History & Legends

Approximately 3 Hours
Moderate Activity 

This leisurely tour of Key West begins with a fully narrated tour on board the Old Town Trolley, covering over 100 points of interest as you take advantage of hop-on/hop-off privileges at 11 different stops around the entire island.

Step back in time to the days before ‘civilization’, when fierce Natives left their enemy’s bones to bleach on the island of Bone Key.

Explore what is now a lush, tropical island, and discover the charm and grace of one of America's unique architectural pleasures.

Get to know characters such Ernest Hemingway and Harry S Truman as well as the magic that is Key West. You will find out about Key West’s unique role in the Civil War, and about Henry Flagler’s dream and how it came true.

From bold Spanish explorers and brave wreckers to the great cigar barons and sponge magnates, Key West’s golden age is yours to discover, from settlement through the exciting days of the railroad, the doldrums of the Depression, World War II and the Kennedy era to the present.

Your tour includes entry into the Hemingway Home -- the house of author Ernest Hemingway (Trolley Stop #5). Enjoy a leisurely tour through the home built in the 1870s by a wealthy ship-wrecker. Ernest Hemingway arrived in Key West in the early 1930s and wrote about a dozen novels and short stories including To Have & Have Not, For Whom the Bell Tolls, and The Green Hills of Africa. After hearing wonderful stories and anecdotes, take a stroll around the beautiful property, complete with some descendants of Hemingway’s original polydactyl cats.

It’s just a short ride to Mallory Square, where you will walk a short distance to the vacation home of President Harry S Truman. President Truman enjoyed 16 working vacations in Key West, and even joked that he wanted to move the White House here. The only Presidential Museum in Florida, the Truman Little White House has been a host to six US Presidents, as well as royalty and dignitaries from around the world.

This is an independent (unguided) tour that allows you to tour at your own pace.


This excursion is led in English