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A Weekend Full of Fun Things to Do in Key West

Last Updated on October 20, 2023

Looking for fun things to do in Key West? We have you covered.

Caribbean House Key West exterior.

From its Conch-style houses, with tin roofs and gingerbread trim, to its dramatic history and rambunctious bars, Key West bewitches visitors like a magical sea nymph.

Camping at sunrise in Key West.

Besotted travelers return year after year, drawn to a place where almost anything goes.

Key West Conch Fritters stand.

The historic center, Old Town, is full of watering holes and kiosks. It also brims with historic attractions, atmospheric restaurants, and plenty of shopping.

It’s amazing how much you can do and see within a 48-hour window of time or a weekend.

Things to Do in Key West

Key West taken from balcony at Marriott resort.
Key West is always picture-perfect.

Key West proudly wears its history on its sleeve. Founded in the 1820s, this city became the southernmost outpost of the United States before Florida even achieved statehood.

Downtown Key West buildings.
Source: Key West

To walk down Old Town’s tree-lined streets, under an island-blue sky, surrounded by inns and houses well over a century old, can be one of the simplest Florida pleasures you’ll ever experience.

Key West Mural at Cuban Coffee Queen

While it would be easy to spend several days savoring all that Key West has to offer, sometimes there’s only a short weekend available to savor this tropical destination.

Audubon House and Tropical Gardens

Audubon House building exterior.
The Audubon House on Whitehead Street.

Let’s say you have already toured the Hemingway Home. In that case, start your island explorations at the Audubon House, also on Whitehead Street.

This lovingly preserved mansion with its distinctive green shutters once housed the family of Captain Geiger, a wrecker who made a fortune salvaging ships that had foundered on the Florida Reef.

Here, you can tour each room and come away with a sense of how a well-to-do family lived at the time.

Audubon House Museum interior.
Source: Audubon House

The painter John James Audubon once illustrated a tree in the Geiger’s garden, which is why the home has been named in his honor.

Another reason to tour the house is the chance to see its spectacular collection of Audubon prints.

Audubon House Address: 205 Whitehead St, Key West, FL 33040

Kino Sandals

Kinos Sandals in Key West.
Source: Kino Sandals

A short hop from the Audubon House is Kino Sandals. Hand-crafted sandals have been made here for decades, and come in all colors.

Kino sandals sitting on the pier.

“Kino’s” has won legions of loyal fans, and a pair of their sandals is one of the most comfortable – and least expensive — Key West souvenirs you’ll find.

Kino’s Address: 107 Fitzpatrick St, Key West, FL 33040

St. Paul’s Church

St. Paul's Episcopal Church vintage postcard.
Source: Authentic Florida Collection

Over on Duval Street, be sure to stop inside St. Paul’s Church, a dazzlingly white, tropical house of worship completed in the 1920s.

St. Paul's Church in Key West.
St. Paul’s Church in historic Key West

An Episcopal church has stood on this site since the 1830s, although fire and a hurricane caused the demise of those earlier versions.

St Pauls Key West building exterior.
Source: St. Paul’s

Today, the quiet interior of St. Paul’s offers a welcome respite from the hustle of Duval Street and a place to pray, meditate, or absorb the stillness.

St. Paul’s Church Address: 401 Duval St, Key West, FL 33040

Date and Thyme

Date & Thyme building exterior in Key West.
Delicious Date & Thyme on Fleming Street

Particularly when on vacation, sometimes you want to eat something light…to offset later indulgences. At lunchtime, if you want to try something off the beaten path, cruise down Fleming Street to Date & Thyme.

Date and Thyme Smoothie Bowl.
Source: Date and Thyme

Casual, health-conscious Date & Thyme serves up fresh wraps, custom blended juices, salads, smoothies, and daily specials.

Date and Thyme Acai Bowl.
Source: Date and Thyme

A crisp salad with pesto, avocado, and pumpkin seeds can make for a tasty change of pace.

Date & Thyme Address: 829 Fleming St, Key West, FL 33040

The Conch Tour Train

Conch Tour Trainin front of buildings in Key West.
Source: Conch Tour Train

Strolling around Old Town, you’ll inevitably see the Conch Train ride by and hear its high-pitched bell. When your feet get tired, it’s worth taking a tour.

Conch Tour Train at the Southwest Point.
Source: Conch Tour Train

The drivers will regale you with wild and wacky tales – and some surprising history. After navigating the streets here for decades, the Conch Train has become a Key West icon in its own right.

The Conch Tour Train Address: 303 Front St, Key West, FL 33040

Tucker’s Provisions

Tucker's Provisions in Key West.
Tucker’s Provisions on Duval Street.

People feel compelled to shop on their island vacations; if you want to bring back treasures you will actually treasure, pop into Tucker’s Provisions.

This charming boutique on Duval Street sells thoughtfully curated clothes, bags, shoes, and accessories for men, women, and children.

Tuckers Provisions sunglasses in a purse.
Source: Tuckers Provisions

You’ll find pieces here with great craftsmanship and classic style, often tweaked with a playful twist. (Be warned: While Tucker’s is an excellent place to buy gifts, you might wind up finding something for yourself.)

Tucker’s Provisions Address: 611 Duval St, Key West, FL 33040

Green Parrot Bar

Green Parrot Bar in Key West.

Maybe you’ve already sampled the margaritas at the ever-popular Sloppy Joe’s, and want to explore a different watering hole.

At the Green Parrot Bar, you will feel like you’ve floated backward into another era before Key West was “discovered” by tourists.

The Green Parrot building interior.
Source: The Green Parrot

It may be a dive, but the drinks flow freely, and at night, there’s often interesting and quite excellent live music.

Green Parrot in Key West popcorn.

Enjoy some of the Green Parrot’s popcorn and settle in for a good time.

Green Parrot Bar Key West Address: 601 Whitehead St, Key West, FL 33040

Pepe’s Cafe and Steakhouse

Pepe's in Key West building exterior.
Pepe’s Cafe & Steakhouse on Caroline Street, the oldest restaurant in Key West.

Another Key West institution is Pepe’s, a restaurant with a humble exterior but solid comfort food.

The oldest restaurant on the island, dating from 1909, Pepe’s once presided over Duval Street but later moved over to Caroline Street, where it continues to feed both travelers and locals.

Pepe's Cafe Meal and sauce.
Source: Pepe’s Cafe

Unapologetically retro dishes include oysters Florentine, barbecued chicken, and New York strip steak served with homemade cornbread.

Green Parrot in Key West Key Lime Pie.

Their key lime pie has become justifiably famous, so you’ll definitely want to savor a slice.

Pepe’s Cafe & Steakhouse Address: 806 Caroline St, Key West, FL 33040

Mallory Square

Mallory Square in Key West.
Sensational, world-famous sunset celebration at Mallory Square.

Whether you visit Key West for two days or a week, don’t miss the sunset celebration at Mallory Square.

Mallory Square in Key West.

The tarot card readers, street performers, and craftspeople remind visitors of a time when Key West was still a rough-and-tumble town, but the view will keep you transfixed.

Sailboat with a sunset in Key West.
Sunset in Key West is always picture-perfect.

Look out on the horizon, as boats sail by and seabirds swoop overhead, and marvel at the sky’s gradations of color as the day draws to a close.

Mallory Square Market entrance.
Source: Mallory Square Facebook

In few other places in the world will you find people from all walks of life, gathered together to appreciate a sunset.

Soak it in. Inhale a lung full of sea air. Before you know it, Key West has cast another enchantment, and you can’t help but wonder when you’ll be back.

All photos by Laura Albritton.

Laura Albritton is the author of four books on Florida Keys history including Key West’s Duval Street and Historic Lighthouses of the Florida Keys, which she co-authored with Jerry Wilkinson. She is also a documentarian.

Key West's Duval Street.

Other Authentic Florida articles by Laura Albritton:

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