Swanky and Snazzy

Jazz up the night in the venue that brings you musical stylings from all of the best talent down here in Key West. This place is a true gem. The bar crafts elevated cocktails. There is even a page on the cocktail menu featuring the favorite drinks of Frank Sinatra and other legends. The regular crowd is friendly and interactive, and the music is just top notch. The room is setup like a cabaret with the stage front and center featuring nightly shows that  "razzle dazzle 'em"! Very enjoyable.

821 Duval Street

(305)741-7515

www.littleroomjazzclub.com

Just a few steps off of Duval Street this upscale neighborhood hangout offers a full range of craft cocktails and great wines and beers. (Go ahead to the back and grab your own beer or wine and let the barkeep open it for ya...) The Roost is super casual but also refined and offers an elevated atmosphere with a fun mix local characters and visitors lounging in velvet chairs or perched upon its stools.  Charcuterie plates and other nibbles are prepared. Please stop in, the staff are lovely and they have created something special here.

508 Flemming Street

(305)294-2600

www.theroostkw.com

One of the greatest cocktail programs in town lives here on Caroline Street between Duval and Whitehead. This is a break from the Pina Coladas. With a speakeasy ambience and a great crowd any given night of the week, the mixologists and bartenders at General Horseplay really are an amazing team who offer guests an amazing time. They know their stuff and they have all of the ingredients to prepare you something that is glorious and indulgent. Out back there is a live music venue and it gets funky sometimes. A good time for sure.

423 Caroline Street

(305)741-7599

www.generalhorseplay.com

Tucked away inside the Pier House Resort, the Chart Room is one of Key West’s most iconic and off-the-radar bars. What it lacks in size, it makes up for in character—this cozy, no-frills spot is where salty locals, travelers, and legends like Jimmy Buffett once gathered before fame found them.

Don’t expect a menu or fancy cocktails—just strong pours, great stories, and a dive-bar vibe that hasn’t changed in decades. It’s a piece of old Key West that refuses to be polished. If you're looking to experience the island’s unfiltered charm and local lore, a visit to the Chart Room is a must.

1 Duval Street

(305) 296-4600

www.pierhouse.com/dining/chart-room-bar

Right on Duval Street and impossible to miss, Willy T’s is a Key West staple known for live music, cold drinks, and walls (and ceilings) plastered with thousands of signed dollar bills left by travelers from all over the world.

The vibe is casual, quirky, and full of energy—exactly what you’d expect from a bar in the heart of Old Town. There's live music daily, a big open-air patio perfect for people-watching, and a menu loaded with cocktails and bar bites to keep the fun going.

Willy T’s is one of those spots that captures the free-spirited, come-as-you-are essence of Key West.

525 Duval Street

 (305) 294-7674

www.williets.com

The Tipsy Rooster is a laid-back little bar with a big island attitude. Located at the corner of Simonton and South Street, it’s just a few blocks off Duval.

This open-air gem is a favorite spot for groups looking to gather, relax, and kick back without the crowd crush. With friendly bartenders & great music, it’s the perfect mix of local charm and good vibes.

Whether you're starting your crawl, escaping the Duval madness, or just want a casual spot to hang with friends, the Tipsy Rooster is that hidden-in-plain-sight hangout you’ll want to come back to.

1325 Simonton Street

(305) 295-5287

https://tipsyroosterkw.com