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✈️ Travel

Key West Guide: The Ultimate Southernmost City Escape

Key West Guide
Walter Hennery·July 28, 2026·6 min read

Key West is quirky, colorful, and completely unlike anywhere else in the US. Here's how to experience the best of this island paradise.

Must-Do Experiences

  1. Southernmost Point Buoy: Photo op at the iconic buoy (line forms early)
  2. Mallory Square Sunset Celebration: Street performers, food vendors, stunning sunset
  3. Ernest Hemingway's House: Six-toed cats, tropical gardens, literary history
  4. Duval Street: 1.25 miles of bars, shops, restaurants
  5. Fort Zachary Taylor: Best beach on Key West, Civil War fort

Best Restaurants

RestaurantCuisinePriceMust-Order
Conch RepublicSeafood$$Conch fritters
Blue HeavenAmerican$$Key lime pie
El SiboneyCuban$Ropa vieja
Luke's KitchenSeafood$$Fresh catch
Bob'sSeafood$$Lobster bisque

Water Activities

  • Snorkeling at Fort Zachary: Best reef access on the island
  • Jet ski tour: Circle the island (3 hours)
  • Fishing charter: Deep sea or backcountry
  • Paddleboard: Calm waters, manatee sightings
The sunset rule: Get to Mallory Square at least30 minutes before sunset for a good spot. The celebration starts 2 hours before sunset and peaks right as the sun hits the water. Tuesday nights have the best street performers.
⚠️ Key West Tips:
  • Don't rent a car " — the island is3 miles long, bikes and scooters are better
  • Don't visit during Fantasy Fest (October) unless you're prepared for massive crowds
  • Don't skip theKey lime pie " — it's mandatory, not optional
  • Don't forget sunscreen " — the Florida sun is intense even on cloudy days
The bottom line: Key West is walkable, bikeable, and completely unique. Budget 2-3 days minimum. Must-dos: Southernmost Point, Mallory Square sunset, Duval Street, Hemingway's House. Best time: November-April (dry season). Expect to spend$150-250/day.