Classic, Historic Key West

By Kai Rambow


“He was the most interesting man on the planet, long before the Dos Equis commercial,” our tour guide at the Hemingway House noted.  Key West has attracted all kinds of enterprising and famous characters, creating a storied history.  Here are great options to explore some of that history:


Conch Tour Train vs. Trolley Tours

If you’re making your first trip to Key West, taking one of these tours is a great way to learn about the city.  The Conch Tour Train is a narrated trip with only a few stops. Trolley Tours is also a narrated trip, but has numerous hop-on and hop-off stops.  Both are good, so it’s a matter of personal preference.

Note: Trolley Tours states it takes you around the entire island. While technically true, the additional length has water on one side and hotels / commercial properties on the other side.

Ernest Hemingway House

This historic house existed before Hemingway moved in; it’s the stories about this colorful, transformative writer that make this a must-see place. While you can explore on your own, recommend you take a guided tour, to get the vivid details of Hemingway’s life.

Even little details are told with flair. A six-toed cat gifted to Hemingway has multiple descendants living in luxury here. All have been given famous names. One kitten was named Howard Hughes.  Shortly after being named, this cat became a recluse. “You can’t make this stuff up,” our guide enthused.


Harry S. Truman Little White House

Under doctor’s orders to get some rest, Admiral Nimitz suggested this spot at the naval base.  President Truman loved it so much, he made multiple visits during the rest of his presidency totaling 175 days.

Changes were made to the original building, turning it into the little White House. Personal insights from guides make this a worthwhile visit. While Truman loved being here and frequently walked through Key West, his wife did not. Truman loved to play poker; his spouse disapproved.

Duval Street

This main street has a wonderful mix of historic buildings, art galleries, restaurants and bars. Day and night walks reveal different aspects of Key West.


Pepe’s Café

Over 100 years old, this is the oldest restaurant in the Florida Keys. It has a solid reputation with locals and repeat visitors. President Truman would stop in for coffee during his walks. Noted for daily specials for breakfast, it’s open all day. Located across from the historic seaport (806 Caroline St.) with plenty of parking nearby, this is a tasty, historic place.

Tips for a Great Trip

Hurricane Irma:  This trip was made two weeks ago.  The Keys are fully recovered with very few indications of last year’s hurricane.

Drive or Ferry: It’s a seven-hour drive without stops to Key West. The ferry running from Ft. Myers may seem like an option, however, several people shared problems they’ve encountered.

Check in time for the ferry is 7 a.m.  It’s a 2.5-hour drive to the ferry, so you would need to leave really early or book a hotel room. You can expect to arrive in Key West around 12:30 p.m.

Ticket cost for one person is more than gas for a return trip by car. A bigger problem is the weather.  If the weather is not good, the ferry will cancel a boat trip.  It will be your responsibility to book a hotel room or get a rental car.

Special thanks to Jim Granan for his invaluable assistance.


The Ernest Hemingway Home and Museum

907 Whitehead St.

Key West, FL 33040

Harry S. Truman Little White House

111 Front St.

Key West, FL  33040

(305) 707-6184