Insider’s Hemingway Experience

Explore Hemingway's Key West haunts while savoring local food, cigars, and rum on a four-hour guided walk

4.9 stars• 839 reviews

From$157/ person

Duration

4 hrs

Includes

Hemingway entry, Tastings, Guide

Highlights

Follow in Ernest Hemingway's footsteps on this guided Key West walking tour, sampling local food, drinks, cigars, and stories along the way. Gain entry to his historic home and enjoy curated tastings at iconic island spots.

Explore the Hemingway Home with included admission
Watch artisans hand-roll cigars at a family factory
Savor Cuban roast pork and iconic Key Lime Pie
Sip rum or non-alcoholic alternatives at Pilar Distillery
Receive a Hemingway Experience booklet packed with coupons

What's Included

Hemingway Home admission
Three food tastings
Three alcoholic or NA beverages

Things to Know

Tour operates rain or shine; wear comfortable walking shoes and sun protection. No pets allowed.

FAQs

Q: How much walking is involved?

A: The tour lasts about 4 hours and includes moderate walking between stops in Old Town.

Q: Are food and drinks included?

A: Yes. You get 3 tastings, 3 alcoholic drinks, a cuban meal, and Key Lime Pie.

Q: Do I need to bring anything?

A: Bring a camera phone, sun protection like a hat and sunscreen, and comfortable walking shoes.

Q: Is entry to the Hemingway Home included?

A: Yes. Your entrance to the Hemingway Key West Estate is part of the tour.

Q: Can guests with dietary restrictions join?

A: Some accommodations may be possible, but options are limited due to set tastings

Cancellation policy

Full refund for cancellations made at least 24 hours before departure. Cancellations within 24 hours receive a 50% refund; same-day bookings are non-refundable. Rescheduling within 24 hours costs $15 per ticket; free with more notice. No-shows are charged full price. Tours run rain or shine; if the operator cancels you may reschedule or receive a full refund.

Review summary

4.9

Excellent

839 reviewsGoogle Maps

If you're trying to decide whether a food tour is worth it in Key West, this one seems to hit all the right notes. The guides really make the experience. Larry gets mentioned over and over, with people praising his 26 years of local knowledge and the way he weaves history into the food stops with humor and passion. But it's not just him. Kayla, Corley, Kyle, Danielle, and Sara all get individual shoutouts for being knowledgeable, engaging, and genuinely fun to spend a few hours with. These aren't just tour guides reading from a script; they're locals who clearly love what they do. The food itself gets enthusiastic reviews, with generous portions that often leave people with leftovers. You'll hit multiple restaurants representing different aspects of Key West cuisine, from conch fritters to lobster mac and cheese to Cuban sandwiches and Key lime pie. Several reviewers mention this tour helped them discover spots they wouldn't have found on their own, especially first-time visitors who appreciated getting oriented to the island. The tours accommodate everything from intimate groups of two to slightly larger parties, and whether you choose the food tour or the craft cocktail crawl, people consistently leave feeling like they got their money's worth. The blend of eating, walking, and learning about the island's multicultural heritage (including interesting stops like cigar-making demonstrations) creates an experience that's more enriching than just hitting restaurants solo.

What people are saying

On Tuesday, January 21, 2025, my family and I joined the Key West Historic Seaport Food & Cultural Walking Tour, and it ended up being one of the most memorable highlights of our time on the island. The tour masterfully blended the rich flavors of Key West with its equally rich cultural heritage. As we strolled along the historic waterfront, we enjoyed a variety of fresh, locally inspired dishes—including creamy lobster mac & cheese, flavorful fish tacos, a perfectly seasoned Cuban pork sandwich, and of course, a slice of the iconic Key lime pie that was both tart and sweet—the perfect tropical treat. But this tour was more than just a feast. Our guide was engaging and knowledgeable, sharing fascinating stories about Key West’s seaport history, its culinary roots, and even its multicultural influences. One unique stop took us into the world of Cuban cigar-making, where we learned about the traditional process, the craftsmanship involved, and the cultural significance of cigars in Key West’s Cuban heritage. It was a hands-on, eye-opening moment that added depth to the experience. Along the way, we were treated to stunning waterfront views, and we even spotted some of the island’s local wildlife—tarpon swimming beneath the docks, iguanas lounging in the sun, and wild chickens roaming freely, adding a fun and quirky vibe to the tour. Each stop along the route felt authentic and thoughtfully chosen, highlighting the best of Key West’s food, culture, and charm. We left the tour full, happy, and with a deeper appreciation for the island’s past and present. If you're looking for a delicious way to explore Key West while soaking up history and local flavor, this tour is a must. It’s the perfect blend of food, fun, and cultural insight!