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Key West Walking Tour

At the end of Grinnell Street, spanning three city blocks, the Historic Seaport is a boardwalk chalk full of beautiful schooners, charter boats galore, open-air eateries and nautical shops.  There is even a small sea-turtle museum/aquarium.  One could literally spend hours here just looking at the sights.  And don’t forget to feed the Tarpon.  Conveniently placed coin operated machines distribute pellet like food to feed the bait fish, birds, and other variety of sea-life living at the marina.  I can assure you that watching the little critters eat entertains people of all ages.

Across from the Seaport, Caroline and Fleming Streets are home to several historic “conch cottages” built at the turn of the 20th century.  Many are now utilized as popular guesthouses.  The best time to view these gems is at night during the Holiday Season when they are all lit up with Christmas lights competing with one another for different titles during the annual holiday tour.

As you come to the end of the Seaport you will find yourself at Front Street.  Mallory Square, located just steps away at the foot of Duval Street, is famous for its sunsets.  Every night when the sun goes down local artisans and performers gather together to peddle their wares and please the crowds that populate the area.  But in the day time you can visit the Shell Warehouse, the Shipwreck Historeum, and the Key West Aquarium, see the immense cruise ships docked at the Hilton Resort and Marina, or shop in one of the many boutiques that populate the area. 

As you complete your tour of the Seaport, turn onto Duval Street, Key West’s equivalent to New Orleans’s own Bourbon Street.  About one mile long, this famous street is bursting with local color; art galleries, pubs, museums, restaurants, shops, jewelry stores, and clubs line the street.  Do the “Duval Crawl” and have a drink at every bar you pass; by the time to get to the end of the street you will be crawling.  (Maybe you should save this for the evening and take a cab back to your hotel.)

Whitehead Street parallels Duval Street to the west.  Here one will find a more residential area of downtown Key West with sights such as the Audubon House and Gardens, the Ernest Hemingway House and Museum and the Key West Lighthouse Museum.  

On the corner of Whitehead and Southard Streets is the Truman Annex, one of the most picturesque neighborhoods in Old Key West, reminiscent of the “Leave it to Beaver” era.  This gated, white picket-fence community is adjacent to the Harry Truman Little Whitehouse Museum and also leads to Fort Zachary Taylor State Park and beach.  Here, you will have great views of both the Gulf of Mexico and the Atlantic Ocean. 

Besides the museums and the Annex one will also run into Bahama Village, a neighborhood occupied by peoples of African decent, and marked by colorful wares being sold out on the corner of Whitehead and Thomas Streets.  This area is also home to Blue Heaven Restaurant which provides for it’s patrons the true taste of Key West; located on Petronia Street, the building itself has been used to entertain locals and visitors alike for over a century.  The spot is famous for their Sunday Brunch and their very relaxed atmosphere.

The Southernmost Point of the Continental United States is located on the corner of South and Duval Streets.  Traveling north on South Street will bring you to the islands beaches, namely Higgs Beach, South Beach, Dog Beach, Rest Beach, Broken Glass Beach, and eventually Smathers Beach which is located on South Roosevelt Blvd.  And where better to relax after a long walk than on the beach where you can catch some Southernmost City sunshine.

If you get tired of walking you can always take an Old Town Trolley Tour or go for a ride on the Conch Tour Train.  You can buy tickets for these tour individually or purchase a Passport which includes several museum tickets as well.