5 of the Best Things to do in Key West

From discovering Ernest Hemingway’s home to viewing a beautiful sunset at Mallory Square, Stephanie Kalina-Metzger lets us in on five of the best things to do in Key West.

Each year, more than two million travellers cross an item off their bucket list by visiting the tropical paradise known as Key West. This small, walkable, picturesque island located in South Florida, spans just four miles long and one mile wide, yet offers an array of activities for those seeking to soak up not only the sun, but also the rich history and culture of the area.

Few areas rival Key West’s climate, so there’s no such thing as a ‘bad’ time to visit the island. Best of all, every attraction mentioned below is open all year round.

Read on to uncover Stephanie’s insider info on five of the best things to do in Key West.


Courtesy of an expert guide, visitors can hear about the lore, legends and history of Key West via the Key West Hop-On Hop-Off Narrated Trolley Tour.

Tourists can get acquainted with the island and hop on and off at their leisure to sightsee, or stay on the 90-minute ride for an overview of the area.

Stops include various hotspots such as Mallory Square, Hemingway House, the Southernmost Point Buoy and the Key West Shipwreck Treasure Museum, to name a few.


Located at the corner of Whitehead Street and Duval Street is a Spanish colonial style house, built in 1851 by Asa Tift. The attractive dwelling later became home to one of America’s most iconic writers and today stands as one of Key West’s biggest tourist attractions.

Guests who visit the Ernest Hemingway Home and Museum will learn all about the prolific author who spent nearly 10 years in the property. Docents share details on the life and times of Hemingway, along with interesting tidbits they might not otherwise have known.

A highlight of the tour for many is the opportunity to view Hemingway’s writing quarters, which he accessed via catwalk from the second floor of the main house. The catwalk no longer exists; instead, visitors climb a set of narrow stairs resembling a fire escape to peek into the room where Hemingway’s novels were brought to life.

Head outside and you’ll find the first in-ground pool to be installed in Key West. This labour-intensive project which was hand-dug by pickaxes, cost a pricey $20,000 and Hemingway was disgusted by its cost so consequently tossed a penny on the ground declaring, “You might as well have my last cent”. His wife Pauline then embedded the penny in cement on the property, so you could say it actually cost them $20,001.

Also, if you’re a fan of cats as Hemingway was, you’ll be pleased to hear that almost 60 of the furry felines roam the grounds. Today, visitors can interact with them, many of which are polydactyl meaning they have extra toes. Now that’s something you don’t see everyday.


The Harry S. Truman Little White House, located at 111 Front Street in Key West, was constructed in 1890 for Naval officers and in 1911 was converted into a single-family residence. Theodore Roosevelt visited several times and Thomas Edison stayed at the house for six months while working on 41 new weapons during World War II.

Truman used the house for 175 days during his administration and the dwelling became known as the ‘Little White House’. President Dwight D. Eisenhower also conducted meetings there while recovering from a heart attack and Bill and Hillary Clinton used the house as a weekend retreat. The structure is considered the birthplace of the U.S. Department of Defense and the U.S. Air Force and tours are conducted daily every 20 minutes from 9 a.m. to 4:30 p.m.


Duval Street is Key West’s most iconic street, buzzing both day and night, home to outstanding restaurants, boutique shops and lively bars like Sloppy Joes which was known as Earnest Hemingway’s favourite haunt.

The 1.25-mile long stretch offers a variety of merchandise from art, to antiques, cosmetics and more. As night closes in, the atmosphere on the popular street turns more lively. Crowds gather to enjoy pub crawls, party and celebrate and it’s not unusual to witness more than a few unconventional characters. For people watchers, it’s a must-see scene.

If you’re looking for a holiday home right on top of Duval Street, Louisa’s Hideaway is an excellent choice complete with a private pool and modern furnishings.


Mallory Square is also chock full of shopping opportunities where tourists can purchase anything from clothing, to accessories, cigars and souvenirs.

Guests can also explore artifacts from an 1856 shipwreck at the Key West Shipwreck Treasure Museum and learn from ‘Asa Tift and his wrecking crew’ about how the maritime wrecking industry provided a living for the early pioneers of Key West (be sure to climb the tower to witness an incredible view).

Those who work up an appetite after a day of shopping can visit any of the many restaurants in Mallory Square like El Meson De Pepe. The family-owned restaurant with the funky decor specialises in Cuban Conch cuisine and its patio bar is a perfect perch for sipping mojitos while enjoying live Latin music.

Two hours before sunset, the excitement becomes palpable. Arts and crafts vendors begin setting up booths and food trucks arrive to offer a variety of mouthwatering fare. Quirky and talented street performers including jugglers, psychics and local musicians turn up to entertain the growing crowd as the sun begins to set in the distance.

Many spectators will consider this nightly Sunset Celebration as one of the top highlights of their visit to Key West so this is something you definitely shouldn’t miss.

Top tip: Stay a stone’s throw from Mallory Square at the hugely popular Ocean Key Resort & Spa, a Noble House Resort which offers stunning views across the the Gulf of Mexico.

Originally published at www.travioor.com.

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