History to Happy Hour: 1 Day In Key West!

If you only have one day in Key West, this is the perfect way to experience it—from history to happy hour! We started with the Old Town Trolley Tour of Key West, the best sightseeing tour on the island, before diving into an iconic Duval Street bar crawl with some of the most famous bars in Key West.

00:00 Intro - 1 Day in Key West
00:50 Old Town Key West Trolley Tour Highlights
05:50 Walking Duval Street & More History
10:46 Sloppy Joe's Bar
15:00 Rick's
17:22 Flying Monkey's
19:50 The Original Margaritaville
23:25 Outro

🚌 Old Town Trolley Tour of Key West – The Old Town Trolley is the #1 way to see Key West in just one day. With 13 stops and unlimited hop-on, hop-off access, you’ll see highlights like Mallory Square, the Ernest Hemingway House, the Southernmost Point, and more. Tours run daily from 9am–4:30pm, and each ride includes live narration filled with fun Key West history and local stories.👉 Learn more: https://www.trolleytours.com/key-west

After exploring Key West history, we took things to Duval Street for a bar crawl you can’t miss in Key West nightlife:

🍻 Sloppy Joe’s – This world-famous bar was Ernest Hemingway’s favorite hangout. Today it’s the heart of Key West nightlife, offering live music, cold beer, and signature cocktails in a lively party atmosphere.

🎶 Rick’s - Known as the largest entertainment complex on Duval Street, Rick’s has 8 unique bars in one spot—from rooftop views to dance floors and live music. A must for any Key West bar crawl.

🍹 Flying Monkey Saloon – tIf you’re looking for frozen drinks, this is THE spot. With famous slushy machines serving frozen daiquiris, piña coladas, and margaritas, the Flying Monkey is a fun stop during any Key West pub crawl.

🌴 Jimmy Buffett’s Margaritaville – No trip to Key West is complete without stopping at Margaritaville, the legendary bar and restaurant inspired by Jimmy Buffett. Enjoy cheeseburgers in paradise, classic margaritas, and laid-back island vibes.

⭐ Whether you’re here for Key West sightseeing tours, Key West history, or Duval Street nightlife, this video shows how to make the most of one day in Key West Florida—from hopping on the Old Town Trolley to bar hopping at Sloppy Joe’s, Rick’s, Flying Monkey, and Margaritaville.

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