on the tour?

The Pilar was Hemingway's boat. The tour takes you to the dock where he kept it in Key West Harbor, one of several stops connected to his life on the water.

Is there a guide on this tour and what language do they speak?

A live guide leads the entire tour and speaks English. They provide context about each location and Hemingway's connection to it as you walk.