We go to Key West every year in the fall. It’s truly my happy place — great weather, easy days, and that little island feeling that only Key West has. It’s the Southernmost City in the continental U.S. and proudly calls itself the Conch Republic (a tongue-in-cheek “nation” from a 1982 protest). Roosters crow, six-toed cats nap at a famous author’s house, and every evening, everyone gathers for sunset. The island’s motto is “One Human Family,” and it shows. The best part? Key West is small — about 4 miles by 1 mile — so you can walk, bike, scooter, or grab a golf cart. If you only have a few days, you can accomplish a great deal. If you have more? Even better.
And oh yes — dining. There are no chain restaurants here. Everything is local, flavorful, and filled with personality. From pancakes under the trees with chickens to rooftop cocktails and decadent desserts, Key West is a foodie’s playground.
What can you do if you only have a few days? A lot. And if you’re lucky enough to have more? Even better. Who knows… MAYBE one day we can all visit Key West TOGETHER!!!
I have so much to say about Key West. Here are all the articles that will hopefully let you know more about this amazing tiny island:
Key West is packed with quirky, historic, and colorful attractions. For kicks and giggles, I’ve created an itinerary that I think would be fun for a short trip to Key West:
Sample Itinerary: 3 Days in Key West
Thursday – Welcome Evening
- Sunset Cruise: There’s no better way to kick things off than watching the sky melt into shades of pink and gold from the water. Hop aboard a classic Key West sunset cruise — picture gentle breezes, island music, and a toast as the sun dips below the horizon. It’s a relaxed way to meet everyone, swap introductions, and start our adventure on island time.
Friday – Old Town & Duval Street
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Morning:Start early at the Southernmost Point Buoy before the lines build, then wander through the Butterfly & Nature Conservatory, and continue on to the Hemingway Home & Museum.
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Lunch: Grab a casual bite at Garbo’s Grill, a FUN food truck with some of the best tacos and burgers in town…. And it’s located at Hank’s bar that has live music all day.
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Afternoon: Tour the Truman Little White House or the historic Key West Lighthouse (depending on interest). Then take a rest back at your hotel or rental — you’ll need it!
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Evening:
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5:00 pm Happy Hour at the Boathouse (or as early as 4).
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Stroll to Mallory Square for the nightly sunset celebration.
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After dark: Duval Street comes alive — bar hopping and late-night appetizers for those who still have energy!
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Saturday – Island Flavor & Exploration
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(Earlier) Morning: Coffee fix at Cuban Coffee Queen, a Key West must.
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Morning: Hop on the Conch Train or Old Town Trolley, with fun stops at the rum distillery, beaches or any of the other wonderful stops in Key West
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Lunch: Sit down at Pepe’s Café, a Key West institution since 1909. It’s cozy, quirky, and proudly calls itself “the oldest eating house in the Florida Keys.” You’ll find sandwiches, fresh seafood, and a laid-back local crowd. Prices are reasonable, and the history adds flavor to every plate.
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Afternoon: Guided bike or walking tour through the historic Key West Cemetery, then down to Fort Zachary Taylor for ocean views and shady trails.
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Dinner: Head off the beaten path to Geiger Key Marina & Fish Camp, a tucked-away waterfront spot with picnic tables under the palms. This is Old Florida charm at its best — casual, affordable seafood, live music on some nights, and incredible views across the backcountry waters. It feels like a secret escape, and the sunset here is just as magical as in town.
Sunday – Farewell Morning
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Breakfast: Wrap up with a leisurely brunch at Blue Heaven, famous for its roosters wandering the courtyard, towering slices of Key lime pie, and colorful Key West energy.
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Optional: Stroll Duval one last time, snap a few photos, or grab Cuban Coffee Queen to go before departures.
What do you think? Join me???
Here’s some other WONDERFUL articles about Key West!
So much to know about a tiny little island 
