Key West Bar Crawl – Cocktails
Explore hidden watering holes with a fun local guide leading the way. You’ll sip craft cocktails—including a flaming TIKI drink—swap stories, share laughs, and leave with new friends, a buzz, or both.
Full refund with 24-hour notice
$79 /Adult
Find the Bars You’d Never Walk Into
This afternoon bar crawl takes you off the beaten path to the best local bars in Key West. With a local guide leading the way, you’ll enjoy creative drinks, hear fun stories about the island, and relax in hidden spots far from the usual tourist crowd.
Perfectly timed for an afternoon adventure, this tour leaves you plenty of time to enjoy the rest of your day. Whether it’s the flaming cocktail, the group laughs, or the discovery of a new favorite bar, you’ll leave with memories and a smile.
- Hidden Bars: Visit local watering holes you’d never stumble upon on your own.
- Unique Drinks: Including a flaming cocktail that’s as fun to watch as it is to drink.
- Lively Local Stories: Tales and fun history from your guide as you explore.
- Make New Friends: Bond with your group over drinks and shared stories.
- Convenient & Relaxed: Perfect for an afternoon adventure, less than one mile from port.
Relax and Socialize with Your Group
With a small group and a guide who knows where to go, this tour gives you an insider’s look at the best bars and drinks Key West has to offer.
3 hours
Tours run daily between 3pm and 4pm
Rain or shine
Small bites & 5 drinks
1 mile of easy walking
Adults only (21+)
Analise Andrews
Analise Andrews, Owner & Founder
Analise Andrews, Owner & Founder
I’m always back in my grandmother’s kitchen in Key West.
When I think about the best memories of my childhood, it’s the smell of fresh Cuban bread. Or, the sound of my grandmother’s laugh as she told me stories about being a little girl in Cuba.
There’s something else she did too, she made every meal feel like a celebration.
And that, is a big part of who I am today.
Food isn’t just something you eat; it’s a bridge to understanding people and culture. The community, the chefs, the artists — they’re all here in our food.
I thank you for letting me share my love for Key West with you.
Sincerely,
Analise Andrews
Analise Andrews
Owner & Founder
Frequently Asked Questions
Stop 1 – Choice of 3 cocktails
Stop 2 – Hemingway Rum Daiquiri
Stop 3 – Rum Runner or Craft Beer
Stop 4 – Choice of 3 cocktails
Stop 5 – Choice of 3 cocktails
Wearing a shade hat will greatly improve your experience! While we will be in the shade the majority of the tour, the Key West sun is very intense. Comfortable shoes, sunscreen, sunglasses, and a healthy appetite too. Bonus points if you bring a camera and share your shots with us!
Cancellations are fully refundable up to 24 hours before your tour. Within 24 hours, a 50% refund applies. No-shows are non-refundable—come on, we plan ahead! All of your food has already been accounted for by the restaurants, so we still have to pay them for your plate.
Yes, parking information is included in your confirmation email and tailored to your tour’s starting point.
Your ticket price includes the cost of the food and vendor gratuities associated with your meal.
Your tour ticket does NOT, however, include tour guide gratuities. If you enjoyed yourself, gratuities are greatly appreciated and accepted by your tour guide, although never mandatory. The standard gratuity for a tour guide in the service industry is 15%-20% the cost of your ticket.
Yes, bathrooms are available at most stops along the way.
No. Only guests 21 years and older with valid ID are allowed on the Cocktail Crawl.
Most tours can accommodate wheelchairs and strollers, but please contact us ahead of time to confirm specific needs.
Tours go on rain or shine! The good news? You’ll be dining inside for most stops. Seating is reserved and set aside at each restaurant, so the rain will only affect short walks between stops—not your enjoyment of the meals.
The Southernmost Tour – 1.5 miles.
The Historic Seaport Tour – 1.5 miles.
The Cocktail Crawl – 0.5 miles.
Insider’s Hemingway Experience – 1 mile.
However, all tours have frequent stops and walk an average of four blocks in-between each stop. The island is flat, and we walk at a very moderate pace.
Stop 1 – Choice of 3 cocktails
Stop 2 – Hemingway Rum Daiquiri
Stop 3 – Rum Runner or Craft Beer
Stop 4 – Choice of 3 cocktails
Stop 5 – Choice of 3 cocktails
Wearing a shade hat will greatly improve your experience! While we will be in the shade the majority of the tour, the Key West sun is very intense. Comfortable shoes, sunscreen, sunglasses, and a healthy appetite too. Bonus points if you bring a camera and share your shots with us!
Cancellations are fully refundable up to 24 hours before your tour. Within 24 hours, a 50% refund applies. No-shows are non-refundable—come on, we plan ahead! All of your food has already been accounted for by the restaurants, so we still have to pay them for your plate.
Yes, parking information is included in your confirmation email and tailored to your tour’s starting point.
Your ticket price includes the cost of the food and vendor gratuities associated with your meal.
Your tour ticket does NOT, however, include tour guide gratuities. If you enjoyed yourself, gratuities are greatly appreciated and accepted by your tour guide, although never mandatory. The standard gratuity for a tour guide in the service industry is 15%-20% the cost of your ticket.
Yes, bathrooms are available at most stops along the way.
No. Only guests 21 years and older with valid ID are allowed on the Cocktail Crawl.
Most tours can accommodate wheelchairs and strollers, but please contact us ahead of time to confirm specific needs.
Tours go on rain or shine! The good news? You’ll be dining inside for most stops. Seating is reserved and set aside at each restaurant, so the rain will only affect short walks between stops—not your enjoyment of the meals.
The Southernmost Tour – 1.5 miles.
The Historic Seaport Tour – 1.5 miles.
The Cocktail Crawl – 0.5 miles.
Insider’s Hemingway Experience – 1 mile.
However, all tours have frequent stops and walk an average of four blocks in-between each stop. The island is flat, and we walk at a very moderate pace.
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