Where in the world can you go and walk from the Atlantic Ocean to the Gulf of Mexico in less than an hour?  The answer is Key West, Florida.  The island actually sits between the two bodies of water which makes exploring this quaint town a fascinating and educational journey.  Because of its small size, walking is the main form of transportation in Key West.  And a walking tour is by far the most interesting and informative way to get to know this island, rich in lush scenery, American history and Bahamian inspired architecture.

Start: The Southernmost Point in Key West

Southernmost Point
Whitehead Street and South Street, Key West, FL 33040
Starting out at the very south end of the island, you will find yourself at the Southern Marker for the southernmost point of Key West; the southernmost point in the Continental U.S.A.  Take in the beauty of the Atlantic Ocean and take advantage of a unique photo opportunity at this famous, historical marker. Walking north on Whitehead Street, you can leisurely view Key West’s classic conch homes and inns, with palatial two-story porches, shutter flanked windows, charming framework and white picket fences overflowing with colorful foliage.  Weaving up and down side streets along the way, you’ll also find various eatery gems off the beaten path. As you head north along Whitehead, you may want to stop and visit the Key West Butterfly & Nature Conservatory. Take a quick right on Truman Ave to Duval Street and pick up some souvenirs at Key West’s Truval Village Market Place.

Earnest Hemingway & Mile Marker Zero

Head back down Truman to Whitehead St and continue heading north a block and you will find the Ernest Hemingway House & Museum. Right after that you will find some great souvenirs at the Bahama Village Market and a few blocks more will take you to Mile Marker Zero. Continue down to 410 Caroline Street where you will come across a tiny cottage once visited by the famous poet Robert Frost. The building is now open as the Heritage Museum.  Trek down a block or so to discover the Harry S. Truman Little White House and the Curry Mansion Inn which was purchased in 1975 by a New York couple named Edith and Al Amsterdam whose family still operates it today as one of Key West’s most popular bed and breakfasts.  Beautiful columns and balconies adorn this 28 room inn filled with eclectic antiques.  Guests can enjoy a full breakfast and happy hour drinks daily.

History, Art, Ghosts & Key Lime Pie

Continue heading north on Whitehead and you will pass the Audubon House & Tropical Gardens, a quick jaunt down front street will bring you to the Museum of Art & History (Customs House) and right on the corner of Front St and Whitehead St. you can book a Haunted Tour of Key West at the infamous Ghosts & Gravestones or visit the Key West Aquarium right next door. Head north-east on Front St and a few blocks down is Ripley’s Believe it or Not. Across the street on the corner of Duval and Front St., you can stop in for a slice of Key West’s Famous Key Lime Pie at Kermit’s Key Lime Pie Shoppe.

The Seaport Harborwalk, Dinner & Drinks

Make your way down Duval and turn East on Caroline Street to Margaret Street and you will soon find yourself at the Seaport Harborwalk. Stroll the seaport to Schooner Wharf Pub and eat fresh seafood while you sit amongst towering ships docked in the marina.  Take a snorkeling or sunset cruise out to a coral reef in the Gulf of Mexico.  Also, visit the Conch Republic restaurant for open air, waterfront dining in a laid back, casual atmosphere.  There are several large hotels and resorts along the water that you can visit for a drink or dinner.

Mallory Square Sunsets

Further down along the water, you will discover the bizarre and beautiful charm of Mallory Square where the sunsets are magnificent and the entertainment – a tad weird.  Fire eaters, jugglers, daredevils and more make Mallory Square Key West’s own little circus.  It’s a must see!

Key West’s Spirited Nightlife: Irish Kevins & Sloppy Joes

Backtrack a bit to Duval Street and wrap up your tour with singing and dancing at the World Famous Irish Kevin’s where singing along with the entertainment is sure to be the highlight of your day. If belting out some fun tunes isn’t your style then Key West’s free spirited nightlife awaits you. Visit Sloppy Joes, Hogsbreath, Margaritaville and more, for tropical cocktails and lively music.  No need to worry about appointing a designated driver, remember you’re on foot and there are plenty of Cabs & Uber drivers patrolling 24/7 to bring your tired feet back to your hotel or vacation rental when you are done for the day!
If you prefer to take a Trolly, Old Town Trolly Tours hits most of the same places from the comfort of the Trolly so you can save your sandals.

Key West Walking Tour Map

To view the map below in a new window click here.

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