Quick Answer: Key West is quirky, colorful, and 100% unfiltered America with roosters roaming free, six-toed cats, and the best key lime pie on the planet. Sunset at Mallory Square is non-negotiable.

Key West: My Quirky Conch Republic

We walked off the ship straight into conch-town chaos — pastel houses, drag queens on bikes, and the smell of Cuban coffee everywhere. Rented bikes (best decision) and pedaled to the Hemingway House first. The polydactyl cats are as advertised (currently 59 of them), lounging on Papa's bed like they pay rent. The writing studio upstairs still has his typewriter — you can feel the ghosts of rum and genius.

Then Duval Street bar crawl on two wheels: Sloppy Joe's (get the original sloppy), Irish Kevin's for live music that makes you dance on tables, and finally the Green Parrot — dive bar perfection. Stopped at Kermit's for key lime pie on a stick dipped in dark chocolate — tart, cold, life-changing.

Southernmost Point buoy photo at 3 p.m. was predictably packed, but we waited 45 seconds and got our turn — worth it for the silly picture. Ended the day at Mallory Square for sunset: fire jugglers, sword swallowers, and that famous green flash as the sun dropped. The whole crowd cheered like we'd won something.

Food highlight: Cuban mixto sandwich at Sandy's Café — pressed roast pork, ham, Swiss, pickles, mustard — eaten on a stoop while a rooster judged us.

The pros: feels like nowhere else in the USA, and it's walkable or bikeable everywhere.

The cons: Duval gets rowdy at night (which is also a pro depending on your mood).

The Moment That Stays With Me: Sitting on the seawall after sunset, legs dangling above the water, eating that chocolate-dipped key lime pie while a busker played "Wagon Wheel" on a beat-up guitar and the sky turned cotton-candy pink.

Getting Around Key West

Walk or rent bikes for the day. Conch Train tour is fun if you're lazy.

Positively Worded Word of Warning

Roosters start crowing at 5 a.m. and Duval smells like last night's regrets by midnight — embrace the beautiful mess.

Frequently Asked Questions

Q: Worth it?
A: Always — even on a cruise.

Q: Best attraction?
A: Sunset at Mallory Square + Hemingway House.

Q: How long for Duval bar hop?
A: As long as your liver allows.

Q: Can you walk from port?
A: Yes — everything is 5–30 minutes away.

← Back to Ports Guide