Key West: Old Town Food Walking Tour & Cuban Lunch

Summary

Key West food tour with Cuban flavors, local stories, and pie

You’ll walk through Key West’s Old Town with a local guide, tasting Cuban dishes at El Siboney, sipping rum at The Speakeasy Inn, and ending with real Key Lime Pie. Expect stories about the city’s history between bites, plenty of laughter, and enough food for lunch—plus those little moments you’ll remember later when you catch a whiff of lime or hear Spanish on the breeze.

What’s the experience like?

"Try the ropa vieja," our guide Maria said, sliding a plate across the table at El Siboney. The place smelled like slow-cooked onions and something tangy I couldn’t name. I’d barely sat down before she was telling us about her abuela’s recipe and how Cuban food became such a big part of Key West. There was this old guy in the corner sipping coffee and nodding along — maybe he’d heard it all before, or maybe he just liked the sound of Spanish in the air. The first bite was rich and salty, but then there was this bright citrus thing going on. I didn’t expect that.

We wandered off Catherine Street after lunch, ducking away from the crowds on Duval. Maria pointed out pastel houses with gingerbread trim while we tried not to look too much like tourists (impossible). At one stop — I think it was The Speakeasy Inn — we tasted rum that burned a little going down but left this caramel aftertaste. Someone in our group tried to say “salud” with a Southern accent and everyone cracked up, even Maria. She kept tossing in these bits of history about cigar rollers and shipwrecks; honestly, I only remembered half because I was distracted by the smell of frying fish from somewhere nearby.

By the time we reached our last spot for Key Lime Pie, my feet were getting tired but somehow there was still room for dessert. The pie had this tartness that made me squint at first bite — in a good way — and the crust was crumbly, almost salty-sweet. We sat outside under some faded umbrellas while Maria handed out coupons for places we’d passed earlier (I stuck mine in my pocket; who knows if I’ll use it). It rained for five minutes—just enough to make everything smell green—and then stopped like nothing happened.

Step-by-step itinerary

Day 1 — Key West food and cultural walking tour

• Meet at El Siboney, 900 Catherine Street
• Walk off Duval Street into historic neighborhoods
• Visit The Speakeasy Inn & Rum Bar

Top questions

How long is the Key West food walking tour?

The tour lasts around 3 hours from start to finish.

Is lunch included on this Key West food tour?

Yes, food tastings are enough for a hearty lunch during the tour.

Where does the tour start?

The meeting point is El Siboney at 900 Catherine Street in Key West.

How many stops are there on this walking tour?

You’ll visit 5 locally-run establishments plus one stop for an alcoholic drink.

Is this walking tour wheelchair accessible?

Yes, all areas and transportation options are wheelchair accessible.

Are children allowed on this tour?

Yes, children ages 12 and under must be accompanied by an adult; infants not eating don’t require a ticket.

What happens if it rains during the tour?

The tour runs rain or shine; ponchos are provided if needed.

Does the tour include drinks?

You’ll get water at every stop plus one alcoholic beverage during the experience.

What’s included

Your day includes five generous food tastings (enough for lunch), one alcoholic drink, water at each stop, exclusive coupons for local shops along the route, all led by a friendly local guide as you stroll 1.2 miles through historic Old Town Key West—rain or shine.