Whitehead Street in Old Town Key West is a leafy, mile-long stretch that runs parallel with Duval Street, from the Gulf of Mexico to the Atlantic Ocean. It’s a street with many tourist stops that manages to feel authentic. Colorful Key West bungalows, sprawling Banyan trees, historic points of interest and roaming roosters make for a pleasant walk that's characteristic of the island.
Start your walk at the Southernmost Point Buoy on the corner with South Street, where Whitehead begins (or ends, depending on your perspective). The concrete buoy is the southernmost point of the continental United States and is constantly flanked with tourists waiting in line for a photo. Head north before cheesing it for the camera.
It won’t be long until you reach the Key West Lighthouse (938 Whitehead St.). The historic Key West Lighthouse is out of commission today, but it served the Key West community since 1825. Built on one of the highest points in Key West, an 88-step climb to the top is one of the best views on the island and worth checking out.
You can find this stunning mural and great food and drinks in Moondog Café at 823 Whitehead St.
Across the street you’ll spot the entrance to the Hemingway Home & Museum (907 Whitehead St.). Hemingway spent most of his Conch tenure at the iconic Spanish colonial. The Hemingway Home and Museum is open 365 days a year, from 9 am to 5 pm. Check the website for current tour pricing. Cash only.
Further up, the Green Parrot Bar (601 Whitehead St.) is bound to catch your attention. This lively dive bar is a popular spot for locals and tourists out to socialize and enjoy live music and drinks.
Onward, you'll cross paths with a towering Kapok Tree on the left and Mile Marker Zero on the right, which marks the start of the U.S. Route 1. The highway stretches 2,369 miles north to the Canadian border. Swing by the End of the Road gift shop to pick up souvenirs and a mile zero marker of your own.
Up on the right, notice the white house-turned-restaurant that was the original headquarters of Pan-American Airways (301 Whitehead St.). Enjoy a meal and tasty home brews from the aviation-themed First Flight Restaurant, which now occupies the space.
Continuing onward, you’ll see a house with green shutters and lush greenery: the Audubon House & Botanical Gardens. While John James Audubon never lived in the house, he was believed to have spent time sketching Key West’s native birds on the premises. You can see some of the naturalist's paintings and sketches on display today. Visit for a walk through the gardens and a look at this restored, American Classic Revival house that is one of the finest on the island. The Audubon House and Botanical Gardens are open 365 days a year, from 9:30 am to 4:15 pm.
As you near the end of Whitehead Street, you’ll come upon Mallory Square, which is a trip in itself! Try to plan this trip to reach Mallory Square before sunset so you can witness the daily Mallory Square Sunset Celebration.
Planning a stay in Key West? Check out rates at 24 North Hotel. We have an on-site Starbucks, shuttle service to Old Town every hour, and our pool area is one of the best on the island. See our special offers - special rates for Florida residents!