Key West Bars

09/17/2026

Best seat in the house: front-row access to the beautiful chaos of Key West.
Grab a drink, claim a chair, and watch Duval do what Duval does best, deliver a new character, story, or questionable outfit every 30 seconds.

09/16/2026

An itinerary is useful until the music is good, the drinks are cold, and a local says, “You should see the next place.” Then it becomes a loose suggestion with excellent potential.
Key West rewards flexibility and a friend who does not panic when dinner plans become a sidewalk discussion. Tag your favorite spontaneous travel planner.
KEY WEST CHECK-OUT TIME IS A SUGGESTION. THE BAR STAYED OPEN.
I DIDN'T LOSE MY ITINERARY. I UPGRADED TO ISLAND TIME.

09/15/2026

WHERE AM I? Key West Bar Edition
Clues: a cold b**r, a hot dog with mustard, a bowl of peanuts, and enough photos on the wall to fill a lifetime of island stories.

Think you know this legendary little spot? Drop your guess below—no Googling!

09/15/2026

I didn't learn this Duval Street survival trick until way too late.
Save your vocal cords and your sanity with one simple rule.
You haven't really arrived in Key West until you've heard a cover band blow the roof off
Sloppy Joe's.
But here is the secret.
Don't try to have a deep conversation while the band is playing.
Just nod, smile, and order another cold b**r.
It is the easiest way to survive the noise without losing your voice.

What is your favorite song to hear a cover band play at Sloppy Joe's?

09/14/2026

Pink on the outside, pure Key West on the inside—Harpoon Harry’s is the kind of place that makes you slow down, grab a seat, and order like you have nowhere else to be.

Breakfast, lunch, dinner, or a well-earned drink… what are you ordering at Harpoon Harry’s?

09/13/2026

Happy Hour is Calling !!! The White Tarpon

09/13/2026

September lineup at Schooner Wharf Bar

Friday vibes are in full swing at Schooner Wharf Bar 🎶🌴🍹

Kick off the weekend the Key West way with live music, cold drinks, waterfront views and that laid-back island atmosphere we all love.

Grab your crew, pull up a seat and enjoy live music all day and into the night at the Historic Seaport. ⚓️🎵

There’s no better place to spend your Friday in Key West!

09/13/2026

Game day buffalo pizza Seaside Cafe at the Southernmost House

Buffalo Chicken Pizza. The real MVP of game day. 🏈🍕

Loaded with crispy chicken, light garlic purée and our basil three-cheese blend over a creamy sauce, then finished with house-made buffalo and ranch sauces. Catch the game at Seaside Café with ocean views, ice-cold drinks and a wood-fired favorite worth cheering for! 🏆🔥

09/13/2026

Happy Sunday at Harpoon Harry's !

Sunday plans: Good food, good company, and a table for two at Harpoon Harry’s! ❤️Happy Sunday, Key West!