Drinking in Key West can mean very different things depending on where you end up. There are bars with decades of stories behind them, live music spilling onto Duval Street, tiny rooms that still feel like Old Key West, and waterfront spots where the view is as much the point as the drink.

You could spend an entire trip attempting to work through the island’s bar scene. I wouldn’t. These are the places I’d put on the list instead — some for the history, some for the atmosphere, and a few simply because I genuinely like being there.

Captain Tony’s Saloon

BEST FOR · KEY WEST HISTORY

If I were choosing one historic bar to make sure you see, Captain Tony’s would be high on the list.

The building itself has lived several lives, and there’s something to look at in nearly every direction — old photographs, memorabilia, and dollar bills covering the walls and ceiling, many signed by visitors who wanted to leave a little piece of themselves behind. This was also the original home of Sloppy Joe’s before that name moved to Duval Street.

It’s dark, eccentric, and unmistakably Key West. Even if your plans don’t involve a full afternoon of bar hopping, it’s worth stepping inside.

→ Best for: A drink surrounded by some of the island’s best bar lore.

Chart Room

BEST FOR · OLD KEY WEST

Hidden inside Pier House, the Chart Room feels almost like a secret compared with the bars a few blocks away on Duval Street.

It’s small, dark, and wonderfully old-school, with a history tied to some of Key West’s most recognizable characters. Jimmy Buffett played here during his early days on the island, and over the years the bar became a gathering place for local writers, artists, sailors, treasure hunters, and plenty of other Key West personalities. The room has retained the kind of character that would be difficult to recreate intentionally.

This is one I have a particular soft spot for after staying at Pier House several times. Order a drink, grab some popcorn — and if you know, you know: don’t pass up the hot dogs. It’s not where I’d go for a big night out. It’s where I’d stop when I want Key West to feel like Key West.

→ Best for: A quieter drink, a little island history, and one of my favorite corners of Key West.

Sloppy Joe’s

BEST FOR · THE CLASSIC DUVAL EXPERIENCE

Sloppy Joe’s is famous, busy, loud, and firmly on the tourist circuit. I’d still go.

Its history is intertwined with Ernest Hemingway and the Key West of the 1930s, although the present-day bar occupies a different location from the original. Today, expect live music, crowds, and a much bigger production than some of the island’s smaller historic bars.

You don’t need to spend the entire night here to understand why it has become such a Key West institution. Stop in, order a drink, listen to the band, and consider the box checked.

→ Best for: Experiencing one of Key West’s most famous bars at least once.

Irish Kevin’s

BEST FOR · LIVE MUSIC & A ROWDY NIGHT

Irish Kevin’s is not where you go for a quiet pint.

It’s energetic, irreverent, and built around live entertainment, with performers who tend to make the audience part of the show. Located right on Duval Street, it’s an easy place to wander into for one drink and discover considerably more time has passed than planned.

As someone who will almost always investigate an Irish pub while traveling, this one earns its place on my Key West list.

→ Best for: Live music, a lively crowd, and embracing the Duval Street version of Key West.

Celtic Conch Public House

BEST FOR · THE OTHER IRISH PUB

Yes, I’m putting two Irish pubs on the list.

Celtic Conch has a different feel from Irish Kevin’s — more pub than performance, and an easy place to stop when you want a drink without committing to the full Duval Street spectacle.

The combination of Irish-pub familiarity and unmistakably Key West surroundings works surprisingly well, and it has become another stop I’m happy to make when I’m on the island.

→ Best for: A more relaxed pub stop when you still want to be close to the action.

Green Parrot Bar

BEST FOR · LIVE MUSIC WITHOUT THE DUVAL STREET FEEL

A few blocks away from the busiest stretch of Duval, Green Parrot has been part of Key West for generations.

The building began as a grocery store before becoming a bar, and today live music is central to the experience. It feels less polished and less interested in being a tourist attraction than some of the island’s most famous names — which is part of the appeal.

Check who’s playing, walk over, and see where the night goes.

→ Best for: Live music and a Key West institution beyond the busiest blocks of Duval.

Schooner Wharf Bar

BEST FOR · THE HARBOR

Schooner Wharf is the kind of place that makes the most sense when you’re actually sitting there.

Set along the Historic Seaport, it’s casual, open-air, and surrounded by boats. There’s frequently live music, but the marina setting is what separates it from the bars farther inland.

Come during the day or around sunset, grab a drink, and stay awhile if the music is good.

→ Best for: A casual waterfront drink with boats, live music, and plenty to watch.

Sunset Pier

BEST FOR · DRINKS WITH A VIEW

Not every Key West drink needs to happen inside a historic bar.

Sunset Pier at Ocean Key Resort sits directly on the water near Mallory Square, with colorful tables, live music, and a front-row view as the sun goes down. It’s hardly an undiscovered sunset spot, but the location earns the crowd.

I’d come here for the setting rather than treating it as a nightlife destination — preferably early enough to get settled before sunset.

→ Best for: Turning one of your Key West sunsets into cocktail hour.

If You Only Have One Night

Trying to cover Key West’s bar scene in a single evening is unnecessary. Instead, I’d use the walk itself to see a few different sides of it.

Start around the Historic Seaport with a waterfront drink, then make your way toward Old Town. Stop at Chart Room or Captain Tony’s for the history, continue to Sloppy Joe’s to see the classic Duval Street scene, and finish wherever the music sounds best.

That gives you the harbor, Old Key West, and Duval Street without turning the night into a checklist.

Continue Planning Your Key West Trip

There’s more to plan beyond where to have a drink. Start with these guides to staying, eating, and getting to know Key West.

• A First-Timer’s Guide to Key West

• Where to Stay in Key West

• Where to Eat in Key West

From The Edit

Key West nightlife is much more interesting when you pay attention to the rooms you’re drinking in.

Some of these places have been collecting stories for generations; others are simply very good at delivering the loud, slightly ridiculous night that Key West occasionally calls for. I wouldn’t try to choose between the two.

Go to Captain Tony’s for the history. Sit in the Chart Room and imagine the Key West that existed before you arrived. Have a night when Irish Kevin’s sounds like an excellent idea. And at least once, order a drink somewhere by the water and stay through sunset.

That mix is much closer to the Key West I keep coming back to.