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Every man’s life ends the same way. It is only the details of how he lived and how he died that distinguish one man from another.

Ernest Hemingway

The Florida Keys are one of my favourite spots to travel in the United States. I recently shared my Florida Keys Travel Guide, a detailed guide of my best recommendations for where to stay, eat, and play in the five main Keys.

In today’s post, I’ve teamed up with Hotels.com to dig a little deeper into one of my favourite keys: Key West. 

Morning 

Your Key West adventure begins with the scenic drive through the Keys. Key West is approximately 128 miles, or a three-hour drive from the Miami Airport. If you leave from the airport first thing in the morning, you can plan to be in Key West by midday. The best part of the drive was no doubt the 7 Mile Bridge between Key Marathon and Bahia Honda Key.

Afternoon

When you reach Key West, you’ll likely have worked up an appetite from the drive, so stop in at Blue Haven, an iconic spot for Floridian-Caribbean cuisine, key lime pie, and live music. 

After lunch, it’s time to check in to your hotel. Key West is home to tons of great accommodations, but my favourites are The Laureate or The Gardens Hotel. The Laureate is an all-new, all-suite luxury Hotel with modern, luxurious accommodations and a prime bay front location. The Gardens Hotel is a quiet, adults-only bed and breakfast that’s perfect for a relaxing getaway in the Keys.

Evening

After checking into the hotel, head down to Duval Street to do some shopping and explore. Duval Street is the main drag of downtown, running north and south from the Gulf of Mexico to the Atlantic Ocean. Although it is not much more than a mile in length – this is where the heartbeat of the city comes to life with a diverse array of restaurants, shops, world famous pubs and attractions.

While you’re downtown, make sure to stop in at Ernest Hemingway’s house. Literary icon Ernest Hemingway is one of Key West’s best-known and well-loved “freshwater Conchs” (a resident who was not born on the island). His former home is located in Old Town and is now a U.S. National Historic Landmark that’s absolutely worth a visit during your time in Key West.

After an evening of shopping and sight-seeing, I recommend dinner at Spencer’s by the Sea, which is a restaurant located inside the gorgeous hotel property, The Reach Key West. Their beachside restaurant offers a perfect setting for a romantic dinner and their menu is full of delicious seafood dishes. When in Key West, it’s crucial to try authentic Key Lime pie, so make sure to save room for dessert!

Night 

Key West is famous for the sunsets, so after dinner head to Mallory Square to catch the sun dipping into the ocean. There’s a sunset party here every night. You can also opt to go on a sunset cruise and watch the sunset from the water.

End your night in Key West at the Green Parrot Bar. The Green Parrot is more than a bar; it is a Key West icon. The bar is open until 4AM 7-days a week and hosts a variety of creatives for live music, tattoo contests, and poetry slams. 


As travel today remains uncertain, please keep your safety and the safety of others in mind at all times. If you are comfortable with traveling, please travel responsibly and within regulation as any travel is at your own risk.