First Time in Key West Itinerary

Key West offers a unique blend of history, culture, natural beauty, and fun activities that make it a must-visit destination for anyone traveling to Florida. If it’s your first time visiting Key West, check out our First Time in Key West Itinerary that we put together and loved! (Pro tip: I used a digital planner to help me plan my trip. I recommend the Key2Success Planner, here.)

key west mural

There are many reasons why you should visit Key West! Here are just a few:

  1. Beautiful weather: Key West has and some of the coolest coral reef beaches in the world. You can spend your days swimming, sunbathing, and enjoying the ocean breeze.
  2. History and culture: Key West has a rich history and a unique culture that’s unlike anywhere else in the United States. You can explore historic landmarks like the Ernest Hemingway Home and Museum, the Key West Lighthouse, and the Harry S. Truman Little White House. Our First Time in Key West Itinerary includes all of these places. Don’t miss the chickens!
  3. Outdoor activities: Key West is a paradise for outdoor enthusiasts, with opportunities for fishing, kayaking, snorkeling, and diving. You can also take a sunset sail or go on a dolphin watching tour.
  4. Nightlife: Key West is known for its lively nightlife, with plenty of bars, restaurants, and live music venues to choose from. Whether you’re looking for a relaxing evening or a night of partying, you’ll find it here.
  5. Stunning sunsets: Key West is famous for its breathtaking sunsets, which you can enjoy from the beach, on a sunset sail, or at a waterfront restaurant.

Our “Don’t Miss” List for Key West:

Here was our First Time in Key West Itinerary:

Day 1:

  • Travel Day, Arrive by Noon. We took a taxi from the airport in Key West to our lodging (The Grand Guesthouse) and rented bikes right from the hotel. Highly recommend doing this as a great way to get around!
  • Lunch @ El Siboney Restaurant (900 Catherine St.) for authentic Cuban food
  • Snack at Kermit’s Key West Key Lime Shoppe (200 Elizabeth St)
  • Truman White House (111 Front St)
  • Dinner @ Conch Republic Seafood Company (631 Greene St) Daily Happy Hour from 4-7pm or Sunset Pier
  • 5:30pm – Sunset Celebration at Mallory Square (Sunset is at 6:16pm) (Every First Time in Key West Itinerary should include this!)
  • A Great photo opportunity is the “WELCOME TO KEY WEST” postcard mural located behind Cuban Coffee Queen on Margaret Street (284 Margaret St to be exact). While there, sample some Cuban coffee and grab some cheap souvenirs at the cute shops next door.
butterfly conservatory key west
Key West Butterfly Conservatory

Day 2:

  • Sunrise @ Edward B. Knight Pier
  • 8:30am – Southernmost Point (do this first before it gets crowded) (1400 Whitehead St)
  • 9:00am – Hemingway Home (907 Whitehead St) The six-toed cats were the best!
  • 10:45am – Mile Marker 0 (501 Whitehead St)
  • 11:00am – Lunch @ DJ’s Clam Shack (629 Duval)
  • 12:00pm – Hemingway Rum Company (201 Simonton)
  • 1:00pm – Key West Cemetery (Grab a map on Passover lane off Windsor)
  • Dinner @ Seaside Cafe at the Mansion (1400 Duval)
  • Sunset at 6:17pm
  • Explore Duval Street at night – Check out Sloppy Joe’s – WEBCAM
Key West Hemingway Cat
Hemingway Cat

Day 3:

  • 10:00am – Key West Lighthouse (938 Whitehead)
  • 11:00am – Lunch @ Blue Heaven (729 Thomas Street)
  • 12:00pm – Go to the beach (Zachary Taylor Park) (bike) (601 Howard England Way)
  • 5:00pm – Two Friends Patio (Duval)
  • Sunset at 6:17pm
Key West Cemetery
Key West Cemetery

Day 4:

  • 10:00am – Butterfly and Nature Conservatory (1316 Duval) – this is the most magical place I’ve ever seen!
  • 1:15pm – Flight home (Be sure to get to the airport early as security can take a while during busy times.)


Key West Southernmost Point
Southernmost Point

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