Key West Florida City Guide

Absolutely everything you need to know about what to do in Key West
By
Cortney Tarell
Key West Florida City Guide

Key West, Florida is one of the most famous vacation destinations in the world.

It’s known for its serene waters, extreme water sports, and thriving night life. But Key West is so much more than that. It has a rich history as a home for some great minds of history. It has one of the best LGBT+ communities in the state, a thriving art scene with live music playing all over the city, and a small-business friendly market. All of this adds to so much to do, you could be busy in Key West for a year. Walk down Duval Street to witness one of the country’s most famous historical streets, still bustling with shopping, art galleries, and entertainment in addition to historical homes.

Most of the action here happens on the Island of Key West, the southernmost island on the U.S. Route 1, but Sigsbee Park, Fleming Key, Sunset Key, and Stock Island are also within the city limits of Key West. The southernmost city in contiguous United States is packed with sites to see and things to do, this is just a small list of some of things that make it great.

History

Key West City Guide
The Key West Lighthouse
 

Key West was the first Florida city discovered by Europeans when Ponce de Leon landed here in 1521 in search of the Fountain of Youth. He named it Cayo Hueso, “Bone Island” in Spanish. “Key West” stuck as the name of the island because it sounded so similar to Cayo Hueso. The city became a part of the United States in 1822 and quickly became a buzzing business town when industries such as wrecking, salvaging, salt manufacturing, and turtling thrived here more than anywhere else. In the mid 1800s, it was the richest city per capita in the country. The Key West Lighthouse was built in 1847.

Soon, Key West became one of the most important military centers. Fort Zachary Taylor was built here in the lead up to the Civil War. It remained under Union control despite the rest of Florida belonging to the confederacy. 

Key West City Guide
Hemingway Home
 

After the war, Key West once again built a booming industry, this time in tourism. After Henry Flagler’s Overseas Railway was built in 1912 to connect the island to the mainland, it became a popular spot for celebrities of the time to visit and even live including Ernest Hemingway, Tennessee Williams, and President Harry S. Truman. Today you can visit The Truman Little White House and the Hemingway Home to get a peak at this moment in history.

In 1982, Key West further established itself as self sufficient city when it declared independence from the United States in response to the United States Border Patrol blocking the Overseas Highway to curb drug trafficking and causing huge traffic jams. They called their new independent country “The Conch Republic”. The independence was short lived, but it is celebrated in the Conch Republic Independence Day each year. The name is still an important title to Key West natives, who call themselves "conchs".

Key West City Guide
Key West Shipwreck Treasure Museum
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There have been plenty of shipwrecks here, and discoveries from those shipwrecks have led to more and more knowledge of the island’s history. Learn more about the Shipwreck history of Key West with a visit to the Mel Fisher Museum or Key West Shipwreck Treasure Museum.

Other great places to visit for the history of Key West are The Custom House Museum and The Oldest House.

Culture

Key West Florida City Guide
Key West Pride
Photo courtesy of gaykeywestfl.com
 

Key West is one of the most richly cultured cities in Florida. The locals (known as Conchs) are proud of their quirky city and all its eccentricities. Here you will find a town full of people who will accept you into the family exactly as you are. The motto of Key West is “One Human Family”. Everything is colorful and vibrant, with a laid back beach vibe and the arts represented everywhere. Spanish-inspired Victorian architecture mixes with Caribbean style to form Key West’s completely unique energy. Everywhere you turn on this island, you will find something new, interesting, and different to explore.

The city has been a mishmash of cultures and artistic endeavors since the very beginning. In the 1800s it attracted everyone from British immigrants to escaped slaves from the mainland and refugees from Cuba. It wasn’t long before gay and lesbian people found that this little island was a place where they could proudly be themselves. All of those people helped shaped Key West into the diverse and welcoming place it is today.

A huge percentage of Conchs are artists, encouraged by the environment around them to create as much as possible. The leading industry is tourism, as expected, but many people also work in the fishing or marine biology industry and many are also restaurant or small business owners.

As mentioned before, LGBT culture is especially represented here. There’s a reason Advocate Magazine called it a “Gay Paradise”. LGBT visitors won’t have to search far to find friendly locals, but if you want to stay in the aforementioned paradise book a stay at Alexander’s Guesthouse, a hotel that has been incredibly gay friendly for decades or the Equator Resort, a male only, clothing-optional resort. Gay and lesbian bars can be found around the island year-round, but the best time for LGBT vacationers to visit is during one of the two pride festivals that happen here: Womenfest in September and Key West Pride in June.

To experience extra of what makes Key West so weird and wonderful visit in October during Fantasy Fest.

Food and Drink

Key West Florida City Guide
Interior of the Rooftop Cafe
 

Key West has one of the most exciting food scenes in Florida. In fact, it was named as one of the World’s Best Islands for Food by Travel and Leisure in 2015.

The Small Business friendly environment of Key West has made it a great place for all kinds of independent restaurants and delicious food you won’t find anywhere. Many of the most famous restaurants on the island have been there for decades. Pepe’s Cafe is the oldest restaurant in Key West, opened in 1909. It would be impossible to list all of the delicious food options in Key West, but here are some standouts:

For a fancy meal:
Santiago’s Bodega, Latitudes, Louie's Backyard, Nine One Five, Seven Fish, Rooftop Cafe

For a casual meal:
Banana Cafe, Mellow Cafe and Gastropub, OnlyWood, Caroline's Cafe, Date and Thyme

Seafood is, of course, a huge part of life on any island. This island is especially known for pink shrimp, stone crabs, spiny lobster, conch chowder, and conch fritters. Conch Republic Seafood Company comes up again and again as the best place to get any and all of those dishes. Also check out Alonzo’s Oyster Bar, Thirsty Mermaid, Half Shell Raw Bar, Eaton Street Seafood Market, and Turtle Kraals.

With its close proximity to Cuba (Key West is closer to Cuba than it is to Miami) Cuban food is also an important cuisine in Key West. Cuban culture has been a huge part of the city since Cuban refugees flooded here during the Ten Year’s War in Cuba in the 1860s. Get some of the most authentic Cuban food at El Meson de Pepe, Sandy’s Cafe, and Cuban Coffee Queen.

Key West Florida City Guide
Sloppy Joe’s Key West, one of Key West's oldest and most famous destinations.
 

When you’re walking around the hot streets of Key West, you’re definitely going to want an icy cold cocktail or beer, and there are plenty of places to get delicious ones. Sloppy Joe’s Key West is probably the most iconic watering hole on the island. To get a true Florida Keys experience make sure you try the Rum Runner, a cocktail that mixes Bacardi Superior Rum, Blackberry Brandy, banana liquor, lime juice, and grenadine, invented on Islamorada. You should at least try some rum, which has a long history on the island. Visit the Key West First Legal Rum Distillery or Papa's Pilar to learn more. Want to skip the alcohol? Grab a fresh coconut to sip on coconut water. 

Key West Florida City Guide
Key Lime Pie from the Key West Key Lime Pie Company
 

And of course you don’t want to leave Key West without trying key lime flavored everything, but especially key lime pie. Kermit's Key West Key Lime Shoppe has every key lime flavored treat your heart could desire. Old Town Bakery, Blue Heaven, Key West Key Lime Pie Company, and Café Solé are all also often sited as restaurants with the best key lime pie, so try them all and decide for yourself!

Shopping

Key West Florida City Guide
Mallory Square
Photo Credit: Cortney Tarell

 

Most of the best shopping to be found in Key West is at independent boutique shops you stumble upon as you stroll the streets of the city. There are no shopping malls in Key West and few large chain stores, but the shopping is some of the best you’ll find anywhere in the state. Duval Street, The Key West Historic Seaport, and Mallory Square are good places to start, but the entirety of Old Town Key West has tons treasures just waiting for you to discover them. Some interesting specialty stores on the island include Besame Mucho, Key West Island Books, Peppers of Key West, and The Green Pineapple.

Key West is also a great place to buy art and handmade items. You’ll find people selling their art all over the island. Also check out the Arts section for a list of the best galleries in the area.

Entertainment

Key West Florida City Guide
Entertainers at Mallory Square
Photo Credit: Cortney Tarell

 

You don’t have to look far to find entertainment in Key West. Tourism is the biggest business here, so there are businesses across the island lining up to take you on themed cruises, rent you a jet ski, and lead you on a special tour. There are quite a few things that you have to do on a visit to Key West, and spending some time doing water sports is one of them. Rent jet skis, go parasailing, and take a snorkeling trip while you’re here, there’s no better place to do it. If you want to do something more extreme, it’s also a great place for skydiving.

Another Key West standard is a stroll down Duval Street to see everything there is to see. Make sure you visit mile marker 0 and the Southernmost Point for the requisite photos.

Key West Southernmost Point
Photo Credit: taylorschaake on Instagram
 

When the sun starts to go down, that’s the time to head to Mallory Square, where tons of street performers come out to entertain beginning two hours before sunset. It’s a party you don’t want to miss. After the sun goes down you can head back to Duval Street to enjoy some of Key West’s legendary nightlife. 

Another thing Key West is famous for is the amount of ghosts that reportedly reside here. With so much history, it’s hard to avoid the inevitable hauntings. If you’re especially interested in ghost stories, there are plenty of ghost tours you can take. Can’t miss places for the supernatural lover are the Fort East Martello Museum as the home of famously haunted Robert the Doll and the Key West Cemetery, with lots of epitaphs that are worth the read.

Want to catch a movie while in Key West? Head to the Tropic Cinema to support the island’s local movie theater.

Arts

Key West Florida City Guide
Interior of the Key West Theater
 

Key West is an amazing art and cultural center. You can partake in every form of art on the island, surrounded by it even if you’re just strolling the streets. Street art and street performers are common here, so you’ll find an artistic experience even if you don’t go looking for it.

If you do want to seek out the arts in Key West, one of the best ways to do it is by checking out one of the many galleries dotted throughout the island. These galleries focus on showcasing local talent and highlighting the beauty of natural Florida. Some of the ones that you don’t want to miss include: Key West Art Center and Gallery, Art On Duval Key West, Key West Pottery, Zazoo Fine Art Gallery, Gallery on Greene, and Gildea Contemporary Gallery. Also check out The Studios of Key West, where artists can rent work space and take classes to improve their work. You can check out the gallery space and attend a performance there to support local artists.

Theatre also has a great home in Key West. Check out the Waterfront Playhouse, the oldest continuously running theatre group in Florida, or the Red Barn Theatre to see a play or musical on your visit. You can also catch a variety of different kinds of shows at the Key West Theater.

The best way to experience music in Key West is to catch it live at one of the many restaurants and bars that double as a music venue. Walk down the streets of Old Town and you will hear music streaming out of tons of places, so head inside to support some of the local musicians. If you want something more classical, catch a show with the South Florida Symphony Orchestra, which often has shows in Key West at the Tennessee Williams Theatre at The Florida Keys Community College

Sports

Fishing in Key West
Fishing in Key West
Photo Credit: Captain Justin Valakis on Instagram

 

As previously mentioned, water sports are king in Key West. There are plenty of places to go boating, jet skiing, or sailing. There are also tons of fishing charters ready to take you out to the best places to go fishing.

 

Key West Florida City Guide
Key West Golf Club
 

Besides that sports are not very common in Key West. There have been no professional sports teams in the city since 1975 with the exit of the minor league baseball team called the Key West Sun Caps, the Key West Conchs, and the Key West Cubs alternatively.

There is one golf course in Key West, the Key West Golf Club on Stock Island. It is a course on over 200 acres of island land with 18 holes for all levels of skill.

Nature

Key West Florida City Guide
Dry Tortugas National Park
Photo Credit: Cortney Tarell

 

Key West is an island surrounded by incredibly blue ocean on all sides, with many nearby islands to explore as well. Most of the coast of the island isn’t made up of beaches, but there are a few beaches to check out. Smathers Beach, Higgs Beach, South Beach, Dog Beach, and the Beach at Fort Zachary Taylor aren’t the most beautiful or expansive beaches in Florida, but they are great places to get some sun and soak in the ocean while you’re in Key West.

For one of the most epic nature experiences in the state, take a cruise or a private plane down to Dry Tortugas National Park, one of only three national parks in Florida, where crystal clear waters surround the historic Fort Jefferson for some of the best snorkeling and sightseeing you’ll find anywhere. You can set up a tent right on the island of Garden Key to spend the night practically right in the ocean and stargaze at a sky that isn’t blocked by electric light. You can also camp closer to the action in Key West at Boyd’s Key West Campground or Leo’s Campground, both located on Stock Island.

Key West Florida City Guide
Dolphins swimming in Key West
 

Other great places to experience the plant life and natural wonder of Key West include the Key West Tropical Forest and Botanical Garden and the Key West Butterfly and Nature Conservatory. Ocean life is abundant here, and you can get up close and personal with it out in the wild by taking a snorkeling trip or going swimming with dolphins. Learn more about the sea life of the area with a visit the to Key West Aquarium or the Florida Keys Eco-Discovery Center. Wild birds, turtles, and marine and land mammals are rehabilitated at the Key West Wildlife Center. Visit to learn more about animal rescue efforts on the island.

Education

Key West Florida City Guide
The Florida Keys Community College
 

Key West is a part of Monroe County School District. It contains one public high school: Key West High School, two public elementary schools: Gerald Adams Elementary School and Poinciana Elementary School, and one K-8 School: Horace O'Bryant School, plus several public charter schools and private schools. There is one college in the entire Florida Keys, The Florida Keys Community College, which has its main campus on Stock Island.

Tourism

Key West Florida City Guide
Cruise ship coming into Key West
Photo Credit: Cortney Tarell
 

Tourism is the leading business of Key West, so if you’re visiting you will find so many places to stay and people who are used to doing business with tourists. You will find plenty of fun at any time of the year, but planning your vacation according to the time of year can help you have the best experience. Winter months are the most crowded with northerners coming for months at a time, and summer months come with lots of heat and humidity. Visiting during hurricane season, from June to November, can be a risk. Spring is the best time to visit for a perfect balance of good weather and lower crowds.

As for where to stay, there’s something for everyone in a variety of price points. Find your perfect tiny bed and breakfast or comfy inn, or stay in a luxury hotel or rental home. The options are endless.

Transportation

Key West Transportation

Getting around Key West is very easy. Much of the island, especially around Old Town, is walkable. If you want to get around faster, there are plenty of places you can rent a bike for the week or so. The city has a public bus system that travels all around the island. The Duval Loop bus that travels Old Town is free to ride and other bus lines are low cost.

Most people get to the island by way of the overseas highway that stretches from mainland Florida. You can fly to the island at the Key West International Airport. The island also has one of the busiest seaports: the Key West Historic Seaport. You might arrive here if you come to Key West on a cruise, or you’ll leave from here to go on all sorts of fun adventures and day trips at sea.

Health

Key West has one major hospital, The Lower Keys Medical Center on Stock Island.

 

Sources:

conchtourtrain.com

keyshistory.org

Key West Florida City Guide
Key West Florida City Guide
Absolutely everything you need to know about what to do in Key West
Cortney