Key West: Craft Cocktail Crawl & Food Tastings Off Duval

Summary

Key West flavors and stories in every glass with locals

You’ll sip five unique cocktails in real Key West bars (not just tourist spots), taste spicy bites and fresh tacos between stops, and hear stories from a guide who knows everyone by name. Expect laughter, new friends, and maybe a recipe or two you’ll want to steal for home.

What’s the experience like?

"You ever tried a Hemingway Daiquiri the way they make it here?" That’s how our guide, Jamie, kicked things off as we shuffled into the first bar—barely noon but already humid enough that my shirt stuck to my back. The place smelled like lime peel and old wood. I could hear someone laughing behind the bar, not at us (I think), just at something that happened before we walked in. Jamie handed us these cold glasses—pale pink, tart, not too sweet—and told us about Hemingway’s favorite haunts. I tried to picture him sitting right there, sweating through his linen.

The whole Key West craft cocktail crawl felt like weaving through someone else’s memories. We ducked off Duval Street after the second stop (the one with the cauliflower bites—spicy, crispy, weirdly addictive) and wandered into quieter neighborhoods where roosters strutted across cracked sidewalks. At one point I lost track of which drink we were on—maybe four?—but Jamie kept us moving and told stories about old bartenders and rum runners like she’d known them herself. She even taught me how to say “cheers” in Conch, which is…well, not actually a language, but she made us laugh trying.

I didn’t expect to like the locally-made beer as much as I did. It tasted kind of floral and salty at once—I guess that’s what happens when you’re surrounded by ocean air all day. There was a moment when we sat outside at our third stop and everything just slowed down: breeze in the palms, condensation sliding down my glass, someone playing guitar a block away. I still think about that view sometimes; it was nothing special but felt like exactly where I wanted to be.

By the time we finished with tacos at this spot Jamie swore had been on TV (“Diners, Drive-ins...something,” she said), nobody wanted to leave yet. A couple from Tampa swapped numbers with us; my partner tried to order another round but Jamie herded us gently toward the streetlights coming on over Caroline Street. So yeah—if you want a real Key West cocktail crawl with local bars and actual stories (plus food so you don’t wobble home), this is it.

Step-by-step itinerary

Day 1 — Key West craft cocktail and food tour

• Meet guide and check-in
• Visit first high-end bar and taste cocktail
• Visit second high-end bar and taste cocktail
• Visit third high-end bar and taste cocktail
• Experience tiki era flavors at fourth bar
• Enjoy taco at featured local spot

Top questions

How many drinks are included on the Key West craft cocktail crawl?

The tour includes five craft beverages: four cocktails and one locally-made beer.

Are food tastings part of this Key West cocktail crawl?

Yes, there are two food tastings: Asian cauliflower bites and a taco of your choice.

Does this tour visit only Duval Street bars?

No, most stops are neighborhood bars off Duval Street where locals go.

Is pickup included for this Key West cocktail tour?

No hotel pickup is included; guests meet at a central location 15 minutes before start time.

What is the group size for this cocktail crawl?

The group is limited to 12 people for a more personal experience.

Is this tour wheelchair accessible?

Yes, the tour is wheelchair accessible.

What if it rains during the tour?

The tour runs in all weather conditions; ponchos are provided if needed.

Are dietary restrictions accommodated?

You can advise dietary restrictions during booking in the Special Requirements field.

What’s included

Your afternoon includes five craft drinks (four cocktails plus one local beer), two food tastings—a spicy cauliflower bite and your choice of taco—plus all taxes and fees. You’ll be guided by an enthusiastic local who shares both stories and snacks as you stroll between lively bars off Duval Street in small groups of up to twelve people.