Coolest Bars in Key West - Best Pub Crawl

I've chosen my favorite unique bars for this bar walk. This route will take you across the whole island from north to south. You can start by dipping your toes in the Gulf of Mexico and finish by wading in the Florida Straits. The walk is just under 2 miles one way and will introduce you to a range of awesome bars in Key West, from beachy vibes to more sophisticated spots. Let's get started!

Lagerhead's Beach Bar is a super casual spot nestled right on the beach—it's a true piece of paradise! You can order from the beach shack and then kick back and enjoy the stunning views. This beach bar oasis boasts breathtaking waterfront scenery, lively afternoon entertainment, Cuban-inspired cuisine, and an amazing spot to catch the sunset.

Lagerhead's Beach Bar

Next stop is one of Key West's most legendary bars - the Chart Room at the famous Pier House Resort & Spa. Originally this space was just another guest room in this 50-room hotel until it was transformed into this cozy watering hole in 1967. Local legends like Mel Fisher and Jimmy Buffet were often spotted belly up to the bar. Jimmy Buffet was known to play his music here in exchange for free drinks. Loaded with memorabilia, vintage photos, and yes actual patrons' ashes embedded into the bar itself, its a great place to stop in and soak up some of Key West's unique history. Don't miss out on the complimentary popcorn, peanuts and hot dogs that have been offered to visitors for decades.

Chart Room Bar at The Pier House Resort & Spa

Next up, you'll head over to The Saint Hotel, which came about by combining the oldest running hotel, The Edgar House, with an old Memorial Hospital. The hotel and grounds are absolutely stunning! You can explore both heaven and hell in just one afternoon. Start by checking out The Tempt Burgundy Bar. It's decked out in red and gold, and you can pick from the Seven Deadly Sins cocktails.

Tempt Burgundy Bar

After indulging in one of the sin cocktails, you can cleanse yourself by heading straight up to the Halo Rooftop Lounge. You can sip on one of the Seven Heavenly Virtues cocktails while listening to live music and enjoying a great view above the always entertaining Duval Street. Daily happy hour is 4:17 p.m. - 7:14 p.m.

Halo Rooftop Lounge

Next up is 22&Co, probably the most cheerful, sparkly, and rainbow-filled bar you'll ever visit. The owner calls it a "dive bar for unicorns," so come on in and grab a seat on a tutu bar stool. Treat yourself to a dessert martini packed with glittery fun. My top pick? The Smooth Operator, a tasty peanut butter martini. You won't regret it!

22&Co

Keep heading south and you'll find The Orchid Key Inn. Just follow the orchid artwork through the parking lot, and you'll arrive at The Orchid Bar, a cozy and charming spot away from the hustle and bustle. This "cool-retro-meets-modern" bar is known for its creative and super fresh cocktails, with a menu that changes with the seasons. My favorite is the Grapefruit Martini!

Orchard Bar at the Orchard Key Inn

We’re wrapping up our bar adventure at the Four Marlins inside The Reach Resort. Aim to get there around sunset to soak in the amazing ocean views. Honestly, the view is breathtaking no matter when you go. Swing by for happy hour daily from 4pm to 5:30pm to snag some discounted drinks and appetizers.

Four Marlins at The Reach Resort

Here's the route - hope you enjoy checking out what I consider the best bars in Key West for cocktails!

Key West Best Bar Crawl