Ultimate Guide to the Most Fun Pub Crawls in Key West

Considering a trip to Key West? Then you’ve got to check out the local pub crawls. If you’re imagining wild, boozy nights that leave you regretting your decisions the next morning—not so fast. Key West pub crawls aren’t just about drinking. They’re about adventure, history, great drinks and great company.

Sure, you’ll sip on some tasty tiki cocktails, but you’ll also discover secret spots, learn new things, and possibly leave with some unforgettable stories. Sound fun? Let’s take a closer look at some of the most unique and exciting pub crawl options in Key West.

Pub Crawls Are More Than Just Drinks

When many people think “pub crawl,” they imagine chaotic nights and pounding headaches. But in Key West, pub crawls are a whole vibe. They’re lively, creative, and often come with bonus experiences like breathtaking views, fun souvenirs, and fascinating stories about this quirky island.

Whether you’re here to meet new friends, experience local culture, or just enjoy cocktail creations you won’t find anywhere else, Key West offers unforgettable adventures for every type of traveler.

Featured Pub Crawls and Cocktail Tours

Here are three incredible pub crawls you can book today, each offering a distinct (and totally Key West) experience.

1. Up the Keys Tiki Bar Crawl

Perfect for: Groups, bachelor/bachelorette parties, wedding celebrations

Forget walking—this crawl takes the party on the road! The Up the Keys Tiki Bar Crawl is a van-based tour that whisks you away to three of the best tiki bars in the Upper Keys.

Here’s why this crawl rocks:

Dress up for fun: Every guest gets flower leis and grass skirts. Lean into the tiki vibes!
Special pricing: Each stop offers exclusive deals just for tour members.
Scenic travel: The van ride itself is part of the fun, with stunning views as you coast your way through paradise.

When: Mondays, Wednesdays, and Fridays from 2 PM to 6 PM.

Whether you’re traveling with your crew or celebrating something special, this crawl is guaranteed to be an epic (and Instagram-worthy) time.

2. Key West Craft Cocktail Crawl

Perfect for: Foodies, cocktail enthusiasts, and history lovers

For a more intimate and educational experience, the Key West Craft Cocktail Crawl is your go-to. This walking tour through Old Town marries the art of mixology with fascinating local history.

Here’s what to expect:

Cocktails and snacks: Enjoy five unique craft cocktails paired with two delicious food tastings.
Hidden gems: Discover spots you’d never stumble upon on your own. You’ll leave with new favorite hangouts.
Insider tips: Your expert local guide has all the best recommendations for food, drinks, and activities. Ask away!
Non-drinkers welcome: Prefer to skip the booze? A non-alcoholic ticket option is available, but you’ll need to be 21+ to join.

Duration: 3 hours

Fun fact? Many past guests say they’ve been inspired to recreate their favorite drinks from this tour at home. It’s the gift that keeps on giving!

3. Hemingway Experience Tour

Perfect for: Literature buffs, rum lovers, and cultural explorers

Take a walk in Hemingway’s legendary (and slightly boozy) footsteps with this incredible tour from Key West Food Tours.

Why it’s unforgettable:

Hemingway House: Begin with a guided tour of Hemingway’s iconic Key West home, complete with its famed six-toed cats.
Cuban vibes: Enjoy a traditional Cuban meal and a slice of mouthwatering key lime pie.
Rum + cigars: Sip Hemingway-inspired rum drinks and learn about cigar making at a historic cigar factory.
Handcrafted cocktails: Try three different drinks, each tied to Key West’s cultural roots.

Duration: 4 hours

If you’ve ever idolized the legendary author or just love the artsy dives he frequented, this tour is an absolute must.

A Few More Fun Recommendations

Looking for even more ways to mix cocktails with exploration? Check out these additional experiences.

Sunset Tours – Because cocktails + sunsets = magic ✨
Haunted Pub Crawls – Spooky stories, creepy vibes, and boozy fun.
Bike Tours – For the active drinkers who want to earn their calories.

And don’t forget, every experience feels fresh depending on the timing, group vibe, and your mood. Even if you’ve done a pub crawl before, you’ll likely discover something brand new!