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A First Impression

 

Sometimes the best way to arrive somewhere is by water.

 

On this trip, we boarded the Key West Express ferry in Marco Island, Florida, a high-speed jet-powered catamaran that glides across the Gulf of Mexico before pulling into Key West’s colorful Historic Seaport. It’s a relaxed and scenic way to begin a visit, and the moment you step off the boat, you immediately feel that unmistakable Key West vibe — casual, sunny, and just a little bit quirky.

 

One of the first sights at the harbor is a statue of Henry Flagler, the man many credit with helping build modern Florida tourism. Flagler was one of the founders of Standard Oil alongside John D. Rockefeller, but after making his fortune in oil he turned his attention to developing Florida’s east coast.

 

Flagler built the Florida East Coast Railway, constructed luxury hotels like the Ponce de León Hotel in St. Augustine, and helped transform places like Palm Beach and Miami into destination resorts. His most ambitious project was extending the railway all the way to Key West via the famous Overseas Railroad, an engineering marvel that crossed the ocean on a series of bridges. It was a bold project that helped cement Key West’s place on the map.

 

Of course, history aside, the first order of business in Key West is often something a little simpler: a cold drink and some seafood.

 

We made our way to Dante’s Key West Pool Bar & Restaurant, a lively open-air spot known for its stone crab, poolside atmosphere, and boat drinks in every color imaginable. While enjoying the scene, we were introduced to some of the island’s most famous residents — the Key West chickens.

 

Chickens roam freely throughout the island. According to local lore, they were brought here by Cuban settlers in the 1800s for eggs and food, and cockfighting was also popular in both Cuba and the Florida Keys. When cockfighting was eventually outlawed, many of the birds were released. Today the chickens are protected and have become a quirky symbol of the island, wandering confidently through streets, patios, and even restaurants.

 

Key West is also famous for its legendary bar scene. Sloppy Joe’s and Hog’s Breath Saloon remain iconic stops along Duval Street, though some locals say they’re not quite what they once were. Meanwhile, The Green Parrot still holds its reputation as a longtime favorite for both locals and visitors, known for great live music and a laid-back atmosphere.

 

To explore the island, we rented scooters, which turned out to be one of the best ways to get around. Scooters make it easy to navigate the busy streets while also slipping into quieter back roads and residential neighborhoods that visitors might otherwise miss.

 

No visit to Key West is complete without stopping at the Southernmost Point in the continental United States, marked by the famous buoy just 90 miles from Cuba. Nearby you’ll also find Mile Marker Zero, the beginning of U.S. Route 1, which runs all the way up the East Coast to Maine.

 

After snapping a few photos, we grabbed lunch and a drink at the Southernmost Point Bar, where the atmosphere perfectly captures the relaxed rhythm of the island.

 

Later we visited the Key West Butterfly and Nature Conservatory, a beautiful tropical space filled with butterflies, birds, and lush plants — a peaceful break from the lively energy of Duval Street.

 

Another highlight of the day was Truman Waterfront Park, one of the most scenic areas on the island. Nearby sits the USCGC Ingham Maritime Museum, a historic Coast Guard cutter now serving as a floating museum. We enjoyed drinks aboard the ship while exploring the decks and exhibits.

 

Late in the day, we wandered through a small artist market near the waterfront, eventually picking up a small painting as a reminder of the trip. The day ended the way many great days do in Key West — watching one of the island’s famous sunsets, where the sky turns shades of orange, pink, and gold over the water.

 

The following evening, we joined a sunset catamaran cruise complete with food, cocktails, and live music. With the breeze off the ocean and the sun dropping below the horizon, it was the perfect way to wrap up a day in Key West.

 

From roaming chickens and historic railroads to scooters, seafood, and unforgettable sunsets, Key West delivers a unique mix of history, character, and island charm.

 

And that’s our first impression.